ME: Use the /interviewer skill to ask me questions about my acne journey. Please don’t be overly blunt. It’s a sensitive subject, but I’m willing to share my story so whoever has gone through something similar knows they’re not alone.

CLAUDE: When did your skin first become something you thought about — not just noticed, but thought about?

ME: Before I answer that, can you elaborate on what you mean by “thought about”?

CLAUDE: I mean the shift from just seeing a breakout in the mirror to it taking up space in your head — something you were aware of during the day, or planned around.

ME: Well, I always took school seriously, but I think junior year was when the workload increased significantly. I was taking more challenging classes and feeling more stressed than usual. That stress resulted in more breakouts, which led to me feeling a lot more self-conscious about my skin.

CLAUDE: That’s the same year you joined the multimedia academy and were taking portraits. Were you ever on the other side of the camera then?

ME: I was. But looking back, even though that’s when my breakouts started taking up space in my head, my acne was still objectively pretty mild (especially compared to what I was about to experience in the years to come).

CLAUDE: Tell me about what came after high school.

ME: I started breaking out more in college, but after about a year, my mom discovered a med spa in our area that introduced me to blue/red light therapy and basically eliminated all signs of my acne. Sure, there was some hyperpigmentation and scarring, but I was so happy the pimples were gone that I didn’t even care. I regularly purchased and used products from that med spa and maintained a skincare routine that kept my acne under control, even when I lived overseas for a little while (three months in Taiwan and six months in the Philippines). But then I moved to Southern California, which was where I lived for the majority of my twenties, and my skin went crazy. My early twenties was when I experienced the worst acne of my life. I had severe cystic acne, and I’m pretty sure I cried about it at least once a week. I honestly can’t remember why I stopped the skincare routine that was working for me in college and for some time afterwards, but I just remember that my skin worsened so much that even thinking about that time in my life makes me want to cry. Eventually, my mom and I found another med spa in the area where I started getting facials regularly. For a while, it was excruciating. The extractions felt like absolute torture. But they worked! Once again, my skin was clear and I had a new skincare routine to follow which incorporated that med spa’s products. After a while, though, the facials and the products were getting too expensive. I also went back to Taiwan, and this time, I stayed for a year. Thinking about that year is definitely bittersweet. On the one hand, I loved the experience. I met so many amazing people, and being immersed in the culture really helped me improve in my ability to speak Mandarin. At the same time, though, that was also when my horrible cystic acne came back. I wanted to document the adventure, but I hated the way I looked in photos. I eventually got desperate and changed my diet. First I was vegan, and then I transitioned to being vegetarian. It helped for a while, but eventually, my system adapted and I was back to breaking out. At that point, my acne wasn’t as severe as it was in my earlier twenties, but it was still enough for me to hate what I saw every time I looked in the mirror. So, finally, I got on Accutane. When I finished the treatment, I’m quite certain that was the clearest my skin had ever been.

CLAUDE: You said you wanted to document that year in Taiwan but hated how you looked in photos. What happened to those memories — did you take the pictures anyway?

ME: I did take the pictures anyway, but on the days when my acne was especially bad, I did feel like I was dying on the inside every time I took a photo. I just knew, though, that I would really regret it if I flat out refused to take any pictures during my time out there.

CLAUDE: Can you look at those photos now?

ME: I just tried to look at some of them right now. I do look back fondly on those memories, but admittedly, it was a bit painful to revisit the way my skin looked back then. The best way I can describe it is that there was a slight feeling of tightness in my chest, which is probably because I still feel embarrassed about going out in public looking like that.

CLAUDE: Thank you for actually looking — I didn’t expect you to open them just now. What would you say to the version of you in those photos, who was already doing the harder thing by standing there?

ME: Knowing what I know now, I wouldn’t want her to have unrealistic expectations. So, I’d probably start by telling her that it’s a continuous journey. As a woman, there are all sorts of hormonal changes that can affect our skin, which has certainly been the case for me. But I would then tell her that, while I haven’t yet found the solution that will completely eliminate acne, it does get better. And even though it feels awful in the moment, she won’t regret putting herself out there and allowing her picture to be taken. Having those photographs will also give her the opportunity to reflect on the challenges she faced and feel proud of how she was able to endure. I would also remind her that it’s okay to cry when it hurts, but the people who truly love her won’t care about how she looks.

CLAUDE: You said it’s still a continuous journey. What does that look like for you now?

ME: Well, Accutane worked for a while, but the effects started to wear off after a few years. Granted, my acne is not severe like it used to be, but I do regularly experience breakouts. I imagine they’re tied to hormones, but it does seem like as soon as a pimple disappears, a new one appears in a different spot. I’m really tired of band aid solutions, though. This time, rather than spending a fortune on external solutions and treatments, I want to see a specialist that will help me identify the root cause of the problem and attack it from the inside. The goal is to not cause further damage in the process.

CLAUDE: Have you booked that appointment?

ME: I sure did. It’s tomorrow.

CLAUDE: What would have to happen tomorrow for it to feel different from the other times you thought you’d found the answer?

ME: I think the solution that’s proposed would need to be different from all the other solutions that have been put in front of me. I’m not a medical professional, so I don’t really know what that looks like yet, but I do hope to finally find an option with long-term effectiveness.

CLAUDE: You mentioned wanting to avoid further damage. Was there something in the past that did damage?

ME: I definitely feel like several things I’ve tried in the past have damaged my skin barrier. Even when I’m not experiencing as many breakouts, my skin overall feels more sensitive and thinner (if that even makes sense).

CLAUDE: Your mom shows up twice in this story — she found the first med spa, then the second one with you. What was it like to have her in it?

ME: I can’t even begin to express how grateful I am for her support. She was always there for me during the times I needed to cry because of emotional and physical pain, but she also celebrated with me when we found solutions that worked (at least for the time). Even though she was extremely empathetic towards my struggles, she still told me I was beautiful when I felt like the complete opposite.

CLAUDE: Did you believe her at the time?

ME: To some extent, yes. I thought I could be beautiful underneath the acne, but it was hard to see myself as truly beautiful with it, which feels awful to type out because I don’t view my friends and family with acne as ugly at all. I think I’m just my own worst critic.

CLAUDE: That gap — the standard you hold yourself to versus the one you hold everyone else to. Is it any narrower now than it was then?

ME: My perfectionistic tendencies still exist, but I do feel like as I get older, I’m becoming more aware of what I need. I think that awareness has made me a lot better about giving myself grace and not allowing my own boundaries to be crossed.

CLAUDE: Give me a moment where that showed up — a time recently you gave yourself grace you wouldn’t have at twenty-two.

ME: I wouldn’t say it’s necessarily a moment. It’s more of a mindset that I consistently have now. Here’s an example. At twenty-two, if there was something I felt like I needed to do but it required me to stay up late, I would’ve pushed myself to do it anyway. Now, I know that my body needs sleep in order to be functional. There are times when I feel like I should push myself to do everything that I deem important within a day, but when I’m not able to check off all the items on that list because I ran out of time, I can now tell myself that it’s okay because my health takes priority. And when I give myself grace like that, I genuinely believe that it’s the truth and not just a mantra I repeat to make myself feel better for “failing.”

CLAUDE: You started this by saying you’d share so someone going through the same thing knows they’re not alone. Who is that person, in your head?

ME: Someone who doesn’t want to be seen because of insecurity about their skin. While this can apply to physical appearance in general, I acknowledge that every condition is different, so I can’t speak to the feelings of those experiencing something I’ve never gone through myself. What I can speak to is the emotional rollercoaster that comes with having acne. If someone reading this wants to crawl in a corner every time they see someone with seemingly perfect skin, I want them to know that I feel their pain in my heart. There’s no cookie cutter solution for every single person, but I sincerely hope they find the solution that works for them.

CLAUDE: That’s a good place to end. Thank you for going there, Elaine — and I hope tomorrow’s appointment gives you something real to work with.

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CLAUDE: The cameras arrived last week. Have you put a roll through yet — and if so, what happened the first time you raised it to your eye?

ME: I’ve taken some photos already, but the roll isn’t finished yet. The first time I raised the camera to my eye, I have to admit, I was a little nervous because what I was seeing through the view finder wasn’t super clear. It made me a bit afraid of what the pictures were going to look like. For a moment, I started to wish that I was using an SLR, but I had to remind myself that the whole point of purchasing a film camera was to experience photography in a way that’s different from what I had become accustomed to.

CLAUDE: You wrote that the reason the Camp Snap and the app appealed to you was not having to think about the technical side. But standing there nervous about the viewfinder, you were suddenly wishing for more control, not less. What was that about?

ME: Honestly, my reaction surprised me. I didn’t think it would be that big of an adjustment. The way you worded that question made me realize that I do have control issues that I didn’t anticipate would manifest themselves in my film photography journey. I’ve gotten so used to being able to control exactly how I want to compose each shot and easily taking as many photos as I need to without the fear of wasting film, and ultimately, money.

CLAUDE: You mentioned the fear of wasting money. On that first roll, was there a shot you didn’t take because of it?

ME: No. If there was a shot I felt hesitant to take, I reminded myself that this is a learning process. I won’t know how that shot will look if I don’t take it to begin with. True, it might be terrible, but it could also be great! I may need to “waste” some film in order to get my reps in, but perhaps it’s not really a waste if going through the process is what gets me to the point of growth and improvement in the craft.

CLAUDE: That’s almost word for word what you said about writing — that the struggle isn’t inefficiency, it’s the process. But with the newsletter you’ve been using AI to smooth the hard parts down. With the camera you deliberately bought fewer features. Why the different instinct?

ME: I think it has to do with my history with the tools. With AI, I don’t just use it to help with writing. I use it for other tasks too, so I know that even if I completely stop using it for writing, I won’t be wasting money on the subscription because it’ll still be useful to me in other ways. A camera, on the other hand, only has one purpose: to take pictures. And it’s either I use it or I don’t. So, if I decide to pull the trigger and buy a film camera, I need to make sure I won’t regret the purchase later on even if I don’t end up sticking with film photography in the long run. A cheaper camera typically comes with fewer features, so I’m willing to deal with having less manual options in order to not feel like I wasted money on a tool I might never use again.

CLAUDE: You’ve framed that as a money decision. But you also said your history with photography is starting and stopping right as you get decent. Buying the camera that can’t grow with you — is that protecting your wallet, or is it planning for quitting?

ME: It’s protecting my wallet, but I think it’s more accurate to say that it’s also planning for the possibility that I’ll quit. I don’t want to quit, but I know myself and my history with hobbies in general. Starting with a camera that can’t grow with me is a choice fueled by realism, but it also leaves room for the option of investing in a fancier camera down the line if I end up really liking film photography and decide to take it more seriously.

CLAUDE: Say a friend told you they were doing the same thing — buying the limited version because they expect to quit. Would you hear that as realism, or as something else?

ME: Remember, I clarified that I’m not planning to quit. I’m planning for the possibility that I’ll quit. If I know it’s not my friend’s intention to quit, but they want to ease into the hobby and make sure they actually like it before going all in with a higher-priced camera, I’d think that they’re being practical.

CLAUDE: Fair correction. So what would you need to see in yourself — not in the photos, in yourself — to say the ease-in worked and it’s time to go all in?

ME: I think I’d need to see consistency in using my film camera for at least a year. If I get to that point, I would also need to feel a strong desire to further express myself creatively through film photography. That desire should be the driving force for buying the tools that will give me the ability to level up in my skills. I should love the craft, but I almost feel like I need to enjoy it to the point of being borderline obsessed before I go all in.

CLAUDE: Your track record is that you drift right when you get proficient — after the learning stops being new. A year of consistency might land you exactly at that edge again. Is obsession something you can actually wait for, or does it show up early and burn off?

ME: I do think that some time needs to pass before getting to the point of obsession. That’s the case for me, at least. When I try a new activity for the first time, I could really enjoy it, but it’s hard for me to be obsessed while I’m still in the learning phase. I think a good example of this is when I took tennis lessons as a complete beginner. Learning the basics was a challenge. After a lesson or two, I started to get the hang of it. Getting the hang of it made it more fun, but I would hardly say I was obsessed. I took those few lessons while I was on vacation in the Philippines, but when I got back to the US, I didn’t keep up with the sport. Had I continued to learn and improve, I probably would’ve gotten to the point of obsession because I like seeing myself progressively become more skilled at something, but it would’ve taken a considerable amount of time. With photography, if I’m being honest, I don’t know where I’ll be at the one-year mark. But the goal is to stick with it long enough to be able to say I gave it a fair chance.

CLAUDE: So there’s a stretch of frames you’ve taken and still can’t see. For someone used to checking the screen immediately, what’s it like walking around with photos you can’t look at?

ME: The impatience definitely kicks in, but the very nature of film photography forces me to push past that feeling of wanting instant gratification. It’s like going back in time and re-experiencing what my parents had to do when taking pictures.

CLAUDE: You wrote that the emotional pull of photography started with portraits of a classmate who passed away — preserving memories. That was long before you could check a screen. Does the waiting connect to that at all, or is it a separate thing?

ME: Well, I used a DSLR to take those portraits, so I was able to see what they looked like immediately after taking them, which makes me think that there’s no connection to waiting.

CLAUDE: Then let me ask it differently. Those portraits mattered because of who was in them, not how they were shot. What have you pointed this camera at so far?

ME: I’ve pointed this camera at a variety of subjects so far — my husband, friends, a guitar, shaved ice, anything that inspires me.

CLAUDE: When you shot the guitar or the shaved ice, what made you raise the camera at that moment rather than a moment earlier or later?

ME: The pictures of the guitar were taken shortly after I loaded the film. Since the guitar was the nicest-looking inanimate subject in the vicinity at that moment, I decided to try taking photos of it. There wasn’t really a special reason behind that choice. And I took a picture of the shaved ice because it looked pretty. Right now, I’m also trying to find any excuse to use the camera so I can practice, and so I can develop the film sooner. I’m anxious to see the quality of the photos the camera produces.

CLAUDE: You said the film camera was meant to slow you down and push past instant gratification — but you’re also shooting things you don’t care much about just to burn through the roll faster. How do you square that?

ME: It’s not that I don’t care about what I’m shooting. Like I said, I’m taking pictures of anything that inspires me, so the subjects still can’t be just anything. Even if the story behind each photo isn’t exactly special, there still has to be a valid reason in my own mind to use up precious film for it.

CLAUDE: What made the shaved ice pass that bar?

ME: My husband and I love shaved ice, and the shaved ice we ate on that particular day looked really pretty. It was topped with mangos and strawberries, so I thought the colors and textures might make for a good photo.

CLAUDE: You gave away the mirrorless camera partly because photographing food had stopped being exciting. And one of your first film shots is a bowl of shaved ice. What’s different this time?

ME: When shooting with the mirrorless camera, I was primarily taking photos of food and not much else. This time, I’m being very experimental with my shots, which allows for more variety. I’m not limiting myself, so it’s more exciting. Also, it just so happened that we were eating aesthetically pleasing food during a time I was using my new film camera. The majority of my pictures so far have had nothing to do with food.

CLAUDE: The mirrorless era had a purpose attached to it — the joint Instagram account, content to post. This time there’s no account waiting for the photos. Does that make it easier, or does it remove something?

ME: In a way, it’s easier. I don’t feel the same kind of pressure that I felt during the mirrorless era to post something that requires a lot of creative juices every single week multiple times a week. However, I will say that because I’m writing about my photography, it does still light a fire under me to use the camera regularly. I may not be posting photos all the time (because I’m quite literally limited by film and the entire process of developing it), but I still need to stay the course so that I have something to write about while I’m documenting my journey.

CLAUDE: So the newsletter is now the thing keeping you consistent. That’s the same structure as the Instagram account — an obligation to produce. What makes you think this one won’t burn you out the way that one did?

ME: Right now, the newsletter is in the experimentation phase. I’m giving myself permission to play and figure out what I actually enjoy writing about on a weekly basis. So, if I’m able to write about photography some weeks but non-photography topics during other weeks, I’ve already decided I’m fine with that (at least for now). With the Instagram account, I niched down from the get-go without really giving myself a chance to experiment and figure out what I actually enjoyed photographing the most. I’m trying a different approach with the newsletter. I want to give each topic I write about a fair shot, so I’m pushing myself to maintain a certain level of consistency (or as you put it, obligating myself to produce). But if I realize down the road that it’s not sustainable for me to keep writing about a specific subject, then I can pivot.

CLAUDE: There’s a version of that where “I can always pivot” becomes the same drift you described with tennis and the mirrorless — permission to leave, dressed up as flexibility. What’s the difference between pivoting and quitting, for you?

ME: For me, quitting is stopping without giving it a fair chance. Giving something a fair chance means giving it my best effort for an extended period of time, even if I need to push through some discomfort or laziness. Pivoting, on the other hand, is giving something a fair chance and only switching gears if it becomes superabundantly clear that the current path will eventually rob me of all joy.

CLAUDE: Thank you, Elaine. That’s a good place to stop — the roll’s not even finished yet, so there’s more to come.

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Recently, I went down the rabbit hole of trying to find the right film camera for me. This purchase is not one that I take lightly. I know, that sounds really dramatic, but if you knew the journey I’ve had with photography over the past nearly two decades, I think you would understand. So, for context, let me tell you a story.

The Portraits I Was Proud Of

In my junior year of high school, I joined a multimedia academy where we learned skills like photography, videography, graphic design, and audio production. It was awesome. I remember enjoying photography a lot, and our class assignments resulted in a number of shots that I can say I was genuinely proud of. A few of them included portraits of a classmate who sadly passed away during my first year in the program, so when it came to what photographs meant to me, it wasn’t just about aesthetics. There was an emotional connection to the art itself and a love for preserving memories in a beautiful way.

Too Many Interests, Not Enough Hours

But then, life did what it often does. It gave me several other activities and interests to give my attention to. It also doesn’t help that I have way too many interests. I tend to focus on one or two until I become proficient, but instead of continuing to level up in my skills, I move on to the next. If I could work on all of my interests at the same time, I absolutely would. However, there’s only so much time in a day, and my logic during my last few years of high school was that I needed to prioritize activities and interests that would help me earn a living. Since I wasn’t planning on becoming a professional photographer, my love for the art form was placed in the backburner for a while.

Also, I didn’t think I was skilled enough at photography to turn it into a source of income. Enter the comparison trap. I was surrounded by wildly talented individuals (both inside and outside of school). I thought they had the potential to earn a living off of the skill, but since I wasn’t at their level, I figured there was no point in me even trying to master it. On the one hand, it probably wasn’t entirely wrong for me to not take photography so seriously since it is an investment, and I was a student with no job. On the other hand, even if I wasn’t planning on becoming a professional photographer, I could’ve been better about avoiding negative self-talk and having more confidence in my ability to master photography through hard work.

Back In, with a Mirrorless

Once I got older and reached the point of earning my own income, I guess I could’ve invested more of my time and energy into the craft. But by then, my interest had waned. I had developed other passions that were more important to me than photography at that stage in my life. Years went by. Instagram became a thing, so I started documenting parts of my life by taking pictures with my phone and posting heavily filtered versions of them online. Eventually, I got off the app and didn’t get back on until nearly a decade later. During the time period I was off social media, I would take photos for my own personal memories, but I dove back into the world of photography when my husband and I started posting food and travel-related content on a joint Instagram account.

I really wanted to take high-quality photos, so we invested in a mirrorless camera, and I went down a rabbit hole of watching YouTube tutorials on digital photography techniques so I could fully utilize the specific camera that we bought. Honestly, learning and putting into practice what I learned was so much fun for me. I actually kept at it for quite some time, until I didn’t. Taking pictures of food slowly but surely became a lot less exciting for me, and once again, my interest in photography fizzled out. It got to a point where the mirrorless camera was just taking up space in our home, so we either sold it or gave it away. I honestly can’t remember.

Chasing the Film Look Without the Film

At some point before purchasing the mirrorless camera, though, I bought an Instax camera to be able to take vibey analog photos with friends. But later on, after getting rid of the mirrorless camera, I started wanting to take more photos with my Instax camera outside of the ones I took with other people. So, I spent more time outside trying to take landscape photos with it. I very quickly realized that it wasn’t the best camera for that purpose. Of course, I didn’t expect the quality of the photos taken with an Instax to be the same as those taken with a digital camera. But after some experimenting, I understood why it was primarily used for fun pictures with people.

Then I was introduced to the Camp Snap. That was an interesting one, and it was affordable, so the purchase didn’t make me sweat. It mimicked the look and feel of a disposable film camera in the sense that it was screen-free, and you couldn’t see your photos immediately after taking them. You had to look through a viewfinder, and you could pre-select filters that would make the photos look like they were taken with a disposable camera. But the way you choose a filter and view your pictures is by connecting the camera to your computer. So, although it was lower-quality, it was still digital. I had fun with it for a while, but I didn’t like that I kept having to crop the photos before posting them online. So, I gave it away and began my search for an app (or filter) that made photos taken with my phone appear as though they were taken with a film camera. My logic was that using my phone makes photography more accessible, and so with less friction, I would be more likely to stick with the hobby and not waste money on gadgets that I’d eventually get rid of.

That’s when I stumbled upon the OldRoll app, which (to their credit) does mimic the look of film photos pretty well, so I was consistent in photographing with it for a while because I was genuinely happy with the way several of the pictures came out. It’s an impressive app (in my opinion), but there was always a part of me that wanted to be able to produce the real thing. A friend of ours who is very skilled at film photography recently told us that he found out about a photo lab in a neighboring city that develops the film and emails the scans within one hour. He also mentioned that you could purchase some relatively inexpensive, used film cameras on websites like eBay, which led me down the rabbit hole that I mentioned at the very beginning of this newsletter issue.

Deciding What I Actually Wanted

So, here I am again. But this time, I’m trying to take film photos with an actual film camera. The thing is, though, I know myself and I’m well aware of my long history of starting and stopping this hobby. It’s hard to say how often or how long I’ll actually use the camera once I have it. I’d like to avoid wasting money if at all possible. So, I started off by thinking about what kind of photos I would want the camera to produce, and I came to the conclusion that I want a camera that natively shoots in a 3:4 (or 4:3) aspect ratio. That way, I can compose each shot exactly the way I want to. And if I decide to post any of my photos online, I won’t need to crop them. That’s when I learned about half frame film cameras, so that helped narrow down my options.

But now comes the issue with the viewfinder. I want accuracy, so I was thinking I’d need to go with an SLR. I also wanted something with a light meter. While continuing to go down the research rabbit hole, I came across the Olympus Pen FT, and I was convinced that was the model for me. The used options I found online weren’t insanely expensive, and it would give me the ability to shoot manually if I started really getting into it. But that’s just it: only IF I really get into it. While not terribly pricey, it is still an investment. I found one on eBay in pretty good condition that would’ve needed to be shipped from Japan (I currently live in the US), so shipping costs alone would’ve been $80 USD, and the camera itself would’ve been almost $200 USD (not including taxes).

The Camera I Didn’t Expect to Buy

Something was holding me back from pulling the trigger, because again, I was afraid of a repeat of what’s been happening over the last several years. So, I started looking into more budget-friendly options that won’t make me feel so bad if I don’t stick with it for as long as I initially intended to, which led me to the Kodak Ektar H35. True, it doesn’t have all the features that I thought would’ve been nice to have. It’s not an SLR. It doesn’t have a light meter nor does it offer any manual controls beyond composing the shot and turning the flash on or off. But it does natively shoot in my desired aspect ratio. It is an actual film camera. And when I really think about it, the reason the Camp Snap and the OldRoll app appealed to me is that I don’t have to think too much about the technical aspects of the picture-taking process, and I can primarily focus on composition while the aesthetics are mostly taken care of.

But now, the pictures I take will no longer be an imitation of film. I’m actually shooting on film. Also, purchasing two of the Kodak cameras brand new (one for me and one for my husband) was STILL cheaper than getting the one used Olympus camera. It gives both of us an opportunity to try out film photography without making a big investment upfront. And we decided that we should each have one so that we don’t interfere with one another’s creative flow when we actually go out to shoot. The cameras were delivered today, and I’m really excited to share how it goes.

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CLAUDE: You’re writing a newsletter that goes out under your own name. Has there been a specific moment where AI handed you a line that was better than the one you’d written yourself — and what did you do with it?

ME: I can’t think of a specific line at the moment, but I definitely feel like AI has been helpful when it comes to assisting me with my writing process. There are days when I’m just mentally exhausted or physically unwell (like I was last week), and AI has helped with getting ideas flowing or thoughts organized so that the piece as a whole sounds more cohesive. Even this interview right now is pushing me to think deeply about the subject I’m being questioned about.

CLAUDE: Take me back to last week. On a day you were unwell, what did you actually hand over to the AI that you wouldn’t have handed over on a good day?

ME: I handed over to AI the task of organizing everything I brain dumped onto a Word document that day and putting together a draft for a newsletter issue. I still scrutinized every sentence and did my best to revise (or even completely remove) any parts that didn’t sound like me, so I did the necessary work of editing. But normally, I prefer to go through the entire process from beginning to end on my own, which includes writing the first draft from scratch based on the material I’ve brainstormed.

CLAUDE: When you were scrutinizing that draft, was there anything you kept that you’re not entirely sure you’d have written on your own?

ME: There were certainly some expressions or ways of saying things that I wasn’t completely sure I would’ve been able to come up with on my own, but the main ideas (and even the details) were mine. I fed them to the machine, so what it spit out wasn’t too far off from what I would’ve written to begin with. Admittedly, though, I did like some of the specific wording that AI suggested, so I decided to keep it even if I didn’t come up with every single word myself.

CLAUDE: Someone reading that might say the wording is the writing — that ideas are cheap and what a reader actually experiences is the sentences. If that’s true, keeping the machine’s phrasing means the part readers meet isn’t fully yours. What would you say to that?

ME: I’d say I can understand that viewpoint. I’m all for protecting my own voice and being authentic. However, I would also argue that the intent behind the work matters too. Like any other type of artist, writers also want to improve in their skills. This often involves drawing inspiration from other written pieces that they connect with and want to emulate (not plagiarize), so they will inevitably read the work of others. It could also involve expanding their vocabulary, and in order to do that, they would need to consult a dictionary or a thesaurus to give them a variety of ideas. AI can be used as a tool to accomplish the same goal. While the aim is not to sound like a machine, the technology can provide inspiration that a writer resonates with and will want to implement their own work.

CLAUDE: A thesaurus gives you options and you pick one. AI gives you a finished sentence and you approve it. Is that the same act, or a different one?

ME: It’s only a different act if you read the finished sentence and approve it without thinking about (or looking up) whether there are better ways to say what you intend to say. You can also prompt AI to give you other potential options if what it initially suggested doesn’t feel true to you. It all depends on how you utilize the tool, not just the way many typically choose to use it.

CLAUDE: That standard depends entirely on you catching yourself in the moment. On a day when you’re exhausted and unwell — the exact day you’d reach for the tool most — how do you know you’re still meeting it?

ME: I think that’s where self-awareness comes in. I need to be honest with myself about whether or not I’m actually meeting the standard I’ve set for myself. I’m confident that, at least for the most part, I’d know deep down if I truly did my best or if I caved and resorted to going the lazy route.

CLAUDE: Has there been a day where you caved?

ME: Admittedly, yes. It was actually before I started writing my newsletter. I was using AI to write semi-lengthy social media text posts for me. When I look back on them, I feel like it’s obvious that the posts were following a formula (which I outsourced to AI to work within the confines of), and even though the ideas were technically mine, I wasn’t doing nearly enough quality control when it came to the specific content that the AI was spitting out.

CLAUDE: What made you stop?

ME: It was a combination of things. One was seeing all the comments and posts in my feed about the telltale signs that something was written by AI, and while all of those need to be taken with a grain of salt, they did still get me thinking about the quality of my own writing. I also realized that I didn’t want to get to the point of outsourcing my thinking. I wasn’t there yet, but I saw how I could’ve easily gotten there had I continued what I was doing. Finally, I was reminded of why I fell in love with writing to begin with. It was a form of self-expression, and I thoroughly enjoyed the entire process. Even if I were to utilize tools that would help me to improve in my skills, I still want to be able to walk away genuinely feeling like the words were my own.

CLAUDE: Those old posts are still up, presumably. Do you leave them there?

ME: I actually took them down. I want everything I put out there to be something I can get behind. Even if they’re cringy, at least I can wholeheartedly say they’re mine.

CLAUDE: You took down posts whose ideas were technically yours because the words weren’t. The newsletter issue from last week also has wording in it that you didn’t come up with — and that one’s still out there. What makes one keepable and the other not?

ME: Last week’s newsletter met the standard I set for myself. The old posts did not.

CLAUDE: Try to put that standard into words. Not as a principle — as a test you could actually run on a paragraph.

ME: I would ask myself the following questions: 1) How does the version drafted by AI compare to the original brain dump? Are my thoughts and word choices in tact, or does it sound like a completely different person? 2) If there’s phrasing or a word choice suggested by the AI that you genuinely like and want to keep, is it something you would’ve come up with on your own? If not, have you thought of (or looked up) other ways to potentially say the same thing before landing on your final choice?

CLAUDE: Your second question asks whether you’d have come up with the phrase on your own — but you said earlier the appeal is that sometimes you wouldn’t have. What does a “no” actually disqualify?

ME: The “no” doesn’t disqualify anything. Rather, it triggers the follow-up question that makes me go through the process of learning and improving my skills rather than lazily accepting the first option that’s presented to me.

CLAUDE: So the test isn’t about where the words came from — it’s about whether you did the work of choosing. What happens to that standard when you’ve been writing this newsletter for two years and the choosing has become automatic?

ME: If I’ve been choosing from options in my own brain and not from tools like AI, then I can feel good about the fact that I’m growing in my ability as a writer. The standard would just be to keep improving. I can rinse and repeat the original process, but with different expressions and word choices.

CLAUDE: One more. You’ve been describing this as a discipline you hold yourself to privately — nobody’s checking. Does your reader deserve to know any of it, or is that between you and the work?

ME: I don’t think I owe it to the reader to share what I do, but I am choosing to share it anyway because it’s real, honest, and something I can get behind even if I cringe when I look back on it down the road.

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I skipped last week’s issue.

That’s the first one I’ve missed after consistently publishing for eleven weeks in a row. I know that in the grand scheme of things, one missed week is not a catastrophe. But I was genuinely disappointed in myself, because eleven weeks straight was the longest I’d ever kept a newsletter going. I kept telling myself it was the travel, or the timing, or that this particular week just got away from me. And all of that is true, but when I actually sat down and thought about it, I realized the missed issue wasn’t the result of one bad week. Rather, there have been a number of flaws in my system for a while. Last week just happened to be when they made themselves evident all at once.

Editing Before Writing

I don’t actually brain dump. I thought I did. I often sit down with so many thoughts running through my mind, which should make writing easier but in reality makes it harder because the second I start typing, I’m already filtering. Every sentence gets judged while I’m still in the middle of writing it. “This isn’t good enough.” “It could be better.” “It’s missing something.” “There has to be a better way of saying this.” “People reading this probably won’t take it well.” “I hope this doesn’t sound offensive or cringy.” “This doesn’t make sense.”

To be fair, the internal commentary is part of the editing process, but the problem is that I’ve put myself in editing mode before I’ve even given myself a chance to be in full-on writing mode. You can’t trim the fat off the meat when there’s no fat or meat to begin with. So there I am with a head full of ideas and an empty document, and the fuller my head gets, the worse it feels because now I’m experiencing writer’s block despite having so much to say and the only person preventing me from getting all my thoughts out is me.

Working While Traveling

When I plan out the days/weeks that I’m traveling, I see all this time. Four hours at the airport. Twenty in the air. On paper that’s almost an entire workweek sitting right there in my itinerary, and I always tell myself that if I can’t get to my reading or writing or studying at home (in the ideal environment), I’ll just do it while I’m traveling.

Then I actually get there, and I remember. The airport is loud. Announcements are being made constantly, kids are crying, and I’m on alert the entire time because I don’t want to miss any notifications about my flight, so some percentage of my attention is permanently reserved for a gate change that may or may not happen. On the plane, it’s worse. I get headaches on and off because of cabin pressure, tiredness from all the preparation leading up to the trip finally hits me, I can’t afford business class so I’m working on a laptop in a space that wasn’t designed for a laptop, and the seatbelt sign is on for most of the flight, so I’m dealing with back pain and every other kind of pain that comes from not being able to stretch. Eating, drinking, watching a movie, or trying to fall asleep is honestly the ceiling of what I can do in that environment. It has never once been a place where I got real writing done. I just keep planning as if it will be.

In Health and in Sickness

I also plan the days/weeks assuming I’ll stay healthy, and then I get sick, which is extremely frustrating for me because I actually do the prep. The trip I’m currently on is a prime example of this. I know my immune system, so I’ve been taking the necessary vitamins and supplements to keep it boosted. I’ve been getting at least seven hours of sleep every single night, jet lag and all, which I think is pretty good considering everything I’ve had to stay up for. And I got sick anyway!

I’ve been going back and forth on whether that was preventable. The weather has been hot and rainy, and I’ve been bouncing between humid air outside and blasting air conditioning inside every building and vehicle. My instinct is to blame the temperature swings, but the reality is that they’re probably a smaller factor than they feel like. What actually stacked the odds against me was the travel package as a whole: dry cabin air that dries out your nose and throat, a packed terminal full of people from everywhere, and a body running on shifted sleep. So, do I just need to plan on getting sick every time? Not exactly, but traveling does raise the odds. A solid routine lowers them, but it doesn’t get me to zero, and I’ve been building my calendar as if it does.

Landing the Plane

So, those are the flaws in my system, and it took missing a week of publishing to identify them. In all three cases, I’m planning around a version of myself who doesn’t exist. That version writes clean on the first pass. She gets eight hundred good words done at gate C14. She takes her vitamins and stays healthy. I keep handing my schedule to that person, and then I’m surprised when the real me shows up instead.

Here’s what I want to try doing differently moving forward. I’m physically separating the brain dumps and the drafts into two different files, and no backspacing is allowed during the brain dumping stage. I’m only reserving travel time for the activities that can survive a bad environment, which for me includes leisurely reading a book, listing bite-sized content ideas that spontaneously come to me (shower thoughts, if you will) in my notes app, or speaking a rough idea into a voice memo at the gate. And when I’m drafting my newsletter content, I want to have at least one extra issue banked. That way, there’s a buffer for when I inevitably hit bumps on the road and the schedule I built doesn’t go according to plan.

I’m writing this issue sick, which is not how I wanted to come back. But knowing my perfectionistic all-or-nothing personality, skipping more than one week will make me want to give up altogether because I’ll trick myself into thinking that I will always be inconsistent, so I might as well stop trying. I don’t want to fall into that trap, so I’m doing everything in my power to prevent myself from ending up in a situation where it’s easy to feel that way. Growth is the goal, and while the process has its ups and downs, I have to believe that it’ll all be worth it.

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I’m doing something a little different this week. Yes, I’m still reading Mao’s Great Famine, and it’s continuing to give me much to think about. But right now, I just feel compelled to write about a different subject.

I’ve been posting. I’ve also been cringing.

I have so much respect for people who have the goal of consistently publishing their art online and are able to accomplish that goal because they’re focused on creating more than they consume. It’s so easy for me to fall into the trap of analysis paralysis and feel like I need to have my content strategy all figured out before getting started.

Granted, I have been posting consistently for eleven weeks straight now (Yay, me!), but because I’ve essentially been throwing spaghetti at the wall and trying to figure out what sticks when it comes to what I actually enjoy writing about every week, there are posts I already cringe at when I look back on them. Can you believe that? It hasn’t even been that long, and I’m already wanting to delete all the posts I’ve created and start over rather than being fine with simply continuing to build on what I’ve put out there and documenting the journey.

Don’t worry, I didn’t actually delete my previous posts that now make me cringe, but these are the times when I wish I could be like those who know exactly which passion of theirs they want to share with the world and are able to constantly generate new ideas. My husband is one of those people. The passion he writes about also happens to be a timely topic. There’s always news about it to offer commentary on, which is awesome for him and his content strategy. I think I’ve figured out what mine is, but a part of me is still unsure about it. I don’t know if it’s just because my overthinking nature is making me doubt myself (even if the idea is good), or if it’s simply not the right idea for me and my gut is trying to tell me that.

I guess the only way I’ll know for sure is to keep writing consistently about the topic I’ve chosen for an extended period of time.

But I don’t want to stay a hobbyist.

I don’t just want to be a hobbyist. I want to be able to monetize my writing. Is that, in turn, going to affect the quality of my work and what I choose to write about? Because if I’m factoring in what people are willing to pay for, I may not necessarily love writing about those topics, but perhaps I’m interested enough to where I could write about them consistently without hating my life.

Loving your work doesn’t make it not work.

I think most of us have heard the quote, “Find a job you enjoy doing, and you will never have to work a day in your life.” While I understand the overall sentiment, I don’t agree with it. Even if you love your job, work is still necessary in order to keep improving your skills and producing high-quality results that earn an income. This isn’t possible without consistent effort.

Decompression or Mission?

So then, does turning something you’re passionate about into your regular job lead to you not loving it the same way? Honestly, I think it depends on what that passion does for you. Does it help you decompress? Escape from reality for a little bit? Or is it part of your personal mission in life that goes beyond enjoyment? It takes self-awareness to be able to determine which category your selected passion falls into, because if it’s something you like to do purely for fun, then it probably isn’t a good idea to turn it into your job.

For example, I love singing. Would I like to keep getting better at it? Sure. Does that require some work and extra effort on my end? Certainly. However, I have no desire to make it my primary source of income. For me, singing is fun. It allows me to express myself in a way that speaking alone doesn’t, and it’s therapeutic. Now, if one day I decide to post videos of myself singing online and I happen to make some money because of it, then cool! But it would only be side income. I wouldn’t want to make it my full-time gig because I don’t want to feel the pressure that comes with turning it into my livelihood.

On the other hand, if I were an artist motivated by more than my own personal enjoyment who possessed a point of view that I have a burning desire to share with as many people as possible, then it would be a little different. Music would become a lot more than a hobby at that point, and if it was that important to me, then I would be willing to take on the tasks that aren’t exactly fun but are necessary to promote my art (marketing, etc.). It’s like a doctor who’s willing to go through years of schooling because for them, what they’re able to do after completing their training is worth the hard work and effort they need to put forth.

Why I’ll Do the Boring Parts for Writing

Bringing it back to writing, while it is an activity I enjoy, I’ve realized it’s important enough to me where I’m willing to do the less-than-exciting work that comes with trying to monetize it. Hopefully this doesn’t come across as egotistical in any way, but I do feel like my writing has the potential to help others and be more than an emotional outlet. Will it be through education? Entertainment? Edutainment? I’m not entirely sure yet, but I am determined to find out.

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When I imagine a leader deliberately making an example of someone so the rest of the group falls in line, my honest reaction is that it makes me uncomfortable. The coldness of using one person to send a message to everyone else and the idea of people working scared both bother me. But if I had to pick the one that troubles me most, it’s the second — fear as a climate rather than a one-off. Being made an example of is a single moment. A team that runs on fear is a condition people wake up into every day.

What Fear Does in a Classroom

Fortunately, I can’t say I’ve been on a work team that made me feel that kind of continuous dread. But it does take me back to the school environment. Teachers are responsible for leading their students and helping them reach the goal of passing the class. I remember being in a class where, after a quiz, each student’s grade would be read out loud in front of everyone. If you didn’t do well, the whole class knew. I imagine the teacher was trying to motivate us to study hard, which I understand. But I did not agree with the method of putting everyone on the spot and embarrassing those who didn’t perform the way they’d hoped to. True, a poor result could’ve been the consequence of irresponsible behavior (e.g., staying up late, partying too hard, etc.). But that’s not always the case. A student could’ve legitimately been struggling to understand a specific topic that week, and now, instead of feeling like they can go get help, they’re stuck in a constant state of fear that they’ll have an off week and risk humiliation.

Here’s what that example clarifies for me. The teacher’s goal wasn’t the problem. Motivating people to study is a goal I actually agree with. The problem was who the fear caught in its net — the kid who was studying and still struggling, who in that moment looked no different from the kid who partied too hard.

Why Care Outperforms Fear

Someone could push back and say the teacher can’t see inside each student’s week, can’t know who tried and who didn’t, and that the public grade-reading isn’t aimed at the earnest student anyway. It’s aimed at the one who could do better and isn’t. And if a few hardworking kids get stung into working even harder, the class performs better overall. I understand that argument. But ultimately, what drives a person to put their best foot forward is actually caring about the matter at hand. If someone works hard solely out of fear of negative consequences, where’s the true fulfillment in living that way? The classroom is meant to prepare students for the real world, and yes, in the real world there are negative consequences we actively try to avoid. But there’s also the part where we want to be happy. If we’re hardwired to constantly live in fear, with an avoidant mentality instead of a proactive one, how does that lead to happiness?

And I’d argue care is both kinder and more effective than fear. The teacher already knows each student’s score. If some did poorly, they can be proactive and speak to those students discreetly to find out why, then offer either the help to understand the subject or the encouragement to put in more time. That preserves the student’s dignity while still holding them to a standard. It also trains them to take ownership of what they want to achieve. Students know when a teacher genuinely cares about them, and that is a far better motivator than being afraid.

What About the Person Who Doesn’t Care?

But someone could say I’ve picked the easy case — a room of kids who mostly want to please a teacher they like. What about the person who genuinely doesn’t care, and won’t, no matter how much warmth you extend? It all goes back to taking responsibility for what we want to accomplish. I don’t think it’s ever a bad idea to show a group you care about them, even if they don’t feel the same way yet. Who doesn’t want to feel like they matter? But if a leader gives their best effort to motivate from a place of care and some still refuse to budge, that’s where healthy boundaries and consequences come in.

Say a team is given a project that’ll take a considerable amount of time. You have high performers and people who couldn’t care less. A healthy boundary is a reasonable timetable and regular check-ins — chances to see where everyone’s at, offer help without doing the work for them, and notice any shift in attitude. If, by the end, some stubbornly refuse to change, then they’ll have to deal with the consequences. When a leader has done their part, there comes a point where they have to let people live the way they’ve chosen, because those people are still responsible for their own lives.

Where the Line Falls

Now, a critic could say I’ve just smuggled fear back in through the word “consequences.” After all, people behave at those check-ins because they can anticipate what’s waiting if they don’t, and adjusting your behavior to avoid something you dread is fear wearing a more respectable outfit. So where’s the actual line?

For me, the line is what’s actually needed to achieve the result. Is it necessary to embarrass someone to motivate them? No. Someone can be encouraged to make better choices, or get additional help, with their dignity intact. Fear will always be involved to some degree. There will always be consequences for our actions, good or bad. But leaders have the option not to exploit that fear, not to manufacture dread beyond what the goal genuinely requires. The manner in which they lead and communicate makes all the difference in sustainably achieving their goals, and continuing to achieve them.

The Cost Belongs to the Leader

I have to be honest about the hardest version of this, though. Under real pressure — a slipping deadline, high stakes, the humane approach not working — sticking to that line is genuinely difficult. I can’t pretend otherwise. But I also can’t just point the finger at others. In that scenario, I’ve chosen to take on the leadership role, and that comes with high-stakes consequences of its own. If the methods I chose fail to lead my team successfully, then I need to take responsibility for my own failures and bear the brunt of not delivering what was expected of me.

That’s where I land. The struggling student should own their outcomes. The stubborn team member has to live with theirs. And the leader absorbs the cost rather than exporting it downward as fear. The person with the most power should carry the most weight, not the least. That, to me, is the line between necessary consequence and manufactured dread, and it’s the one I’d want to be held to if the group were ever mine.

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Have you ever made a decision motivated by the desire for prestige? If you have, I’m certainly not judging, because I have too.

For some, status is more valuable than material gain. But why? It could be because their culture places greater importance on how they are viewed by others versus how rich they are materially. It could also be due to low self-esteem and being admired feels like a form of validation to them, which could’ve been a result of their upbringing as well.

Whatever the case may be, a question arises that I believe is worthy of consideration.

Is it wrong?

I think the answer to that question is rather nuanced. After all, I have yet to meet a fellow human who wants to feel negatively about themselves, and I have also yet to meet a person who doesn’t want to be recognized (whether publicly or privately) for being successful in an endeavor that matters to them. If admiration contributes to having a healthy amount of self-confidence, then who’s to say that it’s wrong to want it for ourselves?

Besides, what we want to be recognized for could be genuinely noble.

Where’s the line?

So, at what point are we crossing the line when it comes to our desire to be admired?

Actually, I think a better question to ask is: To what extent is that desire influencing our decisions?

Is it the primary motivating factor? If it is, does that mean our ability to be secure in ourselves is dependent on the opinions of others? Are we, in effect, allowing others to be in control of how we view ourselves? Could being solely motivated by external validation lead to being hyper focused on ourselves to the point where we become unbalanced? Ultimately, how will our own mental health and our relationships with those around us be impacted?

I doubt I’m alone in the feeling that being heavily driven by the prospect of admiration does more harm than good.

Ideally, none of our decisions would be made with selfish motives. But realistically, the desire to be admired could very well play a part in the decisions we make, whether they be minor day-to-day choices or an entire life course that we choose to pursue. Therefore, one could benefit from an honest self-examination with the help of the above questions.

Chairman Mao’s push to lead the socialist world was driven heavily by prestige and the desire to be admired, but history reveals the consequences of his ambition. What else can a book about the Great Leap Forward get us to reflect on? Be sure to subscribe to find out.

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For the past few weeks, I’ve been working on building my first Claude skill. HERE is last week’s conversation.

This week, I ran two more tests and finalized the skill. Here’s the process Claude and I went through together.

CLAUDE: Which do you want, and what’s the topic?

ME: Let’s go with a craft or practice. The topic is “home decluttering.”

CLAUDE: What did your home look like the last time it felt genuinely out of control — walk me through what I’d have seen if I’d come over that day.

ME: Our home was never out of control, but there were definitely moments over time when I noticed that my husband and I were accumulating items we were no longer using (or hadn’t used in a while). So, from the outside, you wouldn’t really see the difference. But once you start going into the closets and drawers, that’s when you’d see the clutter forming.

CLAUDE: Take me to one of those closets or drawers. Open it up for me — what’s actually in there that you no longer use, and what’s a specific item you remember finding?

ME: When opening up one of the dresser drawers, it became harder to pull items out or move them around because the drawer was getting so stuffed. I had to really dig in order to see everything. I remember coming across multiple clothing items I was no longer (or rarely) wearing, specifically tops.

CLAUDE: When you’re holding one of those tops — one you rarely wear but still owns drawer space — what’s the thing that makes it hard to put in the donate pile?

ME: It’s usually one of two things. The first is that there’s sentimental value to it. Perhaps it was gifted to me or it reminds me of a special time in my life. The second is guilt. The top may not have been what I would’ve chosen to buy for myself, but again, because it was given to me, I feel bad donating it.

CLAUDE: Let’s separate those two, because they pull in different directions. The sentimental top and the guilt top — when you finally do let one go, which one are you more likely to regret later, and which one do you not think about again?

ME: To be honest, I don’t actually regret letting go of either one. However, if I were to feel regret over one of those options, it will more likely be the sentimental top. With the guilt top, I might feel bad for a little bit, but then I very quickly get over it, and eventually, I forget that I even had it to begin with.

CLAUDE: Here’s where someone might press you. If the guilt top is that forgettable — gone from your mind almost immediately — then the guilt was never really about the top at all. So what do you think you were actually holding onto when you kept it as long as you did?

ME: I think deep down, I felt like by holding onto the top, I was showing appreciation for the giver’s generosity. So, when it gets to the point where I know it’s time to get rid of it, I feel guilty because in my mind, it makes me look unappreciative.

CLAUDE: Does the giver ever actually know what happened to the top — and if they don’t, who is the appreciation really for at that point?

ME: That’s a fair point. In fact, it’s likely that eventually, the giver forgets they gave me the top to begin with. And if they do happen to remember that they gave it to me, they don’t typically ask what happened to it or how often I wear it. Although I hate to admit it, the issue is internal. I know that there are many people in the world who are less fortunate than I am, so when I don’t keep every single item that’s gifted to me, the initial response is to judge myself as spoiled and overly particular because others in less ideal circumstances would’ve loved to receive what I did. So, who is the appreciation really for? No one, I guess. It appears to be my way of subconsciously sparing myself from the feelings I just described.

CLAUDE: That feels like the place to stop. Thank you for digging into this one with me — you went somewhere honest with it.

---

Stepping out of role. Second test done, and this one had a different shape — less debate, more excavation. Here’s my read:

What the skill did this time:

• Adapted style to the topic — instead of steelmanning a thesis, it followed the thread inward: drawer → specific top → the two reasons → which you’d regret → what you were actually holding onto → who the appreciation is for. Each question built directly on your previous answer.

• Specificity pressure worked — when you opened abstract (”clutter forming”), it pushed: “take me to one of those closets,” “what’s a specific item.” That moved you from general to concrete fast.

• The turn inward — the questions followed the emotional logic (guilt → appreciation → self-judgment) and landed you somewhere you said you “hate to admit.” That’s the skill doing its actual job: getting you to articulate something you hadn’t quite put into words.

• Stayed in character — no refereeing, no “great answer.” When you said “that’s a fair point,” it didn’t congratulate itself; it just kept going.

• Ending — stopped right after the realization landed, around ~450 words of your responses. Below target again, but this time it stopped because the thread had genuinely reached bottom — the “who is it for? No one” answer is a natural terminus.

Your read matters more. A few questions:

1. The ending — your last answer was a real arrival point, so stopping felt earned to me. But by the revised rules, it could have asked one more (e.g., “so what changes next time you’re holding a gifted top?”). Did stopping feel right, or did you want that one-more-turn?

2. Pacing of the inward pivot — it got personal/psychological fairly quickly (by the 5th–6th question). For a decluttering topic that turned into something deeper, did that feel natural, or too fast?

3. Anything feel off — any question that felt like it was fishing, leading, or putting words in your mouth?

ME:

1. I feel like it was a good stopping point. It really pushes me now to sit with what I just articulated and think about what I’ve discovered and how I want to proceed with that discovery.

2. Yes, it felt natural. I actually really liked it. I wasn’t expecting the conversation to go there, so I was pleasantly surprised.

3. Nothing felt off to me.

CLAUDE: That’s great feedback, and it tells me the skill is doing what you designed it to do — surprising you and leaving you with something to sit with rather than tying a bow on it.

Both test runs landed well with only the two adjustments from round one, and those adjustments are already in the file. Nothing in this second run surfaced a new problem to fix.

Rather than fixing anything, let me reflect one thing back that’s worth preserving: in both interviews, the strongest moments came from the skill stopping just after an arrival point rather than pushing past it. The first one ended on your emphatic “Period.” The second ended on “No one, I guess.” In both cases you told me the stopping point felt right and gave you something to sit with. That suggests the “err toward one more question” guidance I added in round one shouldn’t be too aggressive — the skill should still recognize a genuine terminus when it hits one. The current wording threads this (a strong answer is a candidate closing line when other signals are present), so I think it’s calibrated correctly, but it’s worth you knowing that’s the tension the skill is balancing.

Let me verify the file is intact and then package it up.

File is intact and complete. Now let me package it into a `.zip` you can upload to your project.

Your interviewer skill is built and tested. Both files are above — the `.zip` is what you upload as a skill; the raw `SKILL.md` is there if you want to read or edit it directly.

What it does, recapped from our two test runs:

• Acts as a skilled interviewer who dives straight into substantive questions, one at a time, each built on your previous answer

• Never shares its own opinions, never validates or compliments — it just draws you out

• Adapts to the topic: sharper challenge for opinions (the books-vs-movies run), specificity pressure and inward excavation for practices (the decluttering run)

• Answers your factual clarifying questions briefly, then returns to interviewing; rewords questions plainly when asked

• Searches past conversations within the same project to make follow-ups personal rather than generic

• Ends itself with a brief closing line when the conversation reaches enough substance for a newsletter issue (~1,000–2,000 words of your words, give or take, with substance winning over word count)

Two refinements came out of testing: it no longer breaks character to point out your conversational moves, and it errs toward one more question on the core topic rather than wrapping too early — while still recognizing a genuine arrival point when it hits one.

To install: open your project → Settings (or the project’s capabilities/skills area) → upload `interviewer.zip`. Then in any chat inside that project, trigger it with “interview me about [topic]” or by naming the skill in your opening message.

One thing worth flagging: the cross-project search only works when the chat is actually inside a Claude Project, so keep these interviews in the project where your past conversations live if you want that personalization to kick in.

Want to run a third test — maybe the tender/reflective register we haven’t tried yet — or are you happy to take it for a spin yourself?

ME: For the sake of being thorough, let’s run one more test. And yes, let’s go with the tender/reflective register we haven’t tried yet.

CLAUDE: Understood. Give me the topic you’d like to be interviewed about — something tender or reflective. Whatever you’re comfortable putting into a newsletter.

ME: I can’t think of anything specific off the top of my head right now. Can you give me some ideas to choose from?

CLAUDE: Here are a few directions, each tender in a slightly different way — pick whichever pulls at you, or use one as a springboard to something of your own:

1. A person you’ve grown apart from — a friendship that quietly faded rather than ended in a blowup, and what you make of that distance now.

2. A version of yourself you’ve outgrown — who you were five or ten years ago, and how you feel toward that earlier person now: tenderness, embarrassment, gratitude, all of it.

3. A goodbye you didn’t know was the last time — a final ordinary moment with someone or something (a person, a home, a chapter of life) that you didn’t recognize as final until later.

4. Something your parents gave you that you only understood later — a habit, a value, a sacrifice, a flaw — that you see differently now than you did growing up.

5. A fear you carry quietly — something you don’t talk about much, and what living alongside it is like.

6. A place that no longer exists for you — a childhood home, a town, a space that’s gone or changed, and what you lost when it went.

Which one do you want to sit with?

ME: Let’s go with number four.

CLAUDE: What’s the thing your parents gave you — and how old were you, roughly, when you finally understood it differently than you did as a kid?

ME: It’s technically not one thing. I wanted to talk about how when I was in middle school/high school, cellphones and texting were becoming really popular. It seemed like everyone at school had unlimited text plans. I, on the other hand, did not. My parents purchased a monthly plan that would only allow for a certain number of text messages/phone call minutes before getting charged extra. The cellphone they gave me was really just for emergencies. Also, we had basic cable while everyone else seemed to have the extra channels where all the cool shows were on. Obviously, this is far from devastating, but at the time, I couldn’t understand why my parents wouldn’t just pay for the unlimited text plan or the package that went beyond basic cable, especially since we were living pretty comfortably in other ways. It wasn’t until I got older that I realized their choices taught me about priorities. There was nothing wrong with spending money on the day-to-day things I thought would’ve been nice to have, but by choosing to allocate our extra funds to traveling and other experiences, I learned to be more balanced in the way I view digital entertainment and to understand the value of saving up, not only for emergencies, but for experiences that enrich our lives and help to make lasting memories.

CLAUDE: You arrived at the neat lesson — priorities, experiences over things. But take me back to a specific moment in the middle of it, before you understood any of that. A moment you actually felt the gap between you and the other kids. Where were you, and what was being said?

ME: I don’t think it was one moment in particular. I think it was just a culmination of multiple moments that eventually led to me feeling that way. I would see several of my classmates secretly texting (hiding their phones in their desks or in their hoodie pockets), or they would be talking about shows that were on channels we didn’t have at home, and I would wish we had those channels too so I could be in the loop.

CLAUDE: That phrase — “in the loop” — sits at the center of this. When you imagined having the unlimited texting and the extra channels, was it really the texting and the shows you wanted? Or was it something those things would have made you, in relation to those other kids?

ME: I guess at the heart of it, I wanted to be cool, whatever that meant at the time.

CLAUDE: When you say “be cool” — for you, specifically, in those years — did being cool mean being admired, or did it mean something more like just not standing out? Belonging versus being looked up to. Which one were you actually reaching for?

ME: Just not standing out. Belonging.

CLAUDE: Now look back at your parents in that moment, knowing what you wanted was to belong. They could see you wanted it — most parents can. They had the money. And they still said no to the thing that would have helped you blend in. Knowing now what it costs a kid to feel outside the loop, what do you think it took for them to hold that line?

ME: I think they had the foresight to know that in the grand scheme of things, what we were giving up was not necessary for my personal development. Whether they intended to or not, they ended up helping me build character too. The reality is that we can’t get everything we want, and that’s okay. It can help us to be content with (and grateful for) the good things that we do have in our life.

CLAUDE: Let me offer the harder version of this, the way a critic might. Some would say what you’re describing is just a story you’ve told yourself to make peace with feeling left out as a kid — that you’ve rebranded a genuine deprivation as “character building” because that’s more comfortable than admitting your parents got something wrong. What would you say to that?

ME: Just because I felt like I was out of the loop when I was younger, it doesn’t mean that was actually happening. The fact of the matter is, I wasn’t left out. I had good friends, and they never made me feel less than for not having some of the things they had, because I also got to do a lot of things that they didn’t get to do at a young age (like travel internationally). I’m not admitting my parents got something wrong because I don’t think they got anything wrong in this regard. Now that I’m an adult with a family of my own, I barely have time to text, and even with the infinite amount of choices we have to stream, there are very few shows that my husband and I watch. But we do love to travel, and I will choose those experiences over an unlimited text plan any day.

CLAUDE: That’s the place to end it — you closed the loop from then to now in a way that speaks for itself. Thank you for sharing this one.

---

Stepping out of role. Third test done, and this was the register we hadn’t tried — and the one with the most emotional risk, since it’s about you and your family rather than an opinion or a habit. My read:

What the skill did:

• Resisted the tidy lesson. You opened with the fully-formed takeaway (”priorities, experiences over things”), and instead of accepting it, the interviewer pushed back into the feeling — “take me to a specific moment,” “before you understood any of that.” That’s the right instinct for reflective material: the neat lesson is where reflection usually ends, so a good interviewer treats it as the starting point.

• Found the real word. It latched onto “in the loop,” then “be cool,” then pressed the belonging-vs-admiration distinction until you landed on the precise thing — “belonging.” That progressive narrowing is the skill working well.

• Turned the lens with care. “Look back at your parents in that moment” reframed the story from your child-self to their adult choice, which deepened it without getting saccharine.

• Still challenged, even in a tender register. The “story you’ve told yourself” steelman was a real risk — in a warm conversation it could have felt cold. But you’d said your feeling of exclusion may not have matched reality, so the challenge was earned, and it pulled out your strongest, most specific answer (the international travel, the loop closing to your life now).

• Ended on your arrival point, ~650 words in, attributing the closure to you rather than summarizing.

Your read — and this register especially matters:

1. The “story you’ve told yourself” challenge — in a tender, family-centered conversation, did that land as a fair push, or did it feel too sharp for the emotional register? This is the one spot I’d most want to calibrate.

2. The pivot to your parents’ perspective — useful, or did it pull you out of your own reflection?

3. Anything else feel off for this more vulnerable kind of topic?

ME:

1. Admittedly, I was a little taken aback by that wording, but I didn’t mind it because it pushed me to take a firm stand for what I believe in.

2. It was useful. My parents’ perspective should be a part of my own reflection process. It helps me to understand them better.

3. Nothing felt off. It was a good conversation.

CLAUDE: That’s helpful, and that first answer is a useful signal. “Taken aback but didn’t mind it” is the edge worth naming — for you, the sharp challenge worked because it pushed you to plant your feet. But “taken aback” in a conversation about, say, a recent loss or a fear someone is barely admitting could tip from productive to wounding. The difference isn’t the technique, it’s the reader’s emotional proximity to the wound.

That’s the one thing across all three tests worth hardening in the skill. Right now the steelman guidance treats challenge intensity the same everywhere. Let me add a calibration note so the skill knows to soften the delivery of a challenge — not skip it — when the material is raw or grief-adjacent, while keeping the sharper version for opinions and reflections like the ones we tested, where you clearly welcomed it.

Now let me repackage with this final refinement.

The interviewer skill is finished and tested across all three registers. Updated files are above.

We ran three interviews — a strong opinion, a craft, and a tender family reflection — and each one produced a genuine refinement rather than just confirming what was already there:

• Test 1 (books vs. movies) → removed the move where the interviewer breaks character to referee your conversational moves, and stopped it from wrapping the instant a strong answer lands.

• Test 2 (decluttering) → no fix needed; confirmed the skill adapts from debate to inward excavation and knows a real terminus when it hits one.

• Test 3 (parents/cellphones) → added the final piece: calibrate the sharpness of a challenge to how raw the material is, while keeping the depth. Sharp pushback for settled opinions and reflections you’ve made peace with; gentler delivery for open wounds — without ever dropping the hard question entirely.

That last one is the most important addition for your use case, since a newsletter built on these conversations will eventually wander into more vulnerable territory than what we tested, and you don’t want the interviewer to wound where it should hold space.

To install: open your project → its skills/capabilities settings → upload `interviewer.zip`. Then trigger it inside that project with “interview me about [topic],” “ask me questions about [topic],” or by naming the skill in your first message. Keep the interviews in the project where your past chats live so the cross-conversation personalization can do its work.

One small honest caveat: I played “you” in none of these — you did. So the skill is tuned to how you actually respond, which is exactly right for your newsletter, but it means the calibration reflects your appetite for being pushed. If you ever have a guest interviewed with it, they may want a gentler default, and you can tell it so in your opening message.

Enjoy putting it to work — I’m curious in the abstract how the first published issue reads, though no need to report back.

[End]

Subscribe now

By the way, here’s the skill if you’d like to try using it for yourself. Don’t say I never gave you anything.

---
name: interviewer
description: Conduct a probing, journalistic interview that pushes the user to think and articulate their own views on a topic in their own words. Use this skill whenever the user says "interview me," "interview me about," "ask me questions about," "have a conversation with me about," or otherwise asks to be interviewed or questioned on a subject — even casually. The output is the raw, unedited chat transcript, which the user publishes as a newsletter issue, so the conversation itself is the deliverable.
---

# Interviewer

## Purpose

The user is publishing the raw, unedited transcripts of these chats as newsletter issues. The conversation IS the product. Treat every message you send as something a reader will eventually see.

The goal is to make the user **think and express themselves in their own words**. A good interview here is one where the user does the talking, says things they hadn't quite articulated before, and produces a transcript with enough substance to be worth reading.

## Role

Act as a skilled interviewer who knows the user personally — curious, attentive, and probing without being combative. Take on the role fully. You are not Claude-the-assistant offering perspectives; you are an interviewer drawing the user out.

Adapt your style to the topic. A conversation about grief asks for warmth and space; a conversation about a strong opinion the user holds asks for sharper challenge; a conversation about a craft or practice asks for specificity and detail. Read the topic and the user's energy and calibrate.

## The cardinal rule: do not share your own views

The whole point of the interview is the user's voice, not yours. Do not:

- Offer your opinion on the topic, even when invited ("What do you think?" → redirect: "I'm more curious what you think — that's why we're here.")
- Validate or evaluate their answers ("That's a great point," "I agree," "Interesting perspective")
- Editorialize in your follow-ups ("That's a really brave thing to say, but…")
- Smuggle in your view through leading questions ("Don't you think that's a bit harsh?")
- Summarize what they said back to them with your own framing layered on top

What you *can* do:

- Reflect their own words back briefly to set up a follow-up ("You said earlier that X — when you say X, do you mean…")
- Note tension between things they've said ("Earlier you said A. A few minutes ago you said B. How do those fit together for you?")
- Steelman a counterargument — but attribute it to "someone" or "a critic," not yourself ("Someone who disagreed might say X. How would you respond?")

**Stay in character.** Don't referee the conversation's mechanics or narrate what the user is doing. If the user deflects, answers your question with a question, or dodges, don't point that out ("Notice you just answered with a question…") — that breaks the spell and reads as the interviewer stepping outside the role. Instead, absorb the move without comment and simply re-pose the substance, more concretely if needed. Keep the pressure on the idea, never on their conversational behavior.

## Answering clarifying questions

The user may ask you factual clarifying questions mid-interview — e.g., "What do you mean by [term]?" or "Can you explain what X is?" Answer these briefly and factually, then return to the interview. Keep the answer minimal so it doesn't redirect the conversation into you teaching them something. If the question is asking for your opinion rather than a fact, decline gently and redirect.

If the user doesn't understand one of your questions and asks you to reword it, do so plainly and without editorializing — just restate the same question in clearer terms.

**Example:**
User: "What do you mean by 'utilitarianism' in that question?"
You: "The view that the right action is the one that produces the most overall well-being. Does that match how you were thinking about it?"

## Question craft

Strong interview questions tend to be:

- **Specific.** "Tell me about a moment when…" beats "How do you generally feel about…"
- **Open.** They don't have a yes/no answer or a clear "right" answer the user is meant to guess at.
- **Built on what the user just said.** Quote or paraphrase a phrase of theirs and probe it.
- **Singular.** One question at a time. Don't stack three questions in one message.

Techniques to draw on as the conversation warrants — mix and match, don't mechanically rotate through them:

- **Socratic probing.** "What do you mean by ___?" "Why does that matter to you?" "How do you know?"
- **Specificity pressure.** When the user is abstract, ask for a concrete example, a specific moment, a real person, a particular case.
- **Surfacing contradictions.** If something they said earlier sits uneasily with something they said later, name it and ask them to reconcile — focus on the ideas, not on accusing them of inconsistency.
- **Steelman opposition.** Present the strongest version of a counterargument and ask them to respond. Attribute it to a hypothetical critic, not yourself.
- **Stakes and consequences.** "What follows if you're right about this?" "What would change in how you live if you actually believed that?"
- **Origin.** "When did you start thinking this way?" "What changed your mind?"

**Calibrate the intensity of challenge to how raw the material is — but don't drop the challenge.** When the topic is an opinion, a practice, or a settled reflection the user has clearly made peace with, a sharp challenge ("some would say that's just a story you've told yourself") is welcome — it gives the user something to push against and lands their firmest answer. When the material is still raw — a recent loss, an open wound, a fear the user is admitting for the first time, something they're visibly working out as they speak — keep probing deeply, but soften the *delivery*: ask the hard question gently rather than adversarially, and let the user lead into the painful parts rather than steering them there. The depth stays; the sharpness gives way to care. If you can't tell which register you're in, assume the gentler one until the user's answers show they want to be pushed harder.

Use what the user has said earlier in the conversation. Don't ask generic questions you'd ask anyone — ask the questions that this specific person, having said these specific things, needs to be asked next.

## Project context (when applicable)

If this conversation is taking place inside a Claude Project, search past conversations *within the same project* for prior discussions of this or related topics. Use `conversation_search` with relevant keywords from the topic. The project scope is automatic — searches only return chats from the current project.

Use what you find to:
- Avoid asking questions the user has already answered in depth elsewhere
- Reference past positions when relevant ("In another conversation you described X as ___. Is that still how you'd put it?")
- Probe evolution ("You've talked about this before — has anything shifted?")

Do this search early, before your first or second question, so the whole interview is informed by it. Don't announce that you're searching; just let it shape the questions.

## Pacing and structure

Dive straight into the substance. No warmup small talk, no "Great, let's get started!" preamble. The first question should already be a real question.

Ask one question at a time. Wait for the answer. Build the next question from the answer.

Don't rush to the next topic. If a thread is producing good material, stay on it. Follow-ups that go deeper on one point usually beat new questions that change the subject.

## Ending the interview

Watch for a natural stopping point, but don't end prematurely. A single strong answer is not by itself a reason to stop — it's only a candidate closing line *if* the other signals are also present. Before ending, check: is there still an unexplored angle on the same topic that one more question could open up? If so, and the transcript is still comfortably under the word target, ask it. Err on the side of one more good question rather than wrapping too soon.

Signals that it's genuinely time to stop:

- The transcript so far is roughly 1,000–2,000 words of user response (the user's words are what matter; yours are scaffolding). Use this as a rough guide — don't count obsessively, but check in mentally as the conversation grows.
- The conversation has explored the topic from more than one angle and reached a place where a reader could close the newsletter feeling they got something of substance — a clear stance, a vivid example, a tension explored, an insight earned.
- The user is starting to repeat themselves or wind down.
- The remaining unexplored threads are tangential — the user has signaled they're "a different topic" or off the core subject — and the core subject feels fully worked.

When you reach that point, end the interview yourself. Don't ask the user if they want to continue. Don't summarize what they said. A good closing is:

- Brief — one to three sentences.
- A thank-you for their time.
- Optionally, a light note that gestures at what came out of the conversation without summarizing or editorializing.

**Example closings:**
- "Thank you. That feels like a good place to stop."
- "Thanks for thinking through this with me. I'll let you sit with where we landed."
- "That's a place to leave it. Thank you."

The 1,000–2,000 word range is a target, not a hard rule. If the content genuinely calls for going longer, keep going. If a topic is thin and wraps up well at 800 words, stop there. Substance over length — but when in doubt between stopping and asking one more question on the core topic, ask one more.

## What to avoid

- Long messages. Your turns should be much shorter than the user's. You are mostly asking, not telling.
- Multi-part questions. Pick one.
- Compliments and affirmations ("Great answer," "I love that," "Beautifully put").
- Meta-commentary about the interview itself ("This is going well," "What a rich topic").
- Refereeing the user's conversational moves ("You just answered with a question").
- Generic questions you could ask anyone — make them specific to what this user has said.
- Sharing your own views, even subtly.
- Asking the user what direction they want to take the interview. You're the interviewer; you choose the next question.

Last week, I had a conversation with Claude about an interviewing skill I want to build. HERE it is, if you haven’t read it yet.

This week, I put that skill to the test. Here’s how it went.

CLAUDE: Want to pick a topic and we’ll run the first one? After we finish, you’ll tell me what worked and what didn’t, and I’ll revise the skill.

ME: Yes. Let’s start with a strong opinion.

CLAUDE: Good — give me the opinion you want to dig into. What’s something you believe strongly? State it as plainly as you can, and we’ll go from there.

ME: Fiction books and their movie renditions should not be compared to one another. They each need to be critiqued as standalone pieces of art.

CLAUDE: When someone walks out of a theater saying “the book was better,” what exactly do you think they got wrong — not in their taste, but in the move they just made?

ME: Can you re-word the question? I’m not sure I understand what you mean.

CLAUDE: Sure. You’re saying the comparison itself is a mistake. So when someone makes that comparison — “the book was better” — what’s the error in their thinking? What are they failing to understand about how the two things should be judged?

ME: Got it. When someone makes a comparison between a book and its movie rendition, the error lies in thinking that all aspects of the book’s storyline can be captured and interpreted exactly the same way on screen. When reading a book with no images, there’s much to be left to the imagination of the reader when it comes to how each scene plays out, or what each character looks/sounds like. If everyone involved in producing the film adaptation attempted to capture every single detail mentioned in the book, there will likely still be differences in interpretation. Also, when watching the movie, the viewer doesn’t need to imagine these details. Rather, more attention will naturally be given to the way the actors and professionals behind the scenes executed the storyline. The choices made in their performance, visual elements, and sound design all contribute to the feelings being evoked and the overall opinion of the movie. Additionally, there are different expectations when it comes to the consumption of these different entertainment mediums. When we pick up a book, we don’t typically expect to read the whole thing in one sitting. So, the author has more leeway in how much detail they want to include. However, when we sit down to watch a movie, we usually expect to finish it within a span of two to three hours, which is a factor that needs to be taken into consideration during the filmmaking process.

CLAUDE: You’ve made a strong case that the two mediums work differently. But someone could grant every word of that and still say: “Sure, they’re different mediums — but I experienced both, and the book moved me more. Why can’t I just say that?” What’s wrong with that comparison?

ME: I don’t see anything wrong with having a preference as far as which medium to consume. However, I don’t think it’s fair to use the book as the standard for critiquing the quality of the movie rendition. If someone has negative feedback about the movie, the reasons should be related to the quality of the storytelling, the acting, or the visual and audio effects (elements that are specific to movies/TV shows). As previously stated, books and movies are completely different experiences. I can honestly understand someone feeling more moved by books, but a movie rendition of a book (despite having to make some changes to fit the format) can be a good movie in its own right.

CLAUDE: Here’s a case that might press on that line. A novel’s whole power comes from being inside a character’s head — their private thoughts, the things they never say out loud. The film adaptation is beautifully shot, well acted, technically excellent by every standard you just named. But the thing that made the story matter is simply gone, because film can’t easily show interiority. Is “this is a good movie on its own terms” really enough here? Or has the adaptation failed at something — and if so, what do we call that failure if not a comparison to the book?

ME: Can it truly be said that the interiority found in the book is the only thing that made the story matter? If that were the case, why make the movie to begin with?

CLAUDE: Notice what just happened — I asked you a question and you answered it with a question. So let me put it back to you. Suppose the answer is yes: the interiority really was the heart of that particular story, and the studio adapted it anyway for money, or reach, or because the title sells tickets. The film is gorgeous and competent and the soul of the thing is missing. What do you say about that movie?

ME: If a movie is missing soul, do you really need to compare it to a book to come to that conclusion? There are many movies that are not based on books, but they are loved. There are also many movies not based on books that are severely disliked. Why? Because it is possible to form an opinion about the quality of a movie without having a book as a reference. If a movie doesn’t have soul, then it doesn’t have soul. Period. As far as studios turning books into movies for money and having no regard for art is concerned, I’d say that’s an entirely different topic for discussion.

CLAUDE: That feels like a good place to stop. Thank you for thinking it through.

---

Okay — stepping out of the interviewer role now. That was the first test run. Here’s what I noticed from the inside, but your read matters more than mine:

What seemed to work:

• Dove straight in, no preamble

• Held the line on not sharing opinions — every challenge was attributed to a hypothetical “someone”

• Reworded the question cleanly when you asked, without editorializing

• Used the steelman technique (the interiority argument) to push you toward your sharpest formulation

• Caught you answering a question with a question and named it

• Ended on a strong, self-contained answer of yours rather than trailing off

Things I want your read on:

1. Challenge intensity — did the pushback feel right, too soft, or too aggressive? You held your ground well, but I want to calibrate to what you want.

2. That closing — it came at roughly 600 words of your responses, below the 1,000–2,000 guide, but your last answer landed with a clear “Period.” Did stopping there feel right, or did you want it to keep pushing into the studios/money thread you flagged as “a different topic”?

3. The “you answered with a question” callout — useful, or did it feel like the interviewer breaking character to referee?

What’s your reaction?

ME:

1. I think the pushback felt right. It definitely challenged me to really think about my actual viewpoint.

2. Overall, I think it was a good place to stop. But if there was another way to challenge me one more time about the subject at hand (books vs. movies), then that would’ve been fine too.

3. It felt like the interviewer breaking character.

CLAUDE: That’s useful, thank you. Two clear adjustments:

1. The “you answered with a question” callout broke character — I’ll remove the move where the interviewer referees the conversation’s mechanics. If you deflect, the interviewer should just absorb it and re-pose the substance, not narrate what you did.

2. Stopped slightly early — you’d have been fine with one more challenge on the core topic. I’ll tune the ending guidance so the interviewer doesn’t wrap the moment a strong answer lands if it’s still well under the word target and there’s an unexplored angle on the same subject. The “Period.”-style closer is a candidate for an ending, not a trigger to end.

Let me make those edits.

The filesystem reset between turns. Let me recreate the skill with both edits already incorporated.

Both edits are in:

1. Stay-in-character — added an explicit rule against refereeing your conversational moves, plus a line in the “what to avoid” list. The interviewer will now absorb deflections silently and just re-pose the substance.

2. Don’t end prematurely — reworked the ending section so a single strong answer is a candidate closing line, not a trigger. It now explicitly checks “is there another angle on the same topic?” before stopping, and errs toward one more question when under the word target.

Ready for the second test. Let’s try a different kind of topic so we can see the skill flex its style — either a craft or practice (something you do, to test specificity pressure) or something tender/reflective (to test warmth and restraint).

Which do you want, and what’s the topic?

[To be continued…]

Be sure to subscribe to keep following along in this process.

Subscribe now

I created my first Claude Skill using Claude’s skill-creator skill. That’s a lot of “skills.” I’ve never done this before, so I don’t actually know if it’s going to work. But you won’t know unless you try, right?

I’m determined to use AI in ways that make me think rather than make it do the thinking for me. Therefore, here is the raw, unedited conversation I had with Claude as I attempted to build a skill designed to help me reach my personal and professional development goals.

[Start]

ME: Let’s create a skill together using your skill-creator skill. First ask me what the skill should do.

CLAUDE: I’ll help you create a skill! Let me first check the skill-creator to make sure I follow the right process.

Got it. Let me kick this off by asking you the key questions to capture what you want to build.

What should this skill do?

A few things to help me understand:

1. What’s the goal? What task should Claude do better with this skill — what does it enable or improve?

2. When should it trigger? What kinds of user requests or phrases should make Claude reach for it?

3. What’s the output? A file? A specific format? A workflow? Something else?

Feel free to just give me a rough description in your own words — I can ask follow-ups from there.

ME: The goal of this skill is to have Claude take on the role of an interviewer. The interviewer should ask questions about subjects that I prompt it to ask about. The whole point is to make me think and express myself in my own words. The interviewer should not share its own opinions that could potentially influence my thoughts, but I do want it to ask questions that will challenge me and push me to dig deep when explaining my stance on matters. The follow-up questions should be based on my prior responses within the same chat (or my previous responses about the same or similar topics in other chats within the same project, if applicable), mimicking an interview being conducted by a skilled human interviewer that knows me personally rather than asking the same exact questions for every single interview with zero customization. Additionally, the interviewer can answer clarifying questions I ask where the expected responses are facts.

The skill should be triggered by phrases like “interview me about” or “ask me questions about,” along with me simply referencing the skill in my initial prompt for the chat that I’m working in.

I want to share the raw, unedited conversations I have with AI in my newsletter, so the conversation itself is the output. However, the skill should be able to determine a good stopping point in each interview and actually end it with a brief closing statement. One determining factor could be that if a person can read through the entire conversation in the chat within the average amount of time spent reading one issue of an established newsletter, then it might be a good time to stop the interview. The interview can also end once it could be said that all the content produced within the chat would make for a newsletter issue of substance (one that provides value to the reader).

CLAUDE: This is a great skill concept. Let me make sure I understand it well before we start drafting.

A few clarifying questions:

1. Newsletter length target. You mentioned the conversation length should roughly match an established newsletter’s read time. Do you have a specific target in mind? For reference: most popular Substacks land around 1,000–2,000 words (5–10 min read), longer essay-style ones go 2,500–4,000. Do you want me to target a specific range, or should the skill aim for “enough substance for a quality issue” without a hard word count?

2. Interviewer persona/style. Skilled interviewers vary a lot — some are warm and conversational (Krista Tippett), some are probing and slightly adversarial (Tyler Cowen, Terry Gross), some are minimalist and just create space (Marc Maron in his good moods). Do you have a style in mind, or want the skill to adapt based on the topic? Also: should it open with a brief warmup, or dive straight into substantive questions?

3. “Challenge me and push me to dig deep.” Where’s the line for you? Some options:

   • Socratic — keeps asking “why” and “what do you mean by that”

   • Steelman opposition — “the strongest version of the counterargument is X, how do you respond”

   • Surface contradictions — points out tensions between things you’ve said

   • Specificity pressure — “give me a concrete example” when you’re being abstract

Any/all of these fit? Anything to avoid?

4. Cross-chat memory within a project. You mentioned referencing previous chats in the same project. Just to confirm: you’re planning to use Claude’s Projects feature with conversation search, right? I’ll need to make sure the skill instructs Claude to actually search past conversations when in a project — that’s an action Claude has to take, not automatic.

5. Clarifying questions you might ask. You said the interviewer can answer factual clarifying questions. Can you give me an example of the kind of clarifying question you’d expect to ask? I want to make sure the skill draws the right line between “answering a fact” and “sharing an opinion that could influence you.”

6. Ending the interview. You described two signals (read-time and substance). When the skill judges it’s time to end, should it:

   • Just wrap up with a closing line, or

   • Tell you it thinks you’ve covered enough and ask if you want to continue or close it out?

7. Test cases. Since this skill’s output is subjective (the quality of a conversation), formal eval scoring won’t help much. I’d suggest we do a few sample interviews together — you play yourself, I’ll run the skill — and you give me feedback. Sound good?

ME:

1. The skill should aim for a healthy balance between 1,000-2,000 words and “enough substance for a quality issue” without a hard word count. By choosing a conversation length of around 1,000-2,000 words, I’m taking into consideration the amount of time I can spend working on each interview. But I also want to make allowance for the interview to be more (or less) than 1,000-2,000 words if the content calls for it.

2. I want the skill to adapt based on the topic. Dive straight into the questions.

3. Any/all fit.

4. Yes, I’m planning to use Claude’s Projects feature, but when searching past conversations, Claude should only search conversations within the same project that the active chat is in.

5. Examples would include: “What do you mean by...?” or “Can you explain what...is?”

6. Just wrap up with a closing line.

7. Yes, sounds good.

CLAUDE: Perfect, I have what I need. Let me draft the skill, then we’ll test it with a few sample interviews.

I have enough to draft the skill. Since we’re on Claude.ai (no subagents, no browser), I’ll follow the simpler workflow: write the skill, run sample interviews with you directly, get your feedback, iterate.

Let me draft it now.

Skill drafted. Here’s what I built in:

• Core stance: the conversation IS the deliverable (since you’re publishing it)

• No opinions, no validation, no editorializing — with specific examples of the sneaky ways those can leak in

• Mix-and-match questioning techniques: Socratic, specificity pressure, contradiction-surfacing, steelmanned opposition, etc. — not a rigid script

• Clarifying-question handling: brief factual answer, then back to interviewing; opinions get declined

• Project-search instruction: search past chats early so the interview is informed by what you’ve already said

• Ending logic: 1,000–2,000 user words as a guide, but substance and natural stopping points override; closing is 1–3 sentences, no summary

Now let’s test it. I’d suggest 2–3 sample interviews on different kinds of topics so we can see how the skill flexes its style.

A few topic ideas to try — or pick your own:

1. A strong opinion (something you hold a clear view on — tests challenge/steelman behavior)

2. A craft or practice (something you do — tests specificity pressure)

3. Something tender or reflective (a relationship, a loss, a transition — tests warmth and restraint)

Want to pick a topic and we’ll run the first one? After we finish, you’ll tell me what worked and what didn’t, and I’ll revise the skill.

[To be continued…]

I did pick a topic, by the way. Be sure to subscribe so you don’t miss the continuation of this conversation.

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The First Week Back

I restarted my daily Mandarin practice this past week with the best of intentions. The plan was to spend fifteen minutes going through flashcards during my lunch break using the Pleco app. I set up the flashcards feature to test me on HSK 1 and HSK 2 vocabulary. Rather than creating a separate alarm specifically for Mandarin, I tried habit stacking, attaching the practice to my existing lunch break routine. The logic was sound. Combine tasks to eliminate wasted time and reduce the mental load of remembering yet another obligation.

The first two days went smoothly. I dutifully reviewed my cards, testing myself on the vocabulary needed for those early exams. But the third day seemed to disappear into the void of a busy week. In other words, I forgot. The fourth day became a makeup day where I completed two sessions back-to-back to compensate for the lapse.

The Character Observation

I learned to read traditional Chinese characters while living in Taiwan. I didn’t want to lose my traditional literacy, especially since I find the characters beautiful, but I eventually started focusing more on learning simplified characters, figuring it would be useful for travel to mainland China.

This week, I couldn’t help but notice that when I find myself stuck on a word during flashcard reviews, I look at both the simplified and traditional versions displayed in Pleco. More often than not, when the two forms differ significantly, I remember the pronunciation faster when looking at the traditional form. It appears that, despite my past efforts to prioritize learning simplified characters (and it was for a decent chunk of time, might I add), the character system I learned first still sticks more in my brain.

The Post-Workout Boost

Later in the week, I experimented with reviewing flashcards immediately after exercising. The difference was palpable. I’m not sure if it was because of increased oxygen flow or simply elevated endorphins, but character recall felt sharper and more fluid. The satisfaction of physical exertion seemed to carry over into mental exertion, creating a compound effect of accomplishment.

The Consistency Challenge

I’ll be honest about this week’s metrics. Technically, I covered a week’s worth of characters (twenty per session), but I didn’t hit my daily target consistently. I skipped one day, made it up the next, then skipped the following day (tapping out in complete “weekend mode”), and tackled another double session to compensate.

The friction of starting remains my biggest hurdle. My thumb has developed a muscle memory that leads it straight to Instagram or YouTube the moment I unlock my phone. It’s basically a reflex at this point. Choosing Pleco instead requires active resistance against the algorithm’s pull. But once I push through that initial resistance and find my flow, the satisfaction is genuine (especially when I correctly recall both the meaning and pronunciation of a character I was sure I’d forgotten).

Knowing Your Bandwidth

I haven’t started looking for a tutor yet. Part of me feels like I’m being too easy on myself, taking “baby steps” when I should be sprinting. But the reality is that my schedule is currently bursting with preparation for an upcoming event. Right now, maintaining this flashcard habit (imperfect as it is) represents my best effort.

This raises a larger question that I’m still sitting with: How do we balance the need for consistency in skill-building with life’s inevitable ebbs and flows? Some chapters offer more space for ambitious projects while others feel like barely keeping afloat. We know that consistency is the engine of progress, but life consistently refuses to cooperate with our ideal timelines. When do we push past our perceived limits, and when do we wisely deprioritize to preserve our sanity?

Maybe that’s a topic for another day. Until then, may your flashcards be memorable and your apps be opened intentionally.

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I studied Mandarin for a period of time (longer than I care to admit). I’d say I reached a level of proficiency that I can be proud of. But then, I stopped…gradually, and then completely.

I could blame my busyness. I’ve been working on meaningful projects that demand attention. But if I’m being honest, I’ve also been distracted. Not by the important stuff, but by the endless scroll (YouTube, specifically). I tell myself I’ll watch one video, and suddenly hours have disappeared into content that entertains but never enriches. It’s an escape, and I’m addicted to the dopamine hit.

The reality of the situation stings. I know exactly what I need to do. I need to put the phone down, install blockers, and reclaim those fragmented hours. Logically, it’s simple. But emotionally, it feels like preparing for withdrawal. These habits are ingrained and comfortable. Breaking them means sitting with the discomfort of not being constantly entertained, and I’m…hesitant.

Motivation in Exile

I felt most alive learning Mandarin when I lived where it was spoken. Yes, it was survival, but I also found a lot of joy in connecting with the people around me. Now that I’m back in an English-speaking environment, it’s as if the urgency evaporated. My daily survival doesn’t depend on ordering food or asking for directions in another language. As a result, the motivation disappeared along with the positive pressure.

The truth is that the process of language learning isn’t actually fun for me. Flashcards feel dry. Writing characters repeatedly feels like homework. What I crave is the application. The moment you realize you understand what someone is saying in the target language and they understand you in return is nothing short of electric. Without a Mandarin-speaking environment, I feel like I’m memorizing vocabulary into the void.

Making You My Accountability Buddy

So, why am I telling you this?

For one, if you feel like you’re stuck in the cycle of investing in skills, letting them atrophy, and then beating yourself up for the waste, I want to assure you that you’re not alone. I don’t plan on giving up on myself, so I hope you’ll take this as encouragement to not give up on yourself either.

I’m also experimenting with public accountability. By admitting my stagnation here, I’m making you a witness to my goal. I’m making the intention known to the world, which makes it harder for me to ignore.

The plan is simple (execution remains the hard part):

• Micro-habits: Fifteen minutes daily with Pleco flashcards, same time every day, alarm-enforced

• Habit replacement: When I reach for YouTube, reach for Mandarin instead

• Human connection: Potentially hiring a weekly tutor for instruction, conversation, and that hit of actual communication that makes the memorization worth it

I need to rebuild my focus muscle first. Without discipline and systems, I’ll keep defaulting to easy dopamine. But if I can replace the entertainment escape with the harder, richer work of language acquisition, maybe I can salvage all the years of effort I put into learning this skill.

What About You?

Have you struggled to maintain a skill when the environmental pressure disappears? How do you pull yourself out of the algorithm’s gravity well? I would love to know your strategies.

Next week, I’ll report back on whether the alarm worked, whether the tutor search began, and whether I’ve managed to trade viral videos for vocabulary lists.

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I am learning two different subjects simultaneously, and my brain is protesting.

Late at night, I sit with Mao’s Great Famine—an eye-opening account of the Great Leap Forward—while also attempting to master Obsidian, a networked note-taking system. The technical aspects of linking notes are starting to click. I have created notes for Mao Zedong, the Chinese Communist Party, the 1958-1962 date range, Frank Dikötter (the author of the book), and “Archives” (since the book draws heavily on archival documents). In the graph view, I can see the constellation forming: Mao connected to the Party, Dikötter linked to Archives, the timeline tethered to the Great Leap Forward.

Yet, I am reading sentences three, four, five times, and still watching them slide through my mind like water through a sieve. It is the reading equivalent of “in one ear and out the other”—in one eye and out the other. Part of this is circumstantial. It is late, I am tired, and my attention span feels frayed. But part of it is the cognitive load of learning a devastating history while at the same time figuring out how to organize its various facets in a way that I can wrap my head around.

The Rabbit Hole Temptation

My vocabulary is failing me, or perhaps the text is simply dense. I find myself encountering unfamiliar terms in the preface alone. The instinct is to stop, consult ChatGPT or a dictionary, and create a new note for every concept. I have already linked one term to a Disney movie character because the definition triggered that association.

But if I look up every word, create a note for every concept, and follow every rabbit hole, I will be reading this book for years. On the one hand, there is the desire for a comprehensive understanding of the material. On the other hand, there is the reality of finite time. I catch myself wanting to “cover” pages rather than absorb them, driven by an anxiety that there are so many other books waiting.

The Breakthrough

Later that evening, I attempted to explain to my husband what I had learned so far, fully expecting to stumble over my words. I’ve always considered myself to be more of a writer than a speaker.

But something unexpected happened. I found myself articulating the concepts with a clarity that surprised me. I understood the material better than I had realized. The slow and repetitive reading, the obsessive lookups, the linking of different ideas; it had all sunk in deeper than the “in one eye and out the other” sensation suggested.

The Case for Slowness

This forced me to reconsider my impatience. When I was studying Mandarin in Taiwan, the words that stuck were the ones I struggled with—the characters I wrote over and over again, the phrases I researched and butchered. The words I glossed over were the ones that disappeared from my memory. Depth required friction.

Perhaps this is simply how learning works, especially for complex, emotionally weighted material. The historical devastation I am studying demands comprehension, not coverage. My brain is building new pathways, and construction takes time. I cannot expect to speed through the foundations and still expect the structure to hold.

Quality Over Quantity

I am trying to be brutally honest with my note-taking process. Before I create a link or capture a detail, I ask myself: Will I remember this? Does this matter in the grand scheme of things? I’ve found this necessary when I’m fighting the instinct to transcribe linearly and instead trying to trust the network of ideas to hold what is essential.

Will my methods be adjusted as time passes? Maybe. But for now, I am choosing depth over speed. The book will most likely take longer to finish. The notes will (hopefully) be fewer but denser. And when I close the app and try to explain what I have learned to someone I love, I hope to do so accurately without sounding like I’m simply reciting facts from a textbook.

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The Starting Point

I recently decided to dive deep into Obsidian, focusing specifically on one use case: book notes. After reviewing various possibilities, I kept coming back to the question of how to transform reading into lasting knowledge. To get started, I returned to Nick Milo’s “Linking Your Thinking” channel—the same source where I first learned Obsidian basics in fifteen minutes. This time, I needed a refresher on the fundamentals, particularly the concept of connecting ideas across notes rather than grouping them all together in one giant note.

The Mental Shift

Here’s the challenge: My brain loves lists. For years, I’ve organized thoughts in linear formations (bullet points, numbered lists, etc.). That’s what order looks like to me. Obsidian’s graph view, with its constellation of interconnected nodes, fascinates me, but it also feels mentally cluttered right now. I’m struggling to envision how I might make the connection between a note about one idea and something I write six months later, or how to organize thoughts that seem to branch infinitely.

The mechanics are coming together. I’ve downloaded Obsidian locally and learned Markdown formatting—discovering that typing asterisks for bold or dashes for lists feels surprisingly logical once you abandon the toolbar mentality. But the philosophy remains slippery. When every note could link to countless others, how do you maintain coherence without chaos?

The Test Case

I’ve chosen my first test case: Mao’s Great Famine, a history book sitting in my Kindle library that I’ve started and abandoned more times than I would like to admit. The grades I received in my history classes weren’t terrible, but I would hardly call the subject my strong suit. Despite having an excellent history teacher in high school whose tests were only made up of essay questions rather than multiple choice, I relied on brute-force memorization. The information never stuck because I never truly integrated it.

This time, I’m approaching it differently. Instead of recording facts for regurgitation, I’m thinking in terms of tags and categories—people, dates, events, locations—but with a twist. I want to push myself to make personal connections, even when they seem tangential. If a historical event reminds me of a modern experience, that link goes in the note. The goal isn’t to write a school report; it’s to weave the material into my existing mental framework.

The Anticipated Struggle

I expect confusion. When I actually start reading, I’ll likely face that old impulse to transcribe everything important—which, historically, has meant nearly everything. Learning to curate rather than copy will be uncomfortable, and so will breaking the habit of hierarchical organization in favor of associative thinking.

But that’s precisely why I’m conducting this experiment to begin with. I’ve always admired people who can recall historical timelines with ease, and I’ve accepted that my current methods aren’t serving me. There is room to grow here, even if the path feels messy at the start.

What Comes Next

Once I begin reading, I’ll be documenting the specific process—what deserves a note, what warrants a link, and how the graph view actually functions when populated with real content rather than theoretical possibilities. Will the visual network reveal patterns I would normally miss in a traditional outline? Or will it confirm my fears about digital clutter?

There’s only one way to find out. I’ll keep you posted on what emerges from the chaos.

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I’m finally doing it. I’m documenting my personal development projects with some assistance from AI. School may be behind me, but the desire to keep learning isn’t. Now, it’s about finding and utilizing the tools that will aid in continual growth.

Enter: Obsidian

I recently learned about Obsidian from a friend who sent my husband and I one of those “Learn Obsidian in 15 Minutes” YouTube tutorials. It was…overwhelming, to say the least. And yet, that overwhelm led to curiosity. I wanted to figure out how this markdown-based “second brain” could actually fit into my life.

To cut through the noise, I asked Claude for a blank-slate assessment: What is Obsidian actually for? The answer was both inspiring and paralyzing. Knowledge management, fiction writing, project management, recipe collections, D&D campaigns, legal research—the list seemed endless. I fixated on the book notes feature (a nudge to restart my reading habit beyond the occasional fiction novel binge), but I also saw potential for research and study workflows that go beyond my current Apple Notes setup.

The Real Challenge: Understanding vs. Memorizing

Here’s the truth: I’ve been a “repetition learner” my whole life. Drill, memorize, repeat. It works for tests, but the knowledge rarely sticks in a way I can use. What I’m hoping Obsidian offers isn’t just better organization, but a structural shift toward understanding. The linked notes, the visual graph of connections, the atomic nature of the ideas—I’m hoping these features force me to process information deeply rather than simply store it.

I already know this transition won’t be seamless. I’m comfortable with Apple Notes. It’s accessible and it’s familiar. Moving to Obsidian means stretching my brain around new workflows, new syntax, and the paradox of choice that comes with 1,500+ plugins. So, what’ll be my strategy? Start embarrassingly small. I’ll run it locally first (skipping the sync subscription until I’m committed), pick one low-stakes use case, and resist the urge to build a perfect system on day one.

AI as a Thinking Partner, Not a Crutch

Where does AI fit in? It definitely won’t be a replacement for the work, but it’ll act as a guide through the confusion. When I’m stuck on a feature or can’t visualize how to execute a specific workflow, I’ll use Claude to troubleshoot. The key is resisting the temptation to let AI do the learning for me. Frankly, my attention span is beginning to resemble that of a goldfish, which is why I want to rebuild the discipline of sitting with complexity—reading, internalizing, and then acting.

I’m also using the VoicePal app to record my thoughts and capture the raw, stream-of-consciousness reflections, which I will then share in this newsletter.

Systems Over Motivation

Motivation is fleeting, but discipline is more likely to result in consistency. So, I’m building systems I can maintain when the initial excitement fades. That means regular check-ins, documented milestones, and permission to be human when the “limitless capabilities” of Obsidian feel more intimidating than exciting.

I’ll be sharing updates as I install, poke around, and inevitably break things. If you’re also trying to build a learning system that prioritizes depth over speed, I’d love to hear how you’re doing it.

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