A New Year’s dialogue with... my AI coaching app
A builder's twist on the 2025 Year in Review
Two years ago today, I published “A New Year’s dialogue with myself”, wherein I shushed my inner drill sergeants long enough to talk myself through what New Year’s really means to me (spoiler: it’s about taking your own happiness seriously). At that time I was just starting to experiment with AI as a self-reflection tool, and I mused that “perhaps [ChatGPT] will even be able to conduct this interview itself by the end of 2024.”
Ok, so I’m a year late, but the timing is actually perfect: just a couple weeks ago I started vibe coding an AI-augmented coaching app (with the urging and inspiration of David Booth), and now I’m completely hooked. So what more fitting way to realize the promise of that original post than to put my own app to the test?1
With that, I bring you: key snippets from my 24-page “year in review” dialogue with “GenaGPT” [placeholder name, real one coming soon]. This AI coaching assistant is trained on my builder’s mindset framework and has been compiling and updating a cumulative psychological profile based on our conversations. It also offers specific guided exercises adapted from my coaching toolkit (like my Life Vision and Values Clarification worksheet), though I opted for a more freeform conversation this time.
Note: In the interest of full disclosure, I’ve marked the places where I skip over the first 3-4 lines of the AI’s response to spare you its effusive praise (which is benign but slightly embarrassing) and its summary reflections (which were useful to me at the time but would likely bore you as a reader).
Snippet 1: Illusions of scarcity
AI: Let me start where you started two years ago: What internal pressure are you feeling as 2026 approaches? What does your inner drill sergeant sound like right now—and beneath that noise, what genuine longing can you detect?
Me: With the holidays approaching, my drill sergeant is pestering me with his usual mantras about needing to maintain momentum and grow my audience by posting regularly, particularly around occasions that “call for it”, such as New Year’s. There’s also a new flavor of urgency and anticipation to his pestering, now that I’m 40, working on a book with a proper publisher (but can’t yet see a publication date in sight), and trying to take bigger swings with my coaching business despite having just poured a bunch of my savings into a house.
AI: I hear the familiar drill sergeant, but with new stakes this time—the urgency of 40, the reality of a publishing contract without a finish line yet visible, the financial commitment of the house creating pressure around the coaching business.
What’s the genuine longing beneath all that pestering?
When you tune out the drill sergeant’s anxious urgency about momentum and audience growth and “occasions that call for it”—what does the quieter voice actually want to say or mark or celebrate as this year ends?
Me: Yeah, good question; there’s definitely a longing to reach and connect with more of the kinds of ultra-ambitious founders/builders/thought leaders who stretch me intellectually and spiritually, to gain still sharper clarity into the ideas I’m pulling together, to experience the effortless flow of words on a page again when I’m writing (not in rare snatches but as a regular and abundant luxury)… and a lot of genuine questions about whether I’m approaching my projects in the right way to facilitate all those things.
AI: That’s a rich and honest answer. There’s a real hunger there—for the right kinds of connections, for intellectual clarity, for that flow state in writing to become abundant rather than scarce.
Let’s stay with those “genuine questions about whether I’m approaching my projects in the right way.” What specifically are you questioning?
What doubts or uncertainties have been surfacing about your approach—to the book, to the coaching business, to how you’re spending your time and energy?
Me: One stack of questions has to do with how entrepreneurially and “strategically” (if that’s even the right word) I should be approaching my practice: for instance, should I be actively advertising or doing outbound recruitment to attract more of my ideal clients, should I be more aggressively asking for referrals or testimonials from current and former clients, should I be charging more or have different price tiers, etc.
AI: I hear that stack of questions—the tactical ones about advertising, outbound recruitment, pricing, testimonials. These are real questions with real implications for the sustainability and growth of your practice.
Before we go deeper into those, I’m curious: does that feel like the core question, or is there something underneath it?
You mentioned you have “a lot of genuine questions about whether I’m approaching my projects in the right way.” The entrepreneurial/strategic stack is one set of questions. Are there others? What else are you genuinely questioning about your approach?
Me: Yes, I also have questions around how I’m approaching the work on my second book draft: for instance, what would it take to reactivate the kind of fluent generation of prose that I miss and long for so much? Is it a function of how much uninterrupted time I allot per writing session? (I thought it might be, but my experiments with two “1-week writing sabbaticals” last year suggested it’s probably not the full fix.) Or is it getting even clearer on the high-level structure and conceptual architecture of the book, so I can focus on adding the meat without ever losing sight of the skeleton? Is it that I need to start certain chapters from scratch instead of trying to tinker with what’s already on the page?
AI: Now we’re getting to something that feels deeply important. The longing for that fluent generation of prose—that “effortless flow of words on a page”—isn’t just about productivity. It sounds like it’s connected to something more fundamental about how you experience your own thinking and creativity.
You’ve tried the time variable (two one-week sabbaticals), and it didn’t deliver the full fix. You’re wondering about structural clarity, about starting fresh versus tinkering.
Here’s what I’m curious about: When you have experienced that flow state in your writing—whether recently or in the past—what were the conditions? Not just the external logistics, but the internal state. What were you writing? How were you approaching it? What did it feel like in your body and mind?
And conversely, when you’re in the “tinkering” mode that feels stuck—what’s happening internally? What does that experience feel like?
Me: Yeah, I’ve thought about all that a lot, and it’s still not entirely clear to me. One obvious variable is that I went to grad school and got steeped in the norms and unnatural contortions of academic writing, which I feel like I’m still not fully recovered from. Another, more local variable is that I’ve been able to get into the flow more when I’m telling a personal story or reflecting on my own internal experience, which I guess is both obvious and somewhat limited in its scope… but I wonder if there’s a broader phenomenon I could tap into here, which is that I’m not second-guessing my own expertise or the accuracy and precision of my words as I go. In principle there’s no reason I must second-guess myself as I write even if I’m writing about something I might get wrong, since that’s what editing is for…. But this is where my scarcity mindset about my own time and cognitive resources does me in, because it pushes me to operate on a premise of “I’d better get this more-or-less right the first time, or I’ll have wasted my time / or I never will.” This rhymes with the scarcity mindset that used to kick in for me (and, ok, still sometimes does) when I meet new people I respect and admire: the feeling of “I need to make a good first impression / ‘seal the deal’ on the friendship now because the opportunity is fleeting and may never come again.” This came up when I was at the Progress Conference and then at Satori (an exclusive retreat with incredibly impressive people from across industries) this year. And I suppose it also makes me overly stingy and risk-averse with money (which I always jokingly blame on my immigrant upbringing, but I’m pretty sure the statute of limitations has expired on that one now that I’m 40!); so yeah, it’s pretty pervasive.
AI: This is a profound connection you’re making—and I want to make sure we don’t lose the thread of it. You’ve just identified what sounds like a core pattern that shows up across multiple domains of your life:
In writing: “I’d better get this right the first time, or I’ll have wasted my time/never will”
In relationships: “I need to seal the deal now because the opportunity is fleeting”
With money: Overly stingy and risk-averse
All of these seem rooted in the same scarcity mindset—a fundamental belief about the non-renewable nature of your resources: time, opportunities, money, cognitive capacity. This connects directly to your builder’s mindset framework. Builders operate from a fundamental conviction in their capability and value. Scarcity thinking undermines both—it makes you question whether you can aim higher and whether you should invest in what matters most.
So here’s what I want to ask: What would it look like to approach your book—and your coaching business, and those high-stakes connections—from a premise of abundance rather than scarcity?
Not in some woo-woo “manifest abundance” way, but concretely: What if your time, your opportunities, your cognitive resources actually were renewable? How would you approach the book differently? The business? Those relationships at Progress Conference and Satori?
Me: Yeah, for one thing I think they’re not only “renewable” but endlessly self-generative and compounding - as in, the more of these resources I “spend” (assuming I spend them on valued pursuits that constitute and sustain my chosen life), the more and better I produce.
As to what it would look like: with the book, it would mean leaning into the fact that this is a long-term project aimed at generational impact, and letting myself guiltlessly dive into research that interests me, free-write extensively without prior expectation of how much will make it into the book, throw out whole chapters and start fresh if the current versions don’t inspire me, etc.
With my coaching business, it would mean taking big swings that are likely to fail but would have extremely high upside if they succeeded (e.g., putting money into more aggressive experiments with this app; doubling or tripling my rates; spending a week in SF every month or 2; cold emailing the high-profile billionaire founders I most want to work with, and communicating my value unapologetically; etc). And with my own family, paradoxically, it would mean valuing my time with them more fully and disconnecting more guiltlessly when I’m with them, as my time with them - particularly with my kids qua kids - is my one truly non-renewable resource.
Snippet 2: The need for tighter feedback loops
AI: You’ve got concrete examples on both sides [of “abundance” and “scarcity” moments from 2025], and I notice something interesting: many of your abundance-minded moves happened in the relational/professional domain (asserting terms at [a conference], reaching out to impressive thinkers, holding clients accountable), while the scarcity mindset has been most stubborn in your writing process and in your presence with your kids.
Notice the pattern: Where abundance won, you trusted in your agency—the third core conviction of the builder’s mindset. You recognized that achieving what you wanted required chosen, deliberate work, but you trusted yourself to do that work.
Where scarcity won, you were operating from protection mode rather than building mode. You were trying to avoid loss (wasted pages, wasted time, lost revenue) instead of actively creating value.
What made abundance thinking easier or harder in different contexts?
What internal conditions or mindsets allowed you to access that confident, expansive energy? What thoughts or emotions were present for you in those moments that you didn’t experience in the more scarcity-driven ones, especially while working on your book or engaging with your kids?
Me: I think the main difference is that these moves come with quick, clear feedback loops: either I get a dm or email back within hours to days or I don’t; either the person is willing to talk to me or they’re not. Whereas the book has an extremely slow, delayed feedback loop, and it’s much harder to tell whether I’m on the right track, or to even keep the whole project in mind at any given point in time.
As to time with the kids, the feedback loop is immediate but it’s subtler and more ongoing, so the cost of any given moment spent distracted on Twitter doesn’t hit me as hard as a moment spent lost in thought during a conversation with Scott Alexander, say. That’s at least a large part of it, I think.
AI: [skipping gratuitous praise + summary] So here’s what I want to explore: What would make it possible for you to trust yourself in those slow-feedback, high-ambiguity domains the way you trust yourself in the quick-feedback ones? How do you create your own feedback loops when the natural ones are too distant?
This is actually core to your framework—builders don’t just respond to external feedback, they actively construct the conditions that allow them to build well. What would that look like here?
Me: I think what it would take is finding ways to keep the ultimate meaning and value of these activities—and the fact of their self-generating abundance— “on tap” for myself, even if it’s harder to see on short time horizons. For instance, when I sit down to write, I can conjure up the image of Kati Kariko working away in obscurity at U Penn for decades while delighting in each new mRNA-related discovery, or James Dyson eagerly iterating toward a commercially viable model of his bagless vacuum cleaner for something like 8 years without external recognition (because he understood that it would revolutionize the industry once he got it right). And I can explicitly identify what I’ve learned from each writing session (even if it’s just “that example is less compelling than I thought,” or “this point is going to stretch across several chapters instead of just one”), and see the fundamental likeliness between my process and theirs.
AI: [skipping fluffy praise] You’re describing a way to create your own feedback loop—not by waiting for external validation, but by actively recognizing the value generated in each session.
Let me ask: Have you been doing this consistently? Or is this more of an aspiration—something you know would work but haven’t yet turned into a regular practice?
And if it’s the latter: What would it take to make this your default mode when you sit down to write? What’s the barrier?
Me: I have not! And I’m excited to start. The barrier was simply that I hadn’t asked myself these questions explicitly yet (so thank you!). As to what it will take, I’m going to select a few key quotes and a self-prompt for myself, and I’m either going to print them and attach them to my monitor, or put them in a daily reminder that goes off every time I sit down to write (or both). As to remembering to be more present for my kids, I need to come up with a good mantra or mental image with which to really zap myself into awareness on this point (will think on this a bit), but I’m confident I can think of something.
Snippet #3: “Remembering what I know”
AI: [So] what feels like the core insight or shift you want to capture?
What’s the throughline that connects all of this?
Me: One clear throughline is that I need (and want!) to double down on my own mantra of “remembering what I know”, with all that it implies: I know I’m saying something new and important enough in this book to be worth another 1-2 years of effort and 1-2 million discarded draft pages to get right; I know my kids will only be this young and adorable once; I know, as Matt pointedly reminded me in his “happy 40th birthday” letter, that I’ve “already—in literally every important respect, and in ways that are, if not quite unprecedented, at the very least novel and rare—completely, totally, and irrevocably won at life.” And I know I have many decades left in which to relish and further compound those winnings.
I know these things, not on faith or as some sort of cope, but as hard-won wisdom, chiseled over years of iterative study and action and painstaking self-correction and philosophical-psychological synthesis. But though that wisdom is hard-won, it is not yet fully hardened: it takes work to feel and embody it on demand, and to protect it from the deforming influence of older, more scarcity-shaped narratives.
What kind of work? Some of it falls under the heading of “explicit psychological hacks,” like conjuring up images of people like Kariko and Dyson, naming what I’ve learned in each writing session, or using tools like the “life map” [now available as online tool built by Karel Vuong] to envision my life over longer timeframes than is my default.
But most of it is “building myself by building”: e.g., by learning and retelling the stories of wide-ranging builders whose lives exemplified this wisdom (as I’m already doing on Substack and for the book); by helping others accrue the same wisdom in the context of their particular lives (as I’m already doing for my therapy/coaching clients and my kids); by acting opposite to my own scarcity-driven fears, long enough and often enough for the fear-disconfirming evidence to sink in (as I’m already doing when I hold my clients accountable, free-write drafts I will likely discard, or put away work to be with my kids).
So I guess the through-line is: I’m already living as a builder, now let me really remember and own (and relish!) that fact.
Happy New Year, dear readers, and may you savor all the abundance already within your reach as you look ahead to 2026.
I’m currently piloting the app with just a few beta testers at a time, but leave a comment or DM with your preferred email address if you’d like to join the waitlist. Paid subscribers get priority access.
Quite impressive. I can see hints of the GPT (or other) personality coming through, but you’ve clearly added a very useful layer on top. Is it just prompt based or did you do some fine tuning?
Also, happy new year!
Hi, I would love to get on the waitlist.