WILD BARE THOUGHTS hit an incredibly cool milestone over the weekend and reached 10,000 monthly readers. Thanks to everyone who reads with me and supports my work, it truly means the world to me.
If you’re a reader who is also getting started on your own writing journey, I put together a list of the things I’ve learned, what I’d do again, and my 9 biggest takeaways from the last year of publishing on Substack.
Thanks for being here. x
THERE’S NO DISCOMFORT quite like the kind that arrives when you stumble across your old writing, your old arguments, your old certainties. That full-body recoil when you encounter the person you used to be, speaking with such confidence about things you now know were incomplete at best, embarrassingly wrong at worst.
We have a word for this feeling: cringe.
Most people treat it like a problem to be avoided or a sign that something went wrong. But what if the cringe is actually telling you something important? What if the absence of that discomfort is the real warning sign?
If you can look back at who you were three years ago and feel nothing but comfortable recognition, you’ve stopped moving. The absence of embarrassment is not evidence of wisdom. It’s evidence of stagnation we’ve been calling consistency.
THINK OF YOUR PAST SELVES as geological layers, each one representing a complete worldview that felt seamless and sufficient at the time. When you excavate downward through these strata, you’re not just finding old opinions; you’re finding entire architectures of thought that once seemed load-bearing and permanent.
The cringe you feel is the gap between those architectures. It’s the measure of distance traveled. If the gap is narrow, you’ve been walking in place. If it’s wide enough to make you wince, congratulations—you’ve actually moved.
This is counterintuitive because we’re taught to value consistency. We praise people who “stick to their guns” and “stay true to their values.” There’s real social currency in being the same person you’ve always been because it signals reliability, integrity, trustworthiness. And there’s something legitimate there, but we need to be precise about what actually deserves consistency and what doesn’t.
Because here’s where most people get confused, and it’s a confusion that can paralyze you: they conflate values with beliefs, treating them as if they’re the same kind of thing, subject to the same rules. But they’re not even close.
VALUES ARE THE “WHY”—they’re your commitments about what matters, what’s worth protecting, what kind of person you want to be. Things like: intellectual honesty matters, human flourishing matters, truth-seeking matters, reducing suffering matters. These can evolve, but they should be resistant to change because they’re load-bearing. They’re the foundation you build on.
Beliefs are the “what”—they’re your best current understanding of how reality actually works. These should be constantly updating as you encounter new information. They’re the scaffolding, not the foundation.
The cringe should come from recognizing your old beliefs were incomplete or wrong, not from discovering your values were misguided. If your core values are flipping every few years, that’s not growth. That’s drift. That’s someone who never committed to anything deeply enough to let it actually guide them.
The person who maintains stable values while radically updating their beliefs isn’t contradicting themselves. They’re doing exactly what integrity requires: staying true to what matters while refusing to pretend they know more than they do.
But here’s where it gets genuinely tricky, and this is the part that requires real discernment: sometimes what looks like a value change is actually a belief change that reveals you were confused about what your values required.
Take this example: You might genuinely value human autonomy, deeply and consistently. That value doesn’t shift. But your beliefs about what policies or structures actually promote autonomy could shift dramatically as you learn more about psychology, economics, systems theory, the ways power actually operates in complex societies, etc. From the outside, this might look like you’ve “changed your values” because your positions have changed. You used to support X policy and now you oppose it. But the value stayed constant. Only your understanding of how to honor it evolved.
This is the distinction most people miss. They see someone change their political positions and assume they’ve abandoned their principles. Sometimes that’s true. But often they’ve just gotten better at understanding what their principles actually demand once you factor in how the world really works rather than how you wished it worked.
NOW, HAVING MADE THAT distinction, we need to acknowledge that values themselves aren’t completely immune to revision. They’re resistant to change, but not infinitely so. There are legitimate reasons a foundational value might shift.
The first is that you might discover a value was never really yours to begin with. It was inherited, absorbed from your culture or family or peer group, adopted before you had the capacity to examine whether it actually resonated with who you are. In this case, the “change” is really a clarification. You’re not betraying yourself; you’re discovering yourself.
The second is that sometimes life experience reveals dimensions of reality you simply couldn’t have understood earlier. Suffering changes people. Parenthood changes people. Confronting mortality changes people. These aren’t just belief updates—they’re shifts in what you viscerally understand about what matters. A value like “individual achievement matters most” might genuinely transform into “connection and legacy matter most” not because you’ve been fickle, but because your frame of reference expanded.
The third is that occasionally, rarely, you might discover through rigorous thought that a value you held contradicts another value you hold more deeply, and something has to give. This should be agonizing. If it’s easy, you probably weren’t really committed to the value you’re abandoning.
The key test is this: value change should feel like loss, even when it’s necessary. Belief change should feel like relief.
I try to interrogate my own beliefs often—to pause and ask whether I’m still acting in alignment with my values or just repeating something that used to feel true. It’s the only way I know to keep the scaffolding honest.
I built THE DAILY 5 framework around that exact habit. Just five minutes a day to check in with myself on what I’m building, what I’m protecting, and what I might be defending out of ego rather than integrity.
WITH THAT FOUNDATION LAID, we can now see the real trap more clearly. The problem isn’t that people change their values too readily. The problem is that they confuse beliefs with values and then protect their beliefs with the same fierce loyalty they should reserve for values.
This creates a perverse situation. We live in an age of personal branding where your social media presence becomes a kind of ongoing performance of identity, and that performance demands coherence. You can’t be one thing on Tuesday and a different thing on Thursday because the algorithm doesn’t reward that kind of messiness. Your audience came for a specific flavor of you, and deviation looks like instability.
So people lock down their beliefs, treating every take as if it were a sacred commitment, because admitting you were wrong about anything seems like admitting you’re unreliable about everything.
“Staying on brand” becomes just stagnation with a marketing strategy.
PART OF WHAT KEEPS US trapped in palatability is a fundamental misunderstanding about how much other people are actually paying attention. We imagine our transformations are being closely monitored, cataloged, judged. Every change of mind feels like it’s being recorded in some permanent ledger of our inconsistencies.
But the reality is, most people are so consumed with managing their own contradictions, navigating their own embarrassments, and maintaining their own brands that they have remarkably little bandwidth for tracking yours. The detailed inventory of all your ideological pivots exists primarily in your own head.
This is both liberating and humbling. It means you have far more freedom to evolve than you think, but it also means your careful performance of consistency is largely wasted effort. You’re trying to maintain coherence for an audience that isn’t watching as closely as you fear.
The few people who are paying close attention fall into two categories. First, there are those who are genuinely interested in ideas and will respect the honesty of evolution. These people are looking for thinkers, not monuments. They understand the difference between updating your beliefs and abandoning your values. Second, there are those who are actively hostile and will weaponize any inconsistency they can find—but these people will attack you regardless, and trying to appear invulnerable to them is a fool’s errand.
When you really internalize this asymmetry, it changes the calculation entirely. The cost of staying palatable is paid in the currency of your own development. The cost of allowing yourself to be cringe is paid mostly in imaginary social penalties that never actually materialize.
LET’S TALK ABOUT WHAT growth actually looks like in practice, because it’s never the smooth upward trajectory we imagine. Real learning doesn’t move in a straight line from ignorance to mastery. It moves through phases of confident incompetence that look, from the outside and in retrospect, deeply embarrassing.
Think about any domain where you’ve developed real understanding. In the beginning, you’re consciously incompetent—you know you’re bad, and that knowledge protects you from overconfidence. But there’s a phase that comes after initial learning where you’ve acquired just enough fluency to have opinions, just enough vocabulary to sound knowledgeable, but nowhere near enough depth to understand the limits of your understanding.
This is the cringe zone. This is where you write confidently about things you half-understand. Where you make grand pronouncements that ignore crucial nuances. Where you think you’ve solved problems that have stumped serious thinkers for centuries because you’ve just discovered them and haven’t yet learned why they’re hard.
Every single person who has ever gotten good at anything has passed through this zone. It’s not optional. You cannot iterate toward competence without first producing incompetent iterations. The bad writing comes before the good writing. The shallow thinking comes before the deep thinking. The cringe comes before the credibility.
This applies beyond skill acquisition to belief formation. You cannot think yourself into accurate views of complex topics without first holding inaccurate views. The person who’s afraid to have a wrong opinion never gets to have a right one either—they’re stuck in the paralysis of studied neutrality, which is just another form of not-thinking dressed up as wisdom.
But here’s what’s crucial: this process doesn’t threaten your values at all. Your commitment to truth-seeking remains intact while your specific beliefs about truth get refined. Your dedication to reducing suffering doesn’t waver even as your models of what causes suffering get more sophisticated. The foundation holds while the scaffolding gets rebuilt.
THERE’S SOMETHING WE DON’T talk about nearly enough: real change requires a kind of violence against your former self. Not gentle evolution, not subtle refinement, but the active killing of the person you used to be.
This sounds dramatic, but it’s descriptively accurate. When you fundamentally revise your understanding of something important, you’re not just adding new information to an existing framework. You’re demolishing the framework and building a different one. The old structure has to be destroyed. The person who believed that thing, who organized their thinking around it—that person has to die.
And we mourn this, even when we know it’s necessary. Even when the new framework is clearly better, more accurate, more sophisticated. There’s grief in transformation because you’re losing something real—the security of your old certainties, the comfort of your old patterns, the version of yourself who thought they had it figured out.
This is why growth is never fully comfortable. It’s not supposed to be. If transformation felt natural and easy, it wouldn’t be transformation—it would just be expansion. When you’re actually changing in deep ways, some part of you is always resisting, always trying to maintain what was. The cringe you feel when looking back is the emotional aftermath of that violence.
But notice what’s being destroyed and what persists. Your old beliefs about how the economy works get demolished. Your old certainty about which policies would help gets shattered. Your old confidence that you understood the problem gets replaced with humility about its complexity. All of that dies, and it should.
But your values—your commitment to human flourishing, to intellectual honesty, to reducing suffering—those don’t die. They’re what motivate the destruction. You’re killing your old beliefs because you’re loyal to your values, because you care more about getting it right than about looking like you always had it right.
The cringe is the scar tissue. It marks where the old belief system ended and the new one began. But the foundation underneath remained solid.
NOW LET’S EXAMINE WHAT gets traded away when we choose palatability over transformation, because the costs are higher and subtler than they first appear.
The most obvious loss is intellectual growth—we’ve covered that. But there are second-order effects that matter just as much. When you optimize for never looking foolish, you necessarily optimize for never exploring territory where foolishness is likely. This means the most interesting, most uncertain, most genuinely novel ideas become inaccessible to you. You can only think thoughts that you’re confident you can defend.
