safety: the bad outcome can’t hurt me while i’m here.

reassurance: [x] says the outcome will turn out fine. i trust them and feel better now.

self-assurance: i trust myself and my process, so regardless of this outcome— good or bad— i know the dots will eventually connect. i’ll be okay.

For most of my life I’ve been skeptical of people who are deeply self-assured. These people just… go for it? Undaunted by guilt, shame, or fear? Without overthinking downside risk or hating themselves when things don’t work out?

Totally bizarre. Probably illegal.

The thing is… over the past couple of years I’ve become one of those people. And despite not intending to join their ranks, now that I’m here I’ve never felt more alive. I’m still pretty new at this whole thing, but already I wish I’d gotten here sooner.

If I could give my younger self one piece of personal advice without creating a time travel paradox it would be this:

You are going to figure out how to become the central source of reassurance in your own life. It’s going to turn out incredible. Way, way better than you imagine. Developing self-assurance is part of the main questline, but in the process you’ll unlock powerful branches in a ton of OP skill trees like rizz, courage, emotional regulation, and luck.

Turns out the belief you have to viciously criticize yourself to achieve greatness and avoid turning into a self-centered narcissist isn’t true. It also turns out raw intellect that overrules feelings and physical cues isn’t as honest as you think it is.

I’m not saying you need to abandon worldly desire and turn into a monk: it’s fine for your reassurance system to include social status, Salt & Straw, romantic partners, etc. You’ll figure out a healthy balance that works for you.

What I am saying is this:

If self-trust and affection isn’t the central source of reassurance in your life, when the chips are down you’ll be willing to betray yourself to keep the system from falling apart.

That’s the fatal flaw.

If you rely on your social circle, significant other, high-status job/school, or spiritual community for reassurance more than yourself, then betraying yourself when you’re afraid of losing them is always on the table. And even when you aren’t actively betraying yourself, the knowledge that you’d be willing to is a leaky toxic waste drum of anxiety. It’s a blueprint for living a life full of regrets.

If you had asked me a few years ago I would have said this worldview was self-centered. Now I believe the alternatives are dishonest and fragile.

To genuinely show up for others as your best self, you’ve got to be fundamentally unwilling to betray yourself. That’s the heart of it.

On its face this may sound stupidly simple. Have you considered trusting yourself more?

The thing is, becoming self-assured isn’t actually a test of intelligence. It took me an excruciatingly long time to figure that out. The hard part is letting go of your personal resistance to accepting trust and affection from yourself.

The why of your resistance is unique to you. Maybe you think liking yourself is cringe. Maybe you believe self-hatred is the only way to avoid becoming complacent and instead live up to your ambition. Maybe you’ve been hurt in the past and think exhaustive threat analysis and mistrust will keep you from being blind-sided by that pain ever again.

Whatever the lore, it boils down to this: if you secretly believe you don’t deserve self-assurance or fear that being kind to yourself will get you hurt, then self-assurance will stay out of reach until you change your mind.

No exceptions.

My journey to self-assurance basically followed these steps:

(1) Get sick and tired of the results of trusting your voice of inner doubt. Become skeptical of how honest and accurate it actually is. Decide you have no idea what’s next but refuse to tolerate this pattern repeating.

(2) Cast a wide net for guidance on how to change: friends, books, therapy, internet strangers, reality tv, anime, content creators. Begin to notice a pattern of people you vibe with regretting the unexpected costs of being unkind to themselves.

(3) Pour energy into visualizing a more self-assured version of yourself and pay close attention to why it feels so hard. Where is the resistance coming from? Why do you roll your eyes at the idea of giving yourself trust and affection?

(4) Commit to pay the cost of uncomfortable, vulnerable, possibly cringe inner work to retool your identity and dissolve resistance at its source. None of your beliefs are off limits.

(5) Accept you can’t logic your way into self-assurance: it’s an emotional state of being, and getting there requires feeling your feels without intellectualizing them.

(6) Get out of your head and take action to build self-trust: its bedrock is competence and keeping promises to yourself.

(7) ADVENTURE

(8) Write down your learnings

For the longest time I had no idea how to visualize what “self-assured me” would even look like. I felt too skeptical, too anxious, and too humble to be self-assured. I wanted to picture it but the process felt like drawing a boardwalk caricature. Ridiculous.

Still, I kept at it: refusal to continue with the old pattern, right?

I couldn’t make out a full picture, but I figured maybe I could try to get more comfortable with affection on one day, and tackle trust another? Maybe I should try to do an ambitious project without using terror of failure as my motivation? I tried all that and more. Progress was gradual, but one day it felt a little less impossible. I stacked a few more days after that, and then weeks, and then months.

Self-assurance is really a feeling more than anything: when you face a stressful situation, it’s cool clarity that you’ll make things work no matter how the chips fall.

No eye-rolling, no panic, no arrogance: just calm, steady trust that you can handle whatever comes, and that you’ll never betray your heart.

That’s the vision.

Vibe Pairings

1. Uncle Iroh counsels a conflicted Avatar about making an impossible choice. Sometimes it’s okay to make a move without really knowing where it leads.

2. The “It gets easier” scene from Bojack Horseman. Honestly one of the darkest, most hilarious, and deeply affecting shows I’ve ever seen. I doubt I’ll ever watch it again, but that first time was unforgettable.

3. The Steve Jobs commencement speech is a video I often end up rewatching when I’m in an uncertain season of life. His perspective about connecting the seemingly random dots of your life resonates so deeply with me.

4. The Mountain is You went viral on BookTok awhile back and is one of the most poignant and persuasive explorations of analysis paralysis and self-sabotage that I’ve ever read. 10/10.

Advice is overrated!1

Well, mostly— and maybe not for the reasons you’d think.

I take great joy in helping people I vibe with navigate difficult decisions: it’s one of my core personality traits. In personal and professional life I’ve often been told I’m great at giving advice, which for a long time slightly puzzled me because as a general matter…

…I genuinely try not to give advice at all.

At some point I realized what the disconnect was— how I’m allegedly good at something I don’t believe I’m doing— and that’s the inspiration for this post.

The short of it is that IMO helping people frame trade-offs and narratives can be incredibly valuable, while prescriptions and roadmaps almost never stick— despite how much people want them.

The most important reason (among many) is simple: in my experience, people voluntarily change only if they refuse to continue existing as they have been, and the decision to say “yeah, I’m done with this” usually hinges on a personal narrative that only they can fully know and control.

Motivation is a good first step but a squishy foundation. Refusal is rock solid.

For example, the single greatest fitness breakthrough I ever had happened in the aftermath of a tough pick-up game. I reached the limits of my patience for having an unreliable jump shot when playing basketball (which I love!) and decided to lift weights (which I do not!) as a means to stop falling off so hard as games progressed.

I had previously been on a never-ending quest of trying to find the “right” type of workout or program that didn’t feel like drudgery and found results to be inconsistent at best.

Weightlifting changed from a story of “hey! do this or get fat!” to “shooters can’t shoot if their arms turn to rubber after 20 minutes” and that made all the difference.

—

I don’t remember the exact moment when I realized virtually all classic advice has a completely contradictory counterpart and both are regularly given with a straight face, but it’s one of those things where once you notice it becomes impossible to ignore.

“never give up”

vs.

“know when to cut your losses”

“if it’s not a hell yes, it’s a no”

vs.

“get out of your comfort zone”

“an ounce of prevention is worth a pound of cure”

vs.

“just do it”

???

One-size-fits-all solutions don’t work with any consistency, yet there is so much demand for them even though good decision-making is mostly in the tailoring.

Advice is often treated like a recipe: follow these instructions and voilà, you’ll get a good outcome! Coat in flour before adding to the mix. You should move to the big city. You shouldn’t give your ex a second chance.

Personally, I believe in counsel rather than advice.

That may sound nitpicky, but I think there’s a meaningful difference— or at the very least that “advice” is an umbrella term with such strong connotations of “tell others what they should do” it’s worthwhile to embrace a narrower term that explicitly rejects that approach.

For me, counsel is about helping people map the space around the decision they’re confronting and ultimately make their own call in harmony with their preferences (not mine!) and overarching narrative.

No recipes!

At core, I focus on three specific things when offering counsel to someone important to me:

(1) Trade-Off Framing

(2) Story Framing

(3) Camaraderie

—

Trade-Off Framing

At the root of any meaningful decision is some sort of trade-off. The advice-seeker has an opportunity to gain a benefit, but doing so requires either giving up something they value or weathering pain and discomfort.

Closing doors and losing things we value feels really bad— literally irrationally so. Biases like loss aversion (humans generally value not losing a dollar at least 2x more than winning one) are crushingly influential but tough to self-diagnose when we’re in the trenches.

I’ve personally experienced and observed people I care about getting stuck in a doom loop that goes a little something like this:

• Feel excited/anxious by the potential upside of a decision (I should start a YouTube channel!)

• Consider the costs and hate them: feel fearful or dejected about how things could go wrong (What if it sucks? What will my friends and the Internet say?)

• Recoil and push off making the decision

• Feel guilty/dissatisfied about not achieving the upside, think maybe it’s time to reconsider

• 🔁

Helping people you care for map out the costs and benefits of a decision doesn’t mean prescribing a specific course of action. Yet it’s consistently one of the most influential gifts I’ve received from people I’ve reached out to for guidance. It’s also what people I care for consistently identify as among my best pieces of advice… even though they ultimately come to the conclusion themselves.

Framing trade-offs might sound robotic, but done with empathy it can actually serve a very personal purpose. It leverages two of your most valuable traits (trust from the person asking for your take + having dispassionate perspective) to help them cut through the stories in their head (more on that shortly) to really boil it down to outcomes.

Ideally, anyways.

Oftentimes, a tough decision distills to whether the person is willing to tolerate the cost of making a change. If not, the decision is kinda clear. If so, the decision is… also kinda clear.

The hard part in these cases isn’t actually the decision— deep down the advice-seeker already know what they want to do— it’s making peace with the cost they’ll have to pay, including closing the door on alternate paths.

I’m reminded of this banger from Tim Urban:

It sometimes turns out that the person you care for has locked themselves into a false binary choice and lost perspective on possible alternatives, compromises, or positive externalities. Gently helping them widen their focus can be incredibly helpful.

The nice thing about trade-offs is that they’re often pretty straightforward to outline— so naturally the next step is getting into the messy, ephemeral, and subjective.

—

Story Framing

Most of us live our lives telling stories in our heads to explain what’s happening around us, and those stories generally have a loose relationship with reality.

Have you ever felt furious about something? Grievously insulted or hurt by a thing that someone close to you did, how could they, how is this even possible, the audacity…

…and then you ate a snack?

Then felt totally calm again, and forgot what you were mad about?

Some questions to consider: Were you actually seriously wronged? Was the origin of your rage the hunger, or did eating just shore up your ability to manage the situation?

It’s jarring to realize how malleable our reality is, and how much agency we have over the narratives that define it for us. This cuts both ways. Some people can harness their narrative and become delusionally optimistic, while others end up crushed by pessimism and can’t help but want that for others as well: both are rooted in stories.

A simple example: when I was in middle school I was relentlessly bullied by a group of jocks on the football team. In high school I prided myself on not watching the NFL and took every opportunity to let people mentioning football around me know that it sucked. I had an endless stream of reasons for why the sport was bad, the NBA was superior, etc. etc.

I’m not sure any logical argument could have swayed me out of hating football.

I went to the University of Michigan for college and was legitimately unaware that the school had a football program when I got to campus.2 During Welcome Week all my new friends kept hyping up their excitement for the season, so out of a sense of affectionate curiosity I bought a ticket from a guy outside the stadium and showed up for the season opener with low expectations.

Turns out my ticket was for a seat in the middle of a twenty-person seating group of long-time friends in grad school. They instantly noticed I was not one of them, but found it both endearing and hilarious that I had no idea how football worked or that Michigan even had a team when I applied. They adopted me as their mascot for the day: stress-testing my eardrums while teaching me the fight song, explaining the rules when they weren’t pounding on cowbells, joyfully chest-slamming me after touchdowns. At the end of the game they said they were jealous I was going to experience 4 more years of this and wished me the best with hugs and fist-bumps.

After that day I became the most hardcore college football fan I knew and didn’t miss attending a home game for the rest of college. I organized watch parties. I memorized the roster. I observed elaborate gameday rituals to ensure I didn’t jinx the team.

My high school friends and parents were deeply bemused by this 180 turnaround and asked me about it over the holiday break.

The answer was simple of course: yes I had a great first Saturday afternoon, but more importantly the story of football changed from the clubhouse of my tormentors to the inclusive cathedral of my college experience. My behavior and relationship with the sport changed with it. It’s that simple… although at the time I would have fervently denied that my middle school bullies were still living rent free in my head years later. I wasn’t ready to tackle that particular story just yet.

One thing I keep in mind when talking to people is that the story unfolding in their head about the same set of facts is likely different from mine and almost certainly colored by all kinds of dynamics I couldn’t possibly grasp given that I don’t know their life story: chips on shoulders from ancient slights, self-preservation mechanics to cope with deep wounds, a need to be the main character and hero of the story, etc.

Any gamer that’s ever seen an 0-10 teammate ranting about how their teams are the reason they’re not winning more ranked games knows that the human capacity for storytelling is limitless.

Oftentimes mapping trade-offs reveals narratives because an advice-seeker will look at the list of pros and cons, realize that on paper the decision should be clear, then find themselves struggling to make it. This triggers surprise but also recognition that there are likely other factors at play that aren’t reflected in their conscious preferences.

Changing stories and narratives is incredibly difficult in my experience, but becoming aware of them and their influence is more achievable and an important step. From there change is up to the advice-seeker, but having a map of the battlefield is a lot better than operating blind.

Offering perspective (particularly by asking good faith, non-leading questions) to set them up to understand and take control of their own narratives is in my experience a powerful outcome of taking a counsel approach rather than going for straight advice.

That may sound like advice but uh it definitely isn’t.

—

Camaraderie

Sometimes what you need most is to hear that people you identify with have struggled with similar situations, even if the terrain and season of their battle was completely different. Not feeling like the only person you know that’s gone through something is such a relief.

A sense of belonging is one of the most memorable gifts we can ever receive.

I can’t count how many times I’ve felt like a failure (story!) then heard someone I identify with say they’ve gone through something similar and immediately felt better. Time and time again I’ve found other people sharing their wins and losses to be incredibly powerful not because they offer a blueprint on what to do next but because they help me re-frame the story in my head in a way that feels honest but also heartening to me.

That said, the best can do both: offer perspectives that are easy to mine for lessons and tactics while also making you feel seen:

My attention span isn’t hopelessly broken, I need to better manage the instant gratification monkey.

Listening to my emotions doesn’t have to be incompatible with my analytical personality— they can complement each other, actually?

I’m not drifting aimlessly, I’m collecting dots that are going to connect later

I’m not a failure, I missed my first shot on goal. It’s on to the next.

And above all: I’m not alone in this.

These might sound like platitudes in a vacuum, but in context they’re everything.

After all, good advice is all in the tailoring.

—

Vibe Pairings

1. Uncle Iroh teaches a mugger how to step up his game. One of my favorite scenes from one of the best episodes of Avatar: The Last Airbender.
   

2. The famous Rick Rubin interview where the interviewer’s brain melts as he tries to make sense of how Rubin— a legendary producer— delivers value to musicians as an advisor when he claims to have no musical ability whatsoever. Never fails to make me smile.

3. This pep talk from S2, E7 of The Bear. It’s my favorite show of 2023, and the character arc of Richie— a stubborn jerk who embraces bravado as a self-defense mechanism but inwardly wants more for himself— is done unbelievably well.

This project— The Aileron— is the perspective I wish I had access to when I first got serious about looking inwards, asking myself the big questions, and taking ownership over the arc of my life.

Who am I?

Growing up I was the classic bookish kid who was laser-focused on soaking up reassurance from academic and extracurricular achievement since I had no idea how to generate it from within.

One day halfway through law school I realized I had made a terrible mistake optimizing for stability and status when what I actually cared about was doing work that was meaningful to me. Unfortunately, at the time I wasn’t sure what to do with that realization other than feel paralyzed by dread.

I graduated the next year then promptly emptied my savings to move to San Francisco, deciding I had to give myself six months to try and break into tech and gaming. If I failed, I’d go back to the law but at least have peace of mind that I’d had the courage to shoot my shot rather than wondering ‘what if?’ for the rest of my life.

At the end of the six months (during which time I met so many incredible and generous people— I’ll always have a soft spot for the Bay Area) I failed to break in, accepted my fate, and started studying for the bar. Dream extinguished.

Although… not entirely.

As a final act of quiet rebellion I started a blog about competitive gaming, a topic close to my heart. I couldn’t work in games, I reasoned, but perhaps I could at least write about them for fun as I resumed marching down a path I knew was wrong for me.

It seemed a silly, tiny gesture at the time, but not giving up on the last ember of my dream was one of the braver (and ultimately most important) things I’ve ever done.

I can promise you it didn’t feel like it at the time, though: I had no expectations for what was going to happen next.

My first essay got retweeted by the CEO of Riot Games.

The second front-paged r/leagueoflegends and got me an email from my webhost suggesting I may be getting DDoS’d.

The third got me an invitation from ESPN to write a full-length feature on the esports industry.

The site spiraled upwards from there, and soon the bar exam was an afterthought.

I'll never forget getting an email from a Riot recruiter asking if I'd perhaps be interested in flying out to Los Angeles, CA to visit Riot Games HQ re: a role on the team building esports for League of Legends?

?

The rest is history (stories for another time!) and every day since then has been a gift.

Once I figured out the professional side of my life, it was on to the personal. That’s a longer story, but suffice it to say I live a life of calm confidence these days, which is a far cry from where I was even a few years ago.

I’ve still got a long way to go to reach my vision, but as I continue learning I’d love to help people that can relate to my content gather momentum on their own journeys.

Why’s it called The Aileron?

Simple: I like the name!

• Ailerons are flight control surfaces that allow aircraft to balance and change direction, but (at least to me) work in a fascinating and somewhat unintuitive way.

• I love air travel and have spent a decent chunk of my life in the sky.

• Fighter jets are awesome and I adore them with childlike enthusiasm.

• After a harsh life setback some time ago I felt aimless and unsure about when I would find a sense of purpose again. One night while scrolling aimlessly in bed I came across an MIT lecture about F-22 flight controls on YouTube. For reasons I can’t fully explain— perhaps the sheer competence of the lecturer, or the engineering marvel of the most formidable air-to-air fighter in history, or maybe just the healing properties of hearing my inner six-year-old yelling SO COOOOOL!!!! for an hour straight— watching that video reignited my sense of joyful living and nudged me back on track. One of the most important things I did in the weeks following that night was decide I wanted to create this project.

What are vibe pairings?

My brain works heavily by association. Writing is a medium I love, but a lot of times the vibe of a piece can heighten or contrast beautifully with other types of media.

Life is about making decisions and taking action true to who we want to be.

I wish us luck getting better at both!

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