Please Stop Inspiring Me

Am I the only one who finds"how I built this" stories unbearable?

Somebody once asked me how I choose what to write about on this blog.
The truth is I only write about things I can’t stop thinking about.

This revelation may be obvious or unsatisfying to hear.
But let’s be honest — intense feelings probably drive your life, too.
No one ever did anything great out of ambivalence.

I’m sharing this because, after joining the chorus of voices praising Sinners, I feel the need to balance it out with an equally passionate dissent.

I officially hate “How I Built This” stories (hereafter, HIBT).

HIBT is a genre of content that unpacks how how now-famous people — celebrities, founders, artists — got where they are and did all the things they’re famous for.

It shows up everywhere: in books, magazine articles, YouTube videos, and podcast interviews. It’s cute, comforting, and devourable — like chicken nuggets for capitalists.

It’s a genre born of the 2010s: the startup boom years, when every hobby needed a revenue stream and every white man was given a podcast.

NPR launched their flagship podcast How I Built This in 2016, which has since spawned a 2020 book and a summit at the Yerba Buena Center for the Arts.

Clearly some people can’t get enough of these motivational deep-dives, the cute anecdotes, heartfelt insights, and counterintuitive takeaways.

I can’t stand them anymore.

My aversion runs so deep I sneak it into unrelated blog posts.

Exhibit A: I opened my review of Conclave by noting that:

How I built this stories feel like maps to treasure that’s already been plundered, a parade of victory laps when I’m just trying to lace up my shoes, blueprints for cathedrals when I’m out here pitching a tent in the rain.

Clearly, something is wrong with me, this genre, or both.

HIBT stories are popular because they promise to democratize success — teaching people how to succeed by reverse-engineering the lives, decisions, and insights of exceptional individuals.

But in reality, they often glamorize improbable outliers while ignoring the role of privilege, timing, and access.

The real reason that I hate them is that these stories don’t just trigger ambition — they trigger comparison. And comparison is a hell of a drug.

Unhelpful Insights Galore

Success is notoriously tricky to describe — especially in ways that are both accurate and compelling.

HIBT stories often offer insights that are as shiny as they are useless thanks to a blinding mix of survivorship bias, hindsight, and our cultural obsession with lone geniuses.

Sara Blakely famously maxed out her credit cards to fund Spanx — a bold gamble that made her the world’s first self-made female billionaire. But it’s a classic founder myth: empowering on the surface, nearly impossible (and inadvisable) to replicate.

Brian Chesky calls Airbnb’s early years a financial near-death experience. They had no revenue, no investors, and survived by selling novelty cereal boxes. It’s great podcast material — but in reality, most founders who go that long without revenue don’t build billion-dollar platforms. They just fold.

Howard Schultz traces Starbucks back to a passion for Italian espresso bars and the idea of a “third place.” While he mentions being rejected by over 200 investors, the emotional spotlight stays on conviction, not capital. The $3.8 million he eventually raised gets a brief mention — but without it, no scale-up story exists. Passion makes a great headline. Access makes a great company.

Zooming out, this genre has a knowledge problem: it makes success look clear and linear — but this clarity is only visible in hindsight. The lessons these stories offer — tidy, crystallized epiphanies — only make sense looking backward. When you’re in the middle of your own mess, they can feel more confusing than clarifying.

As I covered at length in my review of Tim Ferriss’s bizarre and short-lived TV show, this material often comes across as weirdly self-congratulatory and completely unrelatable.

As I wrote then:

The conundrum of being a rich and famous person with an iconic personal brand like Tim Ferriss or Oprah is that when you try to proselytize about learning your approach it’s hard for the rest of us to separate how much of your success is attributable to your method, your wealth, or other contextual or intangible factors that aren’t actually transferrable or teachable. I left this “extreme learning” show with the same question his books and podcasts left me with: how much of being as successful as Tim Ferriss is even learnable?

If you’re after entertainment or armchair motivation, this content is fine. But as education, it falls apart.

After all, so much of this advice isn’t really instruction — it’s myth-making. And the myth always starts with someone who already won. These stories can inadvertently cause harm, not because they’re false, but because of how they’re framed: I did it, so can you.

The Benny Blanco Conundrum

A few months ago, Instagram started feeding me a conveyor belt of clips about superstar producer Benny Blanco. In each one, he breaks down how he came up with the hooks, beats, and melodies behind some of the biggest songs of the past 15 years — like Kesha’s Tik Tok, Katy Perry’s Teenage Dream, and Rihanna’s Diamonds.

Each story is charming and maddening. In one clip, Blanco shares that many of his songs are at 120 beats per minute simply because that’s the default setting in ProTools, and he didn’t realize you could change it. In another, he admits he landed on the melody for California Gurls after showing up late and messing around with some old synth sounds. No master plan, no decade of theory — just vibes and timing.

He presents himself as a lovable goofball who just happened to fall upward into pop history. But for anyone trying to build a career through deliberate effort or break into this industry— it’s mildly infuriating. You’re left wondering: is he a genius playing dumb, or is success in creative industries genuinely this chaotic?

Blanco’s anecdotes fall into a familiar pattern in founder and creator interviews: the accidental savant. He epitomizes why the “I didn’t know what I was doing” narrative is so common; it’s a clever way to sound humble while still building your brand. Maybe Blanco adopts this affable “stumbled into success” tone because it’s palatable or maybe this is just how he talks. But most of us can’t — and won’t — get where he went or where we want to go by stumbling.
And even if we do, this isn’t a strategy or a repeatable formula.

Behold the Descendants of Vanished Kingdoms

If you listen to enough interviews with exceptional or famous people, you’ll start to notice a pattern.

These authors benefitted from opportunities and tailwinds you never will — because the world they rose in simply doesn’t exist anymore.

While searching for a good nonfiction writing podcast I found one featuring interviews with famous authors. I listened to the episode with Susan Casey — who wrote The Devil’s Teeth (about the Farallon Islands) and The Deep, two of my favorite books about the ocean.

Listening to her describe her ascent, it became clear that much of her success hinged on timing: she landed jobs at Outside and O, The Oprah Magazine during a golden age for print, when publications still had the budgets to send writers on quirky, remote assignments — like the Farallon Islands.

It’s illuminating for understanding her career. But it’s useless for mapping mine.

The magazine industry that launched her doesn’t exist anymore — and probably never will again.

It’s like someone pointing at the Sierra foothills and saying, “You know, I once found gold in them hills.”

Cool story, bro. Someone should name a football team after you. These days, the gold rush is in Santa Clara.

These stories make it abundantly clear that the winners in business are often those with the first-mover advantage. While it’s useful to understand how powerful it is to be first to popularize something like on-demand taxis — these stories inadvertently function as a tour of ideas you’ll never get to try.

As the economy speeds ahead, this will only accelerate.

Eventually, HIBT stories will start to feel like dispatches from extinct industries — told to readers destined for jobs that haven’t even been invented yet.

These stories are often framed around hard work — but if you listen to them, they’re almost always really about timing and access. And that’s where the shame creeps in: when we feel inadequate for failing to replicate what was never available to us in the first place.

The Devil’s in the Distillation

CrossFit founder Greg Glassman once tried to sum up how to live a healthy life in 100 words:

Eat meat & vegetables, nuts & seeds, some fruit, little starch, and no sugar. Keep intake to levels that will support exercise, but not body fat. Practice & train major lifts: Deadlifts, cleans, squats, presses, C&Js, and snatch. Similarly master the basics of gymnastics: Pullups, dips, rope climbs, pushups, situps, presses to handstand, pirouettes, flips, splits, and holds. Bike, run, row, swim, etc. hard and fast. Five or six days per week mix these elements in as many combinations and patterns as creativity will allow. Routine is the enemy. Keep workouts short and intense. Regularly learn and play new sports

Before I go any further, it’s worth noting that Glassman’s reputation has since taken a nose dive due to racist rhetoric and allegations of sexual harassment.

His pithy lil’ “Live, Laugh, Love” for gym bros, this “Keep Calm and Power Clean” isn’t interesting to me because I also do CrossFit but because it affirms something I’ve long believed: the principles of a happy, healthy life aren’t that complicated.

The hard part is doing them — not researching them, debating them, or understanding them.

Most people claiming otherwise are lying, selling you something, or both.

But here’s the twist: while health and fitness content tends to overcomplicate simple, universal truths — HIBT content oversimplifies what’s actually complex, contextual, and deeply personal.

In health and fitness, what works is remarkably straight forward — despite the endless parade of headlines, books, and podcasts insisting otherwise.

Hence the enduring appeal of aphorisms like “The met ods are many, but the principles are few,” or Michael Pollan’s: “Eat food, not too much, mostly plants.”

In arts, business, and tech, though, there are nearly infinite paths to success. What works for a writer might not work for an entrepreneur — and what works for one entrepreneur might not work again in another time, place, or industry.
In the search for a Rosetta Stone of success, there’s often no there there.

The paradox of HIBT is this: its obsession with cataloging paths to success quietly proves there may not be a tidy pantheon of principles at all — no matter how confidently Tim Ferriss formats them, how intensely Andrew Huberman biohacks them, or how casually Benny Blanco shrugs them off.

Some wake up early, others sleep in. Many come from money, others grind their way up. Most had luck or tailwinds — few admit it. Maybe success is just complicated.

Sure, there are a few best practices that show up across industries: build your network, look for demand where supply is scarce, don’t burn bridges.

But even widely agreed upon principles come with more caveats than an RFK health report.

• You should treat people with respect and empathy but Steve Jobs was a famous asshole and Elon Musk displays behavior ranging from narcissism to sociopathy.

• You should take feedback well unless you’re Vogue Editor Anna Wintour whose temper and dismissiveness earned her the nickname “Nuclear Wintour.”

• You should dress for the job you want, but Mark Zuckerberg wore the same gray t-shirt every day and became one of the richest people in the world.

• You should be transparent — unless you’re WeWork’s Adam Neumann, who used secrecy as a fundraising tactic and walked away with nearly a billion in severance.

• You should fail fast and pivot — but only if you’re rich, white, and male. Everyone else gets zero to one shot tops.

I realize that, in my ire, I’m now committing the same sins as a HIBT podcast: cherry-picking examples to prove my point while sidestepping the more complicated truth. What I’m getting at is that what works is often less a formula and more a confluence: of timing, temperament, and context. No podcast can fully replicate that.

Maybe the only thing harder than becoming wildly successful is teaching someone else how to do it.

The Distinctly American Flaw in Constantly Celebrating Outliers

I’ll concede that HIBT is a sloppy umbrella term for a wide range of formats, genres, and styles. Some of it is thoughtful and in-depth. Some of it, like those Benny Blanco videos, feels indistinguishable from any other 30–90 second TikTok clip. But they all share one thing: the version of success they highlight is, by definition, rare.

The formats vary, but the subjects are always exceptional.

That’s what makes the genre fascinating and frustrating.

For creative people like me, it’s uniquely maddening. Recognition and riches are rare in any field — but in music or writing, they’re astronomically rare. In tech or finance, you might actually have a shot at a seven-figure outcome if you follow the right steps, land the right job, or time the market. But in the arts, there’s no roadmap. Most of the HIBT advice doesn’t apply — and the slivers that do feel superhuman. When a novelist lands a million-dollar advance or a singer breaks out on TikTok, it’s not just inspiring — it’s alienating. The odds aren’t just low. They’re lottery-low.

The worshipping of the profitable, the famous, the edge cases is also what makes these stories so distinctly American: they assume we should all strive to be extraordinary — a premise as seductive as it is unreachable. It’s the business-class section of our cultural obsession with celebrities, People Magazine in a blazer.

To see how uniquely American this is, consider the Swedish concept of Jantelagen. Jantelagen is the cultural norm that discourages pride and promotes humility and conformity. New Yorker writer John Seabrook invoked Jantelagen to explain the “invisible success” of Swedish music producers like Max Martin and Shellback — hitmakers who’ve written dozens of Top 40 songs while staying out of the spotlight.
It’s the Nordic equivalent of Lil Wayne’s iconic line: “Real Gs move in silence like lasagna.”

This mindset isn’t limited to Sweden — or Lil Wayne. When I was working in Spain, I was surprised to learn that, in Spanish,“ambitious” often carries a negative connotation — associated more with ego and power than drive or creativity.
Yet here in the U.S., our relentless hunger to be exceptional is both iconic and quixotic — a dream we can’t quit, even when it burns us out. It’s what fuels our fascination with billionaires, our love of origin stories, and our cultural allergy to being average.

The deeper problem here isn't just philosophical — it’s personal. And it took me a long time to realize how much it was messing with my head and the heads of everyone around me.

The Bay Area Blues

Alexis recently finished business school at Berkeley.

She learned plenty. But what I learned — by osmosis — is that getting an MBA is like living inside a How I Built This podcast.

The more I talked to people in her program, the clearer it became: nearly everyone was battling intense imposter syndrome. Being surrounded by the Bay Area’s brightest, most ambitious, and most relentlessly self-promotional people dredged up everyone’s deepest insecurities.

At Haas, you’re not just exposed to ambition; you’re engulfed by it. No matter how much money you make, someone else is making more — with a flashier title, splashier vacations, and an engagement ring the size of an ice-skating rink. This pressure-cooker mindset extends far beyond the UC Berkeley campus.

In a Reddit post that went semi-viral, a South Bay tech worker described how this perverse status game now infects everything — from work to weekend hobbies. Even casual hangouts turn into prestige Olympics within minutes. They share how if you’re not an engineer at a top-30 brand, you might as well be invisible. God forbid you work at a tier-two company — or worse, outside tech. People will nod politely, then disengage.

No topic is safe. Mention skiing and it turns into a pissing contest about comp packages and Tahoe real estate. Bring up Japan and suddenly it’s remote salaries at Airbnb. Recommend a restaurant and cue the humblebrag loop about underwhelming Michelin starred meals and omakase in San Mateo — or yet another unsolicited plug for Japan.

At one point, the poster tries to snap their peers out of it: “You know you’re in the top 1%, right?” But it doesn’t register. They just spiral deeper into self-contempt, convinced they’re falling behind — all while relentlessly vomiting signifiers of their own affluence and success.

It’s like everyone’s drowning in champagne while convinced they’re dehydrated.

Why is No One Content to Be Average?

I don’t fault anyone for wanting success or more money.
They’re two of the most universal and understandable desires in modern life.

But the uncomfortable truth HIBT podcasts dance around is this: we can’t all be game-changing entrepreneurs, artists, or titans of industry. Most of us won’t found a company that gets acquired, get a Netflix special, or publish a bestselling book about great white sharks that inspires someone to visit the Farallon Islands.

In the great bell curve of humanity, most of us land somewhere in the middle — average at most things, exceptional at a few, if we're lucky. That’s not a failure. It’s a fact. And it shouldn’t be a source of shame.

The problem isn’t being average. The problem is pretending that average doesn’t exist.

We keep glorifying the statistical outliers — the extremes — as if meaning only lives at the margins. But the middle is where most of life happens. It’s where we build relationships, raise kids, make dinner, walk the dog, pay the bills. It’s where we become who we are.

HIBT content distracts us from this kind of success — the slow, quiet, cumulative kind: holding down a job, recovering from heartbreak, cooking an excellent soup, being a good parent, partner, or neighbor. These kind of hard-won victories seldom appear in podcasts.

When we spend all our time squinting at the stars, obsessing over the constellations, we miss the sky itself, the everyday joys, the small triumphs, the astonishing luck of simply being alive.

When we’re busy waiting for our big break, we miss the moment we’re already in.

Rethinking My Media Diet: How I UnBuilt This

I once worked with a woman who was deeply into Ayurveda. She introduced me to the Sanksrit word ahara. It technically means diet, but she explained that it includes everything you consume: food and drink but also the energy of people and the stories you absorb through books, TV, and podcasts.

Everything we consume shapes our energy, mood, and mindset. This changed how I thought about my life.

In my 20s, I binged aspirational capitalist podcasts like How I Built This and The Tim Ferriss Show. Then I pivoted to “being informed,” adding a heavy dose of political despair from The Daily and Ezra Klein.

Even as the world slowly reopened after COVID, and headlines became less apocalyptic — if not exactly hopeful — I still felt full of dread and frustration.

A big part of that dread, I realized, came from my media diet — the constant background noise while doing dishes or running errands. The news shows gave me a mountain of articulate evidence for how doomed our country and planet are. The HIBT ones gave me proof of how many people are smarter, richer, more famous, and more entrepreneurial than I’ll ever be.

Collectively, it gave me mental indigestion.

Pausing these podcasts gave me something I hadn’t felt in years: relief and clarity.

HIBT content doesn’t fill me with awe anymore — just a cocktail of envy, irritation, and rage.
Some of this is probably age. In my 20s, it all felt electric — full of possibility. But now, in my 30s, life feels more set. I have fewer paths, fewer bets to place, and fewer years to wait for a payoff. Career stories that end in multi-million-dollar exits don’t feel inspirational anymore. They feel like tone-deaf victory laps.

This might just be a me problem.
People I love and respect rave about podcasts like Acquired.

Either way, at 34 going on 35, I’ve realized the healthiest choice for my media diet is to avoid How I Built This stories the way some people avoid gluten: not because they’re toxic to everyone, but because they don’t sit right with me.

My frustration with HIBT content says less about the genre’s flaws and more about my own. This essay commits the cardinal male sin: using intellect to smuggle my feelings into the conversation. This entire critique may have been a Trojan horse for a confession about the frailty of my ego.

How I Built This content isn’t inherently bad — it just makes me feel bad.

I didn’t even need to go to business school to feel inadequate — I just needed a few podcasts and access to LinkedIn.

I’m not building a red-hot AI startup.
I’m a contractor writing copy for websites, emails, and social media.
On good weeks, a few hundred people read my Substack.
And when I’m not doing that, I’m chipping away at a memoir no one has read — and that no one may ever read.
Depending on the day, I describe its quality as passable or laughable.

In that context, hearing about someone else’s spectacular success is more likely to make me feel insecure than inspired.

Like many millennials raised on MTV, VH1, and The Disney Channel, as a kid I secretly believed I’d be famous. Every year, I inch closer to accepting that I won’t be.

Coming to terms with that — and with how unmoored constant comparison makes me feel — I realized changing my media diet wasn’t just helpful. It was essential.

The writing advice I needed didn’t come from interviews with Malcolm Gladwell or Susan Casey. It came from Verlyn Klinkenborg’s Several Short Sentences About Writing — a spare, elegant book that’s all craft, no fluff.

These days, the podcasts that bring me the most joy aren’t about business or politics — they unpack great music: 60 Songs That Explain the ’90s and Switched on Pop.

My only recent HIBT-style binge was Sarah Wynn-Williams’ red-hot memoir Careless People — mostly to study her structure and tone.

My main takeaway? If I ever publish my memoir, I hope to get sued less.

(Though I’ll never forget the part where Facebook was enabling genocide in Myanmar while Zuckerberg’s coworkers let him win at Settlers of Catan on a private jet.)

If I ever tell my story, maybe I’ll start here — with the moment I stopped inhaling other people’s highlight reels and started living in my own rough draft.

Building a life doesn’t come with funding rounds or press releases. The margins are low, the hours are weird, and the failure rate is 100% — but it still feels worth it.

I don’t need these podcasts anymore because I now believe that I’m building something too. It just looks different.

I don’t need a better blueprint. I need time, quiet, and the guts to share the thing no one asked for.

Now, if you’ll excuse me, I’ve got some more writing to do.

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Do you consume a lot of “How I Built This Content?” Why do you love or hate it?

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