The Accidental Corporate Apologist
How I learned to stop worrying and love my job at BigCo
It’s been a particularly existential week.
I’ve had not 1, not 2, but 3 separate people call me, spiraling and thinking about leaving their careers. Google just laid off more friends. The Algorithm has decided to jam-pack my feed with posts about quitting, changing careers, reinventing yourself, and how the “corporate deal” has changed. I’ve written about the epidemic of professional ennui before, but it’s only getting worse. The age of the Millennial Midlife Crisis is upon us.
On top of that, on Sunday I scattered my Mom’s ashes—talk about existential. It was a beautiful ceremony: a field of wildflowers next to an alpine lake high in the Rockies. This has been 7 years in the making and brought me a peace I didn’t know I needed. When confronting death, you really start to think about purpose: how you’re spending time, legacy, what’s really worth doing when it all ends the same way—ashes to ashes, dust to dust. Sitting by the lakeshore, I wrote her one final letter. Much was said, but at the end I committed to using the gifts she gave me to live fully on my own terms and do something that makes her proud. The clock is ticking.
You might think, given the context, that I’m all aboard the “quit your job and surrender to where life takes you” camp. Hell, I have entire posts that talk about passion.
Nope. Life is a little bit more nuanced than “corporate = drudgery” and “startup = freedom.” I’m actually deeply worried the feed is gaslighting all of us into feeling like we’ve made a deal with the devil, selling our souls for a salary + benefits, and that having a bad day at work or a stupid coworker should be cause for full-blown existential depression.
Here’s where they get it wrong, what is really going on, and what to do about it.
The deal hasn’t actually changed.
The folksy pastiche about staying at the same company for 40 years and retiring with a gold Rolex is just a bedtime story. I have literally known zero people for whom this is how it worked. Not my parents, not even my grandparents. For all of them, life was a continual, clawing-tooth-and-nail climb out of poverty full of curveballs, mid-life pivots, shitty employers, broken trust, and everything else you can think of. I’m sure someone had a happy ending at some point, but people also win the lottery…don’t hold your breath.
Beyond this, some feel betrayed because ascendancy up the corporate ladder is seen as an inevitability if not a guarantee. All one needs to do is show up, do a good job, and, every few years, you’ll be offered a promotion with more money and a bigger team. lol what? There are only so many manager/director/VP jobs. If you want to lead an org of 200, you are, by definition, occupying a 1-in-200 role. You must enter the coliseum and brutally murder 199 other combatants armed only with a PowerPoint and a Kanban board. The IC ladder is no different—a company only needs so many principal engineers.
You have always had to outperform and outcompete your peers for progression. Layoffs have always been a thing and have occurred at remarkably consistent rates for decades. Be excellent or perish.
Productivity expectations have always increased
Speaking of things that haven’t changed: new technology has always caused an increase in baseline productivity expectations, repurposing of outmoded labor, and exhortations to “adopt or perish.” It’s been the same for the last 10 technological revolutions.
This has happened no less than 5 times within software engineering alone, and the industry hasn’t been around that long:
Punch Cards to Terminals
Assembly to Compilers
Line Editors to IDEs
Desktop to Web
Humans to Agents
AI is not some rare, once-in-a-lifetime, extinction-level event. It’s just the first paradigm shift you’ve had to deal with since becoming a paid, working professional. That does not imply such changes are easy or simple—not by a long shot—but they are de rigueur when careers are 40+ years long.
The people I know who are actually excited are those who have been through one of these transitions before…basically elder Millennials and Gen X. I seriously wonder if the death of junior engineering roles has more to do with this effect than any conviction that only seniors will know how to walk the AI dog.
The deal has pretty sweet kickbacks.
Division of Labor
Corporations enable us to divide-and-conquer the work needed to, ya know, make actual money. Don’t like outbound sales? Great! You don’t have to do it. Don’t like dealing with customer support tickets? Pass. Pandas scares you a little? Make the data weenies deal with it.
If you want to narrowly specialize in performance optimization for assembly subroutines in low-level kernel code, you can do so and probably have a mid-six-figures job doing it. I have worked with engineers who can’t write a single coherent sentence of English. Putting them in front of a customer would be like conducting a CIA psyop…on the customer. And yet, they are marvelously effective technical contributors with thriving careers rather than burdens of the state.
Some people don’t like confining themselves to a single box their whole life, and that’s fine! The structural rigidity of BigCo can be a virtue in disguise. Ladder changes and job rotations allow you to try out entirely new jobs/careers without having to go back to school or break into another field. All the better that it’s in the big leagues with experienced mentors readily available, and not just playing pretend at an internship or as a “side hustle” (shudder).
Big goals demand big teams
It’s certainly possible for a small, nimble team to achieve great things. One person can change the world. But it’s also true that some things require a large group of people cooperating, no ifs, ands, or buts.
A planet-scale SaaS company will operate in thousands of jurisdictions, negotiating deals across the globe with dozens of data center and network infrastructure operators, and needs a multicultural go-to-market team capable of acquiring customers across segments and regions faster than they churn. Get too big, and regulators will slow you to a crawl (the EU’s DMA and Germany’s FCO anyone?)
Every company started somewhere; technically, you can iteratively build your way towards becoming the next Google…but that’s easily a decade+ of effort with no guarantees. Meanwhile, if you want to make a difference in the lives of billions, you can join a corporation that already has the teams, structures, capital, and customers in place and be living your dream by this time next week.
An engine of upward mobility
The American Corporation is an amazing engine for social mobility, and in an age where big tech is at the top of the corporate heap, nothing comes close to a FAANG job in its ability to lift individuals out of poverty and set them on a path to lifetime security and abundance.
I know new grads have it rough right now, but I can’t stress enough how much of a historical oddity it is that one can make such huge leaps in a single generation.
I come from a family of blue-collar hourly wage laborers with nary a college degree to be found. I was literally homeless for part of my childhood. By modern professional standards, I was a hick with a keyboard. Now, on the other side of undergrad + a pretty brief corporate grind, I am fully post-economic. I get invited to donor galas alongside Fortune 500 CEOs. I know which fork to use in a formal place setting and can tie a tie without a YouTube video. I even own a bidet. Incredible.
Brain Trust…assemble!
The mobility on offer extends beyond wealth generation. The best corporations have fastidiously curated their talent, and you will be surrounded by a veritable buffet of interesting people: Ivy League grads, eccentric geniuses, silver spoon elites, international talent from every corner of the Earth, connoisseurs of esoteric hobbies, and everything in between. At a minimum, they’ll be ambitious and conscientious, which counts for something. I have worked with both Turing Award and Fields Medal laureates, the sort of people I would have never met in a zillion years otherwise.
Even if at times you feel surrounded by smiling imbeciles in your current job, I promise the grass isn’t always greener on the other side. Being an early-stage or even solo founder is a very isolating experience—you have no one to talk to while your self-worth is continually punched in the gut. Once success strikes and you start hiring a staff, there won’t be much money to go after The Greats. At my last startup, I spent years wading through a sea of contract-to-hire oafs—water, water everywhere but not a drop to drink.
Speaking of who you surround yourself with, your immediate colleagues constitute a highly selective group implicitly filtered for similar intellectual interests, abilities, socialization habits, and pastimes.
For example, when you join Big Tech, you enter Nerd Heaven. No matter what your special interest or autistic hyperfixation du jour, there are easily hundreds of people at work who share it. Dungeons and Dragons, 3D printing, anime, particle physics, you name it. For folks who felt out of place growing up, it’s often the first time they felt “at home” anywhere.
More than happenstance is driving this: engagement in almost all forms of civic life has declined steadily since the 1960s. Voter turnout, attendance at town halls and school meetings, religious practice, membership in civic organizations like the PTA, labor unions, the Elks Club, and even informal socializing such as having neighbors over for dinner parties or playing cards. It’s all declined.
The need didn’t go away—it’s encoded in our very biology to seek tight-knit social groups. If your neighbors don’t know your name, your family’s a plane ride away, and the Elks lodge shut down in 2009, then the people you eat lunch with five days a week, who’ve watched your kid grow up over Slack, who show up when your parent dies, are your community1.
For many, their place of employment is the only community center left standing.
Alienation in the workplace
I never thought I’d defend corporate life so vigorously 🙃
I’ve experienced my fair share of disillusionment. Political infighting, ladder-climbing psychos, backstabbers, one actual officially diagnosed sociopath, 5-year-long projects that were utterly pointless, outright discrimination/sexism/ageism, an endless string of unforced errors, empty suits, rampant coasting, you name it.
None of it is endemic to big companies, so I’m usually screaming inside my head, “Really people?! Do you want things to be bad? Do you enjoy working like this?” I deeply believe in respecting the opportunity, so the constant shrugging of shoulders and faux-charming conceits “what do you want me to do about it?” send me into apoplectic rage.
I’ll still go on record and say it’s worth it—that there’s a version of BigCo that doesn’t have to be mind-numbing and soul-destroying. It could even be…great.
That said, I don’t think we’d be seeing such a wildfire of depression, quitting, disenfranchisement, and corresponding think pieces if there wasn’t something going wrong. So what is it about these jobs that is just so distinctly unfulfilling?
The answer can be found in Self Determination Theory.
No Autonomy, Accountability Theatre
The median corporation is really just a gigantic machine for avoidance of accountability.
Nearly every meaningful decision is turned into a “group decision”: quarterly planning, hiring committees, architecture review boards, code reviews, design crits, etc. Go figure dogshit leaders can never be fired; it is frankly trivial to launder bad calls as either a blameless consensus or to create so much fog of war you can’t even see your hand in front of your face.
So long as you follow the standard process and do all the reviews, nothing can ever come back and bite you. Likewise, this very same mechanism makes leaders extremely gunshy about exceptions because an exception carries a name—it sticks out and demands consequences if proven wrong.
So even when an obvious decision is needed for the good of the business, it won’t happen. You’ll get sent to prepare a mountain of slide decks and go through 15 rounds of review while customers suffer and projects fail, all so your boss can CYA.
More than just a means of implementing capital punishment, accountability is also the spice that makes our labor feel worth it…like our existence has real import and consequences. When you alone can make a decision that materially changes the course of a team, you feel the burden and weight of responsibility…but the good kind. More “weighted blanket” than “Sisyphean boulder”—a delicious nectar that is one part self-worth and one part self-efficacy (“I matter, I’m so good at this someone trusts me”).
Absent this level of responsibility, everything feels pointless.
No Relatedness, Surrounded by Strangers
I know I talked a big game about corporations creating like-minded communities and a sense of belonging…but you can also find yourself surrounded by people you do not like one bit.
Not all firms excel at creating culture and imbuing their members with an identity. In the absence of a clear mission/purpose and real social bonding, all that’s left is a brutal, animalistic survival of the fittest.
Even when the company does succeed at establishing a strong and distinct culture, did you choose your employer wisely? Does it reflect your own interests and values? We often betray ourselves and “act the part” to get a job, not realizing we’ll have to maintain the charade forever.
The culture shifts over time, especially when an industry or company matures into a “prestige job” (think: doctor, lawyer, and now, software engineer); you start to see more people showing up exclusively for the clout and the paycheck. They lack any passion for the work, and will hold their nose, opting out of the culture entirely, leaving you surrounded by fakey fakers.
This can literally trigger your fight-or-flight response. Spending half your waking hours with maxed-out anxiety is bad, mmmkay?
Even when the social dynamics are going alright, you’re not out of the woods—be on the lookout for contempt loops.
For years I misdiagnosed my own frustration as an authority problem. More scope, 1 more title, 1 more direct report, and surely the friction would go away. It never did, because the actual problem was values mismatch. I have a strong conviction for intellectual honesty: say what you mean and do what you say; candor is non-negotiable, politeness is optional. Meanwhile, in any large org, communication isn’t optimized for truth; it’s optimized for consensus—hedges, “let’s take this offline,” six-paragraph emails that bury a one-sentence decision under padding.
My values put me in a permanent minority position. Showing up daily to a conversation everyone else is having in code, watching a decision that should take 5 minutes get slow-walked through 3 weeks of flowery non-answers, and having to choose between violating your values or sticking out. This constant tug of self-betrayals is what’s known as egodystonia. It creates a doom loop with an inevitable outcome:
A values mismatch means you can never fully sublimate your ego into the group, because sublimation requires believing the group’s norms are correct.
That gap curdles into contempt—first for the mealy-mouthed email, then the person who wrote it, then the whole culture that rewards vagueness.
Contempt doesn’t stay hidden. It leaks out as behavior: you say the blunt thing in the meeting everyone else was tiptoeing around, you reply-all with the direct version of what someone spent a paragraph dressing up, you stop RSVPing to the “quick sync” that’s really just a venue for softening bad news.
That behavior marks you as blunt and difficult. The tribe—the one thing that was making the rest of BigCo bearable—starts closing ranks. Social rejection turns into yet more contempt and the loop begins again.
There’s no equilibrium here. Just rising pressure between how you believe people should act and how you’re expected to, until something gives: you get pushed out, you quit, or you spend the next decade sanding down the very traits that make you good at what you do.
No Mastery, Cargo Cult Behavior
Let’s talk about the actual work itself. Not in abstract—think very precisely about the various microtasks and actions that compose your day. Everyone wants to be good at what they spend their time on—to feel mastery and with it a sense of self-determination.
To do that, you start out by observing what other, successful people are doing and reason that if you do the same, good things will happen.
At first it’s just acculturation to corporate life. For example, you learn that there are certain phrases and ways of speaking which instantly set people at ease and give you some amount of influence. I remember my boss at Two Sigma uttering the phrase “let me lay out a strawman for next steps” as a preface to basically telling a room of peers/more senior people what to do… and they actually listened. I started using the phrase myself, and it just kept working. Magic.
You keep going; soon much of how you approach the job is based on mimesis rather than parthenogenesis:
Every new project that crosses your desk gets a PRD, a design doc, and a work breakdown structure…even when it’s straightforward.
Every status update gets sterilized to only good news. Anything going wrong gets compressed into an optimistic sound bite about “following up.”
Every meeting gets a running doc, action items with named owners and due dates, and a “parking lot” section for future recurrences.
When you break into management, the number of things you have to do quadruples, and each has a typical approach or standard framework practiced by 99% of your peers:
The team runs off 2-week sprints replete with sprint planning, retrospectives, and story points.
You publish a team newsletter because “visibility” is a nuclear arms race.
Every strategy gets flattened into 3 OKRs and a handful of suspiciously tidy KPIs.
Eventually, you’ve mastered the dance steps of leadership. Your slide decks are perfect, your OKRs pristine, your KPIs only go up, and you can deliver a standard stump speech for everything from selling a new hire to delivering a PIP to explaining your strategy.
And yet, you’re stuck. Every single cycle, the same story: meets expectations, good work, keep going.
The problem is that while you can perform the dance, you can’t actually say why you’re doing any of it, or why those particular actions are fit to task or particularly effective for creating results. You are subconsciously evaluating yourself by how much you sound, look, and act like other managers, rather than by how well you deliver actual, impactful business results. Bezos warns of this in his 2016 letter to shareholders, calling it management by proxy.
We keep building wooden planes, but the promotions do not come.
You will go through the motions of performing these actions completely disconnected from the underlying work, and even if your mind doesn’t pick up on it right away, your body will. You will feel the pointlessness of your labor—the simulacrum within the simulacrum. And one day, you will consciously realize all of your hours are really just enacting a giant kabuki theatre about office work rather than taking the shortest route to solving real problems.
Nothing makes this stick out more than when I try to describe what I do to my friends and family, all of whom work at smaller employers. They don’t understand, and their bewilderment is all the more unsettling because these are experienced professionals. Reactions range from politely changing the topic to “is that it? what else?” Your sense of mastery will be entirely diminished, and with it a gnawing self-doubt will begin to eat you up inside.
Agency at BigCo
You don’t have to quit corporate to avoid all this badness; there is a mindset that lets you seize the richness of your environment and the opportunities it offers. You will awaken to find yourself beneath freer skies. The answer is agency.
As the kids like to say, you can just do things.
I will never forget a week last year when my boss was on vacation during which I had the conn for Google Drive. By the time she got back, I was convinced that I would be fired. During that week I had (1) pivoted one of her pet projects, (2) made a backroom deal with the PMs to shitcan our entire roadmap and sold it all the way up to the VP level, (3) agreed to use Drive’s SWEs to help ship a project for her mortal enemy because it was what’s best for the customer, (4) caused a non-trivial outage, and (5) angered Sundar by blocking Gemini CLI from launching a massive security vulnerability. I was fully clenched walking into our next 1:1, waiting for the axe to fall.
And then…nothing happened. Everything was fine. “Thanks for handling all of that while I was out.” What!? So I just kept doing things like that—following my instincts, using my best judgment of what’s best for the business, and not asking permission. It kept working, and I kept getting rewarded.
Agentic behaviors that freed me include…
Stop asking permission; if you know you’re right, then go do it. Be willing to bet on yourself and own the consequences2 if you’re wrong. If you absolutely must, use “I intend to…” statements and then go do it.
Say what you think you cannot say (h/t Claire Hughes Johnson). I don’t have enough fingers and toes to count the number of times I’ve been crazy blunt, and afterward someone takes me aside and says “THANK YOU for finally saying what we were all thinking out loud.”
If you don’t believe in what your team is doing, change it. Just pushing through and hoping the next project is better makes you an ultra-coward squandering the lives of your people.
Tell your peers and superiors what to do (nicely). Don’t equivocate or hold back; figure out who needs to act and then ask them directly, “Chelsea, can you put together a PRD for this idea by next week?” People assume this is rude or outside their authority, so they ask the air instead: “Who’s taking point on writing the PRD?” Crickets.
Demand honest-to-god accountability. If your boss won’t stand up at a podium and say “Jim is the lead for Project Foobar,” then refuse to engage. I’ve played that game of “unofficial” leads and “no titles” before. It all sounds good and egalitarian on paper, but it’s not, and it creates frustration for everyone involved.
Become a polymath. Engage with topics outside your wheelhouse. Take an interest in finance, sales, marketing, business development, operations…all of it! Learn the actual domain your company works in, and you’ll suddenly find your work is a much more target-rich environment.
Most importantly, find a project that is important to you and just do it. Clear your calendar, block your time, don’t ask permission, and don’t let other people’s problems distract you. Feel the joy of actually crafting something with your own two hands.
Moreover, this amazing thing happens when you stop following a script, pretending, and putting on airs. People connect with you. Real collaboration happens. Honesty and truth. I have this shorthand equation which explains it:
When you stop optimizing for appearances and “winning the game,” it zeroes out the self-interest dominator. Your lack of tact and any semblance of self-preservation makes you both unthreatening and predictable to others, and as a result, your presence puts them at ease. Cheat code unlocked.
On the whole, it turns out you have a lot more autonomy than you think at BigCo. It actually makes sense when you think about it: as a manager, I’m not all that interested in bossing you around, but if you ask my opinion, I’m gonna offer it…so stop asking all the time. If you’re right, you’re right. If you’re wrong…wellllll, at least you lived your life with integrity and bet on yourself.
And if the company decides to fire you for that? So be it. Then that wasn’t the right home for you. You probably learned a lot and have an interesting story to tell. There are many more worlds yet to be conquered. I hear startup people have a fetish for agency; one of them will hire you.
Drawing the line at self-betrayal.
Before throwing in the towel, though, you should try to find the real barriers, rather than the imaginary ones. That thing driving you to misery? Maybe you can ignore it! Have you tried? Practice some agency 😉
But if you find that, no, in fact, there are aspects of your job you can’t simply ignore, then it’s time to make some Grown Up Decisions. If you’re shoveling the Augean Stables, there is no virtue in pretending it smells like roses.
Your worst sin is that you have destroyed and betrayed yourself for nothing.
— Fyodor Dostoevsky
It took years of experience and lots of nasty surprises to find my true values…to figure out why I hate something even though my brain is screaming “you should want this! you should really REALLY want this!” But once my values were crystallized, it became incredibly easy to see what sorts of jobs work for me and which ones don’t. If a job demands you betray your own values, then it’s time to hit the bricks.
At the end of the day, I’m still gonna quit…eventually. I’m collecting 401(k)s like Pokémon cards. It is my nature to seek challenges and new experiences, and I increasingly find the corporate jungle gym is out of fun problems. I’ll pump this well dry and move on to the next one. But that isn’t a rejection of BigCo. The only real question is whether the job in front of you requires you to be someone you’re not, and whether you can live with the answer.
By the lake I promised my mother I’d use what she gave me and live on my own terms. I don’t think that means anything as dramatic as walking out. Most days it means saying the blunt thing in the meeting, or doing the project without asking. Small refusals to betray yourself, accumulated over a career.
The clock is ticking. Spend it as yourself.
If the collapse of community and how it intersects with work is interesting to you, check out Carolyn Chen’s “Work Pray Code” and Robert Putnam’s “Bowling Alone”
Since literally no one else does this, even when it blows up, you’ll probably get kudos all the same. I have tried to get in trouble at work…it’s nearly impossible.