Ambition, then and now

Will you have gotten what you wanted from this life, even so?

“I want the certificate.”

In late 2019, Away, a startup that sells luggage, had a problem. Weeks earlier, a handful of Away employees sent The Verge screenshots of Steph Korey, the company’s then 31-year-old founder and CEO, berating staff for, in her view, not working hard enough, not being devoted to Away’s customers enough, not living up to Away’s values enough, and, in one case where she questioned if some employees were “brain dead,” not being cognitively animated enough. After interviewing a number of former employees who described the messages as “consistent with a pattern of behavior from the company’s top leaders,” The Verge published a lengthy piece charging Korey with creating a “toxic work environment” inside of Away. 

Korey tweeted an apology, said she was “appalled and embarrassed” by her behavior, promised to better support her team through an awkward commitment to “work-life integration,” and, three days later, was fired.¹ Away replaced Korey with Stuart Haselden, a former Lululemon executive with over twenty years of retail experience.² Then Korey returned as CEO, saying the initial decision was a mistake and that The Verge story contained “deliberate lies and distortions.”³

Korey’s firing sparked a number of the tech industry’s long-standing cultural powder kegs. The real story was inequality: If Korey, who grew up in a 55,000 square foot home and was at one point worth $130 million, wanted her team to work harder, she should pay them more than $40,000 a year. The real story was about inexperienced management: Rather than yelling at her support team, Korey should’ve been focused on figuring out why Away was getting 4,000 customer service requests a day. The real story was Slack: Away’s reliance on always-on chat and Korey’s insistence that employees “have almost every conversation in public” enabled executives to surveil and intimidate staff. The real story was racism: Several people of color said that they were fired by Away because they made jokes about “cis white men” in a private Slack channel. The real story was sexism: Had Korey been a man, she would’ve been seen as decisive rather than tyrannical.⁴ The real story was the media: The article was a hit piece—targeting both Away and Slack—uncovering nothing remarkable, written by a reporter with an ax to grind. 

It scissored Silicon Valley in half.⁵ For a few weeks, no matter your team or tribe, you had an opinion on what happened at Away, and it proved that you had been right all along.

The biggest nerve it touched, however, centered around the pressure that Korey, who was known for having a fanatical work ethic, put on her employees to work long hours, over weekends, and over holidays. Some argued that this expectation was abusive; others said it was necessary, the cost of doing business as a young company.⁶ 

This debate over work-life balance was not new; it’s a fault line that frequently shakes up Silicon Valley’s chattering class. Elon Musk regularly dislodges it by encouraging people to work 80 to 100 hours a week; Basecamp founders Jason Fried and David Heinemeier Hansson dislodged it when they published a book arguing that long hours are “a mark of stupidity;” every viral #DayInMyLife video from TikTok dislodges it. And Steph Korey inadvertently dislodged it by, among other things, preemptively rejecting her support team’s requests for time off in the name of accountability and empowerment.

In this iteration, most of Korey's defenders didn't condone her approach—people couldn’t quite contort themselves into saying that calling her team braindead was reasonable. But many people, and especially venture capitalists and their social barnacles, defended her willingness to do whatever it takes to succeed. Rather than criticizing her managerial style, they said, we should applaud her “strong devotion” to her customers and her “meticulous care about the integrity of the product offered.” As one anonymous venture capitalist said, "many VCs are reading it and recognizing the culture as the one they would love to see across their portfolio.”

Fair enough; building a company is hard. Most companies won't succeed unless the people building them are obsessively devoted to that endeavor.⁷ 

But that’s where the story takes an odd twist: Away was, by any reasonable measure, already successful. By early 2018, Away was profitable. Korey’s personal stake in Away was likely worth tens of millions of dollars. Away’s flagship product received a “nearly flawless” score on Wired and was called the “perfect carry-on” by Vogue. They had a podcast, a magazine full of celebrities, and a Forbes cover. 

In other words, what was Korey still chasing? Why did Away need to raise another $100 million? Why did it need 50 new stores and to build “a community” for people who bought suitcases? And why did she need to pursue those things with such relentless urgency that she forfeited her own managerial values—Korey had previously said that “you can’t be your most productive self if you’re not taking time to unplug,” and Away’s mission statement once said that “all time away is time well spent”—to do so?

To people in tech, the answers to these questions are so self-evident that we barely recognize them as questions at all. She did it because that’s what you do when you start a company. If your company sells software, you build great software. If it sells luggage, suitcases—and “getting more out of every trip,” another part of Away’s mission—becomes your singular calling. You become passionate about resilient yet functionally minimal roller bags, or enterprise identity and access management, or solving payroll, or whatever. You go big, and then try to go bigger. In Silicon Valley, we’ve drowned ourselves so deeply in this ethos that we no longer realize that we’re in the water.

One ruler to reign them all

In 2011, I was desperate, in a way that only a trophy-chasing twenty-four millennial can be desperate: My first job out of college, a junior analyst at a think tank in Washington, DC, was stalling, my grad school applications had been rejected, and I was running out of blue chip consulting firms, investment banks, and tech companies to apply to. Like so many other applicants for those positions, I didn’t know if I’d like doing these jobs; I only knew I’d like them on my resume. They weren’t passions, or even hobbies; they were the next opportunity for extrinsic validation. Thus far, the arc of my life—apply to college, go to college, apply for a vaguely prestigious job or smug fellowship, take the most notable one—had been mapped by others, and I figured I’d again drift towards my next “success.” 

I did not make it as far as I’d hoped. After a six-month job search, I landed my first offer on my fifty-ninth application: A data analyst at a San Francisco tech startup with a puzzling product, a clumsy name, and, as their MTV Cribs-themed recruiting video enthusiastically put it, “Cheetos, Fritos, and Doritios!” It wasn’t the glowing gold star that I was looking for, but with no alternative, I took the job. 

When I got to Silicon Valley in 2012, I was indistinguishable from many of the other new arrivals. We were young; we were educated; we were mostly white, mostly male, and mostly free of student debt. We preferred to wear jeans, drink IPAs, and talk about things—technology trends, SF housing policy, bourbon—as if we knew more about them than we did. Though it would take some time for me to be fully manufactured into a tech bro—for example, I still wore The North Face rather than Patagonia, SF’s preferred corporate athleisure—I was grade A raw material.

I was also primed for indoctrination in a more important way: I was ambitious. Despite the Bay Area’s cultural and natural richness, I, like most people flooding into San Francisco’s central neighborhoods, didn’t come for those things. I came for my career. I came to succeed. I came to “have an impact.”  At what or on what, I didn’t know. But in a city overflowing with achievement, I assumed I’d figure it out.

Within a few weeks of being in San Francisco, I hadn’t figured out what it meant to be successful in tech—I’d been run over by it. The three most common things I learned about my new coworkers were their name, their job title, and how early they joined the company. Days after I started, we celebrated raising nearly $100 million in funding—until, a few weeks later, Facebook bought Instagram, a company half our age and a fifth our size, for $1 billion. We lionized coworkers who left to join smaller companies or start their own; we wrote off coworkers who left for established giants like Google or Amazon, as if they were retiring.⁸

That was the only ruler by which we measured ourselves in San Francisco: How much money had your employer raised, how much hype did it have, and how early did you join? This singular scoreboard hung over everything—in every bar, at every Meetup™, inside every Yoga studio and CrossFit gym, on every date. In the tech bubble, there were no alternative measures of success, like there might be more professionally diverse cities. If you were to pick 20 random people out of a bar in New York or San Diego or Memphis, and ask them to sort themselves by social status, they’d probably disagree about the arrangement. How do you compare a dental hygienist to a teacher to a bike shop owner to an accountant? Why would you compare them at all? 

But ask 20 people at The Snug on Fillmore Street, and everyone would give the same answer. In fact, you don’t even need to ask—people who work in tech often arrange themselves by their professional strata on their own. In San Francisco, we are our jobs, we keep score, and we all know who’s winning. We have a scale, and we use it. 

The Bay Area isn’t entirely special in this regard; DC, for example, is also dominated by one industry, and full of young careerists who are hunting the same jobs. But Silicon Valley’s giant social scoreboard has one unique complication: The innate ambition of San Francisco’s startup class is also supercharged by the tech industry’s obsession with “growth.” We don’t value people by where they are. We value them in the same way we value our companies—by how fast they’re rising. Nobody talks about the CEO of a public company that’s growing at ten percent a year, or the Oracle SVP who’d been an SVP for a decade. We talked about the people and companies on the cusp—the rocket ships, the wunderkinds, the new new things. 

For better or for worse, in San Francisco, these vertical trajectories feel possible. Unlike other prestige professions, the tech industry celebrates those who skip to the front of the line. Startups have no entry level analyst program, no obligatory MBA hiatus, no rotational associate sequence, no residencies, no defined timelines for becoming a partner or managing director. In Silicon Valley, "paying your dues" is hearsay. Through the breathless profiles that fill Forbes, VC blogs, and countless 30 Under 30 lists, startup founders are regularly reminded about those who became rich and famous by refusing to be told they weren’t ready. 

And so, we all chase a definition of success that can only be measured by how much faster we were moving than our peers. Every step we take, every hour of work we put in, feels like an urgent acceleration towards… something. Fueled by our time and other people’s money, we race one another to the horizon.

A passion for whatever’s nearby

I have no idea if any of this mattered to Steph Korey. But there are a lot of parallels between her career and my own, and I know that they mattered to me. We both graduated from college the same year. We both worked at NGOs before moving to corporate jobs. Both of us started companies—Korey started Away and I started Mode, which built software for data analysts—in our mid- to late twenties. 

Moreover, both of us were opportunistic founders. According to one profile of Korey, she didn’t start Away because of any particular passion for luggage; she started it because her friend’s carry-on split open on an international flight. Despite initially being unsure if she wanted to start a business, Korey’s reluctance turned into cheeky ambition. “We weren’t interested in starting a small business,” she told Forbes, “we wanted to truly improve how people travel on a meaningful scale.”

Similarly, prior to starting Mode, I had no interest in business intelligence software. I started it because two of my coworkers at Yammer built a popular internal tool, and they inexplicably offered me a seat at their founding table. But once in it, I was in it—trying to reinvent dashboards; writing countless blog posts about dashboards; being called, by the cruelest person on LinkedIn, a leader in the dashboarding space.⁹

In other words, Korey and I both stumbled into our respective businesses. Neither of us were building something that the world especially needed. And like so many founders and company leaders who get swept up in feverish ambitions and pace of startup life, we didn’t create businesses to manufacture products for customers; not really. We created them to manufacture accomplishment for ourselves. We just wanted to succeed; to win; to outclimb our peers. 

In tech, that’s not an ignoble cause. Sequoia Capital, a premier venture firm, believes that all of their investments should “have a desperate need to win.” In the wake of Kobe Bryant’s death, Marc Andreessen marked the occasion by reminding people that one of Kobe’s most admirable characteristics was his atomic obsession with winning. Others have explicitly drawn parallels between Kobe and successful founders for the same reason.

I get why VCs say this stuff. It’s visceral; it’s provocative; it gets the people going. As a lifelong amateur athlete, my YouTube history is littered with Tiger fist pumps, kick-sixes, buzzer beaters and double bangs,¹⁰ bat flips, home run mics, Nike and Under Armour ads, and Minneapolis Miracle remixes. Without a court to compete on, startups became our arena. And we become as monomaniacal about winning our game as athletes and coaches are about winning theirs.

There is nothing inherently wrong with that. People need competition; they need meaning; we cannot just gaze into the abyss of our fleeting existence on a lonely mote of dust floating through an eternal void. We all have religions because we all need religions. If someone finds purpose in building Instagramable totes, that is no more or less cosmically relevant than anything else. And on a more planetary scale, it’s probably not a bad thing for some people to be entrepreneurs for the love of the game—or even, just for the trophies. Suitcases may not be metaphysically material, but a nice one does make flying a little less of a headache.¹¹

Instead, what I think is important to recognize about our motivations is not that they are bad; it is that they are circumstantial. Thousands of people in Silicon Valley meander into their ambitions, via pivots, via pranks, or—as seemed to happen for me and Korey—via professional serendipity. But just as we can wander into our life’s calling, we can wander out.

Is that all there is to a firing?

There is one more parallel between my career and Steph Korey’s: We both got fired from our startups. ThoughtSpot, which acquired Mode almost exactly a year ago, let me go two months ago. 

So it goes; such is the circle of life in Silicon Valley. If you don’t like that deal, don’t work here. Still, the moment was striking to me, not in what it was, but in what it was not. For years, you don’t just work somewhere; you are consumed by it. The things that matter to you are the things that matter to it. For better or for worse, it puts blinders on your ambitions: You obsess over success in your field, and wonder why people in other fields stress about the trivial status games in theirs.¹² 

And then…you don’t. Your calendar is cleared; your to-do list is zeroed; your problems are suddenly someone else's responsibility. You're pulled from the water that you long ago forgot was water, and dropped directly onto the land. 

Standing on the shore, your old pond—the pond where you did your life's work, in which nothing seemed more important than being a big fish—suddenly looks like all the other ponds you used to care so little about. It looks distant; foreign; trivial. From that vantage point, you don't mourn leaving it; you mourn having spent so much time there.

That doesn't mean it didn’t matter. It simply means that our ambitions are defined by our environment. On short time scales, this is obvious; in the moments that we desperately crave tacos, or a quiet moment to ourselves, or a cold shower, we know that we won’t want them forever. In a couple hours, we’ll be full and repulsed by food; in a couple days, we'll want to pop out with some friends; in a couple months, we’ll want a hot shower and cozy blanket.

The same is true over longer time scales; it’s just harder to see. When you’ve been on a ten-year trek looking for a taco, you forget that you might one day want something else. 

This has a corollary that is even harder to see, and harder still to act on. You can manufacture ambition. Being a suitcase executive, building data software, chasing status in Silicon Valley—these are not innate in us. We care about these things because we submerged ourselves in them, became acclimated to it, and forgot that it was water. 

But there are other ponds that we could lose ourselves in. If you start going to pottery classes, suddenly pottery will be your thing. If you become a barista, a guy on YouTube might become your idol. If you work in sports media, you’ll find yourself caring about this gossip and not that gossip. We think that we surround ourselves with our interests, but causality often runs the other way: We become interested in what we’re surrounded by.

We can choose that context—it just takes a leap of faith. As long as your environment stays the same, so will your ambitions. You’ll value the same things as you did yesterday, care about the opinions of the same people, and chase the same trophies. If you change this context, these things will change too. But that’s the uncomfortable order it has to happen: You won’t want something new until you walk away from the thing you currently want. 

That’s the real trap of Silicon Valley, and of other prestige industries. For aimless high-achievers—for people whose only honest answer to the question of “what do you want to be when you grow up?” is “successful”—they offer a default scale. And then, its scale becomes our scale. Though we start out working there despite the job being about shifting paradigms across scalable B2B SaaS, we eventually work there because the job is about shifting paradigms across scalable B2B SaaS. That’s the real punchline to this joke: If you work in tech long enough, this might actually become what you love. 

And maybe that’s ok. But at a minimum, we shouldn’t find our ambitions by accident. If we imagine that we’re no longer in our current pond—that we got fired, or are 16 years old and dreaming about what we to do with our life, or 80 years old and reflecting on what we did—what would we care about then? Are the ladders we spent our time climbing the ladders that we really want to stand at the top of?

Whatever we imagine that existential ambition will be then, we we can make it our day-to-day ambition now, but not without sacrificing our current idols. Because there will be a moment when all have to ask ourselves if we got what we wanted from this life, and the greatest trick the devil ever pulled was convincing us he'd come for us after we die, and not when we're still living.

1. All of her tweets, including her apology, have since been deleted.

2. Away initially said that the change had been in the works for months. This was later reported to be partially true. Haselden had been planning on joining before The Verge story, but as COO, not CEO.

3. Nine months later, in October of 2020, Korey stepped down again. 

4. On one hand, the tech industry definitely idolizes men—Steve Jobs, Bill Gates, Jeff Bezos, Larry Ellison, Andy Grove, Travis Kalanick, many more—when they are notoriously demanding. On the other hand, maybe we shouldn’t? To assume that they were great because they were jerks is like assuming John McEnroe was great because he threw tantrums. I get that greatness can often be prickly, and you can’t throw out the outbursts without potentially losing the passion. But we don’t need to celebrate or mimic that behavior; we can aspire to be more decent. For every Steve Jobs, there are thousands of us with less talent whose tempers don’t make us great leaders; they just make us cruel.

5. Away is neither a tech company nor located in Silicon Valley. However, the Silicon Valley metonym has grown to include venture-backed startups in other major U.S. cities like New York, Boston, Austin, and, for a minute, Miami. Silicon Valley isn’t a place; it’s a mentality. 

6. On “work-life balance,” some people take jobs to get rich, because they’re compulsively ambitious, and because they’re hypnotized by the thrill of explosive growth. Some people take jobs to work on interesting problems, to work with supportive teams, and simply to make enough money to have lives outside of their offices. 

A lot of startups try to have it both ways. They try to offer rides on a rocketship while also putting people and culture first. And when the two are at odds, they gaslight employees by camouflaging oppressive hours as “wild and exciting and unexpected and beautiful.” Other industries like finance are at least direct about what they offer: They pay you a lot of money to steamroll you with work. It may be abusive, but it’s transparent.

That’s why I think startups should be more explicit about how they make these tradeoffs. It’s fine to chase growth at all costs, to build a company and culture that prioritizes the lifestyle of its employees first, or to do something in the middle. But everyone needs to know which temple they’re in. 

Also—a lot of people seem to see this as a choice between winning and gently losing. But this misses the point. We don’t have to define winning around money or market dominance. We can also define it through how much we enjoy the responsibilities that fill our days, or how we support the lives of those we employ. We can still be competitive; we can still have a desperate need to win; we can still refuse to process failure. We just have to be independently-minded enough to not let others define what winning and losing means.

7. Similarly, VCs’ livelihoods—or at least their statuses, their Twitter audiences, their invites to the All-In Summit, and their futures as authors of pop management books with glowing introductions from authors of other pop management books—depend on their portfolios surviving. 

8. Later that year, Microsoft “retired” us all by buying Yammer. We scoffed at their offices, their stale software products, and their bureaucratic performance management practices. We quit, sold our Microsoft shares, and started companies that would build things, and not just tell stories about the glory days. 

Most of those companies are out of business. Microsoft’s shares are up 1,500 percent, and it is now the most valuable company in the world. Ah well.

9. I mean, oh man, does a message like this make you question your life choices.

10. It’s funny now, because they’re the same team. 

11. That said, this can also cause problems. In 1838, Abraham Lincoln said this about ambition:

It sees no distinction in adding story to story, upon the monuments of fame, erected to the memory of others. It denies that it is glory enough to serve under any chief. It scorns to tread in the footsteps of any predecessor, however illustrious.

No doubt, society benefits from some degree of gamified entrepreneurship. But there can be a point at which that goes too far, and rather than working together, every great creator wants their own solo career. 

12. For example, there are legions of Zoomers who are obsessed with their social standing on Instagram and TikTok. Do you care about what these people think? Does their game matter? If that totem pole isn’t important, isn’t it possible to imagine that one day yours may not be either?