Confessions of a Millenial Try-Hard

By Leslie Price

Watching the new Apple TV+ show WeCrashed, about the rise and fall of WeWork, is like opening a time capsule containing our feelings about work prior to the pandemic. Actually, let me be more precise – my feelings about work.

Several years ago, I worked at a very small fashion media startup. At the time, I was the oldest employee there by several years (second only to the president of the company) and the only person who was a parent (when I started, I had a six month old). Most of the employees were in their 20s. One of my most vivid memories from the early days of this job was pumping in front of everyone in the open-plan office, because there was nowhere else I could have done it, save for a glass-walled conference room or the sole bathroom.

Though this startup was very different from WeWork, a somewhat similar ethos of living the brand reigned. Employees were at the office late and it was expected that you would participate in many unpaid night or weekend extracurriculars. (To be fair, I experienced this at other startups as well.)

It was the third WeCrashed episode, “Summer Camp,” that truly brought back memories for me. In it, the company throws a weekend camp for employees that turns into a bacchanal. There is a moment where Adam’s wife Rebekah Neuman says something that offends many of the company’s young employees, and then a crisis room scene where WeWork executives beg her to issue a public statement of apology. “We can’t lose the millennials,” says one of the men. “They’re the only people willing to work 80 hours a week for free beer and t-shirts.”

I have to admit that that tossed-off line hit a little too close to home. Because I was one of those people, though I cared less about merch than I did about proving my worth through overwork. How embarrassing for me. 

The startup I worked for also put on a weekend camp, where employees performed the role of counselors. The camp was for our readers, some of whom flew in from overseas to attend. I don’t remember being paid extra for this; I do remember feeling very distinctly like I had aged out of the experience, that I was too old to be sleeping on a cot with a room full of strangers. But I wanted to show my dedication to my job, so I did it.

Last week, Business Insider published a long excoriation (paywalled, unfortunately) of startup success Glossier. The article’s been described by some as a “takedown” of the company, but in my opinion it’s more of an examination of a particular sort of cultish, personality-led, girlboss-era brand that rose to prominence over the past decade. “With Glossier, Weiss didn’t just create a company — she created a spellbinding world,” Melkorka Licea writes. “Glossier employees used words like ‘guru,’ ‘idol,’ and even ‘God-like’ to describe Weiss’ magnetic presence at the office. ‘At first it was easy to get swept up,’ [a] former employee recalled. ‘And then you see what’s actually going on behind the curtain, and it was not all rainbows.’” Glossier also puts on a summer camp for its employees, “Camp Glossier.”

Part and parcel of convincing young, eager employees to work long hours for low pay is to trick them into thinking that work is more than a job and that instead of being a lowly cog, you’re part of something bigger – a family of sorts, or a member of a brand that stands for something. On WeCrashed, Adam sells long hours at the office as a means to all sorts of ends, a way to socialize and perhaps even meet a life partner. 

The way the show portrays it, WeWork bought into the myth of the “ideal worker,” expressed as “a clear, relentless commitment to paid work” including “working long hours and not allowing distractions outside the paid work environment to interfere with the job, including family and personal facets of life.” In my experience, this was a common startup expectation, but not one that was ever overtly stated.

All this comes as many white-collar corporations in cities like New York and D.C. plan to finally “return to the office” this spring after more than two years of remote work. It must be said that a delayed return to in-person work is a trend for an elite few; as Pew Research reports, “most U.S. workers (60%) don’t have jobs that can be done from home.”

This period has given those of our generation who have been remote for most or all of this time a rare chance to reevaluate the role work plays in our lives. So is it true that, as Kim Kardashian says, “nobody wants to work these days?” I’d argue that many of us have become more clear-eyed around work. Perhaps we’ve realized that for-profit orgs will never truly embody the ideals or ethos that they claim, that we were sold on as a way to convince us to work all those hours for not that much money. Maybe you have to get burned a few times before realizing that actually, all you want is a good salary, work-life balance, and benefits like health care.