Hard-edged jobs in tech (like those in say, law or finance) disproportionately attract people who crave external validation and have a penchant for hypervigilance. Those of us who had conventional success early in life (excellent grades, elite athletes or artists) are overrepresented. As are, I imagine, eldest daughters. Anxious attachment is a desirable personality trait, if not a necessary one.
As adults, we’re done with report cards, SAT scores, and elite universities. However, KPIs (or OKRs or V2MOMs or whatever ridiculous new ways the dweebs from Sandhill Rd come up with to say “goals”) and increasingly senior titles, name-brand companies, and the size of your paycheck are how we keep score now.
Yet what makes you worthy of those titles and elite institutions is much more slippery and subjective than getting an A on an exam or scoring the most goals in a season. It cannot be a coincidence that as the subjectiveness of what constitutes success increases, the number of women in powerful and visible roles decreases. Women outperform men academically, there are more women in the workforce with college degrees than there are men, and yet women are still are under-represented in leadership roles. And for each step up the ladder, there are fewer and fewer women.
I cannot separate my burnout and disillusionment about my working life from my gender. I am also white, cis, straight, educated, and now have enough financial resources to feel a measure of security. I am immensely privileged to be wrestling with one kind of “othered” status and not with the intersection of two or more.
For those women who, like myself, have achieved senior leadership positions there can be a massive cognitive dissonance between how you’re supposed to feel (confident, powerful, and bold) and how many of us feel once we get there (uneasy, undermined, and lonely).
Figuring out how to gain entrée into senior roles can be like trying to hang on to a handful of lake water by squeezing it in your fist—the harder you try to understand it, the less it comes together.
And the most pernicious thing of it is that this subjectivity is dressed up in the language of data. Almost every company claims to be “data-driven” but in practice that only occurs when the data is convenient and bias-affirming.
Self-doubt is part of the human condition, dark triads withstanding. It’s something that men as well as women can struggle with. We all can become habituated to whatever level of success (and income) we have already achieved. There is no rest for the weary for there is always another hill to climb on the horizon. And these fast-paced, competitive industries make sure that next hill is always in view so that you feel insecure with where you are.
During the past few years I came to the realization that the status and power I cared so much about and aligned my self-worth with is—at heart—a pyramid scheme. We are not just encouraged but expected to burn ourselves out, to damage our relationships and our mental health, to base our identities on the fact that we work for a company that would lay us off in an instant to become more “efficient” to please The Street or investors. All so that a few (mostly) white men can become very, very rich and some tech executives (again mostly white and male) become rich enough to afford a single family house in a HCoL area.
By the time you get further down the pyramid to your average individual contributor at your average startup, it’s a few scraps from the table, if anything at all. And while salaries may be better than average at first blush, the effective hourly rate may compete with other industries that are more, uh, reality-based.
Then there are the many inherent tensions and contradictions in what these companies say they want from their employees but in practice abandon when convenient.
They want to hire smart people who are creative, can think and act independently, and who can (famously) “move fast and break things.” But they also want those same people to fall in line when it serves the company (or the ego of the guy in charge). They want to hire people who believe that hard work is correlated with money and position and then seek to simultaneously limit both of those things.
They want to offer you equity at their startup (which is more likely than not to fail) so that they can pay you undermarket at a company that’s one under-performing quarter away from demise. In the current state of tech, they like to disparage senior folks who don’t want to “get their hands dirty” so that they can under-resource you and then blame you for not being strategic. If you’re failing (by their definitions) under near-impossible circumstances, it’s your fault because you are somehow deficient, not because they have designed a poor system.
And if against the odds you do succeed, well then, don’t get too big for your britches, young lady. You met all the conditions for your promotion? Well, we have a freeze on salary increases right now. Keep doing the job we haven’t been paying you for. Got that promotion approved? Good for you! This VP position with 25+ reports pays less than than the 25 year-old individual contributor on the sales team who’s responsible for far less revenue.*
This careful management of expectations—which could also be called gaslighting or workplace negging—is the setup. It’s a tenderizer used to manipulate you into feeling grateful when you’re getting less than you deserve, whether that’s title, compensation, or respect.
If you can’t recognize the manipulation for what it is, it can be easy to oscillate between basking in the (temporary) glow of achievement and a self-doubting pit of despair. When you need that external validation to feel good about yourself, you’re just a rat pressing a lever for the praise and status that only sometimes appears. So you keep pressing it. But boy oh boy, when that reward finally arrives, it feels so good.
But wait! Here, right here, is where there is the most danger to your well-being and sense of worth. Because by year 5 or 10 or 20, if you’re still in one of these jobs, you’ve most likely internalized the absurdist logic of the system. You don’t even need the external pressure to “correct” you because the call is coming from inside the house.
I don’t mean to suggest that these relatively well-compensated jobs are the worst jobs out there or even that my personal experience in tech has been unrelentingly awful.
There are many, many people I would not want to trade places with. I write from a position of great privilege, and for that, I am sincerely grateful.
I have, by many measures, been successful in my career. I am proud of my achievements and I have honestly enjoyed many aspects of it. The two things that I have derived the most meaning from have been 1) learning something new that has allowed a mental unlock to a problem I needed to solve and 2) helping other people unlock those things for themselves.
Despite all of the positives, including the increase in my earnings, I have so much cynicism about and distrust of the industry I have spent nearly 20 years being part of. I certainly have not felt this way for the majority of my time in tech. But these last few years—I can’t unsee that so much of the the industry is built upon an utter Kilimanjaro of bullshit. And the fact that bullshitters keep on winning is demoralizing.
All of this—the BS, the greed, ludicrousness, the workers who are expected to sacrifice their personhood and then are summarily dismissed—is certainly not unique to tech.
But it is the lens through which I’ve experienced this particularly malignant variant of late stage capitalism. I came of age in the working world when hustle culture and “rise and grind” and Gary Vee and Adam Neumann and LeanIn and Girlboss weren’t just poster children of Gen Z cringe but actual aspirational role models.
I didn’t find these things gross 10 years ago (actually Gary Vee was always gross), but I sure do now. And tech hasn’t learned its lesson at all. Afterall, Adam Neumann, tech fuckboi extraordinaire, is like a zombie in a horror film who keeps trying to eat your brains long after you thought he was done for.
So, no, I do not think this ZIRP “backlash” has chastened the industry one bit. The CEO mantra during the last 18 months or so have been “do more with less” to their employees while whispering “profitability” seductively into the ears of investors. That will go out the window when investors release all that dry powder it’s going to be pigs in clover all over again.
I’m sure there will be an increase in hiring. I’m sure many people will be thankful to have a job again (which may have been the point all along).
But here’s the thing. Tech has a huge trust problem right now. And not just with the people and companies they sold vaporware to. The record amount of money locked away, the bipolar swings between “hire everybody” and “fire everybody” of the last few years, the continued layoffs at companies that are “doing just fine,” the reemergence (Surprise, Surprise!) of hustle culture, the ghoulish way investors are licking their chops to see how many workers AI can displace—it’s a cheshire smile wrapped in doublespeak inside of a hall of mirrors.
And a lot of tech workers want out. Instead of smothering the bit of power that workers gained in 2021 (remember the pearl clutching around the “Great Resignation” and so-called “quiet-quitting”?) the manufactured fear and scarcity are creating even more Big Nope Energy from tech veterans, especially from senior women.
It’s a privilege to be able to say no. I have said no to things in the past few years I would have never considered turning down in the past.
It’s scary, but wow, I don’t think I’ve felt so good saying yes to an opportunity as I have had saying no to the few that have crossed my path recently. I’ve had no regrets—even about choosing to get into tech in the first place. Afterall, I’m using the skills and the financial rewards I’ve gained from tech to escape it.
It’s scary to think of doing “something else” when you’re in your 40s. But it was hard to start down this path too. I think getting past the inertia of it and onto the doing is the most difficult part. It’s easy to become paralyzed when you think you have to plan out an entirely different working life.
But I don’t have to do that. 20 years ago, I didn’t set out to become a tech executive, but that’s what happened. I just kept turning toward the things I was most interested in and saw the most opportunity for at the time.
What I know about my path now is that it’s on a trajectory away from Bullshit Mountain, but the principles remain the same: I’ll keeping turning towards what gives me energy and purpose.
* I wish that was a joke but it’s not.