Dropout Chronicles: Episode 4 — Feeling Undervaluated

Hallie Lomax
8 min readJan 1, 2019

I was having lunch with a friend of mine the other day who had just spent the weekend catching up with old mutuals while in town for the week, and at some point the conversation moved to an apparently reoccurring theme amongst our peer group: feeling undervalued at work.

It felt like the last time I was here, all of the conversations were about, “How can we change the world?” But today it seems like the only question people want to know the answer to is how to negotiate their salary.

After recovering from what briefly felt like a very real personal attack, I couldn’t help but wonder: all of these people spent most of their early careers being told that they were going to be the ones to build the future. They’d started companies, raised who knows how much venture capital, appeared in magazines and television shows to give other people advice on how to be more like them; and now — for reasons both fortunate and un — a lot of us find ourselves working a 9 to 5 at organizations that would hardly notice if we disappeared tomorrow.

And it feels very much like this fixation on salary is just a proxy for the desire to be compensated for the dreams we’ve put on hold to help someone else realize theirs.

And while I have had my fair share of Sillycon Vallie moments over the past few years — dropping out of school, working at a start-up, raising money to start my own, popping up in a handful of random magazine articles— it would be pretty insincere to pretend that my general sense of entitlement stems completely from continuous external validation throughout my adolescence. In fact, kind of quite the opposite.

I spent most of my childhood as a compulsive under-performer and perpetual disappointment to my parents (and really any adult I came into contact with). I refused to study for tests, rarely — if ever — turned in homework, and never read a single book on any required reading list, because I never believed that anything about school actually mattered, and refused to participate in something I didn’t voluntarily sign-up for.

Through all the years of being told at every turn that I was a failure, who would never amount to anything, I think the one thing that made it easy for me to not take it personally was the knowledge that I wasn’t even trying. In my mind, the amount of effort I put into something was what separated me from my friends and peers who were successful, and all I needed to do to join the club was to actually try.

And I think one of the biggest wake-up calls for me in my adulthood was the realization that that isn’t always true.

The tech industry differs from most in many ways, but I think one of the more frustrating aspects of the “meritocratic” approach to title within any given larger organization is that its based on what the employer knows you can do, rather than what it believes you can do. Meaning that the only way to move upward (ie. get a raise or promotion) is to prove that you can already operate at that level, and do a job you don’t yet have.

At a company that spends so much time iterating on their product that it lacks the energy to strictly define roles (most smaller startups), the idea of showing up and doing more than what you were originally hired for is easier to deal with because your spread thin coworkers are happy to give you that work, to take a load off their backs. Its a model in which the amount of effort you put in can be immediately rewarded with even more responsibility, and greater opportunities to learn. But for those who want a job that is “just a job” (one in which you don’t care to learn or do more outside what you were hired for, or have upward mobility), this model will never work because the company itself is so grossly understaffed that, in order to even continue tread water, all of that work has to be done by someone. And if you’re just putting in your 8 hours a weekday while the rest of your coworkers are losing sleep, they’ll all grow to resent you.

This obviously creates a cultural expectation of overworking yourself, which then makes it harder to justify a change in title (because everyone is required to work just as hard as you are, and expected to take on the same level of responsibility, having levels that vary can and will reduce morale at that small of a size). And then, of course, there’s just the reality that smaller startups generally don’t have the funds to sustain a direct correlation between your effort and real-time salary. Equity is the closest trade-off — an ownership stake in the product that you’re working so hard to build, that will theoretically grow in value when/if you all succeed. But imperfect in that it could easily be worthless when the company inevitably goes under (or gets acquired for significantly less than the original valuation).

This is especially frustrating if you ever find yourself working at a startup who’s future you don’t necessarily believe in, which is most of the reason why you should Literally Never Do That — and why any Good Founder will kick you to the curb immediately, no matter how much of a Rockstar you are.

Unfortunately, this problem isn’t necessarily fixed if you ever decide to switch over to a bigger company, where the expectation is that you put in your 8 hours a day — but no more, and no less.

Bigger companies — with their well-defined roles, product roadmaps and OKRs — have a tendency to be overstaffed, in an attempt to maximize the probability of hitting their quarterly goals, at the cost of career stagnation for everyone helping them achieve that vision. Unlike at a small startup, where people are happy to pass some of their work on to anyone with time to spare, a larger company will just barely have enough work for you to do to continue to meet the bare minimum requirements of whatever role you were hired to fill.

Imagine a scenario in which your team of, say, six people have 5 features on its product roadmap for the half. Of those six people, two are senior developers, who are required to lead at least three projects in order to continue to meet expectations in their biannual performance evaluation. Not only is this already impossible (if divided only amongst them, one would miss expectations by coming up one project short), but it also leaves negative room for any of the more junior engineers on the team to attempt to take the lead, and prove that they have what it takes to be promoted to the next level.

The “office politics” people warn you about comes in the form of your colleagues wanting you to fail, to give them one less person with whom to fight over the scraps of available growth opportunity you all have limited access to.

In this environment, the only way to give anyone a way to gain new skills would be to let them come up with their own ideas of what should be worked on. But the risk there is that it puts the predefined product roadmap in an unsteady state, wherein the people who’s jobs it already is to lead are no longer being properly supported by the junior/mid-level employees, who are all burning daylight with side projects that may or may not add any value to the company overall in the eyes of its primary stakeholders.

For those looking to get promoted, this quickly starts to feel like they’re balancing multiple jobs (one at and one above their pay grade), while only getting credited for the lowest level one (read: Undervalued). If at any point they start to feel overwhelmed, they end up having to make a choice: do they prioritize what the company currently thinks is most important, but won’t advance their career; or do they finish what they believe to be valuable first, and risk failing at both in the eyes of their boss.

If they pick the first, they’ve worn themselves out, and all they have to show for it is “Meets Expectations,” and a soft signal to their manager that they have no idea how to operate at the next level (having now failed 1 out of 1 times so far). If they pick the second one, and their side hustle happens to succeed at the cost of their team’s predefined goal, then they run an additional risk of having their coworkers hate them, and negative peer feedback overshadowing the positive impact of their personal project.

This is why there’s such a huge stereotype in the Valley of people joining a Big 5 (or FAANG) company to essentially retire. The only people for whom this model is sustainable are ones who are happy with never having to do more than what they already know how to do, and have no interest in gaining more power than they already possess within the larger entity.

For everyone else, you get high attrition rates. On the other end of the stereotype above is the belief that the only way to get promoted is to hop from company to company (or team to team within a company), taking on higher and higher titles with each jump.

If I had to guess why companies seem to only fall into one of those two categories, it’d be because founders (and investors and board members) put the outward appearance of their company ahead of the internal health. When a startup is still searching with a flashlight in the dark for Product-Market Fit, and every day you go without knowing what that looks like is a investor dollar down the drain, and an unpromising growth graph for the pitch deck you need to raise the next round, you’ll come up with any reason you can to keep costs as low as possible. You’ll only hire people who buy in to your vision, who are OK with being paid below market-rate for doing work well outside of the scope of their immediate skillset. Who will lose sleep without expecting overtime to meet deadlines on overpromises you made to the outside world, because they need that equity to be worth it some day.

But then the moment that you “make it,” and the cash starts flowing, and the term “data-driven decision-making” becomes less about iterating on projects that don’t yet work and more about justifying allocating resources towards ones that you know will, you unleash the floodgates and grow your workforce as fast as you can. You would now rather have too many people on your team than not enough.

I do think its possible for a company to build a sustainable model for both product and personal growth, but it has to be done slowly. You have to constantly be operating with a headcount that’s open enough that your current staff feels like they can fill in the gaps with a reasonable amount of extra effort, but tight enough that no one believes they have to work nights and weekends to stay afloat.

The problem is that the people who end up being the most uncomfortable in this scenario are the only ones with the power to relieve themselves of that feeling (the founders, or general executive team). And while an argument can be made that they’re also the ones who stand to lose the most if things go wrong, maybe that should just be the trade-off for being able to live your dream.

To be continued…here!

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If this is your first time here, don’t forget to checkout Episode 1!

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