Early startup employee lessons learned, part 2: coping with the coaster

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Sometime last year, an advisor told me that one of the most useful tidbits he’d gotten about being in a startup was that the “roller coaster” description of startups isn’t quite right - it’s not really that you go up and down and up and down. When a startup is growing, it’s that the highs are higher and the lows are lower. It’s less of a roller coaster, and more of a sine wave with increasing amplitude. Somehow, this comforted me.

Coping with the coaster sine wave

As I wrote in Part 1 of this series, the most important thing that helped me cope was recognizing that unless you’re the founder, you can’t change the company. I encourage you to read Part 1 for more on this, but it’s worth reiterating because acknowledging one’s place within a growing company is a pre-requisite for any other coping strategy. Acknowledging this truth helped me let go of the ways I had envisioned myself influencing our company and come to peace with our new growth, culture, and my role in it. That said, I did pick up a few other strategies to help me cope with the emotional roller coaster/sine wave of being an early employee at an early-stage startup. These strategies are what I’ll focus on in this post.

Focus on your timeline

At the beginning of joining a startup, there are what feels like a million possible paths for the company to take. But as the company grows, the options necessarily narrow as you strive find product-market fit and investors ask for focus and demonstrated impact. It’s important to recognize these changes and change your perspective with them. Otherwise, it’s easy to get stuck wishing that things would go a different way, but that route branched off a long time ago on the company’s timeline and is no longer available as a realistic option. It’s easy to give in to the FOMO and want to still be involved in or informed about every project, but that’s become physically impossible as projects have multiplied (for more on this, I highly recommend this popular “Letting go of your legos” post). Or it’s easy to find yourself wanting to do a job that simply doesn’t exist anymore in this version of the company. Just like founders and CEO’s have to change their jobs every six months or so as the company needs different things from them, so do companies change what they need from early employees. It’s important to recognize that and be ready to adapt.

One of the best parts of being an early employee is that you get to be part of exciting conversations full of wild ideas and big dreams of where the company could go. But as the company grows, the people involved in those conversations change, and it’s very possible that you won’t be part of them anymore. This was especially true for me, as my role became consumed by day-to-day operations as we experienced our hyper-growth in a newly-remote working world. It was hard to suddenly find myself so far from the big picture, big dreams conversations I’d been invited to before. But it’s the founders’ jobs to dream - and like we mentioned in Part 1, if they don’t want or facilitate having you in there dreaming with them then there’s not much you can about it. That means that if the company’s growth goes in a direction you don’t love or you start to see some changes in mission that you don’t agree with, it may be really difficult to process emotionally. In general, early employees likely feel the pain of the company’s shortcomings more acutely than other employees, because we were there from the start. The pain of the delta between what could be and what is hurts us more, because we are more acutely aware of all the “what could have been’s.”

In the early stages of startup’s journey, all of the opportunities and timelines are still valid and available. But as the company grows, both it and its early employees must choose between opportunities, picking individual timelines and starting to travel down them. It’s important to not get stuck looking to your side at all the other parallel timelines you and your company aren’t on, because they’re not available - they branched off a long time ago, or were never available in this reality to begin with. I’ve found that the best thing to do is to focus on the timeline you’re currently on, recognize its merits in addition to its shortcomings, and put efforts toward making that timeline the best it can possibly be.

Divest from the mission (a little)

One useful way I’ve found to cope with getting farther from the early stage dreams is to actually divest myself from them. As startups grow, early employees go from being an integral contributor across all aspects of the company to just regular old employees. From the company’s perspective, you go from being key and core element of its survival to just another cog in the machine. So it helps to do the same, and change your attitude toward the company: from a key and core element of your life, to just another part of your participation in capitalism. Recognizing that the job is just a job can be an important way to gain perspective and emotional distance from the sine wave. Of course - it’s still a really great job, ideally with meaningful impact and opportunities for growth, but still a job nonetheless.

Update your comparators

When I’m feeling burned out or stressed, or if startup chaos is generally getting me down, I’ve found that recognizing that it almost certainly could be worse is actually a helpful coping mechanism. Of course, the coping strategy assumes that you do like your work and the work your company is doing, that you enjoy working with most of your colleagues, and have a non-toxic relationship with your supervisor (or at least some combination of those features) - basically, that you do want to stick with this job but just have to figure out how to make it less emotionally draining.

As you grow and hire more people, ask about their horror stories! (This is especially important if, like me, being an early employee at this company is one of your first jobs.) When you vent to them about what’s going on, ask them to compare this situation to their prior experiences. You might realize that your problems aren’t that unique after all, and hearing that can be really validating. Or you might realize that what you’re experiencing is much worse than you thought, which could shed some important clarity on your situation. You might also be surprised - this might be the best job they’ve ever had! In any case, sharing horror stories can provide you with the perspective that while, yes, what you’re dealing with is difficult, it likely could be worse. I found that being constantly reminded of this made it much easier to deal with the hard stuff.

Focus on the baby steps

One concrete strategy I’ve picked up which has helped me deal with situations where I’m frustrated about something that’s out of my control is to focus on the baby step, not the toddler step. When something happens and I get grumpy because that thing could have been done so much better, instead of focusing on how it could be better (which is how things would be, if we were a toddler company), I try to focus instead of the fact that the thing was done at all (which is the first “baby” step we’re at). For example, if the communication of an important announcement is botched, rather than focusing on how poor the communication was, I try to reframe and emphasize that the announcement was communicated at all! Communicating well is the toddler step; communicating at all is the baby step I’m celebrating instead.

Avoiding burnout

Burnout is real, and avoiding or managing it is critical to coping with the early employee startup rollercoaster. For me, burnout hit early and it hit hard - I was operating at above 100% for over a year, and it’s taken me about the same amount of time to get back to a stable relationship with work. As an early employee in a company experiencing hyper growth, I was a critical piece of so many different aspects of our business operations powering our growth, which I imagine is an experience shared by many early employees. If there’s a foolproof way to avoid burnout, I don’t know it - but I have learned some strategies to process and recover.

First, recognize that you can only do so many jobs. One of my colleagues had a mantra that I found extremely helpful: when she said no to something, or intentionally dropped the ball on something, or explicitly decided not to address a problem at work, she’d say: “I could do that, but then it would be a full-time job and I would die.” When you put it that way, the choice is easy: don’t die.

Second, name all the jobs you’re doing, early and often. As I emerged from my most severe burnout, I found that naming all the jobs I was doing (and very much half-assing) was really helpful. For example, for most of 2022 I was a part-time group lead for one of our data science subteams in addition to being a technical lead, my “actual” job. That meant that when I felt bad for not being good at my group lead role, I would remind myself: it’s just half of my job. So as long as I’m doing it at least half as well as my colleagues, then that’s all we can ask for. Early on, this strategy of naming my jobs actually backfired - I would start writing down everything I did and then become overwhelmed with how many things there were and how impossible it all felt, and end up feeling worse than when I started. But I think that if I had started naming my jobs before they piled up, it would have helped me keep tabs on my growing responsibilities, recognizing which jobs I was letting slide and which ones were critical and therefore needed to be hired for. I think it would have also led to more productive conversations with my manager, helping me advocate for myself in more concrete ways than “I’m stressed, overworked, and burning out.”

This strategy feels obvious in hindsight but it took a while for it to set in for me: work intentionally and on your terms. I’ve had slack off of my phone and the red notifications turned off on my desktop for about a year now, and it’s been life-changing for gaining back control of how I interact with work. Next time I’m in a position where I feel that my company is heading into hypergrowth or I’m creeping toward burnout, I will immediately delete all of my after-work notifications and most of my in-work notifications too. Being principled and intentional about whether and when to work after hours and working on your own terms within working hours is key for managing burnout as an early employee. Of course, it’s important to communicate any changes in availability with colleagues so that they know how to reach you after hours if needed, since startups are unpredictable. But otherwise, focus on strategies to hold yourself accountable to respecting after-work hours. I wish I had removed my notifications much earlier, in part because I think it would have helped me get my mental health back much faster. But equally importantly, I think it would have also made it much more clear to my executive leadership just how much work and tricky troubleshooting we were doing after-hours to keep our daily operations running.

I recognize that it’s really difficult to cut the cord in this way, and in fact it felt impossible for me at the time when I needed it most. A huge part of the excitement of being an early employee is being involved in everything. When things are going well at work, it’s fun to operate with a super flexible schedule like back in grad school. And also like grad school, our identities are wrapped up in the work. Furthermore, hustle culture tells us that we should be working all the time, which is resonates even more strongly as an early employee. And in the case of a startup undergoing rapid growth, then it’s so exciting and nobody wants to miss a thing. But to grow sustainably, startups have to improve their bus factors to not just rely on a handful of passionate early employees and instead grow to have fully functioning and appropriately sized teams. Early employees play a huge role in this transformation, but it only works if we set boundaries and hold ourselves to them. In fact, I believe that a key company milestone that nobody really talks about is achieving redundancy for early employees - the sooner you can get in the habit of not being critical, the sooner your company will get there. So take a vacation, uninstall slack from your phone, close your laptop: remember, you’re actually doing your company a favor.

I hope these strategies and mantras are helpful if you are an early employee struggling with the emotional roller coaster of your experience. Or if you’re considering jumping into the journey, perhaps these ideas and those that I discussed in Part 1 can serve as a sneak peek into the types of challenges you’ll face. Stay tuned for parts 3 and 4 on building teams and hiring!