Lessons learned in a year at an early-stage startup

— 8 minute read

Last month, I celebrated my "Bumpediversary." In other words, it’s been a year since I left a job I was unhappy in to take on a broader role in a new-to-me industry at an early-stage startup.

In the last year, I’ve learned a lot—about the stock market and investing, building and marketing a new product, and also about what it’s really like to work at an early-stage startup in Portland.

Being one of the first 10 employees at a tech company is in some ways exactly what I expected and also somehow not at all what I expected. I took some time over the last couple of weeks to reflect on my experience so far. I identified some learnings (six, to be exact) that I think are worth sharing.

Full disclosure, though: I can’t be sure these are true for everyone everywhere. I imagine working in places like Silicon Valley, for example, is very different. Also, I recognize I have a lot of privilege—and that it probably shows up here.

1. Nobody really knows what they're doing. You probably know more than you give yourself credit for. permalink

Imposter syndrome is real, and it’s always the most real for me when I’m venturing into the relative unknown. I didn’t really know anything about investing or stock before I started at Bumped. There are also certain aspects of the job (as the main consumer-facing digital marketing person) I had never done before. I spent my first month at Bumped waiting for everyone to figure out I had no idea what I was doing.

Fortunately, thanks to therapy, previous career coaching, and also experience, I know that a lot of people feel that way. To get through each day, I told myself, "None of us ever know what we're doing." It was calming and it soothed my imposter-like feels.

But I've since changed my mind on that. While I don't think I was necessarily wrong, I wasn't quite right either.

Instead, I think we know a whole lot more than we give ourselves credit for. I started this job not knowing much about the stock market, sure. But I also started it knowing a lot about researching and writing blog posts, creating complex and personalized email campaigns, and crafting approachable product copy.

Next time you catch yourself saying, “I have no idea what I’m doing,” pause and ask yourself if that’s really true.

2. It’s OK to be doing something for the first time. permalink

It is the most cliché but also so true that startup employees Wear A Lot Of Hats™. When you have only so many people but still a variety of types of things that need to get done, you end up taking on a broader range of tasks than, say, at a company with larger teams and more-defined roles.

I regularly find myself doing something I’ve never done before at work. At first, I thought I was supposed to be an expert in all of those things. (See: imposter syndrome.) But it turns out that’s not true. Learning by doing is a thing. Trial and error is a thing. It’s OK to take on a task you’ve never done before. It’s OK to not do it perfectly. It’s uncomfortable—but it’s OK. You’re not the only one. Lean into the discomfort of not being the best at everything.

3. You don’t have to work all of the time to get the job done. permalink

For whatever reason, dudes (and some not-dudes) in tech are really into Elon Musk. I’m not. But that’s not the point. Earlier this year, he tweeted some controversial things about the hours of work per week it takes to “change the world.”

Tweets by Elon Musk: There are way easier places to work, but nobody ever changed the world on 40 hours a week. But if you love what you do, it (mostly) doesn't feel like work.

The idea that if you love what you do, being a workaholic doesn’t feel like work is garbage. It doesn’t matter if you like what you do for work—it’s still work. It will still feel like work. Because it is work. We are more than our jobs. Burnout is real. More hours worked doesn’t equal more work done.

Over the last year, I had several 50-55-hour work weeks. It made me miserable and resentful, so I now have firmer boundaries about how much I’m willing to work.

I tell you all of this to say: not all startups require workaholism. You don’t have to be available all hours of the day. You can take space for yourself to be the human you are, and also do a very good job and get a lot of work done. If you find yourself in a job with unreasonable expectations for your availability, maybe consider what other options you have. It doesn’t have to be that way.

4. Working with a team made up of mostly men is exhausting. permalink

One of the main concerns I had about this job when I first considered taking it was that I would be one of the few non-dudes on staff. Even with the privilege of being white and cis-passing, I wasn’t sure what to expect.

What I know now is that, while I generally feel safe at work physically, I don’t always feel safe mentally. The same subtle stuff happens at this job that has happened at every other job, that has happened in so many different areas of life. It’s exhausting to spend so much time around people who don’t understand my experience with the world—all of which is compounded by the fact that I am invisibly disabled. It’s hard.

The number of womxn on our team has grown in the last year, which is great. I can't wait to see it grow more.

5. If you are chronically ill, you have to advocate for yourself twice as hard. permalink

One luxury of a larger company with an HR team is that they tend to already have processes in place for handling reasonable accommodations under the Americans with Disabilities Act (ADA)—and they fall under the purview of the Family and Medical Leave Act (FMLA).

Employers are only required to provide reasonable accommodations to disabled employees when there are more than 15 people on staff. Thus, I had to wait for our team to grow to more than 15 before requesting an accommodation to be able to work from home when I need to (something that allows me to do my best work when I’m feeling extra awful). Even then, because we don’t have an HR team, I felt like I had to educate more than I otherwise would have had to in order to get the support I need.

And, because FMLA only applies to companies of 50 or more, I know that if a medical situation arises that requires me to take a prescriptive amount of time off, I could lose my job. I don’t necessarily think I would lose my job, but it’s a very real fear that stresses me out.

It’s also worth noting that—with smaller teams—the optics of invisible chronic illness are a bit different, as well. Instead of a private conversation with a manager about when I’ll be working from home or out for doctor’s appointments, I share it in Slack in the same place everyone shares their whereabouts. This visibility makes me worry that my coworkers will think I’m slacking (pun intended) or not doing my part—even though I know I don’t need to be physically present or work the same hours to do my job.

6. For most, working at a startup with healthcare and a salary is no riskier than working at any other job. permalink

A lot of people seem to think that taking a job at a startup is inherently risky. It’s not. ADA and FMLA stuff aside, so long as you have a salary you’re comfortable with and healthcare, it’s not any riskier than working for any other company. Lay-offs aren’t unique to startups; larger companies lay people off all the time. Working for an established organization doesn’t make your job “safe.”

Startup jobs are just that—jobs. They may come with fewer resources (like HR), and that’s definitely something to consider if you’re looking to join one. But otherwise, I haven’t felt like my current job is any riskier than my last one (though I also know I have a fair amount of privilege, and that could be part of it).

There are likely several more things I’ve learned in the last year that I could list out here (like how fast time seems to go by), but I think six is good for now. I’m not very good at ending these sorts of posts, so I’ll just say this: it’s been a good and stressful and exciting year. I’m looking forward to seeing what happens next.