I’d distinguish between hating your current role at your startup vs. hating the startup you’re building. The former is normal, temporary, and has a solution. The latter is a problem.
My dad used to say that the founder is the janitor. You’re liable to do your fair share of unpleasant work over the years. That’s to be expected, and it’s totally fine as long as the business is moving forward. When I was setting up GA London (an events business), a big part of my job involved apologising to our workshop teachers when only three or four students showed up. Or apologising to students when a class with a new teacher was terrible. It stressed me out rather a lot. But it was also temporary. That part of the job disappeared once we had a bigger email list (could reliably fill every class with no hustling) and automated processes around discovering and making up for for bad courses. At the time, I didn’t see it as a transitional period which would be fixed by scale/processes. I thought it was a permanent quality of the job/company, which made it harder to cope with.
A buddy of mine is currently in one of these slogs around team morale. For months, his ex-cofounder has been actively undermining the confidence of his remaining team. He’s spending his time in crisis-mode trying to keep everyone together and moving forward, which is decidedly not what he imagined doing when he started a tech company. But he can take solace in knowing they’ll outgrow it. In his case, the answer is going to be traction. Once they work the growth rate back up (they paused growth to fix activation & retention), either the current team will get re-engaged or he’ll be able to hire a new team.
The founder who asked me this question is stuck in a stretch of manual hustle to build the early user base. She’s doing everything right and getting great early revenue, but sometimes doing things that don’t scale can be so exhausting that you lose sight of the goal for the tasks. She’s now feeling like she’s going to be going door-to-door forever, when really she’s just weeks away from having enough momentum to never need to do it again.
Sometimes there’s no natural “end point” to the painful task, in which case you’ll want to plan a course out of it. At my last company, FC (a service business we repeatedly tried to productise), we were plagued by urgency. We frequently needed information and decision-making that was in each of the four founders’ heads, but our remote working and frequent travel made quick phone calls impractical, leading to a continuous crisis of “I need to reach that person right now.” It sounds like a minor quibble, but when that becomes the dominant experience of day-to-day work, the company isn’t so fun. In our case, traction just made our problems worse, so we had to intentionally slow down and take the time to fix our internal comms and processes. It took some doing, but afterwards we were free to focus on our real goals.
Speaking generally, I’d reckon that if you’re in an “I hate my job” stage at your own startup, you can fix it by either:
- Traction (fixes morale, hiring, fundraising, and do-things-that-don’t-scale)
- Processes & employees (fixes urgency, dull tasks, interruptions, and the stress of repeatedly making certain decisions)
- Time (sometimes the stars align and just make your life unpleasant for a bit, in which case the solution is also time)
- Skills (e.g. if you lack confidence talking to people then doing sales isn’t much fun, which you fix by learning to get better).
Whether the fix will be arrive on its own or require active work, it’s worth figuring out what that day will look like. A realistic view of better days will help you feel like you’re suffering toward a goal instead of just suffering. In any case, it’s important not to confuse hating your current (and temporary) situation with hating your company at large. When you’re feeling bad day-to-day, it’s easy to start second-guessing your whole vision, and that’s no help to anyone.
If you aren’t sure how to get out of the current quagmire, then lean on your advisors and more experienced startup friends. They’ll help you see the light.
But if, on the other hand, you peer into the future and still hate everything about what your startup is doing, perhaps it’s time to find a way to responsibly cut loose. Startups exist in endless varieties and you get to choose; it’s silly to spend your time on one that’s a bad fit for you.
PS. Have a question you’d like my take on? Send it to firstname.lastname@example.org or tweet @robfitz and I’ll try to hit you back with my view.
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