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Seed: A series about tech startup careers. Issue #1.

In the Spring and Summer of 2022, I was underemployed in a job that was sucking the life force out of me. I had virtually zero challenges, a minuscule impact on the business at large, and I just wasn't connected to the work. Some may be happy making just over $100k and only working my 5–10 hour weeks, but I wasn't. I fantasized about using my extra time for writing, growing an audience, building startups, etc. But I found myself wasting it instead because this job was so misaligned with my needs.

So, after years in that job, I finally decided it was time for something new. After what ended up being almost a year of soul-searching (and a five-month sabbatical), I realized what I was looking for: an engineering role at a seed-stage startup.

This is the company I joined in January of this year (scroll down to see me in the list of team members as the second Founding Software Engineer — yes, I was employee #2).

Choosing the startup route over a more established tech company comes with some sacrifices. I would estimate that I'm sacrificing approximately $80k/year in compensation and 5–10 hours/week of extra work (or 250–400ish hours/year) by working at a seed-stage startup vs. working at a larger tech company (and I think I may well be on the low end).

That’s a steep cost, but the benefits are worth it. At the end of the list, I'll share my valuation of what I considered these benefits to be worth (with explicit numbers), so stick around for that.

1. I Wanted to Feel Empowered at Work.

I felt so siloed and unimportant in my last job (and the one before that), and in this job, as one of just seven people working here, my impact is considerable. For instance, one of the first things I did at this company was build our whole sign-up and welcome experience. I get to completely own that experience, from design through execution, and that's just never something I could have done at my last job.

This kind of autonomy and ownership is invigorating, especially for someone coming from a huge organization with a lot more cooks in the proverbial kitchen. But this can also be a tough thing to adjust to. I know I had to go through a few months of adjustment as I learned to work better without rails, remove my ego from my work, and flex my skill set across more disciplines.

Ultimately though, I'm probably a 2-3x better engineer today than I was just four months ago when I joined my current company. And that's what I was hoping for.

2. I Had My Sights Set on Starting My Own Business Someday.

I’ve always known I would start my own business(es) someday, and I figured that working for an early-stage company was the best way for me to get some related experience and exposure that could facilitate those dreams.

Working here, I'm exposed to essentially any aspect of the business I want, from finding product-market fit to marketing/sales to fundraising and more. This experience will be invaluable when I start my own companies.

And it’s not just the exposure to building a business. It’s also the connections I get to make with both my fellow early employees (who share some of my values, given we both ended up in a startup) and my company's founders. And given my experience so far, I think my founders will be more than happy to help me out in the future, with investor introductions and other professional introductions, that may be critically important to starting/building my own business when my time at this company is coming to its end.

3. I Wanted to Be More Than Just an Engineer.

This is related to the previous point, but I wanted to experience a broader set of responsibilities and job types than just being an engineer. Specifically, in recent years, I've considered making a career change to Product Management and working at this startup is giving me exposure to aspects of that job while still letting me remain an engineer.

And as I continue to grow with the company and embed myself more and more into our product, I suspect I’ll get more and more opportunities to take on Product responsibilities in addition to my engineering responsibilities. This means I can try out a new role without committing to it.

4. I Wanted to Advance To Leadership Quickly.

I was a little over five years into my career when I joined this company, and I felt that I still had several gaps in advancing to a senior-level engineer, let alone reaching for a leadership position where I want to be. I also wasn't getting any closer or closing any of those gaps at my last company, and because of that stagnation, I felt like I would never level up and meet my true potential.

Now, though, I feel very differently. Leveling up feels inevitable, as my pace of learning and growth is several orders of magnitude greater than before. And in a place like this, as the company grows through its first few funding rounds, I think I can even end up finding a higher-level leadership position opened up for me if I advocate for it and keep showing up as best as I can.

Putting Numbers to It

Earlier, I said that I was sacrificing about $80k/year in compensation and an extra 5-10 hours/week of work by choosing to work for a startup vs working for a bigger tech company. For the sake of simplicity, let’s boil that down to $110k/year in lost value on comp and work/life balance, combined.

Obviously, I did the math and decided that the benefits of startup life were worth more than that, but I’m going to put some hard numbers to each of the above benefits as a point of comparison. This is not scientific: it’s purely my gut instinct, but it’s also fun.

1. Empowerment: $60k/year. That’s roughly the amount I would trade for my level of empowerment now.

2. Startup environment/business lessons: $90k/year. I highly value this experience as I think it’ll pay many, many orders of magnitude more dividends in the future.

3. Getting to explore other roles: $30k/year.

4. Leveling up quicker: $50k/year. The value of the time saved in leveling up, in terms of additional future earnings and better inner alignment with my career.

5. Equity: $15k/year. What I feel my level of equity is worth in terms of being a lottery ticket. [I didn't talk about equity in this story, but you can read more about my take on startup equity in the second issue of Seed].

Total: $245k/year, which means a net of $135k/year benefit vs. working for a larger tech company (for me).

What About You?

If you’ve been thinking about a career change lately and have been considering working for an early-stage company, I want to hear about it. Drop a comment on this story with your own numbers for the above criteria.

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