Should I Work at Another Startup?

Advice from The Sherwins for February 2019

Climbing Scale Mountain


Hello Sherwins,

I’ve been working at a startup for six months now, and I just found out we’re closing our doors in two weeks. We’ve always struggled to get funding, but the suddenness was a bit of a surprise.

I’m writing because I’m having a crisis over this. This is actually the third startup in two years I’ve worked at that’s failed, the sixth since I graduated. I know that startups are always a risk, all of my friends joke about it, but I’ve been surprised by it every time. I think things are fine and then bam, I’m looking for another job.

I want to do good work, but all of the startups are sorta looking the same. How can I keep doing this when I know I’m just going to be out of a job again in a year? Is there anything that I can do to protect myself? What am I missing?

E in San Francisco

Hi E,

The solution to this is pretty easy: stop working at startups. It’s not that you’re missing anything; there’s just not a lot you can do to protect yourself. If this cycle of failure bothers you, stop doing it. It’s as simple as that.

On second thought, maybe it isn’t as simple as that. Nowhere in your letter do you talk about the type of work that you do. Perhaps your only option is working for a startup. It’s easy for the two of us—for any of us, really—to make assumptions about people based on what we believe are their choices. So let’s start again.

Startups fail all the time. They start with ideas, add money, and cross their fingers that growth happens quickly. They are built for speed and for scale. They are not built to last.

There are some pretty basic questions you should be asking yourself when you’re assessing a startup, before your compensation even enters the picture. Are they solving a problem you’re interested in? What’s the history of the founder? How quickly will you be able to focus more on the job you were hired for as opposed to “wearing different hats”? What ending do they have planned for the company, and how does that ending affect the product, the employees, and themselves?

There are three possible endings for a startup: gaining independence from external funding, being acquired, or folding. Every decision that a founder makes pushes the company towards one of those endings. Sometimes a founder is very clear about this: we’re going public in four years. Other times, a founder won’t say anything, or worse will hide their intentions in flowery motivational speech like “changing lives” or “disrupting industries”.

Folding is usually not the desired end, but it happens often enough that it’s seen as an acceptable part of the tech world, at least the world that is the Bay Area and Silicon Valley. If every startup became independent or was acquired, that entire economic sector would look very different, very quickly. And not in a good way.

Folding only becomes acceptable when it involves transforming what was learned into successful outcomes supported by new behaviors as quickly as possible. This gets bumper stickered into “learning from failure” in the next go around, but as we’ve said before, if your behavior doesn’t change then you haven’t really learned anything.

This is all to get us back to you. You’re not a founder. You’re not making the decisions. You’re just along for the ride. And you repeat the cycle of looking for a startup that might be different this time. That will offer you, if not stability, then something more. But startups are not designed for that. There is no more. Independence, acquisition, failure. Those are the options.

You’re not alone in this. We’ve been told for a long time now that if our work is meaningful that our lives will also have meaning. But having one does not guarantee the other. It’s more complicated than that.

So what to do? If you want to keep going in that world, try thinking about yourself as a startup within a startup. You have three possible endings when you begin. You will make a lot of money, you will get acquired by another company, or you will lose your job. You, as the product of your own startup, begin as an idea. This idea must grow. You need input, funding, and development. You’ll need a plan for this, just like any good founder.

Sure, during the day (and probably at night, and maybe on weekends) you should like the product you’re working on at your employer. You should find that work challenging and your colleagues supportive, and you should return that in kind with quality output. But you can’t neglect your own growth, personally or professionally. This isn’t to say that you need to take a year off to do some soul-searching on a mountain. But if you keep ignoring yourself, when you leave the next startup, you’ll be a year older and not a year wiser. You’ll be one step closer to an ending you didn’t want, but that is yours nonetheless.

Who are you, as an idea? How will you keep your mind and body, the engineers of you, funded and functioning? How will you leverage research to understand the needs of your audiences—your friends, your family, your colleagues? How resilient will you be when another force sweeps in to buy you or try to destroy you? Where is your life going, as a product in the system that is the human race?

Let’s return to your letter now. You said that startups are looking the same to you, E. Do you also look the same to yourself? You’ve been doing this for six years. You’re different now than when you started. It is ok for you to expect more of yourself. If you don’t, this cycle will continue until you finally close the door on startups forever.

You asked about protecting yourself and what you’re missing. To protect yourself, you must grow yourself. Not in the startup sense of improvement or disruption or increased efficiency; neither humans nor human experience should be governed by dialed-in optimizations. Grow as in becoming a presence that enriches the world and that sees itself as linked to that world. And the only thing that you’re missing is you.

All best,
The Sherwins

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Send questions to questions (at) askthesherwins (daht) com. All questions become the property of Ask The Sherwins, LLC and may be edited. Our advice shouldn't be construed as a replacement for the appropriate legal or professional counsel. The advice on this page will pivot on February 28, 2019.