It's Not About Taking Risks

It's about living authentically.

Reckless & Risky

The first job I was offered toward the end of graduate school was at an engineering company in Florida. After the process of sending out dozens and dozens of applications, it was a relief just to find a company interested in hiring me. They flew me down to their offices, poured endless glasses of fresh squeezed orange juice, and grilled me in an interview. I can’t give too many details, as a quick web search shows they’re still up and running, but from the moment I walked in the vibes were off, as the kids say. I never had a good feeling about the people, the work, or their process.

After the interview I sat in the conference room for over an hour while they deliberated. Despite my increasingly desperate reminders that I had to get to the airport to make a flight, they had me wait, alone, while they came to some kind of decision. Finally, they walked in and offered me the job.

It should have felt like a win, but it didn’t — and truth be told it didn’t seem like they were very excited either. On the flight home (that I barely made), an elderly man saw me slouching in my aisle seat, dressed in my cheap taupe suit, and asked what was up. I told him I’d been offered a job, and that I was going to turn it down — even though I wasn’t quite sure why and had no other prospects.

In a near-perfect foretelling of a future meme, he looked at me in shock and said in a thick accent, “You’re turning down a job? In this economy?” He shook his head, returned to his book, and left me alone with my thoughts. As we deplaned a couple hours later, he told me in passing that it was simply too risky to be picky about work. Honestly, in that moment I agreed. It felt reckless to turn down a job. Hell, I’d never made it to the interview stage before. How could I be sure it would ever happen again? I couldn’t.

Yet I did turn them down, and one month later I got an offer from SpaceX. The rest is history.

Living Authentically

I struggle to share stories like this, because they can come off as a case of survivor’s bias. I took a risk, I made it, therefore so should you, dear reader! But that’s not the point. I don’t think you should take risks for risk’s sake. That truly is reckless.

During my sabbatical, as I try to figure out how to keep living a life of spontaneous opportunity, I realized that turning down a job while having no other prospects is just one of the dozens of big risks I’ve taken over the last decade. However, from my point of view, none of them were actually risks; they were each simply radical demonstrations of living authentically.

Even though I couldn’t articulate it back then, deep down I knew I wouldn’t be my best self at that random engineering job on the Space Coast. I would have had to act inauthentically, been around people I didn’t mesh with, and generally changed who I was to succeed. Is that success? For me, it is not.

Does that mean I had to get the SpaceX job to make everything alright? No. I didn’t even know about it yet when I turned down the other job. And if I had never gone to work at SpaceX, I still would have been fine — just as I was fine when I realized I couldn’t be my authentic self at SpaceX anymore and quit that job too!

After I left and moved home to Alaska to be an entrepreneur, I found that I woke up happier each morning on an air mattress, surviving by eating sandwiches out of a cooler in the back of my car, than I ever did waking up in a hotel to build barges to land rockets on. That might sound weird to you, but that’s ok because it was true for me. Things change, people do too.

Enumerating the Risks

What’s funny is that the same people who told me taking the SpaceX job was a risk (a space startup? Are you nuts?) also told me I was risking too much by quitting (leaving a stable well-known company? Doesn’t seem smart!). The change in perspective is enough to give a guy whiplash! It makes no sense! But for people living in fear and scarcity, everything looks like a risk.

To keep this post semi-short, I will now enumerate some of the major “risks” I’ve taken over the last decade, along with an italicized sub-bullet of the kind of feedback I got on those decisions:

• Going to graduate school across the country, in a new place where I didn’t know anyone:

  • So far from home, you’ll be lonely!

• Not taking the first job I was offered after graduate school:

  • In this economy?

• Not taking the second job I was offered after graduate school:

  • It’s a good company with a long history!

• Accepting a job with SpaceX:

  • What? You’re not going to work for GM or Ford?

• Quitting that job with SpaceX:

  • You’re too good to launch rockets? Or you can’t hack it?

• Leaving a first unhappy marriage of convenience:

  • No one is happy in their marriage, that’s why every sitcom shows bored married couples.

• Moving home to Alaska to start a company:

  • SpaceX will hire you back! Don’t throw that opportunity away!

• Shutting down that first company and starting a second:

  • Okay, you tried the entrepreneur thing, and it didn’t work. Don’t dig a deeper hole!

• Trying to bootstrap an aerospace hardware company as a freshly single dad:

  • You can’t build an aerospace company in Alaska. No one has done it. It’s just not possible!

• Inviting a woman I’d just met to road trip around Alaska with me:

  • Are you insane? You don’t even know her.

• Inviting her to move in with me during the road trip and getting married the next year:¹

  • (I didn’t get much feedback on this one, everyone figured I’d truly gone insane).

• Selling the aerospace company I’d managed to build in Alaska:

  • You finally got this company going the way you want it; you can’t sell!

• Quitting that company to take my present sabbatical:

  • Launch is all you know! What else will you do? How will you pay the bills?

That just about brings us up to the present moment. What strikes me reading that list is that on the surface, and from the outside, each of those decisions looks insanely risky! But from my point of view, it was much riskier not to do them.² Not because I knew they’d all work out (some surely didn’t!) but because I actually couldn’t risk not living as my truest self in each of those moments.³

Even the things that didn’t work, or went away eventually, were chances to practice living as authentically as I knew how at that time. Each step was required to find something a little truer further down the road. I couldn’t have built a space company that worked, without first trying to build a drone company that failed. It’s just part of the game. We can’t skip any steps to get to the end, we have to start with the next best move and go from there.⁴ I’ll admit that as I’ve built the muscle it’s gotten easier, but it’s still not always easy.

“So, What’s Next?”

During my little sabbatical, I’ve been catching up with friends, colleagues, and mentors, as well as coaching new entrepreneurs, which has been a ton of fun. But no matter who I am speaking to, the question everyone inevitably asks me is: What’s next?

I don’t know. Truly, I do not know. But the question I’m pondering isn’t “what’s next?” That question implies more, bigger, better, or all the other adjectives generally used to impress others and secretly disappoint ourselves. I think I’m finally learning that life is less about outward success, and more about learning to live as authentically as we can. I also realized that, up to this point, I’ve only truly harnessed that energy in the big moments, like the ones listed out above.

Now the question I ask is, “I wonder what might happen in this new chapter if I learn to practice each moment?”

1. This one still feels crazy to me when I write it out, but man when you know you know! Happy to report that almost five years later, we have a great combined family and my oldest is the proud big sister of a precocious baby brother.

2. Plus, I figured they’d all make great stories :-)

3. Whoever that was at that time.

4. Listen to this poem “Start Close In” by David Whyte