< What is the Entrepreneur's Journey?

Note: This article is from 2017.

Suggested listening while reading: Hamilton: An American Musical1 - Spotify - YouTube - Soundcloud.

I'm not going to write about the challenges of being an entrepreneur2. There are unquestionably numerous. Many have overcome significant obstacles and enormous odds. In my case, I've been extremely fortunate. Both in the way things have unfolded, but also in being able to pursue work I love.

That's not to say it's not hard work, stress and plenty more. Late nights and often (many) months without a day out. It's not an easy ride. I didn't take a vacation for almost seven years3. When I finally did have one, it took me two weeks to remember how.

But that's a choice I made. Looking back over the last decade or so, it's mostly been fun.

Taking the fun with the not-fun, I'm very different now than from the outset. At its core, being an entrepreneur has uncertainty and a lot of learning. Even when that's "fun" growth, that's still having significant changes in who we are.

The surface changes are easiest to describe. I live in San Francisco now. At some stage I moved from engineering into marketing. Or my best approximation of it. When needed I worked on sales, something I couldn't have imagined early in my career. I went from a previous career in spreadsheets, to neck deep in code, and back to spreadsheets again.

Then there are other changes. How I tend to think about the world. What stresses me, inspires me. Even down to how I like to spend my time.

Water flows downhill. Many of those changes are just time passing, getting older. Yet it's hard to deny how much starting a business has pulled and molded my experience.

One thing that has struck me is how little I thought of those consequences at the outset.

You can't predict the future, particularly in starting a business. Especially a tech startup, which canonizes uncertainty and failure2. Being an entrepreneur is buying into this uncertainty.

Once your idea takes off, it can pull you in all sorts of directions. It feels churlish to expect the path to be exactly as we expect it. Yet, we're good at imagining the kind of business we want to build. The sorts of products, markets. If we're making a bet on mobile, or that blockchain will change commerce. The kind of revenue and valuation we want. Despite all this ambiguity, we can be quite specific about what we're setting out to build.

What I see less of, is being as specific and clear about who you want to be. This will be a commitment that is over a decade, often much more. Jumping in two feet into a startup requires change. Sometimes quite profound change. Some will be good; some will be bad. Some will be neither, but significant regardless.

What is more curious if how blithely many of us enter into this4. For what you're about to start, who will that require you to be?

I'm sure this is true of many endeavors. Writing, art, business, moving country, having a family. Being an entrepreneur has a twist. For an entrepreneur that vision is so external. You're building something external to who you are. But in reality, that's completely untrue. You'll need to flex and break to realize that vision.

If you're embarking on this journey, or in the midst of it, it's useful to pause and think about who you want to be. Try working back from there.

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Filed under Entrepreneurs and Philosophy.


  1. Jennifier Garner getting emotional about Hamilton after Dental Surgery is a hit too. 

  2. Silicon Valley tends to buy into the cult of an entrepreneur. Plenty of inspiration there, but plenty of hubris too.  2

  3. All in all, I feel I got off lightly. 

  4. Particularly in tech, and particularly for first-time founders. There are many examples of people that took a more conscious path. 

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