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Building Your Life is the Creative Thing You’re Doing Right Now

I caught up with a long-time friend this week, someone who has known me since I was 19, since before I was “in tech”, since before I had my first job worthy of going on my LinkedIn profile. He’s a writer and a filmmaker now, and I love to talk to him about ideas I have for stories and hear about his parallel world to software — he’s creating movies, commercials, storyboards, and other artifacts while I’m creating software, specs, spreadsheets, and so on.

But this week, I described my writing as “not real writing” because I’m not publishing much of it. In fact, I’m slowly and regularly erasing my tweets, which used to be such a fun outlet for self expression, when they get older than one week. I’ve considered making all these blog posts private, or just removing this website from the Internet, but talked myself out of it. In life, I’ve folded myself into a little cocoon to let something new germinate. I’m not sure what that is yet.

“I’m not really doing anything creative,” I told him. “I’ve become a reader, not a writer. A consumer of tech, not a producer.” But he wouldn’t let me diminish myself like that and said so. “Why do you think it isn’t ‘real writing’? What’s wrong with being a reader, or a consumer?”

It’s hard to be confident as I slowly emerge from my cocoon. I feel so raw, so vulnerable and soft, so easily reached right to my core. Whatever I was using to protect myself, to keep myself above reproach, isn’t there anymore.

I also feel like the work I’m doing right now, building software, somehow doesn’t “count” as creative because it isn’t something I’ve founded (even though it is remarkably similar to past projects like UnicornDB and GitSheet, which is why I chose to join the team even before my sabbatical was officially over). I know this isn’t true, and not even rational, but it’s part of my inner monologue that I’m working through.


Sitting in the couch with my dogs this morning, reading The Paris Review and sipping my coffee, I was suddenly reminded of a CEO coaching session where I admitted my compulsive need to make things… even on the weekend. When I was still CEO, this often took the form of cooking elaborate meals, but I also have a long string of projects including paintings, short stories, poetry, journal entries, all sorts of investment analysis and theory backtesting that came from this compulsion. When I compare my creative productivity now to what it was then, I would say the person I am today is super lazy! It’s intentional, but sometimes I still judge myself harshly.

After selling the company and moving to Denver, I have been working on a lot of personal projects but with a more long-range and less manic and compulsive nature. A major part of my journey has been learning to sit still, to waste time, to make a little room to be with my inner voice and not just jump as the first “you should” it throws out to me. You should cook. You should clean. You should take the car to the car wash. You should start a startup. You should take piano lessons. Should… should… should.

It’s not that these aren’t good ideas. In fact, I’d like to do all those things. But there’s an issue of motive that I didn’t examine for a long time. Why should I? What drives me to choose to spend time this way versus that, and will that motivation sustain me long enough to see it through? In part I wonder this because of how tired I got at the end of Mattermark. Partly that’s because M&A is a brutal process that is far less about building new things than selling what you’ve already created. But partly I did get tired, and from April 2013 to April 2017 is only 4 years… which makes me question my endurance. I know startups take longer than that, I knew it going in, and yet I just could not find the motivation to take it further.


“Your life is the creative thing you’re building now, your beautiful house you just bought, training your young dogs, the year of the burger, your personal project to read the Western canon of literature… it sounds like like you’ve gone from CEO to philosopher.”

I smiled at this, and tried not to think about how much less epic it seemed than building a billion dollar company. Where did I pick up this need for the epic anyway, was it a borrowed belief that didn’t get much consideration or something actually important to me now?

But then this morning I woke up and checked my sleep quality with my new Oura Ring, plus the AutoSleep app, plus Gyroscope… all to plan how active I’ll be today, what I’ll need to eat and what kind of workout I’ll do. It sounds so trivial, but stringing together days of good sleep, good diet, and good exercise is one of the things I’m finally taking care of in life. And this is something that millions of people (billions, though most don’t have the privilege of these tools yet) struggle with every day.

And for the first time I’m starting to think about maybe all these people building all these products are building them for me. The founders of these products/companies may have varying aspirations, but I am the **user** now instead of the system (to borrow from Tron) and these things that are being to sold me to make my life better are pretty incredible. Some of them are crap, or at least a waste of money for what they deliver, but I’m not really interested in spending time complaining about them on my blog.

I’ve become heavily invested in understanding how to use these tools to construct the modern Good Life. I’ve also taken the time to survey a lot of the timelessly good things, like books and travel destinations, and made an intentional plan (curriculum?) for incorporating them into my life.

I’m writing this down mostly to capture it for myself, for when I forget and want to start another startup simply to gratify my ego or silence my anxiety. I remember how meaningful my life felt as I worked on my startup and look forward to feeling that degree of meaning again, from daily life.