Until recently, it has caused me quite a bit of stress to see that my startup friends are clearly ambitious, whereas I am not. At some point, as we talked about our businesses, they would become embarrassed on my behalf and say, “Oh, that doesn’t really scale, no?” And very delicately, as if trying to ask whether my grandparents are still alive, they might suggest that it kind-of-sort-of might sound like it’s actually an agency. Which is true! But which is perhaps not so shameful as their tip-toeing implies.
The lifestyle vs. scalable debate has been played out already and I have no interest in revisiting it. What I feel now is more of a general rift between future ambition and present enjoyment. In other words, how many todays will you sacrifice to the altar of tomorrow? Speaking personally, I’m simply not motivated by the promise of the future. At my first company, we always told ourselves it would be “worth it”. But must we wait? There is a relevant cautionary tale of the man who postpones all life’s joys only to die on the eve of his retirement. In a world where destinations are uncertain, you’d better also enjoy the journey.
In practice, I don’t have a goal or a plan except to keep spending my days doing stuff I enjoy. And I trust that doing so will continue generating enough financial freedom that I don’t need to stop. The only real “planning” I do is that if I’m faced with two similarly enjoyable choices, I’ll pick the one with higher serendipity. So all things being equal, I’d choose to go to a meetup rather than watch online TED talks, since the former leaves the door open for unexpected opportunities whereas the latter pretty much always goes according to plan. Similarly, if I was feeling equally excited by both, I’d spend time blogging rather than playing video games.
Derek Sivers recently raised the question of what you would do after you were rich and famous. It’s worth considering before you commit years in pursuit of a potentially un-needed reward. In my case, if I was rich, I would sit in a sunny cafe during the day, reading and writing and thinking and coding, and then get drunk on a terrace with friends and lovers over dinner and board games. And sometimes I would go to a new country and hang out with interesting startup founders. Having lots of money is profoundly irrelevant to that lifestyle. So a bit over a year ago, I moved to Spain and started doing those things and have wrapped enough of a business around my day for it to be sustainable. But still, my insecurity remained.
And then, I found myself in Latvia, drinking with a guy who built 2 or 3 big tech companies. He’d started in the mid 90’s and had been through both crashes. He’d accumulated more money than he’d ever be able to spend and was still going at full-speed; I was trying to understand why he wasn’t just chilling somewhere. I told him where I was at and he was one of the few people who didn’t seem apologetic for my non-ambition. Instead, he said (paraphrased):
I spent a few years feeling the same way. Don’t stress about it. Just enjoy. And one day you’ll wake up and find that you’ve fallen in love with a new idea and there’s nothing you can do other than to go make it happen. You can’t rush this stuff. Most people just haven’t stayed in the game long enough to go through more than one cycle.
For me, this helped. I don’t know if anyone else is feeling like I did, but it was a deep source of discomfort and made me feel quite an outside in the community I love. It was good for me to hear from someone who’s been there that it’s an ebb and flow. Now, when people ask, I’m quite happy to say that yes, I’m taking a couple years off of tech startups. After 7 years of getting beat up by my companies, it’s a well-deserved rest.
In my first startup, I just thought it needed to be big. By my second, I knew it needed to make customers happy. And now I’m finally ready to admit that it’s also okay to choose businesses which make me happy.