I’ve tried a bunch of work/life balances over the past 7ish years:
Four of us living & working under one roof, with an unhealthy peer pressure around working harder and longer. We always thought things would get better once we raised the next funding round. Turns out that money doesn’t fix bad culture. We’d moved the company from SF to London to be closer to our customers and I decided to stay there.
We went through YC in summer ’07 and subsequently watched Dropbox, Songkick, and Disqus leave us in the dust as we puttered along for 3 more years.
I moved out of my apartment and into a warehouse, half of which I rented out as coworking space to cover my rent and food. I then spent a year not thinking about money, just working on little projects which caught my interest.
This is when I laid the foundation for my current life, making the friendships and contacts I never had time for in the first company. I also took the time to understand my failures, started giving talks about them, and began writing. Looking back, the year was a big investment in myself which I’m still benefitting from. It was a pretty spartan life (e.g. no cooking or shower/bath), but I never had to work, so that was nice.
Nevada Rob’s after heavy renovations. You can imagine what it started as.
Instead of trying to balance work and life (implying a conflict) some folks suggest going the other direction to create a full and supposedly healthy integration. Anyway, I gave it a try, which led to a lot of startup layers in my life. I was building a startup to help universities spin out student startups. I lived in a startup office. My friends were startup founders. I dated startup girls. I played startup poker. I ate at startup burger night. There was no distinction between work and fun.
Despite how monotonous it sounds, this was actually a great period. Loads of fun and very productive. Unfortunately, I was still just scraping by financially with my live-in-office and at some point you need cash-in-hand.
Startup burger night! A startup meetup without the BS.
Maximum money, minimum time
I knew I eventually wanted to do another tech startup and that I didn’t want to be forced to raise early funding. And that meant I needed a way to generate cash. I explored a bunch of options simultaneously: freelance programmer, strategy guy, public speaker, workshop facilitator, bootstrapping little tech products…
I didn’t quite manage to get it down to the mystical 4 hours, but I did reach a 6-hour work week within about a year. I arranged it so that I worked 3 days a month, travelled a bunch, and used the rest of my time to work on fun new ideas.
I couldn’t have done this without the previous 2 periods, since that was when I built the network I was now cashing in on. It also took about 6 months to learn how to sell myself properly and develop some missing skills.
I think this was in Kiev, Ukraine. Lots of fun, lots of airports.
Minor existential crisis
I had a brief existential crisis around this time. The whole point of making money was to free me to work on startups. And if I didn’t have a startup (the last one had just shut down), what was I even doing? Was I just a consultant? Or a public speaker? Or what?
Meanwhile, I was constantly “busy” with emails and meetings while my most important projects hadn’t moved forward in months. I made a misguided attempt to flee by moving onto a boat, and then realised I could just move to Barcelona instead. Thinking back on four British winters, one wonders why I didn’t do this earlier. It didn’t resolve my self-identity question, but it did get me away from the chaos of the city so I could focus on larger, longer-term projects.
Permanent tinkering vacation
So basically I now do a couple trips per month to London to keep business moving and then retreat back to Spain to give myself the head space to work on big projects. I work in the mornings, prepare some lunch, get a bit of exercise, and then play the afternoons by ear. Usually I’ll work, but I don’t feel particularly guilty if I just go out boozing instead. For my London time, I’ve almost completely stopped taking speculative meetings so I can focus on the 3 or 4 most important partnerships.
The first big “headspace” project was figuring out how to scale a consulting business without giving up the team’s flexible time & location. The second one was writing a book, which I’ve long wanted to do. We also got a publisher for the card game.
You can pre-order it at momtestbook.com. It’s about talking to customers. It’ll make me happy!
Up next, I have a couple burning ideas for little software products which I think I’m particularly well-suited for. I also want to increase passive income. It’s currently paying my rent and I’d like to 4x that by year’s end. It’s early yet, but this feels sustainable, both emotionally and financially. The little projects are fun and the big ones are building toward something meaningful.
The trajectory I’ve been on is basically to maximise freedom of time & place while working only on interesting stuff. It means I have to turn down lots of cool ideas which don’t fit those constraints, but there are always plenty others which do, once you know what you’re looking for.
I guess my biggest realisation has been that you can build businesses designed to maximise happiness instead of growth. It takes work and can still go wrong, of course. You’re putting something value-creating in motion, which is never going to be easy. But my experience with the first company suggests to me that if you don’t explicitly make it the goal, it’s certainly not going to happen by accident.
Mandatory margarita meeting. This is during a London trip, despite the sunshine.
 My flatmate/cofounder had been deported for unrelated reasons.
 I now have funny conversations with my cofounders where we sit around and talk about what we want from the business. But whereas previously, my peer-pressure-addled brain would have said, “I want to be #1 in our industry and growing fast,” we now say things like, “I want the weekend to start on Wednesday.”
Does Microsoft have a Good Strategy or Bad Strategy? Next Post:
Everyone is lying to you (the book)