I remained ambitious long after it stopped being good for me.
Ambiton’s upside is the impetus to chase big dreams. Its downside is that it rushes you to such an extent that you end up arriving more slowly. That’s what happened to me, anyway.
I don’t begrudge ambition my first doomed company. I was on an academic track and probably needed a fairly extreme nudge to get me into startupland. But I do resent it for continuing to bite at my ankles throughout the following three years.
As is often the case with first companies, I couldn’t bring myself to cut loose soon enough and ended up far broker than I ought to have been. But instead of taking the time to sort out my finances, I swallowed the stress (mixed into a cocktail you barely taste it) and charged into the next big thing. I lived in a freezing warehouse (not the trendy kind) and showered in the nearby gym (pouring kettle-heated buckets of water over myself but got old fast). I learned that you can fry an egg on a Mr. Coffee heating pad and clutched at some impression of sleep in a hammock strung between industrial pillars. Needless to say, I wasn’t firing on all cylinders in terms of personal productivity throughout that year.
My next two projects were as ambitious (reinventing education) as they were ridiculous. I say ridiculous not because of the ideas themselves, but because of the state I was in. I couldn’t buy food, get sleep, or pay my taxes (which I did eventually take care of, along with 5 years’ late fees). It was preposterous to think I could get any big work done. But in my head, I was on the straightest path, and no amount of sensible suggestion from well-meaning friends could convince me to stray from it.
Once I’d developed some skills, people started wanting to pay me to do stuff for them. They offered good money, but I refused to take any more work than what kept me just above the poverty line. It felt like cheating on my ambitions to give even one more hour than necessary to earning money. But of course, this optimisation just kept me cold, tired, and hungry, exacerbated by the fact that the ideas I’d chosen had no conceivable early revenue model.
Flash forward a few years, and I was deeply embarrassed to have a small business doing nearly a million a year in revenue, because it was “just a teaching business”. As stupendously stupid as that now sounds, it ate at me so deeply that I repeatedly tried to convince my business partners to throw away everything we’d built and begin the uncertain journey of reinventing it as something productised and scalable. Whatever that would be.
Worldviews are stubborn things, hard to shake. I picked up the worldview of “corporate bad, learning good” toward the end of university. Then PG and YC gave me the “scalable startups are the only way” worldview, which I think I internalised as the even more extreme belief that “you haven’t succeeded as a human until you’ve sold a company”. Maybe I never hung out with enough of the bootstrapping or lifestyle folks. Or maybe since London was a younger ecosystem, I was friends with disproportionately many first-time founders whose raw ambition hadn’t yet been refined.
In any case, I eventually got over it. And I looked at my little company, and I was like, this is frickin’ awesome. And I looked at my personal finances (low savings but enough arriving each month from various dinky little income streams), and realised that if I just vacated my warehouse in Shoreditch (the trendy kind this time) and moved to basically anywhere else in the world, I could more or less retire. When I was 24, I’d imagined retiring by 30 after selling my big ambitious startup. In practice, I ended up doing it at 32 without any notable successes to my name (the teaching biz I mentioned ended up shuttered due to shifting cofounder goals).
I’ve spent the past year getting my ducks in a row. Took care of all the lingering admin (like taxes) and dug up all the stressors I’d swallowed or buried throughout my 8 year startup sprint. I learned to sail (top on the bucket list), rebuilt an old boat that I foolhardily ebayed, drafted a couple new books, and completely failed to improve at dota (the video game) despite countless hours of getting my butt kicked. I’m planning to have a go at sailing around the UK this summer (takes about 4 months, I’m told), but other than that the slate is clean. I’ve got to say, it feels good.
And now that my own house is in order, I’m starting to feel the itch to do something a little bit bigger again. Ambition has its virtues. I’m happy that so many people–and especially young founders–feel the drive to dent the world. But I think you’ll be able to do a better, faster job of it if you take care of yourself first.