This is just a story, not advice, but maybe there’s something relevant. At year’s end I’ll be trading away my location independence for something better.
It’s been a fun stretch. Barcelona was my HQ but I figured there was no good reason I couldn’t travel and work from elsewhere as well. In doing so, I drank tea with prostitutes in Kiev, was stood up for dinner by the Slovenian president, wrote the first draft of my book from a hut in Bavaria, got to whack the gavel at the UN, watched the northern lights from an outdoor hottub in Iceland, and played chess with an old man in Hungary whose only English seemed to be “another shot” and “I win”. Meanwhile, the business has grown solidly and started paying [actual] dividends.
Then why give it up?
For some folks, a successful business is a goal. For others (myself included), the business is just an enabler. If you see your business in this way, then you would prefer that it keeps doing its thing regardless of whether you are working or not. Tech businesses theoretically get this for free once the product is built, since most websites can do their thing without you being on call. But unlike my previous businesses, this one scales with people. And once it outgrew the founding team, we hit a wall. The solution to scaling people is “culture”, which is just a way to spread how the founders work and make decisions to the rest of the team.
Our founders have a history together, so we already knew how everyone worked and remote was fine. But our first hire didn’t, so it wasn’t. Top-tier potential hires have slipped through our fingers simply because we didn’t have a good way to train them. “Just come to Bulgaria for a few weeks” isn’t as compelling as I had hoped.
So hiring is one big reason. Before throwing in the towel, I looked at other companies who have succeeded. A couple solutions exist. The first is for the location-independent founders to hire where they are and spend the first 4-6 weeks co-working with the new employee before traveling elsewhere. You can also do the opposite and bring the new hire to the founders for a month or two. The other approach, unique to the tech world, is to borrow the open-source culture. If the whole team is used to working in that way, new members can plug straight in and may not even realise this is an issue for other companies.
A related problem we hit is partnering with other companies (which is important for us). Even if we could fix all our internal issues, we still need to flex toward the our partners’ ways of working. For example, we’ve set up our comms so we can be away from internet for a week or more without negative effects. But the companies we partner with probably aren’t in the same situation. Plus, starting and deepening a partnership requires trust, which requires facetime.
On a somewhat unrelated personal note, I also suspect vagabonding is a bachelor’s life. Good fun while you’re aligned with it, a bit of a drag otherwise.
With all that in mind, we (i.e. myself and you the reader) are faced with a lifestyle trade-off. Remember we said that businesses are enablers for the things we really want? If our goal is to travel the world and get boozed up in exotic places, then we may as well do it now, even if it caps our business’ growth. Just complete the sentence, “After I sell my business, I can’t wait to…” and then find a way to integrate that with what you’re already doing.
For me to give that up, I’m basically saying is that I think getting my business to the next stage will give me more net happiness than the Mediterranean cafe lifestyle (punctuated by travel binges). Which is obviously a personal choice, but for me it’s right, at least for now, since I’ve started valuing the time to be creative and/or idle more than I value adventure. And I believe that by putting myself where our company can benefit most, I’ll be able to work more efficiently in the short-term (creating more free time) and will be able to grow the team that frees me in the mid-to-long-term.
Happily, I’ve also learned a couple things. Barcelona is great (assuming you live in Raval or Gracia and avoid everywhere else). Travel is easier than you think, even if you’re working. You can get a business pretty far even when it’s a total mess behind the scenes. There’s a strong startup scene in mostly every major city in Europe, so you can stay in the community even if you’re in Malmo or Reykjavik or Tallinn or Sofia or Budapest or wherever.
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