Time away

In mid-November, I stepped away from work for over two months. Very few of Keygen's customers even noticed. That made me wonder — if no one noticed I was gone, when should I come back?

When my first two kids were born, I didn't feel like I had a choice. With my second, I had just quit my job to go full-time on Keygen, and the pressure to keep the momentum going was intense — like all my output was input-based. I ended up going back too early. Years later, I'd learn my wife felt abandoned during that time.

With my third, things felt different. I felt like I had a choice now. Instead of feeling pressure to immediately go back to work, or to take the minimum time away, I felt like the business could run without me for a little while. (Timing ended up being in my favor here too, landing around the holidays, a naturally slow time of year for sales and support.)

I was running the same business when all three were born, albeit at different stages, and while technically the choice to take time away was always there, things only recently felt stable enough for it to feel like a real option. Before, the stress of being pulled back in made any semblance of having a choice feel like a mirage.

This time, with my third, I was able to take over eight weeks off (closer to ten if you count some sick time), all while remaining a solo founder. I came back not because I had to, but because I wanted to. I had a lot of cool work I wanted to finish — work I found meaningful — and life at home was settling into its new rhythm.

The big difference this time wasn't luck — it was years of preparation and optimization — years of making sure everything will just work.

At some point, I started removing myself from the loop. I:

• Stopped doing nearly all high-touch support and sales, making self-serve the default — for everybody!
• Eliminated infrastructure and dependencies that didn't scale.
• Hired out operational work like bookkeeping and taxes.
• Cleared the barnacles that distracted me.

None of these were necessarily about stepping away. It wasn't because I stopped caring, either. It was about making my workload smaller, bit-by-bit, so that I could have more choice — more freedom.

Then one day, after all of that, I realized — with some gentle nudging from my wife — I had that freedom now. I could step away for a little while and everything should just work.

It started with short three- or four-day vacations, then a two-week one, and then finally, over eight weeks of paternity leave.

Years ago, I thought that would be impossible without first hiring a team to support that kind of time away.

Even with all that, I still had nights of anxiety, thinking I'm due for some downtime. I nearly always had my laptop in tow. But those nights came and went, and those anxious thoughts came less and less.

They came and went because I had already solved the issues that used to pull me back in. While I was away, I did do some writing, and a little low-touch sales and support some days, usually while I was alone with my morning coffee, but everything else… just worked.

The business kept going without me, and people kept paying me.

The effort spent in years prior was paying dividends.

I guess my point is: founders, you can take time away. Sometimes it takes some up-front work — but most good things do. Or maybe my point is that you don't have to do business like everyone else.

If you're feeling stuck, focus on making the business less dependent on you. Work on fixing the things that keep pulling you back in — the things that make your output feel input-based.

It might be the most important work you do!

Sometimes, that just means don't die long enough to reap the fruits of your labor. Other times, it may be changing how you do business to better fit the lifestyle^[1] you want to lead.

My answer may not work for you. But find one that does.

Then, take a step back. And see what happens.

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[1]: In hindsight, building such a mission-critical business like Keygen wasn't the perfect choice for work-life balance — but it's worked out okay!

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This is an expansion of a thought from a HN comment.