Three years ago, I wrote an article for Buffer about what I learned in my first year of taking my side hustle full-time. I reread it recently, and I thought it would be interesting to revisit the same points here with the context of three more years in business.
Here's what I thought back in year one vs. what I think now!
1) On working vacations
What I thought then: “work from anywhere” sounded better in theory than it felt in practice, and working vacations mostly meant combining the less fun parts of work with the less fun parts of vacation.
What I think now: I still partly agree, but I’ve softened a little. Sometimes a working vacation is better than no vacation, and I do get more time doing fun things if I let some of them spill over this way.
I still make sure I have some true vacations where I’m actually offline, but I don’t mind working from other places as much anymore as long as I know it’s going to feel a little different.
2) On non-linear growth
What I thought then: once the early wins wear off, growth gets bumpier, and looking at the business month to month makes normal fluctuations feel much scarier than they are.
What I think now: I still track growth quarterly instead of monthly and try not to put too much emotional weight on any one month. Seasonality is obviously real, and AI has made those fluctuations feel even more dramatic at times, but I’m still tracking up overall, which is what I care about most.
3) On wellbeing as a business asset
What I thought then: rest wasn’t something to tack on later once I’d earned it. If I wanted the business to be sustainable, it had to be built in from the start.
What I think now: I still completely believe that. I also think this is probably the one I’ve had the hardest time fully putting into practice. I’ve gotten sick a lot this year, and it’s been a reminder that believing something and building your life around it consistently aren’t always the same thing. This is still an area where I know I have work to do!
4) On ditching the 9-5
What I thought then: trying to force myself into a traditional workday just because it looked more legitimate was making me less productive. I worked better once I stopped treating 9-5 as the default I had to replicate.
What I think now: I’ve mostly just doubled down on this. Thankfully, I work with a team that’s pretty flexible, so most days I work from around 7 to 3, take a nap almost every afternoon (!!!), and then do another chunk in the evening. It works so much better for me than the "typical" structure.
All in all, it was nice to reread something older and realize I still agree with the version of me who wrote it. I don’t think I’d write the original article the exact same way now, but I do think I’d land in pretty much the same place.
I'm curious what other people have found here, too - what still feels true a few years in, and what feels more nuanced now?