Taking extended breaks
The practical questions about being a solopreneur are my favorite. Last week someone asked:
If you actually work completely alone, how are you able to take time off for vacations? Like one week or more? How do you avoid getting dragged back in while you’re off, or losing momentum when you come back?
I’ve fiddled around with my vacation strategy over time, but here’s what works for me.
By far the most important piece of advice: build a product that makes it possible to have time off. What I mean is that if you build something that sits in the critical production path for a company—like an authentication service—it’s very hard to be unavailable if you’re the only person who can help! In my experience, shipping a developer-tool product that’s packaged as a self-hosted Docker container has been the sweet spot. Obviously it’s not the only way you can find success, but it’s a good marker of a product that’s both high value and doesn’t require true 24x7 customer support.
Speaking of support, decide on a clear SLA and communicate it to your customers in the legal agreement when they buy. My SLA is a maximum response time of 2 business days, even though I’m often faster much faster. It helps set expectations up front and suss out any concerns.
With that out of the way, before I take a longer break, I do a few specific things.
If I’m doing any hands-on work with customers, like a POC that needs a lot of hand-holding, I let them know when I’ll be unavailable except for critical issues. Again, in my experience I’ve never seen anything other than understanding about it. Everyone needs time off once in a while, and all you need to do is be clear about your intent.
I’ll prewrite and schedule any marketing content that has to go out the door. It’s a big upfront push but it’s worth it for the sake of continuity. When the content gets published, I usually take a minute or two on my phone to make sure everything looks right and otherwise move on with my day.
On the sales side, I’ll also prewrite any critical followups and set reminders for when they need to be sent. Again, this bleeds a little into my time off, but it’s part of the game.
I put Slack on my phone, which is the primary place I do customer support. If I’m on the go, it helps me respond faster to anything truly urgent. Interestingly, I don’t have Slack on my phone at any other time, so I don’t constantly feel compelled to check it during a break.
Lastly before I leave, I spend extended time journaling anything that’s on my mind. It helps me remember what the big picture is so I can relax.
When I come back, I scan my the notes I journaled to help me get back into the right frame of mind. I also lean on my workflow to pick up exactly where I left off with every deal, marketing post, and engineering project.
It’s not perfect, but it’s the right set of trade-offs for me between having work independence and real time away.