Solopreneur Sabbatical: Month One

A checkpoint one month in—reflecting on the past month and looking at the road ahead

It’s hard to believe it’s already been a month into the sabbatical. It feels like just yesterday that I sat down staring at a blank screen and wondered what the heck I was going to do with myself.

As it’s my first major milestone, I thought I should take the time to reflect a bit on how things are going so far.

So how am I feeling? Currently, I’d say anxiously optimistic.

Trying to unpack the that sentiment is the subject of the rest of this post.

My accomplishments so far

Let’s first look at what I’ve managed to get done in the first month. Here’s a big picture list:

  1. I made this website.
  2. I’ve written a lot and gotten some positive input on my writing. The Art of Working Alone got picked up by Hacker Noon on Medium and got a lot more engagement than I expected.

    Medium Stats

  3. I made a little mailchimp tool that has helped a very small number of people manage their pending subscribers.
  4. I’ve picked two ideas that I’m allocating the majority of my time to right now (place cards and code stats).
  5. I made a landing page for the place card idea and have gotten some helpful feedback on it.
  6. A friend and I have put together a working prototype of a git analysis tool we think might eventually be useful.
  7. I’ve explored four new hiking routes in the greater Cape Town area.
  8. I’ve managed to catch my first unbroken wave on a surf board.

I’m quite happy with how that list looks! Compared to my expectations it’s a good body of work for a month and a good mix of different things. If you add learning new skills and technologies to the mix it looks even better.

I would say this is where the majority of my optimism comes from. If every month looks as productive as this one I think things will turn out great!

Charting the right course

The anxiety part of the phrase comes from looking forwards, not backwards. The greatest source of anxiety I think has to do with finding the right direction.

See, my first month was full of change and possibility. I had no idea what I was doing and the future was my glorious oyster. I could do whatever I wanted and try a million things and all of that would be some form of progress.

However, as time rolls on by the process of exploration needs to turn into a process of focus. If I want to come out of these six months having actually produced something meaningful I can’t be in “exploration” mode the whole time. I have to pick something and really commit to it.

But what if I pick the wrong thing?

That prospect is scary. And it’s also the case that the further I get down any single product path, the more the other paths start to look more appealing.

This is actually a phenomenon so common that there’s an entrepreneurial term for it. It’s called “shiny object syndrome“—the problem of constantly moving onto the next project instead of taking things to completion.

From the article, “it’s called shiny object syndrome because it’s the entrepreneurial equivalent of a small child chasing after shiny objects. Once they get there and see what the object is, they immediately lose interest and start chasing the next thing.”


Can I avoid making a pile of discarded toys that weren’t shiny enough?

Balancing passion and practicality

A major contributing factor to my current anxiousness is that I’m just not feeling psyched about the two ideas I’m currently pursuing.

Place cards is definitely still in the running as a viable business opportunity. I feel like I’ve done a good amount of market research, I’ve gotten some positive inputs from people in the industry, and I have a strategy I think could plausibly work. I believe that there is at least a niche market there that I can go after, and I think that of every idea I’ve pursued so far it’s the most straightforward path to bringing in actual money.

The main problem with it is that it’s just not something I’m passionate about. Do I want to spend the next 5 months—or longer—figuring out how to build and market something to the wedding industry?

With code stats it’s almost the opposite problem. The project is fun, and building software better is a topic I’m passionate about. And I think I’m uniquely qualified to solve it well.

The problem there is that it’s still not clear what the market/monetization potential for it is. I haven’t yet come up with anything I think my own company would pay for, and that feels like the absolute minimum bar it would need to hit for it to be a viable business idea.

So in place cards I have a promising looking business with questionable levels of excitement, and in code stats I have a questionable business I’m excited about.

And in the meantime there are all these other shiny objects around me asking me to come play with them…

What’s an aspiring solopreneur to do?

The road ahead

As has regularly been the case with this project, my main source of solace is the acceptance of the flexibility of my path forwards. Every decision is temporary, made with the best information available at the time, and able to be changed at a moment’s notice.

Place cards and code stats are my most promising paths forward until they’re not, and at that point I’ll figure out what to do next. In the meantime, my plan is to press on with the current best path forwards and hope that my process continues to guide me to a good place.

Don’t waste several years trying to come up with the perfect idea, because it will probably fail anyways… At some point, you’ll stumble on the thing you were meant to work on and momentum will kick in. Christopher Gimmer, Co-founder of Snappa

If I can have five more months as good as the first one I believe something valuable will be waiting there on the other side. If I can keep making progress towards larger goals, avoiding shiny object syndrome while still keeping my eyes open for real opportunities, and most importantly putting in the time then I believe I can get there.

How am I feeling?

Pleased with the past. Nervous about the future. Anxiously optimistic. Doing the best I can.

Keeping on keeping on. 💪 🚀