Staying Productive as a Solo Founder

November 20, 2017 holman

Having a team behind you is pretty nice.

You’ve got one of your engineers that, well, she’s probably one of Those People who sleeps with a copy of RFC 5321 under her pillow. Or you can chat with your designer who can visualize flexbox layouts in his head like Mouse visualizes code in The Matrix. Or you’ll ping your favorite pal in Marketing to help you with this gnarly copy you can’t even begin to simplify. Or, without even being asked, that one odd pedantic generalist on your team will probably be the first to proactively nudge you and volunteer that no, you made a mistake, you were actually thinking about Cypher in The Matrix, not Mouse.

Point is, teams are nice. But you’ve gotta start somewhere. And with half of successful exits run by solo-founder companies, many of those startups start out pretty lonely.

I’ve been working solo full-time for awhile on During, with varying amounts of success and productivity, in between times of less productive stretches. Startups are hard, solo startups are harder, and staying productive in a solo startup is the hardest. Here’s a few things that I’ve picked up that have helped me out.

Leaving things undone

I don’t know who said it first — it’s not a unique idea by any stretch — but leaving work unfinished before I quit working for the day has done wonders for me. (Edit: Hemingway’s Iceberg Theory might’ve popularized it.) This works especially well when I have a trivial 5-15 minute task left over before a natural stopping point. This does a couple things for my brain:

Standups and deadlines

I have more standup meetings now than I ever did when I worked a vanilla job. That’s because I do all my standups in the shower in the morning, and it continues on my commute to and from whatever cafe I’m hacking at that day.

This has been more of a recent addition for me, especially as I move from exploratory hacking phase of a startup to the okay-how-do-I-push-to-shipping phase. It’s basically a challenge: what is the thing or the things that I want to accomplish today? Once I started framing it in terms of “what can I accomplish today?” instead of “what can I work on today?”, I started seeing more concrete progress.

This is kind of only half the battle, though. You also have to hold yourself accountable to what you said: always compare with what you said you were going to do yesterday. I’ve been getting much more into tracking this type of thing (in a tracking issue, or kanban board, and similar tools).

Business concerns aside, writing about what you accomplished in a journal can help a lot, and keep you motivated when you ask the question “what the hell have I been doing the last few weeks anyway?” Because you’re going to ask that question of yourself a lot.

Other aspect about deadlines that’s worth noting: get some friends on board early to badger you with external pressure. It’s pretty easy to lie to yourself about your pacing, but it’s harder to lie to other people. Beyond that, yeah, getting others on board in general is helpful when you talk about MVPs and the efficacy of your product and so on.

Work on what you want

This last one is a little odd, but I wanted to include it anyway.

Obviously you can’t just always work on what you want; only delusional companies would say that. And as a solo founder, the buck stops with you, so you by definition have to do all the stupid bullshit, because nobody else will.

But there were many times where I was working on some aspect of the product that was frustrating, or slow, or just generally something I didn’t want to work on right then. I’ve gotten better at listening to those complaints, because extracting code from your brain when you’re really not into it is not going to end up with great code in the first place.

At times like these, and time allowing, I push it to the side for awhile and try something new. Either literally try something new, some new technology or framework or technique I’ve been wanting to use, or I just shift my concerns for awhile. Work on the backend if the frontend is killing me. Or work on the business if the technology is killing me. Or hell, just work outside and play some soccer or something if the business itself is killing me.

There’s something to be said for focus, of course, but life’s too short to constantly throw yourself at the wall day in and day out. If you really believe in your product and think that generally it’s something that can get you stoked, then taking a break for awhile is usually worth it, and is more productive in the long run. It’ll draw you back in again in the future; don’t worry about it too much.

The Fear

Part of writing this is to give myself a kick in the pants, of course. I’m not as productive or as far along as I’d like. Part of that was a realization that I needed to focus on myself for awhile, which itself helped me get to the pace of development I’m at now. But damn, I think every founder — solo or not — has The Fear. You’re not shipping fast enough, your product blows, what are you even doing as a human being anyway.

But that’s cool. Everyone who’s smarter at this than I am tells me that’s all pretty normal, so I’ll parrot the same advice to you.

Stay on target, enjoy the ride, and build some cool shit.