Intentionally Tiny Side Projects

For the longest time now I’ve been fond of indie businesses.

Most of my friends don’t even know this, but the first real company that I ever started on my own was called SimpleStartup.

It was a web app written in PHP that helped single person companies create a website, charge money for their services, and track finances:

It took me about a decade to realize that I don’t really want to be a start up founder. Up until that point, quitting my job, and launching a startup had always been in the back of my mind. It was an obsession that plagued me.

I find myself in a unique position now, where:

  • I have a a great job.
  • I have no desire to stop working for someone else any time soon.
  • I have no desire to ever launch my own startup again, but…
  • I do still feel a strong pull to build, and launch side projects.

I’ve spent a bunch of time trying to define exactly what I want out of my side projects. I figured I’d share my list here.

What I’m looking for:

  • Something I can do while employed (I’m a great employee, I don’t want to quit, I don’t want a startup)
  • To keep it small indefinitely
  • To stay independent – always own 100%
  • Something I can be excited to work on over the course of many years
  • Where I embrace constraints (out of necessity)
  • A product I wish existed
  • Something around helping designers
  • Simple compelling story
  • Time commitment is no more than 1-2 hours per day
  • Focused on businesses (not consumers)
  • Strong brand – fun, sticks in your head
  • Strong on the design side
  • Long-term play (Since I have a job, I’m not really worried about making money with this)
  • Super niche
  • Solves a real pain
  • Low maintenance users
  • Zero overhead
  • Something I can put on auto-pilot for 2 weeks, or even 2 months (if need be)
  • Minimal feature-set
  • Simple tech
  • Authentic (product, and story)
  • My little Utopia
  • Always create more value than I capture
  • Where I can stay balanced – Spiritually, Physically, and with Family/Work

It’s a big list, but I’ve found that it helps me focus my attention. I’m currently using this list to help define what my next side project will look like.

If you have similar aspirations, I’d love to hear about them!


I don’t do comments on this site, but if you have thoughts, I’d love to hear them. You can email me at

Published by

Dave Martin

Dave is a designer at Automattic.

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