Set long-term goals and created a roadmap

After a hiatus, I'm making time to start working on Get In Touch again. Like many engineers, I'm prone to sitting down and cranking out features. Features are fun! Features are (relatively) easy! Features can be a distraction!

So I wanted to start with a goal to work toward. A long-term goal. But in the past, long-term goals I’ve set have felt distant, and have failed to motivate me. The goal doesn’t feel connected to my day-to-day efforts. So I also wanted to develop a roadmap that made the long-term goal feel relevant and realistic.

I set a goal five years out (somewhat arbitrarily): To have a startup that employs 50+ full-time staff, or has $5 million annual revenue.

To develop my roadmap, I decided to use this algorithm: Break my top-level goal up into ~5 milestones, spaced roughly evenly in time. Then take the soonest of those milestones, and do the same process repeatedly, until the chunks are small enough that they could go onto my to-do list.

For me, here’s what my list ended up looking like:

2025-07-01: At my startup, employ 50+ full-time staff, or have $5 million annual revenue

1. 2021-07-01: Have some web product with 1000+ weekly active users (free is ok)
   1. 2020-07-01: 4 users
      • Allocate substantial time to work on app
      • Start talking to potential users regularly
      • Implement features necessary to make it something I’ll want to use regularly
   2. 2020-10-01: 16 users
   3. 2021-01-01: 64 users
   4. 2021-04-01: 256 users
2. 2022-07-01: Get funding (VC or bootstrapped), and reach 10,000 weekly active users (it’s ok if I’ve pivoted since last year)
3. 2023-07-01: 6 staff, or $556,000 annual revenue
4. 2024-07-01: 17 staff, or $1.67 million annual revenue

I don’t think this is how things will play out in reality; I think I’ll end up adjusting this a lot as I continue to work on it. But it gives me a sense of what sort of progress I need to make in order to hit my goal. That’s motivational!