Get wind in your sails

Thursday, October 23, 2025

Those of us who enjoy optimizing our productivity systems are often at risk of getting distracted. Our system should be a means to an end, but it often becomes the end itself.

A useful analogy that helps keep me on track: focus on getting wind in your sails. It’s difficult to build a well-structured system “in general”, but much easier when you’re actually doing things and building the system around your needs.

There needs to be some activity, action, driving force that meaningfully constrains your productivity system into the right shape. This is what I call the “wind in your sails” - the real action that pushes your system, gives it direction, helps shape it into something helpful for your needs.

All of those content creators showing you their perfect system? The reason their video ended up in your feed is that they spent a lot of time doing the hard work of creating. The system they’re presenting is likely one built to help them scale this hard work. But the hard work came first!

I’m focusing this idea on productivity systems, but it can be more broadly applied to any tool that you use to do your work. All this applies to programmers, for example, when we’re configuring our workflow, our operating system, our editor…

The framing of “wind in your sails” has some nice, subtle effects: