System First, Goals Later
Khe Hy is onto something in this Quartz article about the importance of a tracking system, even more so than a goal, in achieving success. It’s an idea I’ve been playing with for a while now with noticeable results. But to me, it’s not a system INSTEAD of a goal. It’s using a system to help you refine your goals.
I used to think it went like this:

The problem is, you’re ALWAYS making decisions. And you often need more time and understanding to come up with the right goals.
So now my approach is:

And the update schedule goes roughly like:

The middle part of collecting data points and analyzing and reflecting ad infinitum is perhaps my favorite. See my personal dashboard here.
For now though, lets make the stuff on the vertical — projects and ultimate goals — more concrete.
Projects fall into two camps: ongoing habits and discrete deliverables. They last around 3 months. Here is an example of each:
- Habit - Read articles for 25 minutes as part of a breakfast routine. I chose to focus on this project given my vague professional goals. It’s mostly to keep up with data science (via the Banana Data Newsletter) and visualization and world affairs (Visual Capitalist, Pew Research newsletters). I track my habits in an app called Way of Life. If at the end of the 3 months I feel it’s a set habit, I’ll archive it.
- Deliverable - Learn [x]. Build [x]. Train for and run a race. I write these in OneNote and review them every week. At the end of the 3 months, I archive the projects (now accomplishments) in Trello.
As for my ultimate goals, here is a working picture:

In short, choose projects that feel right, even if you can’t articulate why. Put your energy and tracking system towards reaching them. Then see if your goals come more clearly into focus, and use that insight to come up with future projects.