As a single-founder, developer, designer and general biz-dev guy, my to-do list in Basecamp has been invaluable in tracking all the moving parts of an aspiring new startup.

But today, I had to stop and take the time to completely reorganize how I group my tasks in Basecamp. Here’s the story of why.

How I originally used Basecamp To-Dos

I keep a project for each product, and over the past year and change, my to-do lists have served me really well.

I always kept multiple to-dos based on the general area of focus (e.g. marketing, a major feature, a general theme).

Basecamp has been right along with me for the whole ride. But surprisingly, after logging into Basecamp today, I realized that I hadn’t logged in for nearly a month!

It’s not like I was on a vacation over the past month (far from it) — I had been doing lots of work. However, it didn’t occur to me to refer back to my to-dos.

This wasn’t OK though — because I still recognized the restless feeling in my OCD self.

That feeling of angst, that fear that I’ve got lots of activities going on, but I’m not 100% sure if I’m achieving the goal, and I’m not really tracking what I’m doing and where my time is going and this could be bad.

But at the same time, I just couldn’t get myself to start creating more to-dos based on what I was working on.

My new design for to-dos

Upon reflection, I realized that my whole paradigm of working has changed now that I’ve got two products that are beyond just defining the MVP but at a point where they need more refinement and more rinse and repeat.

More concretely, now that both Braintrust and Tout are starting to see some traction, it is no longer about just rolling out the minimum viable product and seeing whether it sticks.

It has become more about setting some specific goals for each product and honing in on the set of tasks that will effectively achieve that goal.

And so, I started to reorganize my to-do lists based on the specific goals I had already set for my products in my head. Once I did this, the actual tasks started flying in.

My to-do list is finally aligned with my mental model, and I knew the move of what needed to happen to achieve each of those goals. Basecamp felt like a friend again.

I split to-do lists into the higher level goals I’ve set for Braintrust — and how the specific tasks can add up to effectively achieving each of my goals.

I think this “new” way will be really awesome in both sticking to my goals and keeping me honest on thinking through how to achieve a goal — instead of just attacking individual tasks that do not amount to anything.

Thoughts/Feedback are most welcome! How do you manage your startup’s to-do list?