Over the last 9 months I've been steadily spending more and more of my time on things I want to have done. Here's what I'm doing. All the usual caveats apply.

In March, on a whim, I started going to strength workouts twice a week. (We have a gym at the office that's open 24/7, so I asked the coach to show me the correct form and then just started coming there all by myself. This may or may not be relevant.) At first it was a constant struggle to avoid skipping workouts, but after a month-long successful streak, an interesting thing happened: my fear of skipping and ruining the streak became stronger than my fear of the workout itself. Going to workouts became effortless, and skipping them became an act of willpower instead. It has stayed this way since. I haven't yet missed a workout.

After a couple months I said to myself, hey, let's add another habit and see how it goes. I decided to try cold showers every morning. The first time was unbelievably scary and difficult, standing there and shivering, unable to turn on the cold water, but I fought through it and then it became easy.

Skipping ahead, now I have five daily habits that I never deviate from, plus one twice-weekly habit (workouts) and one weekly. I'm spending a little willpower on the newest habit which I added a week ago, but it's steadily getting easier, and the rest are pretty much zero-maintenance.

This approach seems to require a lot of patience and time. Looking back, I couldn't have added the second habit immediately after the first. I would have just blown the engine. I really needed these first months of following one simple habit without failing even once, all the while still being unhappy about my akrasia in other areas.