Miss a day, fake a day, stop using.

It was 9:30pm and I just couldn’t get myself to get changed to workout. I didn’t want my streak to end, so I opened my habit tracker, clicked complete, and quickly put it away. I didn’t feel great about it. The next night, I hadn’t gotten my 30 minutes of exercise in again. This night was much easier. I just clicked complete and told myself I would definitely do it tomorrow. I didn’t.

I didn’t open the app again for a month. When I felt the itch to start a new habit, I looked on my phone and saw that in the past year I’d downloaded five habit tracker apps. Each one started with promise. Better charts, better notifications, better widgets. But in the end I fell into the same pattern. Miss a day, fake a day, stop using. All of them were dressed up in different colors and graphics, but underneath they were the same app. Why had I abandoned all of them?

I realized that two things were happening. One, the dopamine from hitting complete on the app went away as soon as the streak was over. And two, did I even care about the habits I was tracking? So I drank all my water for 10 days in a row, was that making me a better person? I sat with that for awhile and thought, is tracking all of these small habits really making me the best version of myself?

I wanted simplicity, with a little more insight. So I opened Apple Notes and wrote at the top: “Do I feel better now than when I woke up?” That was it. Each night I’d put the date, write yes or no, and a sentence about why. Sixty seconds. After a few weeks I had a long list of yes and no days, and a bunch of small notes underneath.

It worked, but I wanted more. More simplicity, more I could relate to. Then I remembered a coach I’d heard somewhere talking about how you just have to win the day. That was it. I changed the question at the top of the note to “Did I win today?” Underneath, I’d write a sentence about the day. Win or loss.

After a while I had long notes of wins and losses but no real way to read them. Was I actually winning, overall? Were there days that kept showing up as losses? The Apple Note couldn’t tell me. I’d been dabbling in small apps for my family. Earlier that year I’d built one for my son to track his bowling scores over the season. So I decided to build one for myself. Simple, useful, honest.

Win the Week asks you one honest question a week, something like “did I make myself present with my family?” Every night you answer it Win or Loss and write a sentence about what actually happened. The scorecard goes seven games like a series. Four wins takes it. Four losses takes it. Either way you settle the week and start the next one fresh.

That is where I am now. Weekly giving myself a question that I can focus on each day. Truthfully asking myself, did I win or did I lose? No middle ground. Making sure I put down a reason. Again, sixty seconds. The W or L is almost irrelevant. It is the act of logging, week after week, and finding out whether you are actually changing. A week where you honestly lose 3-4 is always better than a fake 5-2 win.