Productively Miserable: Why Counting Wins Matters in Self-Improvement

“What parts of my life do I need to work on next? Now I can run 5 miles, but what about 10? What new talent or skill do I need to get to the next level in my career?”

Sound familiar? I’ve been gung-ho about self-improvement for the better part of a decade now, and despite much improvement, I’m somehow less content. If something can be improved, that kind of implies something is wrong with it. After years of only looking at the most broken parts of yourself, eventually that’s all you see.

This is very ironic when the same commitment creates positive results in many areas of your life. For a time I actually got really frustrated with some of my friends and girlfriends. I felt like they didn’t understand me because they thought my life seemed great while I only saw what was broken. The thing is, they were the ones seeing clearly, not me. I don’t want others to fall into this vicious “productively miserable” trap that consumed me for so long.

The core problem at hand here is focusing exclusively on the negative. If we only pay attention to things we want to change, then we will completely forget that there are parts of our life worth being grateful for. Things we’ve already polished until they shine. Skills we’ve already built up to an impressive level. Things we never had to change at all. We have to count those wins every day to keep our perspective balanced and healthy.

Journaling is a pretty basic aspect of self-improvement, but I had only ever used it to write about things I wanted to fix – once again reinforcing the negative patterns above. What I started doing recently was a very brief 5-7 bullet summary of each day. No complete sentences, no editing, just what happened and anything I’m grateful for. It only takes 2 minutes right before bed, but the effect is huge. I now have a spotlight on something positive. Most days are full of many small wins. Not promotions or race trophies, per se, but a good dinner with a friend, a productive workday, a deep meditation, and small steps forward towards the big goals you have. 

If you’re serious enough about self-improvement to still be reading, I’m certain you do a lot of small things every day which get you closer to your goals. It’s time to start taking credit for those wins. We can’t just focus on the fires we haven’t put out yet. If that’s all we see then we’ll think we’re in Hell. There’s a lot of good work we’ve done already, and good work we do every day. Pay attention to it. Write it down. Notice the pattern as you consistently find positive things to write about every day. This is an ESSENTIAL part of your mental health. You need to see both sides to the story, because it’s absolutely miserable to bail water out of a boat constantly and feel like you’re never getting anywhere. You need to see the water level go down. You need to understand things are moving forward and you need to count those wins to know your effort is worth it.

Self-improvement is never really done, and that’s okay. There will always be things to work on. But if we don’t appreciate and shine the spotlight on what went well, our worldview slips in dangerous directions. All work and no play makes Jack a depressed workaholic who doesn’t understand how he can work so hard and still feel like a failure. Don’t be like Jack. Count your wins.

Further Reading: If this post resonated with you then I think you’d get a lot out of The Second Mountain by David Brooks. It’s a really deep examination of what makes life fulfilling and what patterns of accomplishment chasing can tear us apart. I still work just as hard as I used to, but this book showed me how to adjust the focus of my efforts to make the process more rewarding. I hope it can help you too.

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