The Upside to Falling Off the Wagon

James L. Walpole
On Breaking the Mold
2 min readSep 6, 2017

Falling Off the Wagon, “To cease or fail at a regimen of self-improvement or reform; to lapse back into an old habit…”

Falling off the wagon isn’t fun. It isn’t satisfying to fail at a goal or revert to old ways. And falling comes with shame.

I’ve been trying to build a few challenging daily habits in my life. Daily writing is one of them. So far, I have written and published something every day for nearly four months. I’ll admit it — I feel good about that. But a day will come when I fail to write, and my “record” will come to an end.

What will I tell myself then? Hopefully I’ll look back at this post. In the midst of every loss is a potential victory, and it’s no different with habit-building.

If you’ve built your habits by holding yourself to a daily practice and keeping track of your days-in-a-row self-improvement, you might be missing something important about self-improvement. Self-improvement is not about records or numbers. It’s about, well, improving yourself.

Am I writing every day just for the arbitrary goal of maintaining a record? If so, I am a slave to the habit instead of its master. I’ve let record-keeping become the goal, instead of actual self and life-improvement. I might lash myself to the work and keep going, but my heart won’t be in it.

When that day comes that I let record-keeping become my main reason for writing, I kind of hope I fail.

When you fail after a long string of success in a habit, you learn your real choices. You can either abandon the habit, or you can take it up on its own merits for self-improvement, with no pats on the back or impressed onlookers.

When I fail to write one day, I will have to wake up the next and decide if writing is really worth it to me. I won’t have the promise of a growing record to tempt me. I’ll have only the facts. Will writing today make my life better? If I can answer yes to that, I will be unstoppable. I will try again — and again and again, for as many times as I break my record and fall off a wagon.

And I’ll have learned how to get back on the wagon and start over from defeat — surely the hardest habit to build.

Originally published at jameswalpole.com, where I release a new post every day.

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James L. Walpole
On Breaking the Mold

I enjoy philosophy, music, tech, living freely, & discovering frontiers. College opt-out, @DiscoverPraxis alumnus. Marketing bitcoin payment tech with @BitPay.