What I Learned From Failing Miserably at My #365miles Resolution

The goal was simple enough: run 365 miles in 365 days. What could possibly go wrong?

It arrived, like many of my best and worst ideas, from out of nowhere and full of urgency: I should try to run 365 miles this year.

Let’s be clear, I am not a runner. In 2016, I logged 31 miles according to my Nike+ account. Nine of those were from two races my wife made me run. The rest were largely confined to a 2–3 week window before each race.

I used to be an athlete, though. Also, I’m married to a crazy person who is addicted to working out. You can follow her on Instagram at @fitjuicemama if you want to be subjected to this kind of nonsense on a daily basis:

That’s our bedroom. I pass under that pull-up bar at least 10–12 times a day. I sleep four feet away from an $800 spin bike. I share my home office with a weight bench, complete with squat rack. I have zero excuse to not be in great shape. So why have I been telling myself I need to lose the same 20 pounds for the last five years?

For one, I have two kids. Also, I work a lot. I travel for work. I have a bad back. My double chin doesn’t show up in photos if I crane my neck just so. Whiskey is delicious. Nachos. Plus, there’s that one guy at the pool who is way fatter than me, and he always has his shirt off.

The truth is I am awesome at excuses. And procrastinating. I burned 20 minutes between this paragraph and the last setting up a timer to track the time I spent writing. Which obviously requires going onto Facebook for no apparent reason.

So when the idea of running 365 miles in 2017 popped into my head, I got excited. It was simple, easy to track and would lead to a very clear pass-fail metric at the end of the year. As a closet math nerd, I like statistics.

It turns out that “Run 365 miles in 365 days” is pretty much a perfect goal according to the S.M.A.R.T. goals criteria. To be honest, I just thought it sounded cool. I mean, #365miles? Uh, #boosh. Right?

Now, one thing I’ve learned is that I have zero self-accountability. So if I wanted to have any chance of keeping this promise I had to make it public. I waited, of course, until I finally completed my first run on Day 3.

The foolish optimism of youth

Two days later I ran two more miles — at night! In 40 degree weather! “Feels like 32!” I was on pace. I was committed. I was a runner. But as the saying goes, “If at first you do succeed…just wait for it.”

The incident occurred on a Monday. My oldest daughter’s birthday. I was volunteering at her school as part of the very terrific Watch D.O.G.S. program. I was playing tag with her class when the recess whistle blew.

Wanting to set a good example, I tried to freeze. Instead, I planted my foot on a clump of wet leaves and awkwardly dropped my 20-pounds-overweight frame onto my right foot, pinning my toes back flush against the top of it.

Dramatic reenactment

My big toe was badly sprained. I could barely walk, let alone run. It would be three weeks before it healed enough to get back to running. Even then, it was painful. I was 26 miles behind my mile-per-day pace. A entire marathon behind, with 360 miles to go.

It was the perfect time to quit. I got hurt. It wasn’t my fault. I’d only posted two runs which could easily be deleted. Or I could wait a couple more weeks — get really healed up — then start over with a new Day 1. No one could take issue with that, right?

Instead I went out and ran. I don’t really know why. For some reason I knew that I had to. I posted, “Day 35: 9/365,” and moved forward. I knew I’d never catch up, but I decided to pretend that I would.

It’s now Day 46 and I’m 27 miles behind. I’ve done 10 miles in the last 11 days. I know there is no chance of me actually pulling this thing off – I won’t fall for hubris twice – but I’m not thinking about that anymore.

I’m focusing on smaller bits. Never going more than two days without a run. Only worrying about the two or three miles I owe myself that day. Seeing how long I can go before I falter again. Committing in advance to starting back up when that happens.

By holding myself to the original goal of 365 miles I’m going to see what I can really do. If I get to July and I’m 50 miles behind? So be it. That would only require running 1.25 miles per day the rest of the way to catch up. At that point, I’d be running on legs with 132 miles in them. Totally doable.

Hearing that kind of thinking appear in my head has been the biggest surprise. Something about this particular challenge made it easier for me to adopt the kind of frame the problem as a positive “winning mentality” you can read about in any post tagged “motivation” or “self-improvement.”

I can’t lie. It feels pretty good. As a natural born cynic, optimism always comes as a shock to my system. Becoming the kind of person who actually follows through on things? That’s scary.

Here’s the thing, though. It’s kind of happening.

What I didn’t say is that I made some other promises along with my #365miles resolution. One was to start writing things for myself – I write advertising for a living – and publish seven articles this year. So Day 46: 1/7.

I love golf, so I set a goal of scoring 24 rounds under 90. Realizing that’s not going to happen on its own, I signed up for lessons with my club pro.

Another goal was to get back on stage and do comedy. Maybe improv, since it’s something I’ve always wanted to try. My first “Level 1 Improv” class starts on March 23.

Obviously, I remain totally capable of screwing all this up. Part of me is screaming, “You are born to ruin this, champ! Pull that ripcord and grab a seat on the couch!”

The only thing is, that’s not going to happen. This time, it’s different. God help me, I’m going to become one of those people.

In fact, get ready to spit them bars, Lupe. It’s Day 46 and I’m going for a run.