I don’t even think I took myself seriously when I first said, “Hey guys, I’m going to run a mile a day in April.” It wasn’t something I fully thought through, but it seemed like a good idea. Doable even. If I’m being honest, once I started, I wasn’t sure I would make it to April 30th.
If you know me, you know I have a complicated history with daily challenges. I convince myself that ‘this time will be different.’ So I start off strong, I inevitably trail off, and then I’m quietly hoping no one remembers I announced it.
I laugh at myself, but this time it was actually different. And I’ve been thinking a lot about why.
The part nobody plans for
I did not account for injuries. That’s not me being dramatic. I genuinely went into this thinking a mile a day was a slow enough build-up for someone who was not exactly in peak condition. I think I was under the delusion that injuries only really happen to athletes athletes, who put themselves through vigorous workouts every day. Maybe even multiple times a day. Not to someone who is just going on a jog for a mile.
But my knee started talking around day 18. Loudly. Since I didn’t have much experience pushing myself this way, it was the kind of pain that had me hobbling down stairs like I turned 85. I’ll admit my first thoughts were a little on the dramatic side. “Well, this challenge is over. I’d pushed too hard, my body tapped out, and that was that. Game over.”
I did take a few days off instead of pushing through. Then I did something radical. I picked up where I left off. Days 21 and 22 became one run. And when I got back out there, it didn’t hurt nearly as much. I was still in the game.
This might sound obvious to the rest of the world. Rest when something hurts. Pick up where you left off. But there’s this feeling deeply ingrained in my psyche that comes with streak-based challenges where taking a day off feels like failing. Like the whole thing is ruined the second I break the chain. Once one day is off, there really is no point in continuing the challenge.
This is a feeling I have to actively talk myself out of thinking. Starting Days 21 and 22 reminded me that the goal was to finish April, not to limp myself to an injury.
Real talk: if you’re starting something like this, build in the expectation that something will go sideways. Not to be pessimistic, but because having a plan for the hard days is the difference between a setback and a full stop.
I didn’t do it alone
One of the biggest factors for finishing this goal and changing my trajectory to that of a fitness-conscious person is definitely my friends. Specifically, the Jaguares Run Club.
It’s a casual thing. My friend started it as a small way to keep each other accountable. It made it easy to cheer each other on through Strava and social media. We are all so busy that a traditional run club that meets on specific days of the week didn’t totally make sense. And it turned out to be exactly what I needed.
There’s something that shifts when you have people checking in, showing up alongside you, and celebrating the unglamorous middle miles. Sure, sometimes the push came from “I have to go on the run or some people would never let me live it down.” But some days that’s exactly what I needed to push me out the door.
I was especially surprised when people would ask me about my challenge irl. Yes, I was documenting this to the public, but I didn’t think others were actually paying attention. This challenge would have become another abandoned project without them. I’m genuinely grateful in a way that feels hard to put into words, so I’ll just say it plainly: I wouldn’t have finished without them.
If you’re considering a streak or a challenge like this, find your people first. It makes a world of difference.
25 miles and some change
By the end of April, I had run just over 25 miles total. I want to sit with that number for a second because on April 1st, I genuinely would not have bet on it.
25 miles is not a marathon. It’s not going to make any highlight reels. But for someone who started this challenge half-joking, it means something. The math is simple: one mile a day, every day, adds up. Even when it’s slow. Even when it’s ugly. Even when I miss a day or have to group some runs together because my knee staged a protest.
That’s the thing about small, consistent efforts that nobody really talks about. They’re boring in the moment and meaningful in retrospect.
The Cinco de Miler
On May 9th, I ran my first race. The Cinco de Miler here in Chicago.
Five miles. I finished in 1 hour and 21 minutes. I am fully aware that this is not a record-breaking time. But I crossed that finish line, and I thought about how much had changed in 30 days. I felt proud of myself. Even more shocking, I was looking forward to continuing this journey.
Unfathomable.
It changed how I see myself
Something quiet happened over the course of those 30 days. I started thinking of myself differently. Not as someone who wants to be a runner someday, but as someone who runs.
I am a runner.
At the same time, I’m being careful with this shift in identity. I don’t want to burn out chasing a streak for its own sake. The goal was never to prove I could grind through pain. I want to build something sustainable. So now I’m thinking about what balance actually looks like: keeping the momentum without letting the pressure swallow the joy.
My body has a lot to say, if I slow down enough to listen. Running every day taught me to pay attention in a new way. There were days I felt strong and days I felt like I was dragging myself through wet concrete. Learning to tell the difference between “this is hard but good” and “I actually need to rest” is a skill I didn’t realize I was building.
I’m still figuring it out.
If you’ve been thinking about trying something like this, a streak, a daily habit, anything that scares you a little, my biggest advice is this: don’t do it alone. Find your people first. And when something hurts, rest. The challenge will still be there when you get back. But get back to it, don’t let one day off keep you from your goals.
the bold dev 
Leave a comment