Becoming a Runner, Kinda
I’m doing that thing again.
That thing where I wake up from a dream that I was doing something, in this case running, and now I believe that I can be a great runner because I was in my dream.
Running sucks.
I hate it.
But man, I feel good when the run is over.
On the morning of my dream, I ran-walked my way to a whopping 11:51 min. mile. I’m embarrassed to even write that.
The next day, I asked my two oldest girls if they would ride their bikes in front of me while I ran. “I know if I can run behind you, it’ll make me faster because I’ll be trying to keep up with you,” I told them.
Second day mile-time with my girls in front?
10:20.
That’s a whole minute-and-a-half faster than the day before. We celebrated like I had just qualified for the Olympics!
My brain has been processing that little victory in two ways:
First, I ran faster because I was running with people faster than me.
Yes, they were on bikes. Yes, they are a quarter of my age.
But I knew they would make me better because they had the ability to go faster.
So often, we think we have to go it alone. Do the hard thing solo. But it’s not true.
There are so many people out there struggling through the exact hard thing you’re going through. You just need to find them. Some will be further along the leadership journey than you, and some will be running at your pace.
The trick is learning from the ones who are a little faster and a little further ahead. Their example proves to you that the thing you’re trying to do is actually possible.
Second, leaning into the discomfort of running is helping me get better.
Would my mile time have been better on day two regardless of whether my girls were there?
Gosh, I hope so. It couldn’t get much worse.
But the bigger point is this: leaning into something uncomfortable and choosing to do it anyway is the first step to getting better at it.
Running is uncomfortable.
Fundraising is uncomfortable.
Leadership is uncomfortable.
But discomfort is often a signal that you’re growing.
So here’s the question I’ve been asking myself this week: When was the last time you leaned into something uncomfortable on purpose?
And maybe an even better question: Who are you running behind right now that's helping you go faster?
I learned today there’s a running club that meets Mondays and Wednesdays near my house.
It’s truly the last thing I could ever want to do.
But if I want to become the runner I was in my dream, it’s going to require me getting even more uncomfortable and showing up in a parking lot of strangers to exhaust and embarrass myself at 5:45 a.m.
Which, if I’m honest, feels like a pretty good metaphor for leadership.
Growth rarely happens in the places where we feel confident and polished. It usually happens in the moments where we feel exposed, unsure, and slightly ridiculous.
For nonprofit CEOs, that moment often looks like walking into a room full of potential donors and starting conversations that feel awkward.
For entrepreneurs, it might look like pitching an idea that still feels fragile.
For anyone leading anything meaningful, it almost always involves doing something before you feel ready.
So maybe the question this week isn’t just what uncomfortable thing are you avoiding?
Maybe it’s: Where is the parking lot you need to show up in?
Even if it’s 5:45 in the morning.
Even if you’re pretty sure you’ll embarrass yourself.
Because chances are, that’s exactly where the growth is waiting.
Something to consider…
I’ve been thinking about launching a small cohort of nonprofit CEOs who want a safe, honest space to talk about leadership, fundraising, and everything else that comes with carrying the weight of an organization.
No posturing. No pretending we all have it figured out.
Just a room (or Zoom) full of leaders who are willing to learn from each other, share what’s working, and talk openly about the hard parts.
Kind of like a running group… but for nonprofit CEOs.
If that sounds like something you might be interested in, just reply to this email and let me know.
