I’ve set a lot of goals in my life: run a hundred miles, help build a trusted company with my dad, and raise five incredible kids who actually like each other. Just to name a few. They’re the big picture, ambitious goals that you’d see someone put on a vision board.

And look, those goals are great. I’m not knocking big goals or aiming high. But you know, a goal without the right process to support it is about as effective as wishing on a star. Realizing that is when I started falling in love with process goals, not just outcome goals.

For a long time, I thought success looked like ease. I wanted to remove every obstacle, optimize every system, and protect myself from uncomfortable jams. In a way, it made sense. I still understand the impulse. But I also realized that looking for ease couldn’t possibly prepare me to be resilient when the rock met the hard place.

Since I had that wake-up call, I've been deliberately choosing hard things: things I'm not sure I can finish, situations where the outcome isn't guaranteed, physical challenges with my ego on the line. 

It’s absolutely one of the best business decisions I've made.

What’s the first image in your head when you think “leader”? I know a lot of people will instantly think of big stages, flashy hype moments, and the electric energy of a great conference speech. And don’t get me wrong, those moments and those people can be effective and inspiring. 

But it’s really just a small sliver of what solid, lasting leadership is. In fact, I’d argue it rarely looks like that at all.

Some of the most trusted leaders I know aren't the loudest people in the room. They're not the ones commanding attention at every meeting or leaving people energized after every conversation.

Skipping meals seems like it could be a net win. Fewer calories in, same energy out — simple math, right? The logic made sense until I started paying attention to how my body and brain reacted to it. 

(Not well, if you were wondering.)

If you've ever tried to power through a long run after skipping breakfast, you know what’s coming: your legs feel heavy, your head goes foggy, and that creeping irritability that has nothing to do with the hill you're climbing and everything to do with the fact that your tank is on empty.

Skipping meals doesn't make you leaner or more disciplined. It just makes you less effective as an athlete and as a professional.

Winners never quit—right?

Oh, but also, know when to cut your losses.

We’ve all heard it repeated like gospel, and both can’t always be right. Is it better to stick it out and see, or make your exit when things start heading south? 

I’ve done both in my career and in my personal life, and not always the right way. Quitting things I should’ve stuck with and realizing too late that I should’ve walked away sooner. Most of us will get it wrong throughout our lives (I know I have), so it’s important that we high-achievers learn how to tell the difference.

I've been an athlete most of my life. Playing soccer through college, coaching for 25 years, running ultramarathons, logging four or five miles most days. With all that going on, I thought I understood my body pretty well.

Then I turned 40.

My body started telling me in no uncertain terms that I did not, in fact, have it all figured out.

Not all at once—that's not how it works. The signs were gradual at first: recovery took a little longer, my energy wasn't as automatic as it used to be. I'd eat the same way I always had and feel... off.

January in Memphis means gray skies, cold rain, and that nagging voice telling you to wait until March to get serious about training. I hear it every year, and every year, I ignore it. 

Most runners I know treat winter like a grace period—a few easy months before the "real" training starts in spring. And look, I don’t blame them. As I’m writing this, Memphis is under a rare “Winter Storm Warning,” which means snow and ice. Not exactly our forte down here.

Now, am I going to go run in that? Unlikely. I’m not suggesting we forgo safety in extreme weather conditions. That’s just asking for an unwelcome injury. But uncomfortable conditions are a different story.

It doesn’t matter if we’re talking about ultramarathons or business ventures: the people who wait for perfect conditions rarely achieve what they're capable of.

I don’t know about you, but sometimes it seems like we perceive time at vastly different paces. December goes by in a flash of holiday cheer, while January is a cold, miserable slog. I swear this month should’ve been over a week ago, but here we are.

Still in January.

That snail’s pace can make everything feel a lot harder than it should. If you're leading a team right now, you might be seeing the signs: slower response times, shorter fuses, that glazed look in Monday morning meetings.

We're barely three weeks into the year, and some of your people are already running on fumes.

I used to treat January like some kind of corporate New Year's resolution—load up the calendar, commit to everything, convince myself this would be the year I finally got it all done.

Then I'd hit a wall mid-February, wondering why I felt like I'd already run a marathon when the year had barely started.

Sound familiar?

I finally figured out what I was doing wrong after the humbling experience of dropping out of the Keys 100 at mile 60. Turns out, the same mistakes that made me bail on that race were the exact ones I was making in business every January.

Most high achievers I know struggle with the same thing: we're terrible at quitting.

We're wired to finish what we start. We've been conditioned our entire lives to see quitting as failure, to push through pain, to never give up. That mindset serves us well most of the time, but it can also trap us into pursuing things long past the point where they make sense.

I've withdrawn from races. I've exited business partnerships. I've discontinued services that no longer align with our direction.

Some of my best decisions have been knowing when to stop—but it took me years to develop a framework for making those calls without ego getting in the way.

January rolls around, and everyone's talking about clean eating, detoxes, and dramatic diet overhauls.

I get it—after weeks of holiday meals, family gatherings, and being way too full of cheese, the temptation to go all-in on a restrictive plan is real. But let’s be real: the nutrition resets that actually stick aren't about punishment or perfection. They're about getting back to the fundamentals that make you feel sharp, energized, and ready to perform.

This means reclaiming the mental clarity and physical energy that got buried under the charcuterie board.

Every December, I block out time on my calendar for the most important meeting of the year. No clients, no team members, no agenda items that someone else set. Just me, a notebook, and a few hours to think clearly about where I've been and where I'm going.

I didn't always do this. For years, I'd roll from one year into the next without really pausing. Sure, I'd set some vague goals, maybe jot down a few intentions…and then get swept back into the current of daily demands. By February, I couldn't remember what I'd even wanted to accomplish.

And I eventually realized that approach doesn't work when you’re serious about building something that matters.

I got passed by a guy who had to be in his seventies.

I was early on in my ultramarathoning journey. I'd trained for months. And at mile 18, this man shuffled past me like I was standing still. His form was efficient, his breathing steady. Mine was neither of those things.

My ego wanted to speed up. To prove something. To at least keep pace with a guy who probably had grandkids my age. Instead, I watched him disappear up the course while I kept plodding along at my own struggling pace.Woof. That was a blow to my ego.

I said yes to everything for years. Board positions, speaking engagements, networking events, consulting calls, race invitations. If someone asked and I could physically fit it in my calendar, I did it. 

After all, that's what driven people do, right? We show up. We deliver. We don't leave opportunities on the table.

Then I noticed something…unfortunate. My best work wasn't happening in all those meetings I'd squeezed in. It was happening in the margins I'd accidentally left open: the early morning hours before anyone else was awake and the rare Saturday afternoon when nothing was scheduled. 

The quality of my thinking, my leadership, even my training—all of it suffered when my calendar looked like a game of Tetris with no gaps.

The word "no" might be the most important tool in your arsenal as a leader, parent, or athlete. But for high achievers, it's also the hardest one to use.

The alarm goes off at 5 AM, and it looks like midnight. I can see my breath in the bedroom. My running shoes are waiting by the door where I left them the night before, but the bed is warm with the weight of winter blankets. Wife snoozing beside me. No race on the calendar. No training plan to follow. Nobody’s expecting me to show up.

I don’t really have to get up and run. Right?

This is December in Memphis, and these mornings tell me everything I need to know about discipline.

I’ve made some of my worst business decisions at 9 PM on a Thursday after a day packed with meetings, fires to put out, and noise from my personal life. I think we’ve all been there, regardless of our position. 

The problem isn’t necessarily that we’re making decisions when we’re tired. That’s unavoidable when you’re in a leadership role in a business. The problem is that we don’t adjust our decision-making framework to account for our depleted state.

I was talking with one of my colleagues last week who was beating himself up over a deal that fell apart. He kept replaying every decision, looking for the fatal mistake, convinced this one failure might define, maybe even sink, his career.

I recognized that spiral immediately. I've been there more times than I can count.

With Thanksgiving around the corner, I've been thinking about failure differently. Because, really, gratitude isn't just about celebrating what went right. It's about recognizing that some of your most important growth came from the moments when everything went sideways.

Most people think ultramarathons are about pushing through pain. They're not wrong, but they're missing the more important part: knowing when not to push.

I've run enough long races to understand that the ability to suffer isn't what separates finishers from DNFs. It's the ability to recognize when your body needs you to back off, refuel, or adjust your pace. 

Runners who ignore those signals often don't make it to the finish line. And guess what? That same pattern shows up in business leadership, but most CEOs don't recognize it until they're already broken down.

I used to think work-life balance was something I was supposed to achieve. If I just worked hard enough, planned well enough, or optimized my calendar correctly, I'd finally reach a state where everything received equal attention, and nothing fell through the cracks.

That was exhausting…and it never really worked, either.

The problem with "balance" is that it implies everything should always receive equal weight. That on any given Tuesday, my five kids, my responsibilities at REI Nation, my training for the next ultra, my nonprofit efforts, and my marriage should all receive the same focus and energy.

Most executives I know are constantly optimizing their businesses by refining processes, developing talent, and improving systems. But when it comes to their own development, they rely almost entirely on professional experience and the occasional book.

The most effective leaders I've encountered all have something in common: they're training for something outside of work. Not just casually interested in it: actually training with a goal, a timeline, and a plan.

It could be a race, a musical performance, a strength milestone, or fill-in-the-blank with your goal of choice. The specific challenge matters less than the structured pursuit of it.