What can you learn in the pain cave?

Happy Wedsnotruesday!

Yes, it's Wednesday, not Truesday. I'm a day late.

This happens from time to time, but as I always say, it's how you know that I'm writing you fresh content each week and this isn't some AI bot of some recycled email.

Life's been a little harried lately. January and February are a busy season for sales kick off meetings (SKOs), and I've been doing a lot of them. Between Transunion, IBM, Charter Oak Financial/Mass Mutual -- "HI!" if you were in my audience and new here, please write back and say WHAT UP! -- I've been on my toes.

Like my newsletters, I customize every talk. So, it's been... a lot.

But, I'd never complain. I am lucky to do what I do. And, I worked hard to do what I do.

I've also been working hard to train for a marathon -- well, sort of. I'm writing this now from 35,000 feet, en route to Tokyo, to run my sixth (and final) World Major Marathon. (My husband, Mr. Hot Stuff, is probably laughing his ass off with my "final" statement there. Hi honey, I'm sorry, I'm me. Forever and always. Love you.)

Things didn't really go as planned with this training though. Just before Christmas, I had a back spasm that laid me so low that I could barely walk for a few weeks, let alone run. So, if I'm being truly honest, this isn't going to be a great experience.

In fact, it's going to suck donkey balls.

It meant I head to drastically reset my expectations of what success looks like.

Four hour marathon white whale? Still elusive.
Getting back in the best shape of my life? Nope.
Finish feeling strong and powerful? Not happening.

But, I will finish. And to do that, I'm going to have to rely on some pretty serious mental conditioning, especially in the depth of the pain cave.

What's the pain cave?

The pain cave is the depth of despair, the "embrace the suck," the "I just gotta get through this" part of any growth process. It's there you figure out what you are really made of, and what you can do.

I wrote about it at the end of Wonderhell. Write me back, and I'll send you the story.

So, what can you learn about yourself in the depth of the pain cave?

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1. What Defines You?

Think about anything you ever worked hard to earn for yourself, because you cared about more than anything before. Were you proud? Did you have to dig deep? Did you have to keep going? Did you have to earn it?

No one gave it to you. And the motivation to continue, even when every part of you was anxious and exhausted and uncertain, had to come from you and you alone.

You had to earn it. And it taught you that you can do more than you ever thought possible.

Because what you earn defines you, but not in the way we’ve been taught.​

It turns out that it’s not about the “earnings” but what we actually earn — what we actually fight for, when we do hard things — that defines who we are and everything we can do next. And, what a gift that those earnings are limited only by our own courage to push our own previously held ideas and boundaries.

2. What Does This Have to Teach Me?

During a marathon, mile 20 is where it all goes sideways. Your brain starts throwing a full-on tantrum screaming "Oh my god, are you crazy? What were you thinking? Everything hurts, you are dehydrated, muscles are failing, you might pee yourself, or worse. You are going to die out here!”

At Mile 20, the life lesson you learn is discovering what you are made of. Your brain will lie to you every single time. Let’s face it: running 26.2 miles is ungodly, unhealthy, and downright mentally unstable. And yet, it is a triumph of humanity that few have the mental and emotional fortitude to withstand.

You’ll notice I didn’t say physical fortitude. Here’s why: anyone — obvious injuries and health histories notwithstanding — can train to cover 26.2 miles. But not everyone can bring the heart to do it.

And, what else does your brain lie to you about? What other things do you quit because you just don’t know, you aren’t exactly sure, you worry it won’t work?

Your brain will lie. Your heart will not. Dig in, one foot after another, and keep on going. You got this.

3. How Am I Growing?

Everyone has a pain cave. Maybe yours isn’t in mile 20 of a marathon, but in the sleepless nights of a startup, the rejection letters of a job hunt, or the impossible deadline at work. The pain cave is where you meet the version of yourself who wants to quit—and the version who refuses to.

This isn’t about suffering for suffering’s sake; it’s about what happens when you push beyond the moment you thought you couldn’t survive. That’s where growth happens. That’s where resilience is built. That’s where you realize you are capable of more than you ever imagined.

The pain cave is not where you stop. It’s where you transform.

4. What's Louder, My Doubts or My Potential?

At the hardest moments in life, the voices in your head get loud. “You can’t do this.” “You’re not strong enough.” “What if you fail?” These voices aren’t real—they’re just the echoes of past fears, old insecurities, and outdated beliefs about what you can and cannot do.

But here’s the thing: your potential is louder—if you let it be. Every great accomplishment in history, in sports, business, or life, was achieved by someone who heard those same doubts and decided not to listen.

You don’t need to be fearless. You just need to make the choice, in that moment, to trust your potential more than your fear.

5. Am I More Compelled By the Finish Line, or Who I am Becoming as I Cross It?

We all set big goals because we think the reward is at the finish line. The job, the medal, the degree, the achievement. But the real gift isn’t crossing the finish line—it’s the person you become along the way.

The version of you who dared to start. The version of you who kept going when it got hard. The version of you who ignored the doubts, took the risk, and proved to yourself that you were capable of more.

The finish line is just the moment the world sees what you already discovered about yourself. And that discovery? That’s the real win.

Fuel for the Finish Line: My Go-To Pump-Up Songs

You know that saying, you’re the average of the five people you spend the most time with? That's actually bullshit. The dude made it up. There is no science behind it.

There is science, however, behind the fact that ideal running cadence is 180 steps per minute. So, my running mix? Yeah, it's 90/180bpm. When I'm teetering between “wow, I’m amazing” and “dear god, why do my legs hate me,” or especially, "why on earth am I even doing this?" you better believe I curate that input like my life depends on it—because, let’s be honest, at mile 20, it kind of does.

For me, the music is everything. It’s the beat that gets me moving, the bass that keeps me steady, and the lyrics that remind me I’m not just running this race, I’m conquering it. So, in case you need your own personal hype squad, I’m sharing the playlist that takes me from pain cave to power mode.

And, by the way, if you have any good wishes or hopes or motivation for me to add to Sunday's slog of 26.2 miles, please -- by all means -- send them my way. Songs, movies, prayers... anything you got. I'll need 'em!

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