When Was the Last Time Reality Tested Your Confidence?

Recently I was talking with a friend who’s a black belt instructor at a martial arts school in London.

He was telling me about a rough day on the mat.

One of his good buddies had really put it on him during training.

And I mean really put it on him. One of those days where nothing works. Every time you try something, your partner has the answer. Every escape gets shut down. Every opening closes before you can get to it.

You know that feeling?

Maybe you don’t train. I’d bet you’ve still had that day.

You’re pretty good at something. You’ve put in the work. You’ve earned the confidence.

Then somebody shows up or something happens and reminds you how much you don’t know.

That stings.

Now, in fairness to my buddy, the guy he was rolling with had a massive head start. As I remember the story, his friend started Brazilian jiu-jitsu when he was four years old. My buddy came to BJJ much later, after karate and judo. They’re close to the same age, but their time on the BJJ mat isn’t close at all.

That’s a lot of extra repetitions, mistakes, lessons, and years.

So getting handled by somebody with that background isn’t exactly a shock.

Knowing that intellectually doesn’t make it feel any better, though.

Here’s where the story turns.

After getting roughed up by his friend, my buddy was frustrated. And in later rolls with other students, some of that frustration came out.

He rolled a little mean. More aggressive, less patient, more determined to impose his game. I don’t know exactly what was going through his head, but the frustration was showing up in how he trained.

When he told me, I laughed.

Not because I thought it was right.

Because I’d seen it before, and because I’ve been on both sides of the equation.

Actually, three sides.

There’s the guy who dishes out the hard round. There’s the guy who gets humbled and frustrated. And then there are the people who catch the ripples afterward.

One uncomfortable experience can land on people who weren’t even there when it happened.

Maybe you’ve seen that in your own life.

You have a bad day at work and you’re short with somebody at home. Somebody embarrasses you in a meeting and the next person who asks a simple question gets more attitude than they earned. You get frustrated with yourself, and somebody else ends up carrying it.

I’ve done it. Most of us have.

The question was never whether we’d get frustrated. Of course we will.

The question is what we do with it.

And I think that starts with understanding something about comfort, confidence, and what happens when reality interrupts both.

You’ve Earned Your Confidence. Is It Still Current?

Think about something you’re good at. Something you’ve spent years learning.

Maybe it’s your trade. Maybe it’s raising kids, running a business, playing an instrument, fixing what’s broken, or handling rooms full of difficult people.

You didn’t wake up knowing how. You built it. You made mistakes that would embarrass the hell out of your younger self. Then you figured things out. You learned what works, recognized patterns, and eventually stopped having to think about every little detail.

What once seemed hard became familiar.

That’s a good thing. That’s what experience is for. You should give yourself credit for it.

But here’s the question worth sitting with.

Is the confidence you have today based on what you can still do, or on what you remember being able to do?

Those aren’t the same.

Picture a golfer who played beautifully twenty years ago and hasn’t practiced since. He still thinks of himself as a good golfer. He may well be one. But until he gets back on a course, he’s trusting an older version of himself.

Same with a job. The industry shifts. The tools change. The expectations move. But people keep assuming that because they were excellent before, they’re operating at the same level now.

Maybe they are. Maybe there’s something new they need to learn.

How would they know?

That’s where reality comes in.

And reality isn’t always gentle about delivering the message.

Comfort Doesn’t Always Announce Itself

I saw a version of this during my years as an electrician.

Some guys got comfortable with a contractor. They’d been with the shop a while. They knew the foreman. They had relationships with the superintendent. They understood how the company operated.

That familiarity has real value. It makes the work easier. It helps people coordinate. It builds trust.

But sometimes something else started happening.

A guy who used to stay sharp would start to coast. Not dramatically. Not overnight. Just a little. Production slipping. Details getting missed. He stopped pushing himself because he figured he’d earned his place.

He wasn’t a bad electrician. He’d just gotten comfortable.

And sometimes he got a rude awakening.

A pink slip.

Now, layoffs in construction aren’t always about performance. Jobs wind down. Contractors slow up. The economy changes. I’ve seen all of it.

But I’ve also watched men get so comfortable that they stopped paying attention to what was happening around them. They assumed because yesterday was secure, tomorrow would be.

Have you had something like that?

Maybe not a layoff. Maybe a relationship that had been drifting for months before you noticed. Maybe a skill you assumed was sharp until somebody asked you to use it. Maybe a financial situation that looked manageable until one unexpected bill showed how little margin you actually had.

Sometimes life changes suddenly.

Other times, the warning signs were there and familiarity made them easy to ignore.

Comfort isn’t the enemy. You worked hard for your stability. Enjoy some of it.

The problem starts when comfort makes you stop paying attention.

My Own Strange Relationship With Comfort

Looking back, I had an interesting habit during my electrical career.

Whenever I started getting too comfortable with a contractor, I’d leave.

We called it dragging up. Quitting. Moving on. New contractor, new job, new crew, new problems. I rarely stayed with a smaller contractor more than a couple of years. There were two bigger shops I stayed with for around four years each, but even there I worked multiple projects with different crews. I was always running into something new.

For a long time, I told myself I did it because I didn’t want to get complacent. I wanted to keep testing whether my skills held up outside the environment I’d gotten used to.

There’s probably some truth in that.

But looking back, I wonder if something else was going on.

Maybe I didn’t fully trust the security I had. Maybe I wanted to leave before somebody laid me off. Maybe walking away on my own gave me a sense of control.

I didn’t understand all my motivations at the time. I’m not sure I understand every one of them now.

But I can see two things happening at once. One was the desire to keep growing. The other may have been a discomfort with feeling secure.

Those aren’t the same thing.

So it’s worth asking.

Am I chasing a new challenge because I want to grow, or because I’ve become uncomfortable being comfortable?

Sometimes it’s both. There’s nothing shameful about discovering your motivations are complicated.

The useful part is seeing the pattern, because then you get choices. You can deliberately seek challenge without automatically running from stability. You can keep developing without blowing up everything you’ve built. You can enjoy what you earned without pretending you’re finished.

The Mat Keeps You Honest

This is one reason I love martial arts.

You get feedback. Sometimes more than you wanted.

You spend months feeling good about your progress. You’re moving better. You’re recognizing positions. Your techniques start working. Your confidence builds, and it should, because you earned it.

Then somebody shows up with more experience, better timing, a different style, or a physical advantage you haven’t learned to neutralize. Suddenly you’re a beginner again.

Happens to me regularly.

There are purple belts and brown belts who can make me feel like I don’t know a damn thing about jiu-jitsu.

And then there’s Artur.

He earned his brown belt at Roger Gracie in London and now lives in Los Angeles. We roll during the noon classes and on weekends. Good grief. That man has given me some serious lessons in humility.

But here’s what I’ve come to appreciate.

Getting handled by somebody better doesn’t erase the progress you’ve already made. It shows you what’s left to learn.

That’s a different interpretation of the same event.

If you’ve trained for years and somebody with more experience beats you, what exactly did you lose? You didn’t forget everything. Your progress didn’t disappear. You met a level of skill you haven’t developed yet.

That’s information. Useful information.

It doesn’t always feel useful while you’re being flattened into the mat. Sometimes it just feels like getting your ass kicked.

That’s fine. You don’t have to enjoy every hard lesson while it’s happening.

You just get to decide what you do with it afterward.

Here’s Where the Real Test Begins

Back to my buddy in London.

He had a hard round. He got frustrated. Then the frustration leaked into the rolls that followed.

I don’t think that makes him a bad person. I think it makes him human.

And if we can look at it without beating ourselves up, there’s a real lesson in there.

The first challenge was physical. Could he handle what a more experienced friend was throwing at him?

The second was emotional. Could he have a hard day without changing how he treated everybody else?

That second one might matter more.

You don’t get to decide when life humbles you. You get to practice how you respond.

So think about the last time something really got to you. Somebody corrected you. A project went sideways. You lost an argument. You found out you weren’t as prepared as you assumed.

What happened next?

Did you get curious? Defensive? Did you withdraw? Did you get impatient with somebody who had nothing to do with it?

I’m not asking as a guy who has this mastered. I’m asking because I’ve had to work on it and still do.

Sometimes I handle disappointment beautifully. Other times, not so much.

The point isn’t to never feel frustrated.

The point is to catch it before you hand it to somebody else.

That takes practice. Like anything else worth learning, you won’t get it right every time.

What Are Your Yellow Flags?

Most of us know our stress signs. We’re tired. Irritable. Can’t concentrate. Not recovering.

Those are useful.

But have you ever built warning signs for getting too comfortable?

Not enjoying your life. Not taking a well-earned break. I mean the point where familiarity starts replacing curiosity.

What would your yellow flags be?

Maybe you haven’t learned anything new in a while. Maybe you haven’t asked anybody for honest feedback. Maybe you’ve stopped letting your assumptions get tested. Maybe you avoid situations where you might look like a beginner. Maybe you keep choosing the same people and places because you already know how it’ll go.

Or something subtler.

When somebody challenges you, you react harder than the situation deserves.

That one interests me. A strong reaction can mean something got touched. Your pride. Your identity. An insecurity you figured you’d outgrown.

That’s not a reason to beat yourself up. It’s an invitation to get curious.

What just happened? Why did that land so hard? What am I protecting? And is there something here worth learning?

Those questions can turn an uncomfortable moment into a useful one.

Getting Comfortable Being Uncomfortable

You’ve heard the phrase.

Get comfortable being uncomfortable.

It’s decent advice, up to a point.

But it deserves more thought.

Discomfort isn’t automatically good. Some situations should be left. Some behavior shouldn’t be tolerated. Some challenges aren’t worth the physical, emotional, or financial risk. You don’t get extra credit for suffering.

The real question is whether the discomfort is building something you value.

Maybe you’re learning a skill. Having the hard conversation. Asking for honest feedback. Training with somebody whose ability exposes a hole in your game. Walking into a room where you don’t know anybody. Going somewhere unfamiliar and seeing how other people live.

It doesn’t have to be dramatic. You don’t need to uproot your life every six months to prove you’re growing.

A different training partner. A new class. A different responsibility at work. A conversation with somebody whose life looks nothing like yours. Even a part of your own city you’ve never bothered to see.

And here’s the part people forget.

You already know how to do this.

Go back through the challenges you’ve come through. You learned something hard before. You adapted to unfamiliar circumstances before. You figured things out when you didn’t have the answers.

None of that disappeared. You can use it again.

The goal isn’t to never feel uncomfortable. It’s to walk into unfamiliar situations with curiosity, humility, and enough confidence to learn something.

And when it goes badly?

Give yourself a moment. Get your bearings. See what it taught you.

Then try not to make the next person you meet pay for the lesson.

Don’t Get Too Comfortable Being Comfortable

Here’s what I keep coming back to.

Comfort can be the reward for work you’ve done. It shouldn’t become the fence around everything you’re willing to experience.

The confidence you’ve earned deserves respect. So does the person you are today.

You don’t need to tear yourself down every time somebody outperforms you. You don’t need to hunt the toughest guy in the room to prove something. And you don’t need to manufacture hardship.

But every so often, ask:

• Am I still stretching?
• Am I still learning?
• Am I still willing to find out that something I thought I understood has another level?
• And when reality tests my confidence, how do I treat the people around me afterward?

Getting better at something is one kind of growth.

Learning to be humbled without becoming unkind is another.

I think we need both.

⚔ The Dojo Drill

Give your confidence a healthy reality check.

Pick one area where you’ve gotten comfortable. Not necessarily complacent. Comfortable.

Maybe you earned it through years of effort. Good. Acknowledge that.

Then work through these.

1. What am I already good at? Name the capability. Don’t dismiss it just because there’s more to learn.
2. What haven’t I tested lately? What assumption about your skill, judgment, or readiness would benefit from fresh evidence?
3. What’s one manageable challenge I could take this week? Useful, not reckless.
4. How do I usually respond when I get humbled? Curious? Defensive? Discouraged? Impatient?
5. Who feels the ripple when I’m frustrated? And what could you do differently before passing it along?

You don’t have to do all five. Start with one.

Ask somebody you respect for honest feedback. Roll with somebody better than you. Try an unfamiliar place. Or just notice the next time you feel embarrassed or frustrated, and give yourself a moment before you respond.

That last one might be the hardest practice of all.

Because sooner or later life reminds every one of us that we still have something to learn.

When it happens, remember.

Getting humbled doesn’t erase how far you’ve come. It shows you where you can go next.

And how you treat people along the way matters as much as how much better you get.

📚 From the Leader’s Library

​Antifragile: Things That Gain from Disorder — Nassim Nicholas Taleb​

Why?

Most people try to build a life that can withstand adversity, but Taleb challenges us to go further: build a life that actually grows stronger through challenges, uncertainty, and change.

Antifragile explores how creating options, reducing unnecessary dependencies, and learning from manageable setbacks can help us thrive rather than merely survive. It’s a powerful reminder that personal leadership isn’t about controlling everything life throws at us—it’s about becoming more capable, adaptable, and prepared for whatever comes next.