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For the past decade, masculinity at large has been the subject of vilification.

And in many cases, rightfully so. There are so many classically masculine character traits that simply aren’t useful, necessary, or justifiable in the modern world.

In recent years, criminals, using the guise of masculinity, were finally exposed. Many people were exploited and hurt. The examples are abundant.

But I started considering: Are there any saving graces of masculinity? As a man myself, I couldn’t simply accept that all 200,000 years of my ancestry could be reduced to toxicity and malevolence.

So I began reflecting on what elements of masculinity we could all adopt, to become better and more complete versions of ourselves. After all, the masculine and feminine resides within all of us.

Seeking balance of the two—I believe—is how we can live as our highest and most complete selves.

The art of the challenge

If you’re a man, challenges are something you—and your 10 year old self—are intimately familiar with.

Being dared to eat worms, ask out a long-shot crush, and the terrifying proposition of “Let’s take this outside”.

Some of these are harmless, many of them are detrimental. This isn’t about the specifics of the challenges we did as young boys, but rather the spirt of the challenge. 

The spontaneity, bravado, and brash foolishness it takes to propose a challenge. And the Chutzpah to look it right in the face and accept.

The spirit of the challenge, is a piece of masculinity we can all benefit from. By learning how to incorporate it back into our lives, we can enjoy a happier, more confident, and more grateful existence.

We can learn to conquer our fears of failure, become more connected with our latent potential, and increase the level of difficulty we can handle in our everyday lives.

We’ve become disconnected from our potential.

You’re an apex predator, and you don’t even know it.

In We’re Much Weaker than We Think, Nat Elison talks about how early Americans used to carry 600 pounds of cargo on their backs for several miles when transporting pelts across modern day Minnesota.

In Born to Run, Christopher McDougall shares how the Tarahumara Indians run hundreds of miles, over razor-sharp rocks in the Copper Canyon. No training, no stretching, no special diets and they do it virtually barefoot.

In modern day London, taxi drivers undertake an arduous memory examination.1 They’ll remember over 25,000 streets, which direction they run, shops, restaurants, and even minor obscure landmarks like “the location of a statue, just a foot tall, depicting two mice sharing a piece of cheese.”

Believe it or not—if you’re healthy and able-bodied—all of these are within your capacity.

Our bodies and minds are marvels.

Most of us have just become…a little mushy.

72 degrees of temperature control, 60 minutes of low impact exercise machines, running shoes with 4 inches of padding, spreadsheets and automations have taken all the things we used to be good at and outsourced them.

Still, a latent potential lives within all of us.

What if there was a way to awaken this potential? What if there was a way for us to reconnect with how bad ass we truly are?

I believe by embracing the masculine bravado—and stupidity—that lives within all of us, we can unlock this potential. We can become stronger, more resilient, and more ready for the unforeseen challenges life will inevitably throw at us.

First some ground rules on challenges

1. It needs to be beyond your current capabilities.

This means there has to be a real chance that you fail. This acts as a one-two punch. It teaches us that failure is not a bad thing—it just comes with the territory of doing new and difficult things. The second is, you are fundamentally forced to change in order to conquer the challenge.

2. It needs to be inspiring.

You’re going to want to quit, but the nature of the challenge has to pull you forward during difficult times. If it’s not something you’re convinced is for your betterment, you will almost certainly give up too early.

3. Success or failure you will be forever changed by the outcome.

The challenge itself will be a defining moment in your life. A great challenge is a win win. If you successfully complete it, you will be a better version of yourself. If you fail however, it will not be devastating, but rather a growth experience in and of itself.

For example:

Teaching yourself to code in 1 year, and then switching careers has a real chance of failure. If you succeed, your life will certainly be changed. Even if you make it only 60% of the way there and fail, you will be changed. It also won’t be something you easily forget.

However, shaving 15 minutes off your marathon time, fails this test.

If you’ve run a marathon before, and now you’re just trying to do the same thing again, but faster, that’s not enough. To make this a true challenge, consider running a 100 mile race in the middle of the desert.

A true challenge, requires you to scratch your head and wonder: “How the hell am I supposed to do that??”

Now, why should you put yourself through something like this?

Remember that you’re a Bad Ass

The funny thing about training for a marathon is, in the first few weeks, it seems completely impossible.

You’ll start by building endurance from the ground up. Each week progressively adding a mile or two to the distance you can cover.

But around your fourth week of training, when you’re panting on mile 6, you think to yourself…”How am I supposed to run 4 times further than this?!”

It’s a real gut-punch.

But you keep grinding away at it, week after week. Eeking out just a few more miles each run. Then one day—not to long after—you cross a 26.2 mile finish line.

You’ve seen yourself accomplish something you previously thought was impossible. With a marathon finish fresh in mind, you believe you can do anything. You believe that there is no distance too far.

One of the most powerful things challenges do for us is, they give us proof of our own bad-assery.

Now I know it sounds crazy, but deep in my bones, I know I can run a 100 mile race.

I don’t know how, I don’t know where, but I know I could do something that right now seems impossible. Because I’ve done the impossible before.

Theres a word for this unflappable belief we have in ourselves, for our ability to overcome unseen obstacles, and to triumph over fear.

Confidence

One of the guiding lights in my life has been the simple reminder below:

Too often we get caught up in a confidence trap.

If I was just more confident, then I could….

• Stand up to my boss

• Speak up in more meetings

• Finally ask him out on a date

• Stop second guessing myself

But we forget that the only way to gain confidence is to do the hard thing first. To look fear in the face, and despite it, continue forward. The truth is, no one is confident without prior experience overcoming fear.

By setting truly hard challenges—and accepting them despite our fears—we’re improving our relationship with ourselves.

We’re compiling a reel of memories that we can re-watch when preparing for the difficult times ahead. By doing hard things first, you’re building up this reel and cultivating confidence.

Infinite Gratitude

Have you ever noticed how people can complain about anything?

• They gave me oat milk instead of almond milk in my iced coffee

• They’re making us go back to the office for 2 days a week

• My taxi was playing awful music for the whole ride

One of the unique powers of human beings is, we adapt to pain—or pleasure—quickly. It’s called hedonic adaptation. As soon as we experience a new quality of life, it becomes our baseline.

I don’t know about you, but I don’t want to complain about what type of milk is in my coffee. I want to be grateful for each and every modern luxury that makes up my cushy San Francisco life.

Luckily, there’s a way to reverse this adaptive mechanism: A hard challenge.

There is nothing more humbling than spending a week in a town with no running water or electricity.

When you finally make it back to “civilization”, you’ll care far less about what kind of milk is in your iced coffee. Rather, you’ll be worshiping the marvelous little cubes of frozen water in your drink.

Everything is a luxury: Hard challenges remind us of this.

This gets to one of the key components of a good challenge.

It has to suck.

If you’ve designed it properly, you should consider quitting often. The challenge itself has to fundamentally break your concept of a comfortable life. When you’re eventually thrown back into your weekly grind, you’ll have an entirely new perspective.

Just think, how hard would presenting at 2-hour all-hands work meeting feel, if just weeks before you ran an 6-day 156 mile race across the Sahara Desert.

It would be a cake walk.

The more the challenge sucks = The more grateful you will be afterwards. 

Do something extraordinary

Before we go any further, let me tell you the story of two swaggering Italians, and their chest-thumping dare.

Enzo Ferrari was a prideful man. So when the owner of a little Italian tractor company came to his office, he didn’t think much of it.

The tractor man had a problem.

He’d been successful enough with his tractor business to purchase two Ferraris, but the cars kept breaking. The clutch was bad, and in the course of just a few short month, he had bring his car back up to the Ferrari factory for replacements several times. One day he had enough, and requested a meeting with Mr. Ferrari himself.

They got straight to business. The man brought up the problem with his repeatedly broken clutch.

Ferrari refused to accept that his cars were anything but perfection. His Italian bravado bubbled to the surface “You are a tractor driver, you are a farmer. You shouldn't complain driving my cars because they're the best cars in the world.”

And at that moment, and inspiring challenge was born.

The man sped home, infuriated by Mr. Ferrari’s disrespect. He vowed all of his time, money, and resources to build the greatest automobile the world had ever seen. Proving to Ferrari that he was the superior engineer.

The “farmer” was of course, Ferruccio Lamborghini.

A rivalry was born that would change the landscape of supercars forever.

The spirit of the challenge is about accepting these chest-thumping dares. It’s about, every once and a while, letting our egos run free.

The reality is, without this argument and the jabs by Enzo Ferrari, the Lamborghini automobile would have never existed. Ferruccio probably would have continued building tractors, and tending to his simple vineyard.

No one would remember his tractors, or his wine. They’d only remember his cars.

By taking on great challenges, we have the opportunity to break free from our daily grinds, and attempt something truly extraordinary. By occasionally letting our bravado get the best of us, we can do something worth remembering.

Voluntary Transformation

Many of life’s challenges spawn out of necessity.

Our weight balloons, and one day we wake up 50 pounds heavier than we were in college. After years of working in the same career, we have a mental breakdown and need to learn an entirely new set of skills to survive. Something is wrong, so we need to make a change.

This is the classic transformation we find in a Hero’s Journey.

Outlined and popularized by Joseph Campbell, the Hero’s Journey is a classic storytelling framework. Virtually every movie, book, and fairytale you’ve ever heard of follows this same architecture.

In it, we always start with a unsuspecting hero. This hero is then called into action. They leave the safety of their home, and accept a challenge. This challenge will radically change them forever.

Think Frodo Baggins—living a simple life in the Shire—until he is called to destroy the Ring of Power. The journey radically changes him. It unlocks his latent potential, he learns and grows along the way, and ultimately is a completely different hobbit at the end.

He is transformed.

We can wait until we’re called to our own adventure—and forced to change—or we can steer our own ship. We can choose our own journey, our own lessons, and our own transformation.

By creating our own challenges, we are embracing transformation voluntarily. We are opting into life, rather than waiting to be taken away with the current.

This is the spirit of the challenge.

Post Script

This week, I was hiking deep in the Patagonian forest with Ashley. We’d already been on the move for 3 hours. We’d climbed 3,000 ft in elevation, our legs were shot.

After trudging up a particularly steep hill, we looked ahead and saw, yet another massive climb on the horizon. Ash turned to me, and did something that surprised me.

She said “I dare you to run up that!”

I was tired, my pack was heavy, so as I was catching my breath I said “No, not this one.”

She looked shocked, “What, you’re gonna say no to a challenge?”

I grinned, she grinned. We kept walking.

Just when we reached the base of the hill, she broke out into a full sprint.

I followed at full speed.

Without slowing, we reached the top of the monstrous climb.

I panted “That was fun.”

This is the spirt of the challenge. It’s about the guts to do stupid, counterintuitive, and difficult things for our betterment.

It’s about having the chutzpah to propose a challenge that’s beyond our current capacity. Then, in the face of uncertainty, accepting that challenge.

It’s about the acknowledgment of fear, and the nerve to keep going.

Its about the courage to take on something you could potentially fail, and when you do fail (you will), learning the lessons it teaches you and continuing forward.

Happy New Year

—Zac

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