How to Embrace Challenge in Life

It goes by legend that in 1914, Shackleton placed an advertisement in a London newspaper seeking men to join him on an expedition to Antarctica. 

The ad reputedly read: ‘Men wanted for hazardous journey. Small wages, bitter cold, long months of complete darkness, constant danger, safe return doubtful. Honour and recognition in case of success.’

Whether this ad actually existed or not (there’s no evidence it did), thousands of men did apply for this expedition—knowing full well that it was potentially perilous. 

They certainly didn’t apply for the job due to its healthcare benefits or money. They applied because it appealed to something deep in the human psyche: the desire for challenge. 

(As a side note, one of my favorite books in the world is Endurance: Shackleton’s Incredible Voyage. It’s insane. Highly recommend checking it out). 

This same desire for challenge is why you see athletes who retire from their sport only to immediately jump into something else challenging, like a business pursuit. They crave challenge.

It’s part of the reason why you see post-exit entrepreneurs get depressed: they’ve spent years in intense challenge, and now they have enough money to never work again. Travelling the world and pursuing pleasure only works for so long. At some point, they re-embrace challenge. 

It’s why Carl Jung said “Man needs difficulties; they are necessary for health.”

Part 1: The Psychology of Challenge (Why We Need It)

“Virtues that are not practiced die. Resilience that is not practiced weakens.” – Eric Greitens

Challenge and Enjoyment

Fundamentally, we pursue challenge because it’s enjoyable

In his book Flow, Mihaly Czsiksentmihalyi talks about the difference between pleasure and enjoyment.

“A person can feel pleasure without any effort… But it is impossible to enjoy a tennis game, a book, or a conversation unless attention is fully concentrated on the activity.” 

There’s an enjoyment that comes through pursuing challenge, even if it’s not a pleasurable experience in the moment.

There’s a reason people get addicted to hard things like ultramarathon running, serial entrepreneurship, fighting, and so on. These things are enjoyable, even if they can be intensely challenging and painful. 

When pleasure is your only positive experience, it leads you to an unhappy place. That’s why the endless pursuit of hedonism doesn’t work—it’s pleasure for pleasure’s sake. And you don’t reap the rewards that come only through embracing challenge.

There’s a satisfaction that comes with challenge too. Getting to the end of a long work week or finishing up a challenging project and taking some time to truly relax.

But go through a day, or week, or month, or maybe even an entire year where you avoid challenge at every corner, and you won’t experience this satisfaction. A life centered around procrastination and avoidance is marked by persistent low-level anxiety and pervasive lack of fulfillment. And that is deeply unsatisfying.

You were made for challenge. You were made to embrace responsibility. To avoid it is to neglect your purpose. 

Challenge produces motivation, momentum, energy & fulfillment

Without sufficient challenge, motivation wanes. Momentum reverts into inertia. Excitement and exhilaration cease, and so does the energy they produce. 

Think back to a time where you set a challenge for yourself and committed to it. You likely felt an intense burst of motivation. The challenge created a sort of activation energy that made it easier for you to take action.

When I think back to some of the times in my life where I was most fulfilled and energized, they were times of challenge.

Many of the times in my life where I’ve felt most fulfilled and energised have been times of challenge. Writing a book in 30 days, hiring my first employee, going on long backcountry hunts and hikes—walking for miles on end, or pushing through difficult projects… worthwhile challenges that were inherently enjoyable—even if they were hard.

Conversely, the times in my life where I’ve felt the lowest are those where I’m not embracing challenge but know I should be. Where I’ve rested for longer than necessary. Where I’m stuck in stasis and overthinking. Where I’m avoiding the work I know I need to do. Where I’m setting goals that I know are easily achievable and don’t challenge me sufficiently. 

Pleasure vs. Enjoyment

Mihaly Csikzentmihalyi writes: 

“When people ponder further about what makes their lives rewarding, they tend to move beyond pleasant memories and begin to remember other events, other experiences that overlap with pleasurable ones but fall into a category that deserves a separate name: enjoyment. Enjoyable events occur when a person has not only met some prior expectation or satisfied a need or a desire but also gone beyond what he or she has been programmed to do and achieved something unexpected, perhaps something even unimagined before. Enjoyment is characterized by this forward movement: by a sense of novelty, of accomplishment.”

Feeling pleasure doesn’t require effort. It doesn’t require challenge. 

You can get pleasure from your morning coffee. You can get pleasure from drugs. You can get pleasure from procrastinating and watching Netflix when you should be doing work. 

Enjoyment, on the other hand, often goes hand-in-hand with effort and attention

Mihaly goes on to add: 

“A person can feel pleasure without any effort… But it is impossible to enjoy a tennis game, a book, or a conversation unless attention is fully concentrated on the activity.”

He uses the example of a child. During the first few years of a child’s life, they’re like a little “learning machine.” 

They are trying things out. Speaking new words. You can see the concentration on their face when they are trying to play with a toy or figure out how something works. This is effortful enjoyment. It’s good challenge. 

Challenge and activation energy

Ever noticed that you tend to procrastinate on easier tasks more so than challenging tasks?

I’ll have no issues sitting down to do hours of research on a complex topic, but completely put off something simple like replying to an email. 

Why is this? It’s because of activation energy. The energy required to activate yourself and start taking action. 

There are three main drivers of activation energy: physical/mental energy, curiosity/interest, and challenge. 

If you’re exhausted, then it’s hard to get yourself to do anything. Activation energy depends on “real” energy to some extent.

If you have zero interest in the task, even if you’re energized physically, it’s still easy to avoid it. Like me replying to an email.

If the task isn’t challenging at all, then it’s unlikely to produce necessary activation energy. 

But when you have all three, it’s almost hard not to do the work. 

That’s why the best “hack” for productivity is, as much as you can do so, choosing the work that naturally interests you and you find sufficiently challenging (but not too challenging. When you find this, every other productivity hack basically becomes unnecessary. 

Fulfillment comes more from the challenge itself than it does overcoming the challenge

As cliche as it is to say, “the journey” is truly what matters. There are countless examples of athletes and competitors who reach the pinnacle of their career only to realize that it’s far less satisfying than they expected, and in fact it was the training and daily effort that brought them fulfillment. 

There’s a mistake in thinking that overcoming a challenge or reaching the end of a project will fix everything. That if you just work hard enough and achieve something, everything will fall into place. This is false. You know it’s false, because you’ve likely experienced it before. But if you’re like me, you fall into the trap of believing it anyway. 

Instead, recognize that the fulfillment you’re after doesn’t come only from the achievement of the goal, or the overcoming of the challenge, but from the ongoing embrace of challenge and responsibility.

The “event” of finishing, winning, achieving does far less for your personal growth than the daily effort. 

Overcoming challenge raises your internal sense of capability & builds resilience

I remember the first time I went backcountry hunting here in New Zealand—up in the mountains. 

I went out with two friends. The plan was to do an “easy” day hunt, hopefully find an animal (a deer), and carry the meat back out. 

It was one of the most physically challenging days of my life. We started walking at 7am in the morning after a 2 hour drive, and finally got back around 10pm. The walking up steep mountains with 50 pounds of meat in the pack, getting numb feet from walking through ice cold rivers, and trying not to slip down gnarly terrain in wet conditions made for a painful experience. 

But having done that, I know I’m capable of way more than I give myself credit for. When you think you’re done, you’re not. You can keep going. 

When you pursue extremely hard challenges—or in my case you pursue what you think is a normal challenge that turns into a much harder one—you raise your internal sense of capability. You develop a self-confidence that carries you through future challenges, and drives you to pursue harder things. 

And as we just looked at, it’s fulfilling, anyway. As soon as we got back to the car, sat down and warmed up, I said to the other guys, “This has been one of the best days of my life.” 

Part 2: How to Actively Pursue Challenge in Your Life

You might be watching this and you already have more than enough challenge in your life, whether it’s been intentionally applied or not. If that’s the case, then keep pushing through.

But what if you lack challenge? What if you’ve been stuck in stasis for too long, and feel like you’re weakening? 

Well, let’s fix that. I’m going to share three challenges you can pursue, followed by three principles to live a challenge-oriented life. 

The Misogi Challenge

The Misogi challenge is based on the Shinto practice of “Misogi”—where you purify yourself through ritual cleansing, often by standing under cold waterfalls. 

The modern adaptation is that you pursue a personal challenge or endeavour, once a year, that’s far beyond your perceived limits to reset your perspective on life and make it seem more manageable in comparison. 

Here’s how Jesse Itzler describes it:

“Misogi is about taking on something that’s so difficult, so far beyond what you think you can do, that it forces you to dig deep and find a new level of strength and resilience.”

It needs to be difficult. Marcus Elliot gives us a more specific idea of how challenging a Misogi should be”

“Take on challenges that radically expand your sense of what’s possible. There are just two rules: you have a fifty-per-cent chance of success at best, and it doesn’t kill you…

Does it make your jaw drop? That’s a good litmus test for whether something can be a misogi or not.”

Stuck for ideas? Try one of these:

  • Endurance challenge: run a marathon without any training. Walk for 16 hours straight. Do something like the Goggin’s 48 hour challenge
  • Climb a mountain peak
  • Cold water immersion – multiple times in a day

I do think physical challenges are the fastest path to growing mentally, but I’m sure you could undertake a “mental misogi” too. 

Double your goal (or triple it)

If you have a goal you’re pursuing right now, then double it. Make it twice as ambitious. Or three times as ambitious.

Is your goal to build a business in 12 months? Do it in 6 months.

Is your goal to earn 20% more income next year? Make it 40%. 

Something interesting happens when you do this. 

First, you don’t want to do it, because you instantly think “well, I can’t achieve that—hence why I’ve set my goal as it is.”

But you do it anyway, because what’s the harm? You fail, but you probably achieve your initial goal anyway. Shoot for the moon and land among the stars, as they say. 

What happens is that it raises your activation energy so much more. I talked about this in my hyperproductivity video. That you act with high velocity when you set an ambitious goal. It’s challenging, and exciting. 

Doing this enables you to cut through what are often arbitrary limits we set for ourselves. There’s no reason why you can’t do what you want to do twice as fast, or do it twice as big. 

You can take this even further. I love Peter Thiel’s question of: 

“If you have a 10-year plan of how to get [somewhere], you should ask: Why can’t you do this in 6 months?”

I talk more about setting ambitious goals in my guide to high velocity action.

Do a WorkSprint

Some of the most enjoyable times in my life have been where I’ve engaged in large volumes of intense, focused work over a short time period. 

I call these “Work Sprints.” And run a cohort by the same name, which you can check out over at

Here’s how it works:

  1. Set one project or goal over a period of 2-4 weeks. It should be challenging. It should involve some uncertainty. If you know for sure you can achieve it, then it’s not challenging enough. 
  2. Optimize your schedule to allow for massive volume and intensity of work. If that means dropping some responsibilities, do so. If that means less socializing, do so. It’s only a short time period. 
  3. Work. Extremely hard. And enjoy it.

The goal with a WorkSprint is not only to push an important project forward or achieve a challenging goal, it’s also to prove to yourself that you’re more capable than you think. In its own way, it’s like a Misogi challenge.

There’s something that happens to you as the individual when you work with intensity and consistency over a period of time like this. When you work harder than you ever have before. It changes you. As Alex Hormozi said on a podcast, “The work works on you more than you work on it.”

And if you want to do it alongside a bunch of other ambitious action-takers and get daily accountability, then consider joining the next WorkSprint cohort. 

Also read: How to be Ultra Productive With The SPRINT Method


These challenges are worthwhile, but you also want to live a challenge-oriented life. It’s not a one time thing where you do a WorkSprint or a Misogi and then go back to normal. 

Here are three principles to help you do so. 

Avoid Incrementalism 

Incrementalism, in the context of this topic, is the idea that you should increase challenge in life slowly and incrementally.

Instead of signing up for and training for a marathon, run a half-marathon first.

Instead of doing a 4-week WorkSprint, do a 2-week one first. 

There is some value to this way of thinking. For example, if you’re extremely unhealthy or have a heart condition, then running a marathon next week might actually be life-threatening for you—and it might make more sense to work up to it (or avoid it altogether and find another challenge).

It’s a useful philosophy in some contexts. But it slows you down immensely in other contexts.

It comes back to the “2x your goal” challenge. How can you make a quantum leap? How can you get exponential results in work and life? I can tell you that it’s not through incrementalism. 

You can avoid incrementalism by:

  • Setting goals & projects that have outsized returns if completed. Usually these goals and projects feel less comfortable to you. They might have a higher level of uncertainty. But a goal that has a 10x return potential but a 50% chance of success is a much better bet than a goal that has a 1.5 x return potential but a 100% chance of success. One has the potential to radically transform your life, the other only a little bit. 
  • Not lying to yourself. Do you need to do this incrementally? Do you need to build up to it? Or is that just what you’re telling yourself.
  • Embracing incrementalism where it makes sense to do so. For example, you can avoid incrementalism by signing up for a marathon instead of a half, but you still need to train for it. And in your training, you should embrace incrementalism because otherwise you’ll ramp up too quickly and injure yourself. 

Fight Stasis Every Day

Even if you’re someone who’s motivated by challenge more than others, there’s still a tendency to fall victim to stasis. The body and mind want to conserve energy. And if you’re not careful, you can find yourself stuck in inertia—and hating it.

Do something every day that challenges you.

Do the hard, deep work that moves you towards your goals. Do it well, with high standards.

Exercise. Move. Strain your body. 

Find the golden mean between challenge & capability

“Enjoyment appears at the boundary between boredom and anxiety, when the challenges are just balanced with the person’s capacity to act.” – Mihaly Czsiksentmihalyi

As much as you can, operate within the right level of challenge. If it’s too easy, you’ll find it easy to procrastinate and lack the activation energy to do the work. If it’s too challenging and you lack the capability to achieve it, you’ll also find that you avoid the work. 

You’ll know you’re positioned well when you enter flow states easily. 

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