The Pain Cave

January 11, 2025

As you’re reading this, I’m out here in the rugged peaks of Switzerland — my legs are burning, my quads feel like they’re on fire and my lungs are gasping after three hours of relentless uphill climbing.

I’ve already tackled a gruelling 1,600m of elevation and conquered the toughest peak of the race at 3,200m. But with two more peaks ahead, the race has only just begun.

It’s been tough so far, but there’s still a long way to go to finish the Matterhorn Ultraks.

I’ve prepared as much as I could: hours of training, meticulously planning my nutrition and endless visualisations of this exact moment. But no matter how ready I am, it’s inevitable that (if I haven’t already!) I’ll face moments of intense struggle.

In the world of ultra running, we call this entering the pain cave.

For those unfamiliar with the term, the ‘pain cave’ is a concept used in ultra running to describe that crushing moment when fatigue sets in and — physically, emotionally, and mentally — your mind and body are plunged into a place of struggle, pain and discomfort.

Generally speaking, it’s the moment when you face a level of struggle, pain, or discomfort that you don’t know how to navigate or haven’t faced before. It’s a place that most people wish to avoid at all costs, or where they tap out and retreat back to ‘safety.’

However, for those willing to enter the cave, it’s an opportunity to meet ourselves — to be reminded of our strength, wisdom, creativity, and leadership skills. It’s a chance to test and strengthen our resilience, to discover our true capacity to endure.

And that capacity? It hinges on two crucial factors:

How we react to whatever challenges arise the moment we enter the cave, and how well we’ve prepared ourselves for that moment BEFORE it even comes.

This is the core message that I want to get across to you today.

As Seneca said:

“The man who has anticipated the coming of troubles takes away their power when they arrive.”

Think about it.

If you aspire to do anything extraordinary, unique, or memorable in life — in my case, ultra running — it’s inevitable that entering the pain cave is just a part of the process that needs to be accepted — but more accurately, prepared for.

It’s not a question of ‘if’, but ‘when”.

When you’re 40 kilometres into a 100-kilometre race, your legs feel like lead, your stomach is in knots, and your mind is screaming at you to stop — that’s the pain cave. It’s a place where your resolve is tested, where your reasons for running are questioned, and where your true character is revealed.

And while I’m speaking mainly about my trials and tribulations as an ultra runner, the same principle holds true in other walks of life.

It’s true for starting a business, where cash flow problems or unexpected competition can plunge you into darkness. It’s true for committing to a new relationship, where vulnerability and the fear of getting hurt can feel suffocating. It’s true for taking on a leadership role, where the weight of responsibility and decision-making can feel crushing.

The fact is, if you aren’t prepared for your pain cave — whatever form it may take — the fallout (or avoidance of!) will likely be far more detrimental than whatever actually comes up when you’re in the cave in that moment.

I’ve seen runners stick to familiar, running the same miles at the same pace but never tapping into their true potential and the exhilaration of pushing past their limits because they weren’t willing to face the discomfort that true growth demands.

I’ve seen entrepreneurs crumble under the pressure of their first major setback, closing shop and retreating to the safety of a 9-to-5 job because they hadn’t mentally prepared for the uncertainty and setbacks that come with building a business.

I’ve seen partners walk away from potentially beautiful relationships at the first sign of conflict, unprepared for the work and compromise that deep connections require.

The point is, that you will be overwhelmed if you aren’t prepared.

This is why, to me, the overlap between ultra running and life, love, leadership and business is one of the most vital, fundamental lessons you can learn. It’s about finding meaning and maintaining hope despite inevitable pain, loss, and suffering.

It’s about accepting, acknowledging, and — perhaps especially — EXPECTING that life will contain discomfort, hardship and hurt. But then being both able and willing to keep moving forward with a positive attitude nonetheless.

The question is, will you anticipate your arrival at this juncture?

Will you have already taken stock of your ability to handle what you find inside?

Or will you be caught off guard, surprised, and ultimately left stuck, hurt, or worse by your encounter with the pain cave?

This very anticipation is what will determine how I react to and experience my own inevitable pain cave as I run this race. All of the training, mindset preparation, stretching, and physio — it’s not only there to make sure that I have the athletic capacity to cross the finish line, but to make sure that I have fully stocked inventory of choices for when that time comes.

When I find myself in the darkness of struggle, I’ll have a torch to find my way out.

So, think about how this applies to your own life.

When you’re prepared for those moments of intense difficulty, you’re not blindsided by them. Instead, you’re equipped with strategies, mindsets, and the resilience to push through. You’re able to draw on your preparation, to remind yourself why you started this journey in the first place.

Because when you flip the script and look at would could happen when you aren’t prepared, the consequences can be devastating. Not just in the failure to achieve a specific goal — but for the toll that it takes on your confidence, your self-belief, and your willingness to take on future challenges.

But the vital distinction to make here, (and something I want to make clear!) is that being prepared for the pain cave doesn’t mean you’re seeking out suffering. It’s not about being a masochist or constantly putting yourself through hardship. Rather, it’s about being ready for the challenges that inevitably come with pursuing any worthwhile goal.

Just because I see and accept the pain cave — and just because I’m prepared to do what it takes when the situation arises — it doesn’t mean that I constantly seek out situations to suffer.

I don’t wait to be surprised by challenges when they come up — and when they do — I remind myself that it’s not happening to me — I chose this experience. I chose to run this ultra (and the other ones before it!). Nobody forced me to do this.

I WANT to be an ultra runner.

I WANT to run a successful coaching consultancy.

I WANT to be in a committed relationship with my partner.

And I WANT to be ready, able, and willing to anticipate that certain pain caves will be an inevitable part of the process.

I say YES to the outcome, so I also need to smile and say YES to the pain.

That’s why for me, whenever I enter the pain cave — in running, in business, in my relationship — I’m reminded of my resilience. I’m reminded of my creativity in overcoming obstacles. But most importantly, I’m reminded of my ability to LEAD myself.

So this is what I invite you to do today.

The first step is to identify your pain cave — or more specifically, get radical clarity over the part(s) of your life that you currently feel the most resistance to.

So ask yourself:

What parts of my life am I (un)consciously resisting?

What am I avoiding, putting off, or downright procrastinating because of the associated discomfort of the task at hand?

In what ways am I shying away from not doing what I know needs to be done?

Once you’re clear on this, the next best step to prepare for this reality is to expose yourself gradually to your pain cave. Step by step, little by little, until you’re fully aware of its existence — but more importantly, until you’re aware of what choices you have when the time comes for you to enter.

Think about whatever big ‘thing’ you have going on in your life at the moment. Something that you may be well on your way with, putting off, or pretending doesn’t exist. Consider the parts where, if the worst-case scenario happened, you’d be completely overwhelmed by the fallout from the pain cave.

Begin to gradually expose yourself to the aspects that make you most uncomfortable.

For example, prior to this race, I would run 21km without water to prepare for the moment that I run out in a place where a refill isn’t an option — so that my mind and body are prepared for this scenario.

In a similar way, I’d go for a run on the hottest days of the year to prepare for the exhaustion that comes as an inevitable part of doing so — or I’d lace up my shoes and hit the trail when I felt weak or unmotivated.

The point is to make your mind (and body!) aware that failure may happen, but you’ll have your inner strength to fall back on.

Acknowledge that rejection may occur, but you’ll have your self-worth to rely on.

Accept that setbacks may arise, but you’ll have your problem-solving skills to overcome them.

And most importantly — remember why it’s important for you to persist. To push through. To endure.

Because the cave you fear to enter holds the treasure you seek.

And if you really want what you say you want, it’s inevitable that one day you’ll step inside that cave.

The question is — will you be prepared?

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