My Fear of Failure & How I’m Working on Reorienting It

My relationship is complicated. 

My relationship with failure, that is. My relationship with my wife is pretty solid. 

What is your relationship with failure? 

It’s not l something you’re likely to sit down and think through. 

But for one reason or another, I’ve spent a good deal of time on that exact question this week. 

And my answer is; it’s complicated. 

The upside of failing is undeniable. And yet I’ll openly admit I’m not exactly keen on running directly towards the next failure. 

I’ve found four reasons why we should want to put ourselves in a position to fail more. 

I’ve come up with 3 reasons why I don’t enjoy failing. 

Then, most helpful, I found 6 ways in which to handle and deal with failure.

The hope is that by creating a framework that helps me see the upside, contextualize the downside and lay out the tools to handle failing, I’m more willing and more likely to work towards goals and put myself into positions where failing is a real possibility.  

So, let’s start at the top. Why do I think I should  fail more? 

As usual, you can listen to this post on Spotify or Apple Podcasts.

1. Failing is How We Learn & Adapt 

At SwimFast my job is teaching adult,  age group triathletes, to swim faster. 

Every day, I work with people in person and online, helping them work through the messy process of learning a new skill. 

Swimming is a skill that’s pretty hard to master as an adult. It’s not an entirely logical and rational process. The amygdala and the prefrontal cortex argue  with each other from the moment you get into the water. 

The amygdala detects danger and wants you out. It’s focused on survival.  It cares very little for the end goal of learning a skill. It’s what causes you to stop & stand up. It’s the reason you panic. It’s the reason you slow down.  

It’s the source of a lot of failure. 

Having coached 100’s of athletes through the years, I know this. I see it play out every day. It’s part of the process of learning to swim. It’s how we learn and adapt. It’s how we rewire our association with the water and build proficiency. 

As I walk an athlete through this process I will draw a parallel between what they are doing and watching a child learn to walk. 

No child has stood up. Mastered balance. Taken their first step. All without falling down. 

Everyone falls down. 

Each time you fall, you’re failing. 

And each time you fail you learn something about the process and get better at it. 

Failure shows us the way – by showing us what isn’t the way.
~ Ryan Holiday 

2. It teaches resilience 

I’m coming to see resilience as one of the most important skills we can develop as a human. 

We are and we live in an open system. That means change and chaos are built into our lives and are a part of our reality. 

To survive we need to be resilient. We must be able to withstand change. Adapt, learn and progress because of chaos. 

I think failing and resilience are complementary skills. 

The more resilient I am, the more open I am to pursuing things that can or will fail. 

The more goals I pursue that fail, the more resilient I become. 

3. It Will Adjust Your Trajectory 

The older we get, the more likely we are to get stuck in our ways. 

Your life builds momentum in a particular direction. As momentum builds you think less and less about why you’re doing things. 

Instead, you do what you’ve always done. You develop habits, routines and a worldview that builds more and more momentum. 

There may not be a rational conversation or argument that can get you to change your ways. 

But failure can. 

Failure can act as a catalyst for change. It can shock the system or reorientate your mindset. 

A simple example of this is health. You may have smoked 30 cigarettes a day and done no exercise for 20 years. 

No conversation with a Dr will get you to change your ways. 

Then you survive a heart attack. 

And suddenly, things change. 

“Difficulty wakes up the genius”
– Nassim Taleb 

4. The pursuit of something likely to fail is full of opportunity 

In 2001 I decided I wanted to go to the Olympics. 

Objectively there was no way that was possible. Statistically speaking, I was way too slow. 

11 years later, I failed to make the 2012 team. 

Measured purely on time, energy and resources invested vs objective outcome, I’d consider this the biggest “failure” of my life so far. 

But that 11 year journey between 2001 and 2012 was epic. 

The places, the people, the experiences, the memories. Incredible. 

I wouldn’t have had any of those experiences had I not put myself on a path towards failing. 

On top of that, that journey set me on the path I’m currently on. 

The Olympic journey led me to a deep dive 

  • Into psychology. 
  • Into coaching. 
  • Into mindset. 
  • Into training.
  • And recovery. And nutrition. 

What I do today was significantly influenced by that journey. Who I am today was too. 

All because I was willing to run towards the potential of failing. So, if the upside of failing is undeniable, why aren’t you and I signing up with gusto? 

Thought a lot about this over the last week. There’s 3 reasons why I’m not keen on it. 

1. Failing Hurts. 

Facts are facts. 

I think that how it hurts will depend on what was motivating you towards the goal. 

If you are intrinsically motivated to move towards your goal and you fail, I think that it hurts when you reflect on the time & energy sacrifices you made. All of which did not give you the return on investment you wanted. 

If you’re extrinsically motivated, the hurt is all ego. You were in it to prove to someone you could, and you didn’t. That sucks. 

To fail well, you need to be able to process negative emotions well. If you struggle to understand and process negative emotions, as I have in the past, then failing can be much harder. 

2. Failing can impact self worth. 

The tighter your identity is coupled with the goal, the more likely your self worth will be impacted when you fail.

If a big part of who you are is linked with what you do, when you fail at the doing, you feel like a failure. 

If you run a business and that’s your sole focus, if the business fails, it’s hard not to feel like you are a failure. 

If you’re a swimmer aiming at the Olympics. And you fail to make the team. It’s hard not to feel like you are a failure. 

 If I fail, I am a failure. If I fail a lot, over and over, I’m reinforcing the message. Who would want that? 

3. The Perception of Failing 

The less we have failed, the less experience we have with dealing with it. 

Typically, the less experience we have with something, the more likely we are to get anxious about it. The bigger and badder our brains make it out to be. 

Similar to anxiety, I think the story we tell ourselves of how we might fail and the consequences of failing plays out in your head way worse than the actual failing. 

The perception of failing is often worse than reality. The fear is almost all in your head.

Which brings me back to my complicated relationship with failure. Is it all in my head?

  • Objectively, I should go towards.  
  • Subjectively, I want to run away. 

Admittedly, I’m writing and contemplating this for myself, maybe more than for you. 

I’m working emotionally reorienting the relationship with failing. I’m just happy to have someone (you) to talk to about it. 

So the question I have been asking myself is; what framework can I use to help further persuade me to move towards opportunities that hold a higher risk of failing? 

Aside from the 4 reasons I mentioned at the top, I’ve come up with 6 more (or variations of) to help me move towards it more confidently: 

Think Macro, not Micro 

When I fail, I’ll zoom out and look at the big picture. 

That bigger picture may be in the context of the goal. Like, “I screwed up a race, but I’ve got two more races in my season” or “I lost a sale, but there’s another 2 weeks to hit my quota for the month”. 

Or it could be in the context of my life, “Remember that this moment is not your life, it’s just a moment in your life.” as Ryan Holiday put it. In the context of 80(ish) years, is this failure that significant? Can you not recover from it? 

Now those two strategies should be enough. But, if I’m reaching for one more layer because neither of them work, I can look at it in the context of the universe. 

I warn you, this can get existential, but it’s liberating in a way. 

You and I are insignificant. 

There are few names in history we are taught about and remember. 

Cesar. Shakespear. Newton. Einstein. There may be more depending on your curiosity and attention in history class. 

But everyone else, just fades into history. 

Anything you do will fade. It will disappear, just like the human race will disappear and the planet will disappear. No one is going to remember you past a certain number of generations, whether you’re an artist, a poet, a conqueror, a pauper, or anyone else.”
– Naval 

My failure  is insignificant in the context of the universe. 

So is yours. Use that to your advantage. 

Reframe 

So I hit an obstacle on my way to my goal. 

If I am creative enough to look at it from the right angle, there’s an opportunity in failure. It’s got power. “Failure is showing you the way, by showing you what isn’t the way”. 

As Nassim Taleb frames it, “The wind extinguishes a candle and energizes fire”. 

If you see yourself as a candle, the wind is detrimental to your progress. 

But reorient your perspective, reframe your position and see yourself as fire. Now the wind has an appealing power that will help you blaze a new path. 

So, step 2 is asking  if I can reframe the failure and use it, instead of hiding from it? 

You want to be the fire and wish for the wind.”

Separate Yourself from the Failure.

 I think we can learn something from sport and apply it to life here. 

If I have a bad swim workout, I get out of the pool and I leave. If I have a bad bike ride, I get off the bike. 

Giving myself some space from the area in which I faced an obstacle or a failure is highly effective at putting it into perspective. 

I think the same is true for all other moments of failure. Give yourself some space. 

Go for a walk. Do a workout. Use the time to separate yourself and who you are from the situation that has just occurred. 

Step away from the moment. 

Clear your head. 

When you do, you have the chance to think macro, not micro and to reframe the problem more effectively. 

Talk to Someone

In a way, the way I see the problem, is the problem. 

There’s the object event I’ve bumped up against. 

And then there is my interpretation and perception that identified it as a failure in my mind. 

A good way to help reorient my interpretation and perception of the event is to talk to someone that can remain objective about it. 

There’s enormous value in talking to someone that’s not involved. Someone that has had experience with a similar failure in the past. Someone that has your best interest at heart, but will stay objective and tell you the truth. 

Listen. Process. Learn. Adapt. 

Write 

An option that is potentially better than talking; write. 

The goal is to get the thoughts out of your head. Writing forces you to articulate the problem and your perceptions that surround it. 

When I think, my thoughts morph. They evolve and contort. They grow and escalate. If I get stuck inside my own head, thinking makes things a lot worse. 

When I write, I can draw boxes and boundaries around an issue. It defines it and gives it structure. 

With definition and structure, I can separate myself from the issue. And I put myself in a much better place to reframe & change perspective.

Move Again. And do it Fast.

The longer I ruminate or think deeply about the failure, the bigger it is likely to become. With enough time and enough thought I can create a very destructive monster. 

Do not allow this failure to become a monster. 

You don’t have to have everything figured out perfectly to move again. There’s no need to rush, take a moment to separate yourself from the event, compose yourself, gather your thoughts. And then get back on the horse before it runs away from you. 

Six tools that set up a framework to help me see the upside, contextualize the downside and keep moving forward after failing. 

I’m hoping they work. 

Because I’m intentionally stepping into two goals that both excite me and scare me. 

  1. Pivoting my business in a new direction 
  2. Training to break 4 hours in an Ironman 70.3 race.   

Both are equally important to me. Both are going to test me. 

Both are going to teach me lessons and deliver experiences and opportunities that I would not otherwise have the chance to experience. 

Here’s to running, a little less apprehensively, in the direction of the unknown.