#unfiltered #31 The Art of Running into Walls – How to Confront Fear and Fear-Setting

Last night, I happened to re-stumble across a sentence in my collection of quotes that caught my eye.

“The greatest pleasure in life is doing what people say you cannot do.”

Walter Bagehot
Journalist, businessman, essayist

The founder story

I’ve had this long-standing belief – which if you’re a regular reader of this blog, you’re no stranger to – that founders need to have a personal vendetta when building a business. They must have something to prove or someone they’d want to prove to. Building a business is finding where selfishness meets selflessness. In fact, I’d argue that’s true in every ideal professional career.

The path of entrepreneurship is one where resilience is the floor, not the ceiling. While I understand, it is not the only career path that carries this trait, it is the one I am most familiar with. And having asked 31 people, 18 of which are or have been entrepreneurs, I’ve learned that everyone, despite their job title or background, can be scared in the face of obstacles. Everyone feels fear, myself included. The question is what do we do next, after the feeling of fear enters our heart and mind.

The question of fear and doubt

As Matthew McConaughey said in his recent interview with Tim Ferriss when speaking on solitude and the art of running downhill, “What I think we need to remember to do is when we’re asking ourselves these questions, just make sure we answer. If all we’re doing is asking ourselves questions, but never coming up with an answer, well, that can lead to some very imbalanced insanity at times.”

The questions are the feelings of doubt, fear, anxiety, stress, frustration, and depression. Am I good enough? Can I really do it? What if…? But too often, and I know I’m guilty of this as well, we don’t sit down and try to find the answers to these questions. For me, that is part of the reason I journal every day. To chronicle my life, but also to help me think through the dilemmas I come across.

As luck would have it, one of my friends asked me not too long ago, “How do you confront your fears? How do you get comfortable confronting your fears?”

I call it the art of running into walls. I call it an art and not a science because I have yet to finish proving this hypothesis. And because of that, this post is by no means meant to be prescriptive, but rather another tool in your toolkit should you ever feel the need to equip it.

Running into walls

I’m human. I make mistakes. I’m imperfect. And as a (shy) introvert, for the larger half of my life, the scariest thing that I could ever confront was talking to strangers. Seems odd to think about it now, where my career is predicated off of it. While it may or may not be obvious, I’ve failed at talking to people. Not just 6 years ago, but sometimes, still today. While my batting average is definitely a lot higher than before, there are I still mess up. But each time I learn. Well, a tub of ice cream, then learn. Over the years, my practice of solace has gone from ice cream to journaling.

And when I’m stressed, I tend to remember the times I failed more often than the times I’ve patted myself on the back.

People telling me “You’re not the person I thought you were”. More than 20 times.

People telling me “This isn’t working out” 10 minutes into a 30-minute conversation. 3 times. One of which was from someone I looked up to.

And a conversation with a founder resulting in “Can you delete my phone number from your cell? I’d rather us not keep in touch”.

I don’t ever try to antagonize anyone. In fact, I often do my best not to. Each time I hit a new low, I learn “S**t, so this is how low I can go.”

But I still go on. Because the small chance of a huge upside makes every other downside worth it.

The art of running into walls

As a kid, I used to look at how amazing other people were. How each became a local icon. A global icon. Behind every story was a story of adversity. Yet I feared and fear adversity.

So, over the years, I’ve learned to protect myself from adversity – while going through it. I learned how to put on Kevlar and run through a battlefield.

I understand that to grow, you must try, fail and learn. No textbook can teach you how to fail. And while they may teach you how to learn, you don’t really learn until you’ve experienced it. The difference between the French savoir and connaître.

My Kevlar comes in 4 parts – 4 questions I ask myself:

  1. What do I want people to say in my eulogy?
  2. What will happen if I don’t do anything?
  3. What’s the best that can happen?
  4. What’s the worst that can happen?

1. What do I want people to say in my eulogy?

To live, I think about how I will die. If I could set the terms to how I die, how would I set it? If I could be a fly on the wall to my own funeral, what would I want to hear?

Frankly put, what is my ideal self-funeral?

Do I want to be remembered as the guy who’s great at Excel? A guy who got good grades (I didn’t)? Not really. No.

What friendships, relationships, accolades, achievements, and impact do I want to leave the world with?

2. What will happen if I don’t do anything?

Will I be able to handle the short-term, but more importantly the long-term, consequences of my inaction?

Ray Dalio, author, investor, and philanthropist, calls it the 1st and 2nd order consequences in his book, Principles. Usually, the 1st and 2nd order consequences are in direct contradiction with each other. Simply analogized, eating a piece of candy now will give me cavities in the long run. Positive 1st-order, negative 2nd-order consequence. Or hustling 12 hours a day, throwing away your social life, will net you enviable success in the long run. Negative 1st-order, positive 2nd-order consequence.

3. What’s the best that can happen?

What’s the best that can happen? When I was training as a swimmer, we were taught how to visualize. The more detailed your visualization is, the more likely you are to succeed. What needs to happen for everything to work out smoothly? What will your celebration look like? Yes, it’s just as important to visualize the aftermath as the actual event going down. This helps to motivate you even more when you attach the emotions, along with the rationale, behind what success looks like. Get the adrenaline pumping.

4. What’s the worst that can happen?

Equally so, it’s important to visualize the worst. And what you will do – before, during and after – the worst happens. How will you react? And in doing so, you can hedge your own emotions when the worst happens. It rarely does. But it’s possible. And if it’s possible, it’s worth preparing for.

Every new global minimum, from experience, becomes ammunition for visualizing in the future. The more times you do so, the less likely you will be victim to emotions and irrationality when/if it happens. It’s easy to regress to the seemingly impossible odds that are stacked against you, especially if you practice finding answers to this question. But I just focus on remembering one thing. “73.6% of all statistics are made up,” as Mark Suster of Upfront Ventures puts it. So, who knows? The odds are all made up.

In closing

In sharing this post, I’m reminded of what one of my friends brought to light in my last research project. A quote by the great Charlie Chaplin,

“Life is a tragedy when seen in close-up, but a comedy in long-shot.”

Photo by Joshua Sortino on Unsplash


#unfiltered is a series where I share my raw thoughts and unfiltered commentary about anything and everything. It’s not designed to go down smoothly like the best cup of cappuccino you’ve ever had (although here‘s where I found mine), more like the lonely coffee bean still struggling to find its identity (which also may one day find its way into a more thesis-driven blogpost). Who knows? The possibilities are endless.


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