Entrepreneurship can be painful – learn how to deal with it.

You might not believe it if you met me today, but I used to be a pretty serious skateboarder. For just over a decade, I used to spend countless hours on a skateboard..

This wasn’t an easy process. Often, a soft part of my fragile human body would crash into something hard— the board, the pavement, a railing. And by repeating the same trick (or attempting to) over and over again, these mistakes would result in a bruise. A dark, deep blue-purple that only got worse as I continued to practice.

I’d be lying if I told you it didn’t hurt.

But dealing with this pain became part of my life as a skateboarder. And I learned, through this ridiculous self-punishment, how to deal with pain. The realization came to me— pain is 90% mental.

How to Erase Physical Pain

Somehow, I managed to reason with my body. I managed to separate my emotions, my reactions, my interpretation of pain from the actual feeling of pain. I learned that while I couldn’t change the existence of pain in my life, I could change how I reacted to that pain.

With enough practice, I was able to almost completely forget I was in any pain in the first place. Have you ever had two injuries at the same time? Have you noticed that the one that hurts most commands your attention, where you can almost forget the second? Imagine if you can do that same forgetting act actively— whenever you needed to.

It becomes exactly like that innate ability you have to ignore things that pose no danger to you, but are still a little uncomfortable if you think about them. Like the feeling of your shoes wrapped around your feet. Or your wallet in your back pocket. You’ve learned to ignore this level of discomfort, because it’s not immediately dangerous.

This concept is essential how I learned to manage pain in my life. By recognizing that I’m in no immediate danger, and simply refusing to pay attention to it.

Dealing With Your Emotions

As the years passed I dropped my skateboard, wore smarter shirts, got a professional haircut and spent more time in the business world. In a nutshell, I grew up. But the lessons I learned as a skate park kid stayed with me. And in the world of grown ups I continued to practice this detachment from pain.

Adults deal with a lot of pain. Often, this pain is emotional. And emotional pain is hard to shake. You can’t take painkillers for it. In fact, dulling or numbing emotional pain can lead to bigger problems down the road. You often have no choice but to face this kind of pain head on.

So how do you deal with it? How can you put it aside a deal with your life more calmly?

The principle is exactly the same. Detach yourself from whatever emotional pain you feel and study yourself. How are you reacting to this pain? Is it controlling you? Or are you controlling it?

Remember, you often can’t change the circumstances surrounding pain. You may be feeling loss, maybe you’ve been betrayed— whatever it is, allowing it to affect your behavior is not healthy; accepting it is. You can’t control these circumstances; all you can truly control is yourself.

What the heck does this have to do with Entrepreneurship?

I believe that you as an entrepreneur have to be able to keep a cool head no matter what happens in your life or business.  If you get too consumed by the problem you will not be able to make a calculated move. Learning to be stoic will make your entrepreneurial journey a lot more pleasant.

The Stoic Approach

A friend of mine introduced me to stoicism recently, and I’ve realized that I’ve been a bit of a stoic my life without even realizing it. The stoic approach to pain is right in line with my own approach. A Stoic philosopher might argue that often, you can’t control your own body. The only thing, according to stoicism, you truly have control over is your mind. You can control your reaction to pain, but not the pain itself. To master your pain (physical or emotional), you need to master yourself.

As I’ve grown up, I’ve learned to do just that. On a skateboard, I trained my mind to ignore pain and focus on my performance. As an adult, I now do the same thing when feeling pain, discomfort, or even just plain old social awkwardness. The key is the same: keeping a clear head, focusing on the task at hand instead of my own discomfort.

In your own life, where are you feeling pain (emotional or otherwise)? How do you deal with these feelings? Are you governing your reaction to it? Or simply waiting for the pain to pass?

If you’re interested in learning more about this topic, check out Fight Mediocrity’s fantastic rundown of the classic stoicism text, Meditations by Marcus Aurelius. Until next time!


I’m a serial entrepreneur and I write about things I have learned along the way. I’m passionate about helping entrepreneurs and executives to find success and harmony in business and in life.

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