Why You Shouldn’t be Afraid to Fail

Don’t live a less meaningful life trying to avoid pain like I did

The truth is fear has been in charge of my life for as long as I can remember.

That was a difficult line to write. In fact, it took me 8 minutes to type it out. The reason… I was raised that men — especially 37-year-old men — aren’t afraid. Well, at least they don’t admit to other people that they are afraid.

My fear is also difficult to explain because it isn’t a physical object. It isn’t like I am afraid of dogs, or spiders or heights even. No, what I fear more than anything is failure.

A fun side-effect the 2020 year has graced me with is more time than I ever imagined to just sit around and think; and the one thing I have been unable to avoid is recognizing how much my fear of failure has controlled my life. I took jobs that seemed more secure as opposed to those that would be more challenging and fulfilling because I feared not making as much money or being as successful as my friends. I avoided asking women out because I feared being rejected. I avoided being the center of attention to ensure I would never screw up and embarrass myself in front of EVERYONE.

Failure has been such a difficult demon for me to fight because it lives in the most frightening place in the world to me — my head. Who the hell knows what is going on up there? For so many years I thought I did. I assumed I was in charge — telling my brain what to do. I mean it’s my brain. I control it, right? But in reality, I have built so many bad habits that my brain has already decided what I will do — or more importantly what I won’t do.

On the surface it would appear letting fear guide my decisions has been a good thing. I have held jobs that pay well and enabled me to travel the world, I am financially secure, I have a good family and I have great friends. It is a good life really; I am just not sure it is a happy and impactful one.

I have always had the ability to tell myself now wasn’t the right time or things just weren’t meant to be.

I loved playing soccer; and while I wasn’t athletic enough to play professionally, I always thought I could be a coach. But then I quit playing after high school because I wasn’t getting recruited by colleges. However, I never reached out to any coaches to inquire about playing for them. Never reached out to coaches to ask about helping them out or becoming an assistant. Why? I convinced myself if it was meant to be that a coach would find me — by some miracle I guess since I wasn’t playing or networking.

As I abandoned my soccer dream, I started college with a new dream — sports radio host. I attended a school known for a strong Communications program and television and radio networks. So I applied to be a part of both programs, right? What better way to pursue my dream? No, instead I decided I needed my free time for studying and partying. I needed to get good grades, but also school wasn’t supposed to be all work, right? So apparently despite the fact my classmates were getting real world radio experience, I figured I would still make it big just because I knew sports better than my friends.

I have always envisioned myself getting married and having a family, but I stayed at home when my friends went out and would never talk to anyone outside my circle of friends. I mean I was an introvert. Plus, school and life were hard enough so I didn’t want to “work” on finding a relationship. So, I determined the right relationship would just find me. Apparently I figured a smart, beautiful woman was just going to approach a goofy, awkward guy and ask him out?

But now at 37-years-old I recognize it was my fear that crafted stories for not pursuing these dreams as a way to avoid failure. Instead of admitting I was afraid of giving my all and coming up short, of letting myself and others down, I told myself stories about why it made more sense to kick my dreams to the curb with no other goals in mind. Now, instead of having the gratification of knowing I tried my best to do something I loved and felt could make a difference — successfully or unsuccessfully — I am left with regret and questions.

How much more could I have accomplished? How many more people could I have helped? How much happier could I be?

I am not sharing this for sympathy, because quite honestly I don’t need or deserve that. I had plenty of resources and opportunities to change direction but have yet to be courageous or strong enough to do so. There is only one person to shoulder any of the blame for my regret — and it’s the guy writing this.

No, I am writing now with the hopes that what I share resonates with someone else and helps them avoid the mistakes I have made — and also, quite frankly in a selfish way to hopefully motivate myself, to finally change. I hope someone reads this and senses the regret I have over many of the decisions I have made and chooses instead to pursue their passion. Or ask that person they like out. Or stand up and fight for what they think is right.

The great Michael Jordan said, in order to make the winning shot, you also must be willing to miss it. Jordan himself has said he has missed many game winning shots. But it was in those moments of trying and failing that he grew and developed the ability to become the fearless champion we all know him as. Jordan doesn’t live with the regret of not having known how great he could be because he let his desire to be the best overrule his fear of coming up short.

The problem I had — and I think many of us have is that we don’t have someone to tell us when we are older how much more painful the regret of not chasing our dream will be as opposed to the pain of potentially failing in the pursuit of living a more fulfilling life. So, if you haven’t heard that yet take it from someone with a boatload of regrets from playing it safe — chase your dreams.

Work hard. Set goals. Educate yourself on how you can achieve what you want. Then pursue it with all you have — because even if you fail you will have accomplished and lived a more fulfilling life than had you not tried at all. Failing isn’t something to be ashamed of — no, it is something to learn and improve from. We all fail. Not trying and living with regret — that is the thing you should really fear.

2020 has been wrought with craziness but one thing I am trying to take away is to finally defeat my fear. I have started working with a career coach and talking to my friends and family more openly about the changes I want to make. Changing habits is difficult fight though and I fight myself to change every day.

Every day I fight my old way of thinking and that tiny voice in my head telling me I am not good enough. I never feel like I am moving quickly enough in the right direction. Slowly but surely though I recognize that voice and tell turn it off and turn some positive thinking on. I have started to recognize when Negative Dan is trying to tell Dreamer Dan to just play it safe.

I think this article is another step. I am not a writer and I am definitely not a person who shares his feelings. But here I am admitting my fear out loud, asking anyone who reads this to help keep me accountable and also asking others to join me in the journey of fighting their fear of failure — or any other fear you need help fighting.

Anyone who has achieved success has tried something new and failed, but the difference between me and them is that they picked themselves up and challenged failure again. The difference between me and them is they recognized failure isn’t nearly as scary a proposition as regret.

I want to be like them. I want you to be like them. The world needs new leaders (I think the first Presidential debate validated this), ideas and products more than at any other point in my lifetime. Let’s push one another to stop being afraid of missing the game winning shot and start convincing one another to take chase our dreams so we can achieve the success and happiness we all deserve; and in the process make this world the place we all know it is capable of being.