Overcoming anxiety and the fear of failure (episode 30)

We all know that feeling of failure. That feeling of inadequacy. The feeling of rejection. The feeling of embarrassment. The anxiety that comes along with entrepreneurship and generally anything that is worth doing in life.

Mine was a basketball game in southern Indiana. Basketball is intense in southern indiana. I was a sophomore and I was a role player on the varsity team. I was our second leading scorer but I think it was only 8 or 10 points per game. We had a star player who ended up getting a full ride D1 scholarship at Indiana state. We passed the ball to him. He averaged 25 points per game. Because he was on our team and just because of the general culture in Indiana our games were popular. On friday and saturday nights people went to local basketball games. Thats just what they did for fun. It was common for 2-3 thousand people to show up and pack a small gymnasium and the atmospheres were electric. Picture the movie hoosiers.

Its the biggest game of the year. Against our rivals on the other side of the county. On their court so we were away. Its extra crazy. There were full student sections standing and screaming the entire game. It was standing room only in the gymnasium.

Star player gets in foul trouble before half time. The first time he got taken out of the game all season. All of us young kids were just looking at each other. I think we were winning the game by a few points when he went out.

About two minutes to go in the half. One trip down the court I get passed the ball in the corner and shoot a three. Airball. The entire crowd starts chanting Airball, Airball, airball. I start to get a little nervous now. The other team comes down and drills a three pointer. The crowd goes nuts. Next time down the ball gets passed around a few times and ends up in my hands again. I drive to the middle leave my feet for a shot and realize its going to get blocked and make a bad pass. The ball gets picked off and the other team goes down and gets a fast break dunk.

Dunks aren’t that common in high school basketball so now the crowd is really going nuts. Our coach calls a time out. We try to regroup.

We go down the floor the next time and I end up driving to the basket and taking a contested layup that wasn’t even close. The other team was turning up the defensive intensity knowing we weren’t comfortable and weren’t going to be able to get aggressive. The other team goes down and scores again.

With just a few seconds before halftime I once again get thrown the ball and I drive the sideline and go up for a layup. A defender got a great position and took a charge. Foul on me. Another turnover. Clock expires and its halftime. We’re now down by 10 points.

As we walk off the court with our heads down the people there in our cheering section begin to boo our team. Our own fans begin to boo me. A few fans stood up and started pointing and yelling at me.

We go to the locker room and sit there in silence. After a minute or two, which seemed like an eternity, our coach storms in with a red face and a clipboard. He walks right up to where I’m sitting and points at me. He screams “you are not our best player! You will never be our best player! Stop trying to be our best player!” Then he slammed down his clipboard and walked out. That was the extent of our halftime talk.

I will never ever forget those 10 minutes of my life. That voice is deeply ingrained in my mind and I’ll never forget the look in my coach’s eye. All this as a 16 year old kid just trying to figure out life and where I fit in.

That experience pales in comparison to what some people deal with.

Its ingrained in our mind from a traumatic experience as a kid. A cruel bully. Maybe its a parent who just didn’t build us up and instead tore us down and criticised our every move. Maybe an abusive girlfriend or boyfriend. A sports moment or just the insane sport environment in general growing up where every action we take is measured and failure is obvious.

It still plagues us today. That inadequacy. That voice inside our head that is telling us that we just don’t have what it takes to be successful. That we’ll never be good enough. That we just don’t measure up. Other people can do it. Other people can win but I never will.

This isn’t just men. Not just women. It is extremely common for all human beings.

Every single one of us, at times, have that anxiety that arrives and that self doubt that arrives when we are in an uncomfortable or unpredictable situation. That heightened sense of self criticism. That voice telling us that we just aren’t quite good enough. That reluctance to trust ourselves and instead trust what that one bully or that one coach told us when we were 12. Trust that we just aren’t good enough and we can’t do this. The anxiety is crippling.

This is incredibly prevalent in our personal relationships. Maybe somebody is doing something amazing but we are afraid to tell them that because of our own insecurities and our own inadequacies and thus our own jealousy. Maybe our own insecurities lead to trust issues and kill most relationships before they get serious.

Maybe its the inclination in our lives to conform to what other people are doing. In middle school we call that peer pressure. That goes away when we get older right? Wrong. Now its called keeping up with the Joneses. Thats called getting an expensive college degree so we can afford the car payment on a $60k Chevy Tahoe and the payments on a $500k house in the swanky part of town and the credit card payments on the bills we rack up while dining with our friends at the expensive restaurants three times a week.

Maybe that fear of rejection cripples us and keeps us playing the safe game. Maybe our #1 goal in life is to make sure those feelings of failure and inadequacy never show their faces again. Those feelings of being the target of boos from a crowd and a screaming coach never happens again.

There is nowhere in life this is more prevalent than when it comes to entrepreneurship. Entrepreneurship is just like that basketball game. The stakes are high. Failure is obvious when it happens. Its uncomfortable. Its risky. Your friends are going to make jokes and talk down to you when you buy that first $1500 cargo van on craigslist. They sure did to me.

That failure is scary.

Maybe it affects you in the opposite way and forces you to overcompensate. The anxiety forces you to try the long shot venture capital backed company. To try to be the next steve jobs. To try to be the next elon musk. To try to change the world.

Maybe you just want to prove to everyone that you are indeed spectacular and they were all wrong. That your coach was wrong. Your dad was wrong.

In either case there is a fear that you will lose your status. There is a fear of failure. There is a fear of what other people will think of you.

So how do we manage this fear of insecurity and failure and rejection? How do we surpress those negative emotions so we can achieve our goals and find happiness in life? It starts with answering one simple question.

Who am I seeking approval from?

I have news for you. The only person you need approval from is yourself. You are the person that controls your emotions. You are the person that determines if you are happy or not. You are the leader of your own life.

The sooner you stop chasing stamps of approval from other people you will be much much better off and happier. Instead of letting the joneses set your standards you need to feel good about yourself its time to set your own.

How do you want to live? What 20% of activities do you do in life that bring you 80% of your joy? What moral code do you want to live by? What makes you happy.

What about other people? What about my husband or wife? What about my best friends? What about my family members?

These people love you and care about you because of who you are. Because of your moral compass. Because of what drives you. Because of what makes you happy.

So if you approve of yourself and you are happy and confident in your own skin these people will automatically love you and stick beside you. You will get their approval as a byproduct of only needing your own approval.

Let me repeat that. You will get the approval of the people closest to you as a byproduct of only needing approval from yourself.

Set your own standards of success and work towards them. If you can train yourself to realize that other people’s opinions don’t matter failure really isn’t that bad.


A funny thing about that basketball game. The second half I obviously played horribly. I was rattled. I cried on the bus ride home from the game. I cried later that night at the kitchen table as my father and I talked over the game. Luckily he worked hard to build me up. He focused on the positives. The next night I had the best game of the season. I scored 26 points including a steal and a layup as time expired to win the game. The same fans who bood me the night before cheered me on and celebrated the win the very next night.

Now I have even more news for you.

Getting uncomfortable and facing uncertainty is fun.

What is the worst that could possibly happen if you take a leap and start a business? I’m serious. Think about it and answer this. If you’re in America you surely won’t starve to death. In most places in the world you won’t miss a meal. If you do it right and in a low risk way you might lose a little bit of time and money. Its not so bad. Its probably not even as bad as getting yelled at in front of your peers by your high school basketball coach.

Its the possible failure that makes the victory so sweet.

Building something is fun. Entrepreneurship is so amazingly fun because you never know what is around the corner. You never know what is on the horizon. You never know if the phone is going to ring and an employee is going to let you know he just rear ended a mercedes benz on the highway or ripped the top off the company box truck. I’ve gotten both of those calls.

I’ve also gotten the call from a school administrator letting us know that we won the contract to be the preferred provider at a big ten university. I’ve seen the email inbox go nuts with new customer signups beyond our wildest dreams. I’ve had a customer send a thank you card to my house after she packed her passport in her storage squad box and didn’t realize it until it was 3AM and she woke up to catch her 7am flight to China. We answered the call at 3am, dug through the box, and delivered the passport to Boston Logan just in time for her  student to catch their flight back to china.

So what drives you?

Is it the money? You might think its the money and the things you can buy with money but I bet it isn’t. The scientific data on happiness would disagree with you as well. How much money do you need? Really how much money do you need in order to spend your time doing what you enjoy most? Get your number. Write it down. I bet its a lot smaller than you think. Most of the 40 somethings grinding 60 hours a week have already surpassed the money mark long ago but they keep working. Why? This leads me to the next one.

Is it the status? Maybe. That drives a lot of people. But those people are rarely happy. There will always be something else someone has that you don’t have. There will always be that next level of wealth. There will always be someone who has more than you do. Someone who went on a more expensive vacation than you did and put the photos on facebook for you to scroll through. If you chase status you’ll spend your life chasing something that is impossible to fully quantify.

Is it time? Do you want to get your time back so you can spend it with people who mean the most to you? Do you want to watch your kids grow up? Do you want to be at their little league games? Do you want to go on Daddy daughter dates once a week with your amazing 5 year old? Most children don’t get to ever experience timelessness with their dads. Will your children?

The first step is to find out what drives you. Build out your own sets of standards and your own goals. Your own stamp of approval.

I’m going to send you with a challenge. Tomorrow morning wake up an hour earlier than normal. Make a cup of coffee and have a snack. Don’t touch your phone or computer. No input. Go to a quiet place in your house and think. Get a pad and a pen and write.

What do you want your day to look like 5 years from now? What do you spend your time doing? How much money do you need?

Don’t let your anxiety and insecurities hold you back. Don’t let the fear of rejection hold you back. Don’t let standards put on you by society keep you from making decisions that align with your own personal goals. Get comfortable with and embrace the uncomfortable. Buck the 9-5. Embrace the possibility of failure. Get out and build the life you want.

April 9, 2019 9:37 am