Chapter 7

Facing Failure: Be Wrong to Be Right

Sometimes you have to be wrong to be right. Making shit up also means that plenty of shit goes wrong. One of the hardest things to get comfortable with as a leader as well as a creator is admitting that you are wrong. It can be a scary thing, and, let's face it, doesn't feel good. You can feel pretty damn stupid at times.

Failure is an undeniable part of any creative process. There's no such thing as a perfectly formed and executable idea. Where something begins is never where it ends, no matter the initial spark of genius that ignites the idea. Iterating, failing, and advancing the concept are all part of the process of making stuff up.

There are many experts who can speak on the various different ideas around failure – failing fast, failing forward, failing early, and failing often. I come at it from the perspective of playing make pretend on stage and trying to get people to laugh at my nonsense. While I agree with every one of those types of failure, only in comedy do you experience all of those again and again, night after night in front of people who immediately let you know that you are in fact failing. A comedian failing on stage is not a theoretical endeavor. It is a very real and tangible thing. And it can leave marks.

The beauty of this kind of failure is that like real bodily injuries you start to build up psychic scar tissue. I have never met a single person in this industry who has not bombed on stage. Anyone who has ever done comedy, no matter what level they have achieved, has spent a significant amount of time being painfully unfunny in front of people. Some find their funny and their voice faster than others, but the fact remains that when you are creating something out of nothing and trying to elicit an emotional response from people, you can only figure it out through trial and error.

I think at this point most people understand that failure is necessary. What I want to discuss is the idea that the fear of failure can be overcome and does not need to stop you from pursuing your dreams. Tolerance to failure can be built up just like tolerance to physical pain, exercising, or heat or cold or alcohol. And the way you build a tolerance is by repeated exposure to the thing you want immunity from.

Coming up as a comedian has helped to build within myself a resiliency against failure. When you allow yourself to fail again and again on stage you begin find that the actual act of failing becomes less and less painful and important. By failing a whole bunch of times in a low‐stakes environment – in my instance on open mic stages in crappy bars and clubs around Boston – you begin to develop that scar tissue.

As that scar tissue becomes thicker, you feel the pain less and less. As the pain subsides, so does your fear. As your fear goes down, your confidence in what you are doing correspondingly goes up. As your confidence grows, you begin to associate pleasure with the act for taking risks and creating. Your mind starts to comprehend that small short‐term failures aren't really setbacks at all, and that as long as you keep pushing forward and putting in the reps, you are bound to get stronger at whatever it is that you are doing.

The fear of failure is right up there with the fear of looking stupid in terms of things that we can control and often stop us from moving ahead with our ideas and dreams. Especially in the beginning stages of any new endeavor, pushing through our own fear of failure is pretty much up to us.

I clearly remember the first open mic comedy set I ever did. I knew I wanted to try stand‐up comedy. I first started by taking small actions that were within my control and that had very little risk. I found out where the open mics were. I went to see some shows. I started writing down my ideas in a notebook. All of these actions that I could take really didn't expose me to any sort a failure.

I didn't have to tell anyone I was doing any of these things, so there was no judgment from others that I had worry about. Since each of these actions was personal and private, there were no consequences good or bad that came from them.

I finally mustered up the courage to take the critical step from being a passive observer and private creator to putting my thoughts and actions out there in the public realm. I got the number of the person who booked the open mic acts at Dick Doherty's Comedy Vault, a comedy club in the basement of Remington's restaurant on Boylston Street in Boston. It was called The Vault because the basement had once been a bank vault, and the huge mechanized door with all of its wheels and gears was still there in the basement. I wrote, prepared, and did my five minutes along with 18 other people on the bill that night. It predictably went about as well as you'd expect from a person who had never done standup comedy before in their life. That is to say, I sucked and wasn't particularly funny.

I remember hanging out for a while after the show and eventually making my way to the exit where, with my tail between my legs, I thanked the organizer for giving me a chance. The guy, barely looking up from his binder, gave me a quick look and said “Not bad for your first time. I have a spot next month if you want it.”

I was shocked. I figured this was my one shot, and that I had failed so badly and so publicly there was no way I was going to be invited back to perform. As I took the Green Line trolley back to my pantry apartment in Cleveland Circle, something clicked in my head. It occurred to me that as long as I was willing to get back onstage, they were willing to let me get back on stage. I came to understand that the organizer of the show didn't particularly care if I failed, and that if I didn't care if I failed, then there was no barrier to keep me from performing.

Now of course this was the appropriate setting for where I was in my own skill set, and the consequences of my failure were really just my own ego in psychic pain. I kept getting back up there on that stage and, needless to say, I improved. I was doing the same thing with improv groups around the city as well. If somebody would let me improvise with them, then I did it. It made no difference to me if I was good or they were good or an audience thought that I/we were good. I was willing to fail, and then try to dissect the feedback regarding what worked and what didn't and improve from one show to the next.

Developing the ability to push through the fear of failure has helped me far beyond anything I've ever done on the stage. At some point it becomes relatively easy to create onstage. No matter how big a show is, the stakes are in all actuality pretty low. They think you are funny or they don't, they go out for drinks either way, and some portion of the audience is willing to come back and see another show and some won't. Nobody dies or loses their life savings and we all get on with our lives.

This isn't exactly the case when you're creating or taking risks in the “real world.” There clearly can be far greater consequences and therefore the idea of failing can be far more daunting. But the tolerance that I built up to risk and failure has served me incredibly well as I have helped conceive, develop, and grow my businesses. By building up that scar tissue I have been able to move through the fear of failure in many different areas of my life.

The creation of Improv Asylum is a perfect example. When I and my two partners at the time identified that we had a chance to take over a 200‐seat theater and bar in the heart of Boston's North End, the only thing that was holding us back was the idea that it may not work.

At the time, improv comedy was not known as a popular commercial entertainment form. There was no successful precedent for this kind of business in Boston. Nobody was shouting from the rooftop “Lord, please bring us live improv comedy, we the masses demand it!”

The odds of failure were great and in fact most everybody expected we would. And why wouldn't they? I was a 26‐year‐old who lived in a pantry and was so broke that I my car had recently been repossessed. There wasn't a lot of there to indicate that a stellar career in entertainment and business lay ahead of me.

What was very clear to the three of us, though, was the idea that we wanted to find out if this would work or not. All of us agreed that when we were 40 we wanted to know that it was either a success or a failure. What we couldn't live with was the idea of not trying and having to wonder what might've been.

Being “wrong” is different from failing. A decision can still be right even if it fails. Because I love football and belabored sports analogies, consider a coach's decision to go for it on fourth and two. If the team picks up the two yards, they can run out the clock and win the game. If it doesn't, they give the ball back to their opponent who still has time to march down the field to potentially win. Going for it on fourth and two may still be the “right” decision even if the team fails to pick up the two yards. The lack of execution may result in the “failure” to pick up the first down, but the decision to go for it is not necessarily “wrong.”

Being “wrong” typically means that upon reflection you would do something differently, or that an outcome that you were very sure was going to happen didn't materialize. Failure is something we can live with. We learn from our mistakes and hopefully improve from this new knowledge. Being wrong? That's personal. Being wrong feels much more like a critique of our talent, intelligence, or moral compass. Saying “I failed” implies that you at least tried. Being “wrong” just seems like you are an idiot. Nobody likes to feel like an idiot.

But when you open yourself up to acknowledging you were wrong about something – a decision, idea or concept – you open yourself to being right. Other, better options often appear. You learn something new from being wrong as well. Things become clearer and you begin to understand concepts that you may not have before. Being wrong allows you to definitively eliminate certain things and focus on the ideas or actions that are working.

Admitting that you are wrong, as anybody who has had a romantic relationship with anybody already knows, can be incredibly difficult. What is also true is that usually, by that simple admission, the problem is defused and solutions begin to present themselves.

For me, this happened 19–20 years into the life of Improv Asylum. And I am not talking about some creative concept or show idea. I'm talking about very real world stuff. As my companies have grown in size, scope, and complexity I had been resistant to adding in more controls, specifically HR controls. My attitude had always been “We don't need that. It will kill the culture of creativity and freewheeling exchange and development of ideas. We create comedy, for shit's sake, now we are going to have HR telling us what to do and say? No thanks.”

Good people, people with whom I had worked closely for 20 years and who are smart and talented told me many times that we should do more, that the company was growing and in need of this kind of support. Employees as well. Great people who cared about the company as much as I did. And yet I didn't listen. I knew better. Or at least I didn't want to face the fact that if we needed that kind of support, then that meant I, too, probably needed to change the way I was doing certain things.

You change, sure. Me, change? No thank you very much. It was easiest to hide behind the mantra of “HR will change the culture for the worse.”

I was wrong. We needed to grow. The company we owned at 20 years was not the same company it had been at 1, 5, 10, or even 15 years. It was different. I was different. Unfortunately, it took several difficult incidents to galvanize me into action. But once I decided that I was wrong and we needed to change and seriously look at what we were doing with this segment of the company, I was all in.

And then a funny thing happened. That thing that I feared, the culture changing, started to happen. The culture definitely started changing. For the better. I could feel it. I could see it and hear it. And I started to change too, for the better. This thing that I feared, HR for more professionalism and structure, things that I thought were overrated and not all that important, became far less scary. I started working with amazing professionals outside the company who showed me so much more than I ever thought was important on that side of the business. I started to learn again. I was getting coaching, notes, ideas from incredible people who knew a hell of a lot more than I did about this stuff.

Here is the scary part. I liked it. I mean, like really, really enjoyed it. I never thought that I, as a guy who came up in comedy, who went into comedy and started businesses because I didn't want to listen to or be like other people, would totally dig having deep philosophical conversations about HR, culture, employees, and all the things that come with this subject. No one wanted to “change” our culture in a negative way, they wanted to help make what we have at this stage in the company's life much, much better. That became something I could get excited by. Why the hell wouldn't I want to get better, both personally and as a business leader?

I was wrong. I feel stupid looking at it now and realizing that I should have embraced a new way of thinking long ago. I'm stubborn, confident in my ideas, always convinced I can figure it out. Great traits to have as an entrepreneur most of the time.

Being willing to be wrong proved to be more important than any of those characteristics at this point in my company's history. By being wrong, I was able to look at things in a whole new way. It has given me a brand‐new confidence in what I'm doing and where I know my companies can go.

Admitting you are wrong is hard. Change is hard. We still have a long way to go and I know I'll screw plenty of things up along the way. And when I do, I'll have no problem admitting that I was wrong. Because it will give me the opportunity to be right again.

“Great story, dude. But what the hell can I do to feel more comfortable with the fear of failure and admitting when I am wrong?” you aggressively ask.

Let's take a look at some very simple actions or exercises you can take to build up your own psychic scar tissue. Again, I am biased, but enrolling in an improv class is hands‐down the most tangible way to safely experience the fear of failure. While the emotional and physical response to that fear will be very real, the stakes are actually quite low. Lower even than any kind of public performance.

By putting yourself in an improv environment you'll gain tangible experience pushing through the fear of failure and realizing that failure isn't the end of the world. And I can almost guarantee that wherever you are, there is an improv class being taught somewhere nearby. If there isn't, contact me, no matter where you are or what country you live in, and we will figure something out.

While my specialty is improv, you could choose any number of new skills that will flex your psychic muscles. Take an acting class or dance lessons. Join a painting group or take a public speaking course. Sign up for scuba‐diving classes at your local YMCA or beginner rock‐climbing classes at your local rock gym.

Basically, explore any activity that is tangible that you have never done before. Going to a lecture or a talk doesn't count because this is a passive activity and you do not get the firsthand experience of doing it.

You will experience some sort of a failure in anything new that you try, and that is a good thing. Because the consequences are, well, inconsequential in any kind of beginning class, this will allow you to experience and push through small failures. These first‐hand experiences will start to rewire your brain and how you experience and think about failure.

So how does one practice being wrong? I would suggest that it's not about practicing being wrong, it is about practicing admitting when we are wrong. And that can be done simply by stating or writing down “I was wrong” whenever we are incorrect. For example, how often have you been in this scenario:

This mini argument goes on for a little while and it turns out that Dana is correct, it was a left at the lights. Instead of saying what most people will typically say, “Huh, I thought it was a right” or maybe a begrudging “You were right,” here is a chance to simply say “I was wrong.”

It may seem incredibly simplistic, but by finding basic things that you are wrong about and ideally verbalizing them (another way to do this is to keep a running list in a notebook or your phone or wherever the hell you keep your notes) helps take the self‐conscious sting out of admitting we were mistaken about something. Verbalizing or writing down “I was wrong” helps us to be more comfortable with the idea of not always having to be right.

It completely decreases the time and energy we waste arguing over inconsequential details or about things that don't really matter much. When you say “I was wrong” in almost any argument, it completely diffuses the situation and brings an end to the conflict. Once the admission has been made, the other party typically quickly settles down and looks to find a solution or way forward. And making shit up requires that we move forward and not dwell too long on the past or get stuck in the present.

Another occurrence that happens is that when you say “I was wrong,” the other person often becomes conciliatory and may minimize your mistake.

So here are your marching orders: Sign up for an activity that you haven't done before, and find daily small things that you are wrong about, and say out loud or write down in your notes, “I was wrong about X.”

These simple things, which in many cases cost zero dollars, are within your control. And if you do take these steps, you will begin to see that the fear of failure and of being wrong are barriers that we place in front ourselves. Since we put those obstacles there, we have the ability to remove them, as well.