Your Fear of Failure is Your Greatest Enemy
You'll never tap into your full potential until you take a leap and are willing to fall flat on your face.
It was 3am and we were 6 hours away from a press conference where we were supposed to demo our product.
But the product didn’t work… yet.
Our leaders had set a deadline without verifying with the operational and technical teams if it was a realistic timeline. And it wasn’t just a deadline, it was a very public deadline where if we didn’t make it, the broader world would know.
I was working at NBC to build the first-ever online video syndication unit. Our leaders were smart, ambitious business strategists who were excellent strategists but with zero technology build-out experience.
Lucky for them, they hired people on their team that did — people like me and my managers. We worked nonstop for months, 16-18 hour days, 7 days a week to prepare for this arbitrarily, randomly scheduled launch.
My managers might not have been freaked out, but I was. The only reason why I pulled those hours was because failing this was tantamount to setting myself up to get fired.
So what happened at the press conference? Did we manage to get a product that wasn’t fully built fully built in 6 hours?
Well, it definitely wasn’t fully functional, but we were able to demo parts of the product to give the appearance of something worked.
What ultimately happened to that product?
From the precipice of disaster, after many more months of work and a much larger team, it became hulu.
Worrying about failure leads to inaction which is the only guaranteed way to not succeed.
When I think back on that story today, I no longer feel incredible frustration with the leaders who made impossible promises and then weren’t the ones staying up all night to make them happen.
They didn’t model my version of leadership, but they also did something I was far too afraid to do — envision something entirely new and get people excited enough to fund it.
They took the leap that so many others never do.
Instead of only thinking about an idea, investigating an idea, and talking about an idea, they actually did something to advance the idea.
If you spend your time worrying and never give your idea a go, how can you ever be successful?
Our relationship to failure bears investigating.
When I learned in college that 90% of startups fail, I took that as a clear signal to never become a founder.
To be fair, I had already developed a bias against starting my own business. My father is a serially unsuccessful entrepreneur. I don’t mean to be derogatory. It’s just a fact. He tried over and over again, but none of his ideas took off.
To me, being a founder felt like a guaranteed way to overwork with failure guaranteed on the other side.
And yet being part of a startup, an early member of the team somehow didn’t feel as scary. I loved being an early employee. It meant I was able to have a significant impact on strategy, execution, and the organization’s culture.
For some reason, in my mind, the risk of failure was diminished if I wasn’t the inceptor of the idea.
It doesn’t make much sense. Starting the startup was too scary, but being part of a startup wasn’t?
I, like many people, don’t have a rational relationship with my fear of failure.
In fact, in much of my life, I have been rather fearless.
One of my earliest bets was in high school.
After my middle school art teacher shared a newspaper clipping with me about a new technology-driven magnet school that was opening in the fall of my 8th-grade year, I was intrigued.
It didn’t bother me that it was unproven. It didn’t matter that there was only one class before me. The vision was intoxicating — a school where every student would get a new computer to take home ever year on loan along with a modem. We would take college level science and math courses. School would be from 8am-4:30pm and at the end of 4 years, we would have attended school for the equivalent of 5 years.
It sounded amazing.
In 1992, I became a member of the second graduating class of what is now called the Bergen Academies.
When I attended, the school still had to market itself heavily to get parents and students to apply. Today, the school is regularly ranked as one of the top of the high schools in the U.S. and the entrance exam starts blocking a local highway at 6:30am on a Saturday morning because there are so many students trying to apply.
What was my reward for taking a chance to go to this school?
I was able to influence the curriculum, the programming, and the activities. I was part of the early group of students who established the school as legitimate in the eyes of the top universities in the country.
I was able to gain acceptance into schools like Stanford, Princeton, and the University of Pennsylvania not just because of the rigorous coursework, but also because I could tout things like being on the varsity soccer team and playing in the flute ensemble — both being the result of being part of an incredibly small school where I was one of only a few students who even wanted to play soccer or flute. I wasn’t strong at either, but there was literally no one else who could play.
These types of risks and rewards played out throughout my career and life.
The start-up unit at NBC that became hulu gave the opportunity be part of a company that changed the media landscape
Joining an e-commerce startup resulted in my first CEO appointment
Choosing to be an early adopter of online dating allowed me to meet my husband, someone who I would have never met otherwise
Restarting oil painting last year, after a 35-year hiatus, allowed me to discover a latent talent that I didn’t know existed
But my life hasn’t been all fearless decisions.
In 2019, as my family was contending with extreme sleep deprivation over multiple years, and I was embarking on a major revenue transformation at my company, I became paralyzed with fear… daily.
I found it difficult to make decisions and I second-guessed everything I did. I incessantly asked for feedback and input and often delayed key actions until there were negative impacts.
My body was perpetually in fight or flight. I assigned unreasonably high stakes to everything at work and was unwilling to ask for help as I struggled to keep my head above water.
When the pandemic hit in 2020, that only exacerbated my fear response. I was a high-functioning, anxiety-ridden leader who was charging into burnout.
I held it together because I perceived I had to. But when I look back at how I navigated that period in my life — including the few years that followed, I can see how much of what I did and didn’t do was all driven by fear of failure.
Give yourself the space to assess the level of risk before you go into decision-making mode.
What I wasn’t able to do during that difficult period was distinguish the level of risk of each of my actions and the context around me. Sleep deprivation and other forms of trauma can do that do you.
When you lose perspective, it’s easy to be cavalier when you should be conservative or be overly cautious when you should be more aggressive.
I tended towards being overly cautious, but sometimes fatigue can take you in the other direction and before you know it, you’ve rushed a decision that should have been handled with more care.
When a negative outcome is significant and permanent, you might need to be more thoughtful. Examples include marriage, having kids, getting surgery, making a big investment or doing substantial cost-cutting.
But most decisions aren’t likely to lead to extreme outcomes.
The only way to properly understand the risk is to give yourself room to step back from your emotions and with a more calm perspective, make your assessment. Some great ways to do that include:
Take a walk to move your body and let your emotions flow through you and not drive you
Meditate. Breathing mindfully and observing your thoughts instead of being swept up by them can help you get the perspective you need
Journal. Writing out your worries and observations can help you make more sense of the issue
Sleep on it. Your subconscious can do an incredible amount of processing if you give it time to work through what your conscious mind cannot
Define failure with the people who matter most before you make your own assumptions.
What may feel like a failure to you may not be viewed the same way by someone else. When I was in the throws of self-doubt at work, my boss, the CEO came to me numerous times to help me recalibrate my orientation toward failure.
A simple way to do is the “and what if that goes badly?” exercise. When you have something that you perceive is high stakes, find someone you trust and have them ask you “and what if that goes badly?” and you answer. You repeat it over and over and over again until you get to a point where there is no other answer.
You’ll find that most issues will end up with “and it’ll be OK.” By talking it out, you can get a second opinion about whether your assessment of risk is accurate and whether your fear of failure is out of line. This is particularly helpful when you are overly fearful.
What you do after you fail is far more important than the fact that you failed.
In the end, it’s important to remember that failure is not only a part of life, but it’s part of how we develop. We don’t chastise babies for dropping things, toddlers for falling as they learn to walk, or young children for stumbling as they master new skills. Only through failure can they learn.
Everyone fails. That is just a part of life.
Part of what we learn when we are young, and sometimes lose when we get older is the perspective that failure is necessary and helpful to our development as leaders, as adults, and as humans.
Those who know how to pick themselves back up, learn from the fall, and then get back in the game are the ones who will ultimately succeed.
Here are some of the ways I bounce back from failure:
Remind myself that the journey is what matters and that through failure, we can find our way to success
Find the learning in what took place and commit to incorporating the learning into my behaviors
Talk about and share my misses so that others can learn alongside me
Do an activity I love and remind myself that one failure isn’t going to make or break my vision or path forward
Your biggest failures are simply your biggest learnings.
How fast you can learn from a miss is how fast you can grow and improve and reach your goals. It’s OK if it takes you longer to navigate certain periods of fear and self-doubt.
As we get older and become more senior as a leader, we often face more complex issues with more variables.
Learning curves are not linear. Expect to get knocked down a few rungs at times. When that happens, just remember that it’s not a sign you have lost your touch or your ability to be effective. It’s a sign that you are ready for a deeper, more fundamental growth moment.
The deeper the challenge, the greater the growth. I like the visual of a deep pit. When you fall into a pit, the deeper the pit, the more capable you have to be to get out of it.
For me, it took me leaving my last company and last role to create the space I needed to reorient myself to my fear of failure. I also needed my family to move to a healthier place in terms of how we were all sleeping. It’s still not 100%, but it is remarkably better than it was 6 years ago.
My creativity has returned and my sense of possibility and playfulness has reentered how I do my work and engage with the people around me.
I am not the same as I was before facing my deep fears of failure.
I am stronger. You will be, too.
Key Takeways
Worrying about failure leads to inaction which is the only guaranteed way to not succeed
Our relationship to failure bears investigating. Don’t be surprised if your thinking isn’t rational
Give yourself the space to assess the level of risk before you go into decision-making mode
Define failure with the people who matter most before you make your own assumptions — their perspective might be the information you are missing
What you do after you fail is far more important than the fact that you failed
Your biggest failures are simply your biggest learnings
Take a moment this January and reflect on your relationship to fear of failure. Tell me what you discover!
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