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The Fear of Failure: Here’s How to Get Past This Boogeyman

The Fear of Failure Is Human

The feeling that there’s something better around the corner - some juicy prize - is what keeps us moving. Not just you and me, but the whole dang species.

But then there’s the other part of being human - fear. Worrying that there’s something bad around the corner. It may have been what kept our ancestors safe in the wilderness. But now it’s what keeps a lot of us frozen. Especially entrepreneurs.

When I started business coaching for entrepreneurs, this was a revelation for me. I’d see all these self-destructive habits in ambitious, super smart people. And it would hold a mirror up to my own bad habits, my own fears. I’d think…what are we all so afraid of?

I’m guessing you might know the answer firsthand. It’s the fear of failure.

The fear of failure is real. It’s not confined to business, but it’s a freaking superstar in the business space. I’m pretty sure every freelancer, small business owner, entrepreneur - whatever - feels it. No matter what their Instagram posts say.

The fear of failure can dictate your business strategy, damage your productivity, shrink your visibility, and - worst of all - drain your self-esteem.

But even though the fear of failure is human. It doesn’t have to dominate you.

You just have to face it, name it, and manage it.

In this blog, I want to unpack your fears. And mine.

We’ll take a look at a bunch of ways the fear of failure can hide in your life. Then we’ll talk about 3 solid ways to manage, maybe even benefit, from it.

So, Seriously - What Are You Afraid Of?

Well, according to the U.S. Bureau of Labor Statistics, 1 in 5 businesses fail in the first year. That could put some cold water on your enthusiasm.

But if you have a service-based business, which is most of my clientele, you’re likely a pretty nimble entity with sustainable overhead. So…what’s the problem?

Well, the fear of failure operates a bit like a shapeless boogeyman under your bed. Sometimes it’s the threat of financial insecurity driving it. But sometimes the fear of failure is about costs that are more personal and harder to count.

  • The loss of your perfect future - You have a dream in your head, you’re afraid to let it go.

  • The opportunity cost - What could you have done instead of pursuing your doomed dream?

  • The loss of status - What if you end up humiliating yourself?

But look, let’s not jump ahead. Let’s first try to track down the fear of failure in your life. There are some less than fabulous habits you might have. If you dig a little, you’ll discover that old boogeyman - fear - is at the bottom of some of those struggles.

Over-Preparing Can Signal the Fear of Failure

“Just one more class. One more tweak to the website. One more book I have to read.”

Are you forever…preparing…to…start? Do you get caught up in talking about what you should do instead of doing it?

These are the signs of the fear of failure masquerading as work -The Curse of Preparation! And it can really do a number on you.

“Instead of being on the phone trying to get a customer, you are sitting there talking about why we need to call more customers, why we don’t call customers anymore, or why we should start emailing them,” an entrepreneur told fear of failure researchers and Harvard Business Review, “So, you are talking about it and not doing it.”

Preparation is good. But this is something else. I should know. I took so many classes, read zillions of books, and signed up for mastermind after mastermind. Finally I had to call BS on myself.

Yeah, it felt like work. It was nothing but cold feet.

Moonshots Can Go Two Ways

I’m hesitant to mention this one, because - in my role as a business coach - I see way more people dream too small when goal setting. But every once in a while I get a client that would make Elon Musk say, “Whoa Superman, take it down a notch.”

So what’s wrong with that?

Well, it’s not the big goal that’s necessarily the problem. It could be what’s behind it. Sometimes big goals are a smoke screen for the fear of failure.

If you regularly plan big and fall short. Like WAY short. Like never really started. This could be the fear of failure boogeyman holding you hostage..

Sometimes big-ass goals are there not to be reached, but to excuse us for never getting started.

Think about it, when the target is to go from $0 to 6-figures by the end of the month, you can’t really blame yourself for not progressing. No one could do it.

Realistic - or better yet - slight stretch goals are way more threatening. You can measure that work. And you can hold yourself accountable for what doesn’t get done. The fear of failure hates that.

Hiding in Plain Sight

I recently did a livestream about - among other things - “hiding in plain sight.” This is when you show up in public and make some noise…but that’s all that’s happening.

Oh - you’re posting. You're being inspirational. You’re chatty, warm, and available…buuuut you never really say what the hell you do.

Hiding in plain sight is yet another way the fear of failure camouflages itself as “being productive.”

But folks, the goal is to get paying clients. And if you’re posting a lot without ever really being clear about what you’re inviting people into…

If you’re not saying what you want them to do next with a clear CTA…

Then it’s all just a performance to cover that fear of failure. And that’s not what you came here to do.

Escalation of Commitment

The fear of failure doesn’t always delay starting. Sometimes it delays quitting. It’s called escalation of commitment - and we all do it sometimes.

Escalation of commitment is a bias that makes us keep shoving energy, money, and time into a course of action that‘s clearly not working. You can’t bear to face all the wasted resources, so you just flush more of them down the toilet in hopes that something will change.

Like waiting for a bus that’s never coming - because you’ve already been sitting there for an hour. With each moment you just waste more and more of your life.

The fear of failure can make it hard to face that something’s just not working or that it’s something you don’t want to do. But learning to cut your losses is part of brave business too.

3 Hacks to Manage Your “Cold Feet”

So if we wanna get anywhere, we need to manage the fear of failure.

You’ll notice I said manage, not banish.

We want to face our fears and put them in perspective. But you don’t get rid of the fear - not completely. Not if you plan to do anything you truly care about. But you and the fear of failure can become better at working together.

Here are some management tools.

  • Emphasize Process Over Product

The fear of failure can be undercut if you define success in a more useful way. The notion of “Success” needs to be attached to your Process more than on the outcome.

Emphasize what’s in your control. Set goals according to what you’re going to do or learn. And celebrate those successes.

Yes, you want to hit your numbers. Yes, you have to measure your output. But your identity as a successful entrepreneur needs to be linked to the actions you take every day to hit your outcome - more than to the outcome itself.

  • Fear Setting

This is an idea made popular by Tim Ferris and his viral TEDTalk. It’s a riff on the Stoic practice of pre-mediating your fears.

I don’t mean ruminating on them for hours. But sometimes - with the fear of failure -naming and dealing with it in advance can take the teeth out of the boogeyman.

It’s almost like a goal-setting template - but for fears. You name the fear. Be specific. Like name your worst nightmare.

Are you afraid you’ll go broke? Afraid you’ll end up living in your car?

Whatever it is, name it, write it down.

Then think of some actions you can take to prevent that from happening.

Keep my day job until I can save 6 months income.

Start some freelancing gigs.

Minimize the cost of living.

Then write down what you could do to repair things if the worst-case scenario happens.

“Live with my sister for 3 months then reach out to my network for jobs.”

The point is that sometimes the fear of failure makes things seem bigger and scarier than they are. Even if your worst case scenario happens - you’ll feel more equipped to deal with it.

More likely, you’ll see how unlikely most of your fears are.

  • The Failure Quota

Set a failure quota. If you’re afraid of speaking on camera - make the goal to publicly fail on camera 5 times this month.

If you’re afraid of being rejected, set a goal of 100 rejections.

If you just can’t bear to start writing because it’s going to be awful - make a deal with yourself to write 5 bad pages today.

I know this sounds weird. But it can make the difference between staying stuck and kicking ass.


When you really go after failure goals - those rejections, those bad pages, any epic fails - they'll start to become the trail of your success story. Your achievement. Your badge.

Fail with pride, gusto - and you’ll be shocked how fast you start to move past it. So, roll up your sleeves and aim toward your failure quota.

This is kryptonite to a fear of failure.

It’s No Sin, Being Human

Look, I’m not exactly going out on a limb here. I guarantee that the fear of failure is in you. And that’s okay. It’s great. It means you’re a human - awesome - and that you care about something a lot. Which is terrific.

But the more your face that boogeyman, the less scary he’s going to be.

The fear of failure - for those of us who stare it down and manage it - can be like fuel. Like a little warm bubbling inside that moves you faster and faster into a great future.

So - no need to worry about being human. Just be a badass human. Go show your boogeymen who's boss here.

Did you set your specific goals? Do these goals involve taking your passion and creating a profitable business out of it? I could be the mentor for you.


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