Is a willingness to look stupid the ingredient you’ve been missing?

The higher your tolerance for embarrassment is, the faster you’ll grow, both as a person and as an entrepreneur. Yet, most of us avoid embarrassment at all costs, that is, until something short-circuits our caution.

One summer, that something for me was a gorgeous young woman from Arkansas.

My family had driven down to the Florida pandhandle to enjoy the white, powdery sands and emerald waters but my attention was otherwise occupied with a stranger.

She was about my age but with two adults maybe twice her age and a couple of young children. Was she the nanny? A much younger sibling? A cousin?

With each passing day, the desire to talk to her grew. Eventually, I couldn’t stand it, and as my dad, mom, and two sisters watched, I strode across the impossible stretch of sand to where she sat.

She saw me coming, and the family she was with did, too. I felt all everyone’s eyes pressing in on all sides like tiny suns.

“Would you like to go on a walk with me?” I asked.

She was even prettier up close. Brown, curly hair, tasteful red two-piece, tanned gorgeousness.

She smiled up at me and said, “I wish you’d asked me sooner. We leave tomorrow.”

I asked her where she was from. She said, “Arkansas.” We exchanged a few more pleasantries, and though my memory is fuzzy, I’m fairly certain I made a last-ditch effort to change her mind: “Are you sure?”

Again, the dazzling smile as she said she was going to finish her book.

That was that. With a fiery face and belly full of snakes, I retraced my steps to my family. They wanted all the juicy details. I told them I’d gotten shot down, but she’d been nice about it.

The heat of embarrassment faded, a spike of pride took its place. At least I had tried!

After I graduated college, I taught high school English for a year, and one of my roommates at the time told me I had “game.”

“I don’t know about that,” I said, “but I am willing to go up and talk to an attractive woman I don’t know.” That willingness, I think, is half the battle.

In other areas of my life, I have struggled to put myself out there because I didn’t want to fail. For example, for as long as I can remember, I wanted to write a book. Other than a children’s book in 2018, I didn’t finish a full-length project until February 2024, two months shy of my 42nd birthday.

What took me so long?

One of the more powerful factors in my inertia was not wanting to publish a “bad” book. The more we want to do a thing well, the more resistance we encounter when doing it at all. Steven Pressfield talks about this Resistance at length in his book The War of Art.

Desire squats like a great, warty troll on the path to progress, and this troll is especially pugnacious in those of us who have a deep, abiding love of craft, of excellence in creative expression, of engendering beauty where there was none before.

Creative types experience the gap that Ira Glass once described in an interview with Scott Myers:

“There's a gap. For the first couple years that you're making stuff what you're making isn't so good, okay, it’s not that great. It’s really not that great. It's trying to be good. It has ambition to good, but it's not quite that good. But your taste, the thing that got you into the game, your taste is still killer, and your taste is good enough that you can tell that what you're making is kind of a disappointment to you, you know what I mean? You can tell that it's still sort of crappy? A lot of people never get past that phase. A lot of people at that point they quit. And the thing I would just like say to you with all my heart is that most everybody I know who does interesting creative work they went through a phase of years where they had really good taste they could tell what they were making wasn't as good as they wanted it to be they knew it felt short. Some of us can admit that to ourselves, and some of us are a little less able to admit that to ourselves. But we know that it didn't have this special thing that we wanted to have, and the thing I would say to you is everybody goes through that. And for you to go through it, if you're going through right now, if you're just getting out of that phase, if you're just starting off and you're entering into that phase, you got to know it's totally normal, and the most important possible thing you could do is do a lot of work. Do a huge volume of work. Put yourself on a deadline.” (bold mine)

What Glass said is certainly true of the creative process. One of the more helpful recommendations I received during grad school came from a professor in the form of an idea, “shitty, first drafts,” from Anne Lamott’s book Bird by Bird:

“Now, practically even better news than that of short assignments is the idea of shitty first drafts.  All good writers write them. This is how they end up with good second drafts and terrific third drafts.  People tend to look at successful writers, writers who are getting their books published and maybe even doing well financially, and think that they sit down at their desks every morning feeling like a million dollars, feeling great about who they are and how much talent they have and what a great story they have to tell; that they take in a few deep breaths, push back their sleeves, roll their necks a few times to get all the cricks out, and dive in, typing fully formed passages as fast as a court reporter.  But this is just a fantasty of the uninitiated.  I know some very great writers, writers you love who write beautifully and have made a great deal of money, and not one of them sits down routinely feeling wildly enthusiastic and confident.” (bold mine)

The only way to close the gap is through a willingness to do mediocre work that doesn’t satisfy your taste. Okay, we get that on the creative front.

We must give ourselves explicit permission to do creative things poorly, and that’s just as true of business as it is of other creative pursuits.

Somehow, somewhere, we pick up this idea of “professionalism” as an attainable quality. Or, perhaps, without fully realizing it, you thought respectable solopreneurs must fit a certain mold.

In order to not appear incompetent, injure people’s perceptions of us, and thereby crush our own opportunities with clumsy missteps, we become too calculating. We succumb to a chronic hesitancy that whispers, “Wait to move until you can do so safely.”

Perfectionism is an armor fashioned to protect us from embarrassment, and yet it makes moving quickly impossible.

That’s a problem because business is an unending process of experimentation. You can’t know what with certainty what will work until it works. The sooner you make a move, the sooner you get new feedback.

Only with that feedback can you make meaningful improvements.

So in that respect business isn’t like writing or other creative disciplines at all because most of the embarrassing mistakes happen in private.

If I besmirch a page with the worst dialogue ever written, no one has to know but me.

However, when the feedback we need to grow profitable, satisfying businesses comes from real people outside of our little mad scientist studios, well, the stakes are higher.

Those early LinkedIn posts I wrote fall short of my own taste, just like Ira Glass said, and if I make a wrong assumption, share an idea that wasn’t fully thought out, or otherwise flub the delivery, a different kind of troll shows up.

No wonder so many solopreneurs experience intermittent paralysis! Freeze, unfreeze, freeze again. The expected mental pain of looking foolish clears enough for you to draft the post, then you never put it out into the world.

Or you do, and the result is failure (”The post got ignored”) or rejection (”Everyone disagreed with me”). Then, you must contend with your emotions, disappointment, discouragement, and sadness, embarrassment, anger, and fear.

Believe it or not, this moment right here is a crux. I don’t always get the results I want. You won’t either.

You might not have considered a willingness to appear foolish, inept, or incompetent an advantage in your work and career. It is.

The challenge and delight of entrepreneurship is the never-ending parade of obstacles and problems that ensure we never know everything we must know or have all the experience and competencies we need to have. We’re perennially deficient, or to put it a different way, you’ll always be bad at something you need to do right now.

As Alex Hormozi pointed out, “It would be unreasonable for you to be good at this skill given the amount of investment you’ve made.”

To acquire new skills and competencies, we must persist in being bad at them long enough until we become good enough.

This persistence plays out in many areas of business: marketing, networking, sales, pricing, negotiation, writing, communication, cashflow management, process and system design, mindset, and the list goes on.

The way we lead ourselves in our own businesses is by making decisions, right or wrong, and doing new things to develop the business, right or wrong, in order to gain new insights, learn, and become less wrong.

Chronic hesitancy is so costly because it denies you the education of both good and bad outcomes from your decisions. Indecision traps you in the school of stupid.

I’ve coached dozens of freelancers, consultants, and agency founders, and the ones who get extraordinary results have overcome chronic hesitancy and formed two habits that enable them to create real, felt momentum:

1. They make decisions quickly.
2. They take messy, imperfect action.

(Related: The Marketing Principle That Helps Freelancers Stay Consistent Even When They’re Busy)

Of course, they must raise their tolerance for appearing foolish because, roughly six out of ten times, they fall face first into a pile of dog doo.

We can't improve unless we start. We won't start if we're afraid to appear foolish.

Yet, when you are a beginner, looking like a beginner (at least, to experts) is a 99.8% certainty.

So fear of foolishness or embarrassment blocks the path to improvement and eventual mastery, and that’s why a high tolerance for looking stupid is an advantage.

To put it a different way, temporary incompetence is the only path to competence and the satisfaction it brings. I doubt that girl from Arkansas remembers shooting me down, and my wife appreciates my courage.

When you’re feeling stuck, my friend, raise your tolerance for looking stupid.

P.S. Along the way, you’ll discover that no one was watching nearly as closely as you thought, and the odd person who took the time to call attention to your embarrassment, and humiliate you if they could, well, history forgets people like that.

When you’re ready, here are ways I can help you:

1. Free Money. A pricing and money mindset guide for freelance creatives. If you’re unsure about your freelance pricing, this is the book for you.
2. Morning Marketing Habit. This course will help you build an “always be marketing” practice, become less dependent on referrals, and proactively build the business you want with the clients you want. My own morning marketing habit has enabled me to consistently make  6 figures as a freelancer.
3. Custom Business Roadmap. Gain clarity, confidence, and momentum in your freelance or consulting business.
4. Business Redesign. Raise your effective hourly rate, delegate with confidence, and free up 40 hours a month.
5. Clarity Session. It’s hard to read the label when you’re inside the bottle. I've done well over 100 of these 1:1 sessions with founders, solopreneurs, and freelancers who wanted guidance, a second opinion, or help creating a plan.