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How To Quash The Pressure Of Expectations and Defeat Self-Sabotage

There’s a woman who celebrates her wins with a donut. As in, she literally buys herself a donut every time something good happens in her career and then she posts a photo of it (click at your own hunger risk).

It’s made her more appreciative of the little things, identifying more wins, blah blah blah we’ve all read the book – celebrate your wins! gratitude! more will come your way!

For the awakened humans, this is true. And it’s great. God bless, keep on. For the rest of us, we choose the path I like to call “Bad Mom’s Christmas.

That’s when we follow up an otherwise great thing with a shit sequel.


Jurassic Park.

Grey’s Anatomy.


Those of us on the path of Bad Mom’s Christmas are what society might call “self-sabotagers.” We get a win and we’re like “NO! TOO MUCH GREATNESS! MUST CRAWL IN A HOLE AND DIE! DESTROY WHAT MADE ME GREAT! NO DONUTS FOR YOU!!”

We get blind-sighted by the applause. And start producing shit work. 

[To extend the sequel metaphor: It’s when Narcos Medellín turned into Narcos Cali. They took complex interesting characters and turned them into stock types, leaned into predictable cliches, and inserted a whole bunch of gratuitous violence. BOO CALI BE BETTER]

If you don’t have a strong core to begin with, success will kill everything great about you.

Because you become reactive. Reactive to the market, to critics, to short term wins, to applause. THE APPLAUSE. That shit makes you high as a kite. And with some very rare exceptions, no one makes good decisions when they’re high.

Especially if those decisions are fueled by ego and a desire to please. Which, speaking for myself, they always are. Hand me some applause and I’m like, “Please, sir, I want some more.”

We turn to approval seeking (that’s what “wanting more applause” is) when we don’t have a strong core. When we don’t know our values, we don’t have a vision, and we don’t know who we are or what we stand for.

In fact, you need the opposite skill to succeed: the ability to endure being disliked. Weirdo first, pioneer second. That’s how you get good. You keep being the weirdo, you keep defying expectations, you keep your eye on what the market actually wants instead of what they say they want. And you learn to be a shrewd judge of your own work. 

The mistake happens during what we in altMBA call “crossing the chasm.” It’s when you go from being niche to being mainstream (some call this “scaling”). And very few brands navigate this well.

We think that crossing the chasm means being something the mainstream will understand. Being “palatable” or “vanilla.” But jokes on us because the mainstream doesn’t exist. It was made up in the 1930-50s to describe “people who watch TV, read papers, and listen to radio,” which isn’t a market. That’s just everyone.

Marketing rule #1: When you market to everyone, you market to no one. 

Not everyone likes Game of Thrones (GOT). But to those of us who do, we cannot. get. enough. We will literally stay at our subway stop and miss our exit just to take pictures and text them to our friends. 

And, no, I was not the only one in Grand Central doing this.

The way to protect against the sequel effect (aka: self-sabotage after success) is to let go of the expectations success creates. But that is terrible overly-simplistic advice because who can (realistically) do that without 12 years of therapy?? 

I do, in fact, recommend therapy, but in the meantime, I have a suggestion that also works to quash the pressure of expectations:

Keep things an inside joke with your audience.

If you don’t have the confidence to retain your weirdo roots (hi guilty), then you’re going to end up one of the many creators who died of the disease to please. To please new fans, to please the critics, to please the masses.

When you seek acceptance from a market that you didn’t set out to impress, you will perpetually disappoint.

Stay👏🏼focused 👏🏼on 👏🏼your 👏🏼tribe.

That’s the only effective way I know to drown out the noise from the applause and expectations.

The trick I use is to circumvent disappointment is to use it as a success metric. If I hear, “I don’t get it,” from someone who is NOT my market, then I probably nailed it. Because all great work is divisive. Not in a combative way – divisive in a unifying way. It should create a demarcation line between “those who get it” and “those who don’t.”

You’re either someone who’s “into GOT” or you’re not. You’re either a Trekky or you’re not. You either like Alexander McQueen or you don’t. There are few people in the middle.

Celebrate that you will disappoint some people. That’s a sign you’re doing this right. 

Imma go buy myself a donut. 

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