The Hidden Shame of Entrepreneurship—And Why For Some People, It’s Really Frigging Hard to Sell Themselves

I sell people online.

All day, every day, this is what I do for a living: I make people sound like golden-voiced prophets with thighs of steel and very good ideas. I am very good at this. I can take a farmer in Kansas and make him sound like the CEO of Gucci in two lines or less. (Lord, you should see how I spun my ex-boyfriends.)

You think your sister Sarah enables her drug dealing kid? Woo Nelly—try being a copywriter.

The reason why I have a job, however, is because good people are notoriously bad at selling themselves. There are a few reasons for this:

  1. Most people don’t know the point of their work.
  2. They don’t know the promise of their work.
  3. They don’t know how to differentiate their work.
  4. They don’t know how to make what they sell sound memorable and sticky and brand worthy.
  5. They don’t make the client the star. (AKA they talk about themselves too much.)
  6. They describe what they do instead of sell it.
  7. They (heartbreakingly) have no idea why they’re a badass.
  8. And—most notably—they speak as if they’re playing dress up with mummy’s high heels.

It’s this last point I want to address here—and not just because I suddenly, spontaneously combusted into a British accent. ?‍♀️

You know when you meet a shy eight-year-old and they mull about with their head down, kicking in the sand and mumbling only “yes” or “no” when you ask them whether or not they like math and if they know who Freddie Kruger is, and whether or not they think the stock market’s going to bounce back this quarter? You know, typical eight-year-old questions?

Well that's what a business can feel like on paper: a shy, nervous eight-year-old, unsure of itself and what it's supposed to say when the world shows up and starts asking it questions.

A great deal of the copy I read feels…insecure. Wobbly. This sense of “I don’t really know what I’m doing here, but maybe you’ll like me enough to buy.” It feels like you’re playing dress-up as an entrepreneur, but you don’t really believe you’re one.

This is where the problem lies in its dark, damp, bat-filled cave.

Because you can’t see yourself objectively, the way you talk about your work is minimized. It’s powerless. I don’t think you’re looking at yourself as “real”—and it comes across when I see so many brilliant people trying to convey who they are and what they do. It’s as if they're playing make-believe business, giving themselves titles but not really owning any of them.

So the question becomes:

  • Is this an identity problem?
  • Or an articulation problem?

Wellllllllllllll—*munches morning cereal*—I’ll argue it’s both. One feeds into the other, making the latter—articulation—impossible to nail when the former—identity—is constantly changing.

And the former is constantly changing because that is the nature of entrepreneurship: unlike having a fixed title bestowed upon you such as “Lead Lord Accountant at Martin Xerox Company (401K, baby!),” your job must, by necessity, be in constant flux as you pivot, tweak, change, evolve, think on your feet and move in an opposite direction than you originally planned. And it must be that way in order for you to excel at it—the only failed entrepreneur is the one who isn’t failing at something every day. It is how we iterate forward. The way an iguana sheds its skin when it no longer serves them, so does the entrepreneur…because if they don’t, they’re dead in the water.

In this way, being an entrepreneur is like having a never-ending existential crisis…on purpose.

It’s how you do your job. And therefore, most entrepreneurs struggle with their identities every single day of the week…by design. What am I doing today? Does this make sense? Is this in line with our goals? Is this in line with who I am? Well, who am I? What do I want? What do they want? Does this play to my strengths? Will I be able to transition? Is this MY NEW THING?

So, yes, that’s one reason why entrepreneurs sound as if they’re playing dress up all of the time: in many cases, they are. Being an entrepreneur is a game of reinvention like no other.

BUT—that causes an awfully big problem down at Articulation HQ.

All that iterating, tweaking, pivoting is bound to make it hard to state what you do in one succinct, memorable, brand worthy line on a piece of paper. And then, right when you think you’ve got it, you’re pivoting your product yet again. It’s a bit Groundhog Day-ish, really. And even though this reinvention is a necessity, it causes a steep drop in confidence because we’re taught that change means uncertainty when, in fact, it means power.

It means insight.
It means eagerness.
It means constantly doing your best to be your best.

But for most change-makers, change still inspires doubt. And that doubt shows up in big, fat, guilty red letters in your bio, in your copy, and in the way you present yourself to the world.

And man does it kill me. By “kill me,” of course I mean “makes me incredibly sad and also sort of protective like a mama bear even though I’m not maternal at all but IT COMES OUT WHEN I SEE GOOD PEOPLE WITH LOW SELF-ESTEEM.”

I’m using that word deliberately even though it might not fit the technical definition of the bill: it’s the only term, when read aloud, that encapsulates the unexpected byproduct of shame that comes with being entrepreneurial.

Which sounds totally contrary to everything you think about entrepreneurs, right? We think of them as confident, bold, brave! They’ve put themselves out there and they’re doingggg it! And yes, they are. In fact, they’re some of the most capable people on the planet. But, that doesn’t always make them sure of themselves. Most of the time it makes them…insecure. Wobbly. This sense of “I don’t really know what I’m doing here, but maybe you’ll like me enough to buy.”

But—that sense of wobbliness kills sales.

It becomes a self-fulfilling prophecy. You’re wobbly because you’re an entrepreneur, so you articulate yourself in a wobbly fashion, which then ensures that your latest iteration doesn’t sell, which then forces you to readjust your position (again) and be on constant wobble. It’s one long, constant wobbly spiral to the end. And god I hope I rank on Google for the word “wobbly” from here on out.

So may I suggest something?

I’d like to suggest that you assign your words a job. Hire them, the same way you would an employee. These words are now under your employ, and their role in your organization is to represent your business at its highest potential. They are your knights; your guards. That’s what they’re there for: to protect your business goals, even from you. They do not suffer fools and they do not suffer self-doubt. They are given their marching orders on behalf of your business and they execute. Because your words are not you: they are your representatives. And you want strong, focused, powerful representatives. Nobody wants a limp dick representing them, do they? Certainly not. There shall be no limp dick representatives, which means there shall be no words that do not do their job of making you feel like the CEO of motherfucking Gucci.

Choose your words the way you choose your employees.

And then give them the job of protecting your business interests…whatever they are today.

Later, when you shift your focus to a different business goal, you know what you do? You swap out your seasonal “employees” for new ones: new ones that can work on your behalf to reposition you accordingly.

You don’t need to have ONE bio, you know.

Nor do you need to have ONE landing page.

Or even ONE website.

You can have many, all under your employ, all performing different jobs depending on the season, the goal, or the target. Some people even call this “segmenting.” ? But none of them have anything to do with you, personally, as much as they do your customer.

Do not make the mistake of thinking that your words must reflect this one universal statement of truth about who you are: the job of your words is to help you do what you want to do.

Today. Then tomorrow. Then next month. And next year.

And yes, while entrepreneurs might very well be playing dress up in their mummy’s high heels, you know what else they’re doing?

Marching in those same high heels down to the basement, pulling up a seat at the table, demanding to be dealt in, and then taking everybody's money.

And there ain’t no shame in that.

Turns out, your footwear doesn’t matter, so long as you show up.



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