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How To Poke A Hole

This week a friend of mine quit the online business world, quit self-help, and quit thought leadership. I encouraged his quitting because I don’t believe you should do things that aren’t aligned with who you are. But some of the reasons he cited for quitting were disturbing because they’re the same reasons I often want to bail out.

Exhibitionism. False gods. Grandiosity. Untenable claims.

I remember sitting in an audience where a woman, A Thought Leader, gave a talk where she cried and punched things on stage. Then, she made some claims about emotion and the brain using words like “dopamine” and told us how we should live our lives based on something that happened in hers.

Except she didn’t frame it that way. She framed it as, “This is the Truth. You’re welcome.”

I wanted to punch her on stage.

It’s not that she was wrong, it’s that she was unequivocally wrong about the claims she was making about the world.

There’s no good check-and-balances system in the content and online business world (FTC, pay attention). I can say almost anything I want to you in these emails. I guess it’s technically freedom of speech, but I’m less interested in my right to say dumb shit and more interested in how people of integrity can maintain their integrity when they want to make big, untested claims about the world.

I’m less interested in my right to say dumb shit and more interested in how people of integrity can maintain their integrity when they want to make big, untested claims about the world.

Do you remember the difference between a theory and a hypothesis?

  • Theory = a scientifically sound and tested explanation
  • Hypothesis = untested claim, sometimes a belief

It’s ok to make claims. We need claims. We need assertions. We need beliefs. We need hypotheses and opinions and skepticism and ideas. But if you’re in the business of hypotheses and opinions and ideas and punditry (which, you are if you publish online or produce content), you need to seek out the holes in your ideas.

I first learned about “Hole Poking” from a Y-Combinator grad named, Matt.

Matt is the worst to talk to about your ideas because he is always asking reasonable questions you do not have the answers to:

  • How will you test that?
  • Do you really need to build out a full custom website for that?
  • Is there a way to use existing software to make this work?
  • Where do you see demand for this?
  • When you say “make a difference,” what do you mean, specifically?
  • Why is this a good headline?
  • How will this work?

Like I said, infuriating.

Matt will never ever tell you something won’t work. He will only ever ask you questions that lead to why something will or won’t work. He’s actually neutral. Which is how you become a Hole Poker: You’re neutral.

I’m not neutral. It was one of my failures as a social scientist. I have a point of view and it comes out. I’m what they call, “VERY BIASED.” But the great thing about The Academy, and why I wish we’d stop talking about education like it’s useless and why you should not drop out of school, is that they teach you how to have your bias and become aware of it so you can go on doing good tenable work.

That’s why watching Thought Leaders explain one study that supports their point makes my blood boil.

Confirmation bias is not interesting to me. I can find studies that confirm just about anything.

What I want to know is who DISPROVED you.

Then we’ll know we have something interesting to talk about.

Hole. Poke.

Where are you wrong? Where is this argument weak?

A nice shortcut to discovering this is marrying someone who’s made it his sole mission in life to debunk anything you say. I won the lottery on this one.

Husband: “You can’t make that claim.”
Me: “But I’m a writer! I write what I see.”
Husband: “That’s not license to be wrong and make grandiose statements about the world based on one interaction.”
Me: “In fact, it is.”
Husband: “It is not. Don’t be dumb.”

[And scene.]

So, how do you stay a person of integrity in a world of charlatans?

So, here’s where it gets muddy:  For those of us who wear the title “creative,” or “artist,” or “writer,” or if you deal in the business of information and ideas and expertise – part of what people pay for is your point of view.

And my point of view on how to reconcile all this is:

  1. Step 1: Surround yourself with Matts and people like my husband. Make sure your claims can stand up to scrutiny. Don’t niche so hard that you create an echo-chamber.
  2. Step 2: Make it clear when something is your opinion (“a hypothesis”) versus a Truth About The World.
  3. Step 3: Stay emotionally honest.

Ok so step 3 is the really important one and what I’ve been trying to lead up to this entire time. It comes from the world of fiction where honesty is the currency, which makes no sense because fiction, in effect, is lies. To quote Neil Gaiman, “We are using lies, people who do not exist and things that did not happen to those people, in places that aren’t – and we are using those things to communicate true things to each other.”


In my comparative literature days, we called this “suspension of disbelief.” You can, as a rational person, accept and understand that Asgard is not a real place. While also deeply relating to Odin’s relationship to Loki. We can hold two contradictory thoughts together in our minds at the same time. We possess the ability to “imagine.”

The scenes in fiction don’t work unless there are two things present:

The reader knows she’s being sold a lie (“the fiction”). The emotional truth is real.

So as you pursue your path as a writer, author, speaker, marketer, thought leader, visionary, owner, pundit, Person With a Point Of View – make it clear what fiction you’re wielding in order to communicate the emotional truth.

Making more money is great. Selling things is part of this work. But selling false hope, simple solutions, and domain expertise in an area in which you have none – don’t do that.

Surround yourself with people who don’t tell you “this is dumb,” but ask you questions to make it less dumb.

Debunk your own ideas until they hold up to scrutiny. Stay emotionally honest.

Hole. Poke.