Let’s talk about boring.

Oh my god. I’d forgotten why I was interested in boring. I had all of these notes about it, and I just couldn’t remember the point. But I FOUND IT last night while re-listening to my conversation with comedian/writer Benjamin Brown (coming to your ears on 9.19.23).

I remember now.

It’s a magic trick! A simple, little spell.

When you’re pressured to conform, when you’re made to feel low about your particular divergence, you can simply think – “that is SO boring.” – and POOF! The end. The end of it.

I love its lack of meanness, lack of malice. It doesn’t need to bite. It’s too bored! It just…waives the naysay away.

Ope! You pulled the string, and you’re getting a sneaky Deep Dive!!!!!

Joan talked about boring. I love where she takes it! Like me, Joan finds boring unbearable. The worst! And for Joan, fleeing from boring means making a habit of finding herself as the weakest person in the room. What a gorgeous life-hack. Motivate yourself into places/skills/subjects on the farthest possible edge of your comfort zone, simply to avoid boredom. As she says, “it’s fun that you can find things that you’re good at, that you never knew before.” What simple brilliance.

Tito talked about boring! For Tito, it takes a different shape. He’s interested in boredom as a catalyst for raw creativity. As a father, he wants his kids to experience boredom, so they can learn to problem-solve their way out of it. Because – boredom is SO boring. What else is there to do, but innovate? Again, simple. Brilliant.

For McKenna, there’s a joy in being busy, in being productive. And this makes sense! She runs a FARM. It’s chores, upon chores, upon chores. But McKenna knows a trick (and it is a GREAT one) – in everything you do, there has to be a core of fun, of wanting. You can’t force this. It has to be true, on its own. You must first be interested.

I find such wisdom, here. It tells me that when you point yourself at a goal, you have to want to take the steps that will get you there. It’s not enough to want to be there.

Maybe this sounds obvious, but I’ve been a teacher and a coach long enough to know that it’s anything but. I see so much denial around this. Students (sometimes peers) tell me where they “want” to end up, but they’re bored to tears by every possible step along every possible route to that place. That core of fun, the core of wanting isn’t there, at all.

And that brings me to Ryan. I don’t even HAVE to look at my notes to know what I want to say about my conversation with Ryan.

[ok, I’m gonna pause here to say that I was “supposed” to write the boredom essay in June, after Joan, Tito, and McKenna’s episodes had just come out. I’d reviewed my notes, I’d chosen “boring” as the through line. But I was drowning in an acute mix of grief and exhaustion, so.]

[And then – I was “supposed” to write the Ryan/Angie/Max essay in July – but at this exact moment, it’s September and I haven’t even glanced at my notes for these gorgeous conversations]

BUT I DON’T EVEN HAVE TO LOOK AT MY NOTES, because I have been thinking about this non-stop since I TOOK said notes on June 19th (disclaimer: I did check the notes just now to confirm the date).

This conversation with Ryan is my first ever second interview, so we got to skip all of the chronological lines of questioning, and dig right into philosophy. And boy, did we dig in.

I couldn’t wait to talk with Ryan about medium.

For reference…

  • August 9, 2022, I wrote this.
  • October 31, 2022, I interviewed Ryan for the second time.

Ryan and I spoke broadly about the idea that each individual’s creativity (including medium) is bespoke—no two of a kind. He talked about an overarching goal to develop “the courage to create what is ordinary to you with confidence, and openness…if you’re reaching, you’re actually losing that unique perspective.”

And I think THIS is the name of the denial I see when my students (or any fellow humans) are too bored to take even a single bite out of the proverbial whale. I’ve experienced this myself a time or two, as well.

I think it’s just actually terrifying to do what only you can do. There’s nowhere to hide. You can’t blend in with anyone else. So, you may find it tempting to aim at someone else’s bespoke point of arrival, instead.

And listen, of course these things aren’t mutually exclusive. We are all in little Venn diagrams with so many other people, so many mediums, so many communities. Of COURSE we can learn from others, take steps we’ve watched other take, etc. But when every step between yourself and your stated goal is excruciating, when you can’t bring yourself to even scoot your toe toward it…you might be lying to yourself about who you are, what you want, what you need, where you must go.

Your path needn’t be the one of least resistance. But certainly you must be, by some intuitive means, suited for the resistance you take on. That resistance must be palatable to you in some way.

So, I’d say – take a closer look at the fear that brings you to such an unpalatable resistance. Where did it come from? Could it have been, I don’t know, someone/something pressuring you to conform, making you feel ashamed of your exquisite, breathtaking, absolutely one-of-a-kind divergence?

Remember that magic trick we learned?

That. Is so. BORING.

If you don’t want to eat this whale, not even a single bite…which whale DO you want to be eating, babe?

THE END. String well pulled.

We’ll plumb the Angie + Max notes another day.

Thank you for being here.



P.S. Whitefish, Montana (where I breathed pollen, gasoline generator exhaust, and freezing oxygen for several hours last Saturday, then woke up Sunday with a sinus infection #weddingseason #soprettytho).

On Boring