Turtles All the Way Down

What to do when the questions never end.

Why did I say yes to this?

A few years ago, I got invited to a product management dinner in Seattle. At the time, I had Chief Product Officer in my title so the invite made sense on paper. Leaders in product management getting together to discuss ideas, share best practices, network. I said yes.

I arrived for drinks and mingling before dinner. But within minutes, I wanted to leave.

I was head of product for a medium-sized company, running my small corner of the world. The people around me? Ex-Amazon. Ex-Google. Current Salesforce. Early-stage startup founders raising oh so much money. They talked about AI integration like it was a given. They referenced product trends I’d sorta, kinda heard of. My company wasn’t exploring new tech. We just did what we did, quietly, in our niche. I felt so behind.

I can small talk with the best of them, so I hung in there. But the imposter syndrome kinda smacked me in the face.

In my head I started running through things like: “Good lord, am I even qualified to be here?” Then: “Wait, what does qualified even mean?” Then: “Why do I care so much about being qualified?” Then: “If I didn’t care, would that make me seem aloof?” Round and round I went in my little brain. Just questions stacked on top of questions.

Philosophers call this infinite regress. The rest of us call it exhausting.

There’s an old joke that does a pretty good job of explaining this. What holds up the earth? A giant turtle. What holds up the turtle? Another turtle. And under that? Turtles, all the way down.

Imposter syndrome works the same way. You can’t think your way to the bottom. There is no bottom turtle.

So this week, let’s talk about imposter syndrome, what it actually is, why it spirals the way it does, and how you can stop searching for ground that doesn’t exist.

The Loop That Feeds Itself

Infinite regress is when every answer you find just creates another question. Fun right?

It shows up everywhere. In philosophy, it’s the problem of proving anything is true. For example, how do you know that? Well, because of this. But how do you know that? Because of this other thing. And so on and so on. It’s also why people hate philosophy majors.

John Green wrote a pretty great novel called Turtles All the Way Down about a teenager with OCD who gets stuck in these thought spirals. She searches for certainty, for the thing that will make her anxiety stop. But every answer just generates more questions. Every reassurance needs another reassurance.

Imposter syndrome works much the same way.

You start with a simple question: “Do I belong here?” Seems reasonable enough. So you look for proof. You check your credentials, double check the old nametag. You compare your resume to others. But then you think, “Okay, but everybody here has some pretty good credentials.” So you look for what makes you different. Maybe you find something. But then you think, “Maybe that doesn’t count.” So you dismiss that. Then you wonder if dismissing it proves you’re actually unqualified. Round and round.

The trap isn’t the first question. The trap is believing there’s a final answer.

And the longer you search for it, the worse the spiral gets. Because now you’re not just questioning your qualifications. You’re questioning why you’re questioning. You’re anxious about being anxious. You’re stuck in a recursive loop where each ever more desperate attempt to solve the problem becomes part of the problem.

You can’t think your way out because thinking is what creates the trap. It’s rough have a dizzying intellect.

What You Miss While You’re Spiraling

Okay, where was I?

Right. So here’s what happens when you’re stuck searching for the bottom turtle: you end up missing all sorts of stuff.

At that dinner, I spent the cocktail hour in my own head. Just running through all the ways I didn’t measure up. You know what I didn’t do? Actually engage with people. Ask questions. Learn something. Make a connection. I was so busy trying to determine if I belonged that I completely wasted the opportunity to just be there.

That’s a real cost of imposter syndrome. Not that you feel like a fraud. But that the feeling consumes so much mental energy you can’t appreciate what’s actually in right there in front of you.

Of course, there’s a difference between imposter syndrome and healthy self-assessment. Self-assessment is: “I don’t know that much about AI, I should ask some questions and learn.” That’s useful, it moves you forward.

Imposter syndrome is: “I don’t know much about AI and everyone here probably thinks I’m an idiot. Why did they even invite me? Am I capable of learning new things or am I just faking it?” That’s turtle thinking.

One is specific. The other is existential. It’s action vs paralysis.

And while you’re paralyzed, life keeps moving. Conversations happen and opportunities pass. Connections get made. Just not with you. Because you’re too busy asking questions that don’t have answers.

How to Stop Looking for the Bottom Turtle

So what do you actually do about this?

First, remember what I just said, the goal isn’t to prove you belong. The goal is to be present enough to engage with what’s in front of you.

And here are some other things that actually help:

• Name the spiral when it starts. You don’t have to stop it. You don’t have to solve it. Just notice it. “Oh hey, I’m spiraling again.” The act of naming it can create just enough space for you to get some breathing room in your thoughts.

• Ask a better question. Instead of “Do I belong here?” go with “What can I learn here?” or “Who can I connect with?” These kind of questions actually have answers.

• Adopt a little delulu as the solulu. Sometimes the healthiest response to imposter syndrome is to just decide that you belong and move on. Not because you’ve proven it. Not because you’ve found an answer. But because searching for proof is a waste of time. And because sometimes you just have to believe something that can’t be proven and get on with it.

• Use the discomfort as data, not evidence. At the end of the day, feeling uncomfortable in a room full of people who seem more qualified than you is just information. It tells you you’re in a place where you can learn. It doesn’t tell you that you’re unqualified. It tells you that you’re stretching and you have work to do. That’s not bad, it’s helpful.

• Remember that everyone is winging it. For realsies. The ex-Amazon person? Winging it. The startup founder? Absolutely winging it. The difference is they’re not stuck asking themselves if they should be winging it.

So stop searching. Start participating.

In Conclusion

A few months ago, I got invited to a dinner again with many of the same people. I’d been laid off by then, so showing up felt a little weird. No fancy title. I had my own company name on the name tag. It was just me and whatever I’d learned since the last time.

Which, it turns out, was quite a lot! That first dinner had motivated the hell out of me. I DID NOT want to feel that way again. So I learned. I became a sponge. I started paying attention to what I didn’t know instead of pretending I knew it all. That dinner was eye-opening about how much the company I worked for and I weren’t doing. And in the time since, I’ve come a long way baby. Hell, I even teach classes on AI now.

And yeah, at the next dinner, I still felt the imposter syndrome creep in. But this time I managed to catch it sooner. I named it. I asked better questions and <gasp!> I actually talked to people.

About halfway through the night, I found out that more than a few others there had also been laid off recently as well. They were probably spiraling about the same things I had been.

I bet a lot of us are looking for that bottom turtle. Nobody ever finds it.

Ever forward,
— Derek (aka Chief Rabbit)

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