Still Looking: I Don't Know How to Explain You

This one is personal in a different way.

Twelve episodes in, a recruiter at a company you’d recognize said something I’ve heard, in one form or another, my whole career: “I don’t know how to explain you.”

It wasn’t really a compliment. It was a diagnosis — of a system that’s very good at reading specialists, and not very good at reading anyone else.

This episode is about that gap. About a blue gummy bear on a Tokyo sidewalk, and why I went back to look at it. About the voices that shape who we become, especially when the people physically closest to us aren’t shaping us in the direction we want to grow. And about why the things that are hardest to explain about you are often the things that built the most capability.

It’s also the most direct I’ve ever been about why I made this show, and who I made it for.

This is the last bridge episode before Season 2.

The cities aren’t the point.

The seeing is.

TRACK LIST (in order)

1. Walking In the Rhythm - Fishmans

2. Jet Fuel - Mac Miller

3. Theme from Lupin III - Yuji Ohno

4. Middle Child - J. Cole

5. Marunouchi Sadistic - Sheena Ringo

6. São São Paulo - Tom Zé

7. Little Green Bag - George Baker Selection

8. Motasoa - Eidha Al Menhali

9. Can't Wait - Chon

10. Atomic Dog - George Clinton

11. Fight the Power - Public Enemy

12. Where Everybody Knows Your Name - Gary Portnoy

13. Mannish Boy - Muddy Waters

14. Million Dollar Baby - Tommy Richman

15. Under the Weather - Mac Miller

16. Waterfalls - Luke Christopher

17. After Hours - The Velvet Underground

18. Carolina Carol Bela - Jorge Ben Jor

19. Lot To Learn - Luke Christopher

TRANSCRIPT

There's a path near my apartment in Tokyo where I sometimes walk on my way home.

It's the kind of walk where your brain finally gets a chance to catch up with your day. I go there when I have nothing scheduled, nobody asking anything of me, just 5 or 10 minutes of a nice, manicured path and whatever I've been carrying. That’s one of the reasons I love Tokyo. It’s the biggest city in the world, and still, a couple streets away from the loudest places, there’s almost always a small place to disappear.

One particular night, a couple of weeks ago, I had been carrying a lot. You all heard the last episode. You know.

I was almost back at my door when I saw them.

Three kids, maybe eight or nine years old, crouched over something on the sidewalk. One giggled. Another shrieked. A third appeared from nowhere, with a stick, and started poking at whatever it was.

I kept walking. I had dinner to make and a brain that needed to check out.

But I got maybe thirty meters past them and stopped. Stood there on the pavement for a second. I turned around…they were still poking.

I got to my door and went upstairs, dropped my things… but I wasn’t quite ready to melt into my apartment for the night. I couldn’t help it… I went back to look.

This is EveryCity Whispers. I'm Steven. This is the third and final bridge episode from Season One before whatever comes next. And I want to use it to tell you something I haven't said in twelve episodes.

Why I made this show. And who it’s for.

***

THE LEGIBILITY PROBLEM

I want to tell you about a conversation I had recently with a recruiter at a company all of you would recognize.

They had already decided they wanted me. The interviews had gone well. There was genuine enthusiasm on both sides of the table. And then, almost as an aside, the recruiter said something that I've heard, in various forms, more times than I can count:

"You're impressive. I just don't know how to explain you."

I smiled. I thanked them. Went about my day.

But that line…I keep thinking about it. And it kind of pisses me off.

It's not really a compliment. It's a diagnosis. And what it's diagnosing isn't a problem with me. It's a problem with the system doing the evaluating.

Here's my résumé in plain terms. Five countries. Five continents. Ten cities. A career that has touched marketing, communications, design, strategy, content, and about six other things that don't fit neatly in a dropdown menu on a job application. A startup I co-founded that failed. A podcast I had built from scratch. My life has been, by any reasonable measure, genuinely interesting. And that looks, to a certain kind of hiring manager, like a mess.

The professional world has very good systems for reading specialists. The ten-year expert. The category leader. The person whose résumé tells one clean, linear story from A to B. It rewards legibility. It optimizes for the candidate who is easy to explain in a committee meeting.

What it doesn't have good systems for is people whose value comes from something harder to name. The adaptability built across cities. The pattern recognition that comes from failing at something with real stakes. The instinct for reading a room that you can only develop by walking into enough wrong rooms and surviving.

I've spent a significant portion of my career having to explain myself. Justify the gaps. Translate the non-linear path into language the grammar of careers can process.

And what gets me—what has always gotten me—is that the things that require the most explanation are exactly the things that built the most capability.

The startup that failed taught me more about resilience, decision-making, and reading a market better than any year or two of kissing someone’s ass into a promotion ever could. The years spent across five continents built a way of seeing and an ability to roll with a few punches that no training program can deliver. The cities—all ten of them—trained something into me that doesn't have a job title but shows up in every room I walk into.

The system isn't filtering for capability. It's filtering for legibility.

And those are not the same thing.

***

THE BLUE GUMMY BEAR

So, you know what was on the sidewalk?

It was a blue gummy bear.

Just sitting there on the concrete, slightly melted and, oddly…like, looking back at me.

I stood over it for a moment. And then I started laughing. It wasn’t funny. But I had just waited for three children to leave, walked back 100 meters and crouched down on a Tokyo sidewalk to inspect a piece of candy.

And then I noticed that I had noticed it. And that that was weird. And realized how weird it was that I went back…that nobody would actually notice, or care, enough to do that.

I went back inside to make dinner.

And I didn't think about that blue gummy bear again…for awhile anyway.

***

WHAT CITIES ACTUALLY DO

When I started EveryCity Whispers, I opened with two questions:

What does this city want from us? And what should we give to it?

After twelve episodes—after Tokyo and São Paulo and Amsterdam and Dubai and San Diego and North Carolina and New York and Boston and Chicago and Virginia—I want to answer that question more precisely than I did in the pilot.

Cities don't just want something from us. They train things into us. Through what they reward, what they punish, and what they make look normal. It’s quiet and it’s constant.

Tokyo trained me to read the silence. To notice what isn't being said. To understand that the pressure of a place—any place—only has power if you give it permission.

São Paulo trained me to stay in the game when the game breaks. To understand that resilience isn't a personality trait. It's a practice. And that how long you stay in it matters more than how good you are at it.

Amsterdam trained me to be direct. To say what I think without over-packaging it. That clarity, delivered with respect, is a form of generosity.

Dubai trained me that performance isn't automatically dishonest. That showing up, again, in the right posture, is sometimes the most intelligent move you can make.

San Diego trained me to stop mistaking peace for stagnation. That it’s okay to just sit for awhile.

North Carolina trained me to revise. To scratch out the bad draft without making it mean something about who I am.

New York trained me to enter rooms before I feel legit. That you only can build momentum by taking the first step, even when it’s scary.

Boston, through my Mom, trained me to read the real rule, not the surface one.

Chicago, through my Dad, trained me that it’s okay, sometimes, to claim something before I can prove it.

And Virginia—the place I barely thought about for years—trained me to notice. To read the air of any room, any system, any situation before anyone explains it to me.

But here's what I've come to understand after sitting with all of this:

The cities aren't the point.

The seeing is the point.

Cities are the most vivid, most dramatic, most universally legible version of something that's happening everywhere, all the time. Your office is whispering. Your family is whispering. Your friend group is whispering. The country you grew up in has been whispering to you since before you could walk.

Cities whisper louder. That's why I use them. That's why they're the anchor.

But what this show is really exploring—what I've been trying to dig into, one episode at a time—is how we can find a way to hear the whisper in any room we walk into.

And here's the thing about that skill: you don't develop it in a straight line. You don't develop it by staying in your lane, accumulating the right titles, and following the expected path. You develop it by going into places, and situations, that challenge you. By trying things that don’t work out. By making yourself the outsider enough times that reading the room becomes more than just curiosity, more like a way of survival.

In other words, you develop it by doing exactly the things that make your résumé hard to explain.

***

THE FIVE PEOPLE

There's an idea you've probably heard: that you're the average of the five people you spend the most time with.

It may be common sense, sure, but I only explicitly heard it phrased that way a year or two ago. And it really bothered me.

Because I have good people in my life. Friends I love, people who would show up if I needed them. But if I'm honest—and this show has forced me to be honest about a lot of things—the people physically closest to me don't always reflect the person I'm trying to become. Friends from home who are rooted in ways that I'm not. Colleagues in Tokyo who are corporate in ways I'm actively trying not to be.

So I went looking. Not for new friends exactly. But for voices. For people whose way of seeing the world felt close enough to mine that spending time with their thinking actually moved something in me.

And it’s quite a range of people, people you’ve heard of and haven’t heard of. Shane Parrish. Anthony Bourdain. Dave Chappelle. Matthew Dicks. A handful of writers and thinkers who don't know I exist but who have shaped how I see more than most people I've sat across a table from.

If the five people closest to you shape who you become, and if the people physically closest to you don't reflect the person you're trying to become, then you have to be intentional about who you let into your head.

Podcasts. Books. Essays. The voices you choose to spend time with are doing the same shaping work as the people in the room with you. Maybe more, because you actually choose them.

Which is why I made this show.

It’s not because I have everything figured out. I sure as hell do not. But because I couldn't find the voice I needed anywhere else. The one that took cities seriously as forces, not just backdrops and restaurant pins. The one that was honest about failure, fuckups, without performing humility. The one that believes the non-linear path is a feature, not a bug.

Even those people I choose to follow—the ones I’m practically begging to influence me—there’s something about each of them that bothers me, like a dart that’s really close to the center but not quite on the bullseye. I love The Knowledge Project's work on mental models and living better, but there is every now and then a moment that I find it completely unrelatable.

Let me give you an example. Shane has occasionally interviewed some investors, and I've heard this from many investors, and it drives me crazy. So there's this idea that investors might sometimes say: “I won't invest in someone who's building their business on the side, or on the weekends, nights, things like that.” That "If they can't go all in, why should I put my money on the table for them?"

And I find this to just be so lacking in self-awareness because I know how VC works, and every venture capitalist in the world, every angel investor in the world, is investing money they can afford to lose. They're not investing money that's gonna prevent them from eating or having a roof over their head if it doesn't work out. And secondly, they're also investing—knowingly—into a wide variety of companies with the full awareness that most of them are gonna fail. So it's not quite the same risk/reward level, and I find that lack of self-awareness at times off-putting.

There was another anecdote about Joe Liemandt, who founded Alpha School, who I find completely inspiring. I love the interview. But he expressed a similar view, but then in the same interview, he talked about how his father was a personal associate of Jack Welch. Legendary CEO Jack Welch, who's written every management book from like the late '80s, and that he would spend summers with him. And it's like, man, most of us don't have the safety net of having personal access to Jack Welch.

So I find it…let me reemphasize, I love The Knowledge Project, and I get what they're trying to do, but when I hear things like that, it kinda is like, "Ah, this is unrelatable."

Another huge influence, 99% Invisible. I love it. I love the storytelling. The content sometimes veers into something that I can't relate to or maybe don't really care about.

Maybe I see Everycity Whispers as a cross between those two: The Knowledge Project and 99% Invisible.

And this is true of other content I choose to consume as well. And I get it: we're listening to these people because they are successful, because they have a proven track record. But sometimes I find this humble bragginess a little bit off-putting.

Another guy—I can't say I like HR, but I'm kind of fascinated by the human aspect of it. Adam Grant: he's a famous industrial organizational psychologist. And he's very thoughtful, and I like a lot of his work, but then I'll hear him in his podcast talk about feeling like a failure, and “I'm so lazy”, and “I'm not productive enough.” And, you know, this guy was, like, the youngest-ever tenured Ivy League professor, published already a bunch of best-selling books. He's, like, same age as me. Things like this, I just find…he may believe that. I'm not even saying it's disingenuous, that he's an underachiever. But I don't find it relatable, and I'm pretty sure there's a lot of others who listen to the same stuff and actually feel worse about themselves because someone who, by all measures, you're listening to because they are so successful is talking about how they're not successful, which of course makes everyone else feel like shit in comparison.

So these are just examples of when I say… I've been searching for, like, the bullseye for the voice I need to hear. This is an example of how these five people that I've chosen to let influence me, if you will—it's not exactly five, but the content I've sought out to shape me—it all is sort of hovering around the bullseye, but not quite there.

So I guess I've been searching for the voice that said, "The things that are hardest to explain about you are probably the most interesting things about you." I made this show because I needed it, and I figured if I need it, somebody else probably does too.

***

THE LOVE LETTER

So here's who I made EveryCity Whispers for.

I made it for the person whose résumé tells too many stories. Who has lived in enough places that the question "where are you from?" takes a beat to answer honestly. The person who has walked into rooms they weren't supposed to be in and stayed anyway. Who has tried something real, something that mattered and maybe felt risky, watched it fail, and built something from the wreckage anyway.

The person who has been told, in so many words, by someone who should have known better: "I don't know how to explain you."

And who knows, quietly, that the person saying that is revealing something about themselves, not you.

I made it for the person who stops for the blue gummy bear.

Not because it's useful or impresses anyone or shows up anywhere that matters on paper.

But because something in them cannot walk past a thing without wondering what it is. Cannot sit in a city without feeling its logic. Cannot have a conversation without noticing what's underneath it.

That instinct—the one that makes you go back and look—is the same one that makes you good at reading pressure before it reads you. Good at hearing whispers. Good at walking into a new room and feeling its rules before anyone explains them.

It doesn't show up on a résumé. It doesn't have a job title. The hiring committee doesn't have a rubric for it.

But I am now completely convinced, after ten cities and twelve episodes and one very strange stretch of professional life, that it is the most valuable thing you can bring into any room you enter.

Cities taught me that. All ten of them.

And if you've been listening, really listening, they've been teaching you too.

***

I keep coming back to the blue gummy bear.

Not because it means something cosmic. But because of what it told me about myself in a moment when I really needed to hear it.

I was in the middle of three years of being told, quietly and repeatedly, that the way I see things doesn't have value. That my instincts don't map to anything useful. That the thing I bring into a room—the noticing, the reading, the pattern recognition built across ten cities and five continents—isn't something anyone can package nicely in a box, so it must not be worth much.

And there I was. Crouched on a sidewalk. In the dark. Over a piece of candy.

Still looking.

The pressure hadn't gotten all the way in.

And that's the whole show, right there on the pavement.

The pilot opened with a sushi master who had spent fifty-five years making sushi and still called himself a beginner. I didn't fully understand why I started there until recently.

It's not about humility. It's not about craft for craft's sake.

It's about what it takes to still be curious after fifty-five years. To still notice. To still go back and look at the thing on the sidewalk even when you have dinner to make and a brain that needs to stop.

That's what every city I've lived in has been trying to build in me.

And that's what I want this show to keep doing, for me and for whoever finds it.

Season 2 is coming. It's going to go places I haven't been, find stories from places I haven't lived, and bring in voices that aren't mine. The show was always meant to become less about me and more about the idea. That time is coming.

But the whisper will be the same.

Pay attention. Notice what isn't being said. Understand that whatever environment you're in right now—city, office, relationship, system—it’s running a quiet training program on you. Shaping your instincts. Rewarding certain ways of seeing and letting others weaken.

The question was never whether you're being shaped.

You are.

The question is whether you're paying attention to the shape that’s forming.

***

I'm Steven. This is EveryCity Whispers. Thank you for listening.

I’ll see you next time, and until then, remember. You don't have to move cities to move yourself forward. Cities don't shout. They whisper. Stay curious, and listen closely, and you’ll hear them.

EVERYCITY WHISPERS

KNOW THE WORLD. KNOW THYSELF.

hello@everycitywhispers.com

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