Be Beautifully Boring with Charlie Gilkey – SMJ 001

You're about to Learn ...

• What happens when a “Do Epic Shit” yields to “Be Beautifully Boring.”
• What thriving can look like in life’s liminal seasons.
• What to do about creative constipation and its relationship to seasonal productivity.
• Why ordinary, un-Instagrammable moments can be the most beautiful.
• How to hold both gratitude and global chaos at the same time … without denying either.
• How good of a Snarf impression I can do.

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Resources and Items Mentioned in This Episode

Books

• The Animal Connection
• Factfulness

Where to Find Charlie Gilkey Online

• Productive Flourishing

Timestamps and Topics

• [00:00] Podcast revival after seven-year hiatus
• [03:12] Friendship, spontaneity, unscripted conversations
• [07:48] What changes over 13 years
• [12:34] Fibromyalgia, chronic fatigue, diagnosis clarity
• [18:20] Redefining ambition and energy limits
• [24:55] Overwork, burnout, and cultural expectations
• [31:10] Holding gratitude alongside global chaos
• [42:03] Three reflective questions and closing challenge

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Transcript

Joel: Well, hey there, and welcome to Surprise Me Joel, with your host Joel Zaslofsky. It's a revival and a rebirth, so let's get to podcasting.

Joel: Oh my goodness. I'm grateful to be back podcasting after a seven-year hiatus. My last episode was number 130 for my original podcast, Smart and Simple Matters, which I stopped producing in 2019. I have missed being on the mic and bringing you conversations with super rad humans — or, you know, going solo occasionally.

Joel: The premise of Surprise Me Joel is fairly similar to Smart and Simple Matters, except this time I've made it obvious. I talk about whatever the heck I want, with whomever the heck I want, for as long as I want, and publish when I want. I don't have anything to promote this time around, though. Surprise Me Joel is just a hobby — it's not connected to any business pursuits like my first podcast was. So you'll have less in the intro and outro of each episode if you have any context from the first podcast, but still plenty of unconventional Joel energy sprinkled everywhere.

Joel: This first full episode of SMJ features a conversation with my seriously groovy friend, Charlie Gilkey. You'll hear us paddling around a bit because we enjoy each other a bunch — after 15 years of friendship, we just hit record. There's no script, no agenda, and no idea for either of us where the conversation would end up.

Joel: You'll hear us discuss a whole bunch, because that's what happens on Surprise Me Joel. We'll talk about things like how Charlie moved from “do epic shit” to “be beautifully boring,” being candid about grief, and what thriving really looks like in life's liminal seasons. Creative constipation and seasonal productivity. Wrestling with holding both gratitude and global chaos at the same time without denying either. A 1980s Thundercats cartoon impression of Snarf — yes, there will be sound effects on Surprise Me Joel. And three powerful questions Charlie asks himself and other folks, plus a surprising challenge at the very end.

Joel: I have to say, this episode starts slow and builds steam like a chugga-chugga-choo-choo. I won't make you wait any longer. Here we go.

—-

Joel: Welcome, Charlie. I'm stoked to have you join me for a conversation.

Charlie: J.Z., I'm so happy we're having this conversation. I particularly love that neither one of us knows where this is going to end up. Those are some of the most fun podcasts — when you're both the guest and the host. And hopefully, listener, if you're listening to this, you're like, oh, this is not a pitch, this is not a canned thing. There's no stump here. It's just folks out and about in the world doing cool things.

Joel: It's a conversation. It's a two-way thing — it's not just me asking Charlie question one, two, three, four, five, six, seven. We'll go back and forth and riff like we have for about 15 years. I looked before we started and we recorded our first podcast episode 13 years ago.

Charlie: Wow.

Joel: And we did a second one a decade ago. Maybe that's a good starting place. What things, at the macro level, have changed for you as a human? And what things are just core to you that haven't changed at all?

Charlie: I don't know that at the core level a lot of things have changed. What has been significant, over the last couple of years, is that I sort of stumbled into the diagnosis and reality that I have fibromyalgia and chronic fatigue syndrome. That's been actually pretty fascinating for me because I'm still a high-energy guy, still doing a lot of things. Really understanding, oh wow, there are a lot of shifts I need to make. But it also gave me a lot of peace. It's one of those things where when you don't know you're fighting gravity and you're always wondering why you're hitting the ground, you're like, what is going on? But then it's like, oh, there's this gravity here and that's what's going on. I can adjust to that. I know what's going on.

Charlie: That's probably the biggest difference — where so much of my work now focuses on helping people get out of overwork and burnout. That wasn't necessarily the arc I knew I was on until the diagnosis came. And I was like, oh, I probably was overworking for a normal human, but in this body, with these limitations, I'm definitely overworking. So how do I redefine things? How do I really strip back to what matters most? I just don't have the same amount of energy for the world that I used to. Sitting with that, but also being like, okay — so what part of the world do I want to spend more time with? It's a good clarifying thing. I've been an essentialist for a long time, and this just took it to a different level. That's probably the biggest change in how I think about time, energy, attention, relationships, and projects now versus 14 years ago.

Joel: Right on. We were talking recently and you said sometimes you have maybe six good hours in a day, whereas before — who knows how far back you go — you were doing eight, ten, twelve hours of creative work. Now that you've pared it down, what does that mean for where you're putting that time and energy right now?

Charlie: Very tactically — I got sick in September, just a normal fall sickness. Historically, what I would do is acknowledge I'm sick and let things start falling off. Social media is one of the first things that falls off because I don't have that energy for the world. But once I was done being sick, I was like, if I already know it's depleting for me, if I already know it's not one of the things I need to maintain, why not just get rid of it? So for the most part, I have. The world's a lot better for me, actually. I've taken the energy I used to spend on the news cycle and all that, and I spend more time doing human things — texting people, sending videos — just shrinking the world to think about who I have true mutuality with, versus maintaining parasocial relationships where you have to ask who that's actually benefiting.

Charlie: When you saw me looking pensively out the window, I was actually thinking of SimpleRev. That was 2014 or 2015, so that's a deep cut. And you mentioned essentialism — that's a term I haven't heard in a long time.

Joel: Keep going.

Charlie: At that time, 14- to 16-hour days were pretty usual for me. Around that time, I was also helping the Live Your Legend community transition after Scott Dinsmore passed. That really ratcheted up another level of work because I had my own business and essentially half of another business I was trying to transition after Scott passed. It just took a long time to get back to normal. Then came the pandemic, book launches, all those things. Going from that high energy to six, maybe seven hours on a good day — seven if I pay for it, ten if I'm really going to pay for it — it's been interesting.

Charlie: One of the things that's been challenging is figuring out where writing goes. I'm a professional writer, an author. Around 2014 and 2015, writing didn't count as work for me, even though I still had these full days. Writing two or three hours and then doing a full day — at a certain point I was like, I can't, this is too taxing. When I started counting writing as work in the same way as client work, it shrunk my advising and business day down. But I'm still wobbling with that balance. If I don't write enough, I'm not my best version of myself. If I write too much during a cycle where I've got a wonderful, healthy crop of clients, I'm working against my body's limits.

Charlie: I've adopted more of a seasonal approach. What I'm really good at now that I wasn't good at before is when there's a lull — especially in advising and business work — I just accept it. I might work two or three hours a day. Whereas before, in a prior version of me, it was like, great, I've got time to do all this other stuff. But now I'm just like, it's a lull. It'll pick back up. And when it picks back up, I lean into it and don't have a lot of agita about it. And when it goes back to a lull, I'm like, okay, it's a lull. Just really accepting that there's a seasonality to creative flows and engagements and just being human. It's not a problem — it's probably a feature.

Joel: There are still consistent things, and writing is one of them. One of my favorite terms I ever learned from you is being “creatively constipated.” I bring that up in conversation every once in a while and I get those scrunched-face looks — but everybody gets it immediately. So do you feel that creative constipation if you're traveling, out on the motorcycle with Angela, road tripping, and you don't have an opportunity to write?

Charlie: Absolutely. I've gotten better about not making a problem out of it — it's a situation, not a problem. On a three-day motorcycle trip through the Pacific Northwest, I'm not going to stop and write for half the day because I've got an idea. I'm like, if it's important, it'll come back. So I don't have that same sense of urgent need. But it does still back up — except instead of thinking in weeks, I'm thinking in months now. If an idea is still chasing me after three months, then I know I've got to write that. It's just not one of those things where I had a thought on Monday and it's got to come out in two weeks or the world will end. Ain't nobody got time for that.

Charlie: So it has changed my prolificness in a way — probably for the better. The other major change from 13 or 14 years ago is that I've seen I've overproduced blog material and essays and underproduced books. So now more of my writing and ideas are going into book projects — I've got a serial going, plus some parallel arcs. Instead of thinking I've got to write this idea and publish it, I'm more like, oh, this is a piece of that body of work. And it's feeding that way, which at this point in my career feels much more satisfying. I'm building more coherent bodies of work.

Joel: Do you ever write fiction or poetry, or are you strictly nonfiction?

Charlie: I'm mostly a nonfiction guy. Every three or four times a year, a sci-fi novel that's been working on me for the last eight years pops up and I'll write some on that. It changes because technology changes. But it's probably not going to be a major piece of my public writing for the next three to five years. There's a season for everything.

Joel: As a parent, I remind myself of that. Now that my kids are older, many new seasons are available to me. I wanted to go back a few minutes, because you said something the last time we spoke that I knew I wanted to talk to you about — the only specific thing I had going into today. You said you've undergone a shift from “do epic shit” to “be beautifully boring.” Those Charlie-isms — that's got to be original. I heard that and I was like, be beautifully boring — oh, that is so beautiful. Can you tell us more about what that means day to day?

Charlie: I'll do the prologue first. In the early 2010s, I wrote a post called “Do Epic Shit” and it was one of the most viral things I'd done. But people actually didn't understand what I was saying. The point was — if you want to do something that gets attention and is remarkable and easy to market, then do epic shit. It's easiest for people to have that big story, which is why we see so much of it. But it wasn't some kind of prescription to go out and do epic shit. It was conditional: if you want that sort of thing, then do this.

Charlie: But then I became “the do epic shit guy,” because social media truncates everything to the cool line. Even in that post, at the bottom, I wrote that one of the most remarkable and epic things you can do in our world is be yourself and live life on your own terms. In our society, that's actually radically epic. That paragraph got snipped in the social media fray. So I was that guy for a long time. Even then I had problems with it, but it was a good marketing angle.

Charlie: When people ask what I'm doing these days, it actually sounds pretty boring. I write books — nothing super exciting about being a nonfiction author. It's not an Instagram moment where you're like, look at me in the coffee shop writing. I hate that. I spend most of my days advising, doing leadership development and change management, helping people do their best work. Nothing fundamentally epic or exciting about that either. Even today — being beautifully boring means I'm probably going to assemble a new cat tower for my three Thundercats, and I'm looking forward to the weather getting a little nicer for a motorcycle ride. It's all this sort of stuff that's boring in a way, but in my own life it's beautiful. I'm not going to post it on Instagram. Who cares? But the whole point is — find the things that really light you up and stop caring about external validation. Let it be beautifully boring. It doesn't have to be beautiful to someone else.

Charlie: I've never wanted to be a social media influencer. That was never my vibe. But I had enough of that sort of happening along the way, and I just stopped a lot of it. With the fibromyalgia and chronic fatigue, I don't go to conferences as much, I don't speak as much — it's more taxing. And in a way, it's like you walking around bare-chested in Minneapolis. It's quirky and idiosyncratic, but it's not epic in that Instagram way. And yet it fuels your life. It's beautiful in its own way. The reason I'm really pushing the “boring” part is so that people don't fall into what we have now with internet culture — where everything has to be packaged as some kind of video or photo montage reel of your life. No. You can just be boring and be happy and not have a story to tell. And that's actually really, really good.

Joel: [Snarf impression] Snarf, snarf, snarf. That got me back to the 1980s. And I know none of these three cats are named Snarf.

Charlie: You're too good at that. We call them the Thundercats because when we got them, we got a litter of three that were five months old. I'm totally a cat dad and I'm proud of that — boring as it is. We had three ancient cats that all passed. Our last one, Petey, passed in 2024 at about 22 years old. Socks was 21 or 22. When I say ancient, these were old cats — we'd had them since high school. They weren't running around fighting anymore.

Charlie: So when we got these new cats, they're a litter, they're playful, they have no boundaries — with themselves or with us. They were so excited to finally be out of the cage that they just started running around the house and upstairs, and it sounded like thunder. Hours of them running and chasing each other. So thunder plus cats, plus I'm an 80s kid — Thundercats.

Joel: Yeah, I totally get it. I want to talk a little more about Petey. I remember talking to you a number of years back and you said Petey was on his last legs — that was probably 2021 — and he lived until 2024. I had Lucia, our Samoyed — that's a dog breed, in case you've never heard of it — and she lived until 17 and a half, which is certifiably ancient for a large dog. I learned some things about death and dying in the process of guiding her through those final years. When she hit 14, we were like, any day now — and she still had a pretty good life until 17 and a half. Did you learn anything about life through the death of your last crew of cats?

Charlie: Let me roll back on this. If you haven't read the book Animal Connection, it's a great book. The thesis is that our relationships to animals — especially dogs and cats — have been the single biggest thing that has spurred human evolution. Without those relationships, we would not be the humans that we are. Another way of saying it: you can't be fully human without these types of interactions.

Charlie: For what it's worth, that was one of the seeds of the sci-fi novel I've been working on. Humans get spaceflight and we leave Earth. But if you look at what the engineers are actually solving for, they're only solving for humans — not for dogs and pets and cats. So what happens to humanity when we get separated from these animals that have been essential for our emotional regulation, our understanding of life and death? They're just gone because the Elon Musks of the world aren't thinking about whether Charlie's going to be able to have two cats on a colony ship. And yet — what makes us human? Relationships to each other, and relationships to animals.

Charlie: Yes, I did learn a lot. I think animals and the lives they live — and how quickly they go — are here to guide us and teach lessons that over the course of an 85-year human lifetime we might not learn fast enough. One: how precious time is. Two: unconditional love. Three: resilience. Petey was getting to the point toward the end where he couldn't really walk and was in a lot of pain, but he was not giving up. Dude was not going anywhere. It was only because something specific happened on his last day that made it clear — that's it, there's no coming back.

Charlie: Sunshine died first, around 2014 or 2015, at about 14. Socks passed during the Start Finishing book tour — she died about a week after the book came out. So I was out traveling and doing the speaking tour, and grieving her loss at the same time. And Angela also had a miscarriage that month. I was out doing the speaking thing, and people would come up in line afterwards and say, “Charlie, you don't understand — my brother is sick, my mom died last year. This is so easy for you.” And at that very same moment, I was grieving the loss of a cat I'd had for over 20 years and a miscarriage. It wasn't useful to say that in the moment. But it really brought home how much we are always in transition, even when we're not aware of it.

Charlie: How do we honor those different transitions and seasons? A lot of my work started at that time thinking about the reality that the trick to thriving — I think — is how you manage these liminal periods and transitions, not necessarily what you're doing when you're in a groove or when things are great. It's: how do you develop emotional and practical practices such that you get back on the horse faster when you fall off, rather than just focusing on staying on the horse longer?

Joel: Gratitude is a huge one for me — as a practice and as a defining element of who I am and how I show up. Sometimes I freak people out, especially if they don't know me well, because I'm just in radical amazement of the world. I'm so grateful to have a friend like you, to be able to do this. I know it's 2026, but we're talking in real time across a couple thousand miles with no hitches. Like — are you serious? I get to have these friendships, do this kind of work, my family is incredible. My parents are still alive. My brother and sister-in-law and their kids are just across the Mississippi River in St. Paul. There's so much I've built — both practices and just the way I've trained my brain to not downplay the darkness and heaviness of life. There's a lot wrong with the world. But constantly asking, even in the moment, “Can I be grateful for something right now when things seem pretty crappy?” — that's the pillar I build so many other things on.

Charlie: I'll build on what you just said, because I know there are a lot of people listening right now thinking, these dudes are so tone deaf. Are you kidding me with what's happening in the political space? I get that. But at the same time — if you're in that space, I really do encourage you to read the book Factfulness, because it turns out when you look at the facts, the world is better than it's ever actually been. More girls are going to school across the world than people think. More people are living healthy lives. Fewer kids are dying before the age of three.

Charlie: Okay, so pause — I'm a combat veteran. I served in Operation Iraqi Freedom, traveled to places that are not on any tourist itinerary. They're just hard places. And when you look at those places and how much better off they are, even relative to when I was there — go to South America, go to Africa, go to Southeast Asia — I think you'll have a profound gratitude for how amazing the world is. Even amongst the darkness, even amongst the uncertainty in our political institutions, even amongst the incivility that has developed especially in the United States, even amongst the resurgence of fascism and different things happening around the world — part of that is just: wait a second, all of that is true. We can be concerned. We can be ready to resist. We can be resisting without denying the many, many wonderful, good things.

Charlie: Most of my efforts these days are to take the full rainbow of experience — the good, the bad, all the different colors — and not try to separate that rainbow into just one thing. We're used to the mental model where things are hard and bad, or good and easy. We are not used to something being hard and good at the same time. But it turns out a lot of life is hard and good simultaneously. How do you take in both without brightside-ing one thing and Eeyore-ing the other? Both are true right now, and I can sit with that. It takes a lot of open-heartedness.

Charlie: You might not end up as buoyant as Joel, but you also realize — going the Buddhist route on this one — how much of our agita and suffering comes from attachment to one of these things. We're attached to the good, and when it wanes or fades, we can't adapt. We're attached to the bad, and when it lingers longer than we want, we can't let it go. In this moment, things are beautifully boring and amazing. They're also frightening. People are getting married, having kids, experiencing the best moments of their lives. And in this same moment, people are dying, letting loved ones go, going through crippling things. All of that is true at the same time. It helps you sit in the complexity and the tension and interrogate your attachments — which gives you just enough distance from what's going on to find your center.

Joel: Most of my attachments are to things — the troublesome ones, at least, I'll put that in air quotes. Sugar, for example, still has some pretty major challenges with the role it plays in my life. Despite my best efforts in a number of different ways to loosen that, a lot of it just feels like resignation. I have pretty uncomplicated relationships and attachments to biological beings — humans and dogs. But it's the inanimate objects — like hitting my head for the umpteenth time on something in my basement. The predictable anger, even though that wall, that ceiling, did not do anything to me. I'm clearly responsible. So messy. There's so much to get caught up in and wade through, and yet I can get instantly caught up on something so small and insignificant. I even know it logically the moment it happens — and emotionally it's just, yeah.

Charlie: Really, what it sounds like is that you're attached to the illusion of control.

Joel: Oh my goodness. Yep. Yep.

Charlie: Because you realize that with organics — with living things — you don't have control, so you accept that. But you think you're in control of your body, and of not hitting that wall. When really the body is doing its own thing. And that's the same with sugar — you want to be more in control, you want the illusion of control, and when that gets shattered, that's the suffering.

Charlie: The deep, intense pandemic period was rough for a lot of different reasons — objectively rough. But I think it shook people largely because it shook their illusion of control. It shook the idea that things were predictable. You know where to get the toilet paper. Everything has its place. We thought we had mastered things that we had not. We were reminded in a very human and humbling way that there are bigger forces at play than just your comfort and your supply chains.

Charlie: We're animals. We want to control our environments — that's part of being the type of animal that we are. Sophisticated animals do this: octopi alter their world, cats and dogs alter their spaces, ants do it. It's a fundamental animal drive. And at the same time — Aristotle said this — animals have these emotions and urges, that animus. That's what makes animals animals. So a lot of times when I find myself in that reactive space, I use what I call chaotic medicine. I just laugh at myself: I am upset right now because I walked down the stairs and one of these cats left a little toy mouse there, I stepped on it, I stumbled and janked my knee, and I'm mad. But what am I actually mad at? Am I mad at the cat? The mouse? The stairs? My knee? When you think about it, it's just a random thing. It doesn't have to be more than that.

Charlie: Have you heard the story of the empty boat from the Taoist tradition?

Joel: If I have, I've forgotten it. Now you're going to tell us.

Charlie: Sometimes it's called the empty or the open boat. So if you're on a boat on the river and you see another boat coming toward you, you'll yell at it — get out of the way, what are you doing? Until you see there's no one in it. And if it bumps you, you're not mad about it anymore. There's no driver. It's just a random boat floating down the river. You might have questions about how it got there, but you don't have that sense of, “How dare you hit me? Move, I'm right here.”

Charlie: It's a Taoist story with a double meaning. On one hand: what if you treated all the bumps of life as if they were an empty boat? Just one of those random things that bumped into you. No agenda, no intention, no fate teaching you something. It's just a boat floating down the river. But there's a second meaning I love even more: how can you be the empty boat? How can you release your attachments and desires and need for control, so that when you bump into somebody, you can say, “I'm sorry — I didn't have an agenda. I was just an empty boat floating along.”

Charlie: So when you bump your head on the wall, it's not fate. It's not you being dumb. It just happens — predictably three times a month, apparently. When you have a sugar craving, if it's not in a place where it's truly unhealthy for you, turns out you're an animal. Maybe that's telling you something. It doesn't have to have a whole story attached to it. I have a client who always says, “I know you're going to let me off the hook on this one, Charlie.” But first — being on a hook is painful. You're being impaled by a sharp object. Second — what does being on the hook actually serve you? She did what she needed to do. It met her priorities. It got the thing done. What's the remainder she thinks is so important? Why do you want to be on the hook? That's the question I end up asking her.

Joel: She hates when you ask that.

Charlie: But it is the question. Why do you want to remain on the sugar hook? Why do you want to remain on the “I bumped my head” hook when you know it's passing? If you drop something on your toe and it hurts and you yell and cuss and get mad — that's just being an animal. No further story needed. That is the appropriate response when you drop a hammer on your toe. Ouch. What the heck? Okay. That's just neurons firing. It doesn't have to be more than that.

Joel: And now I'm curious about the neurons firing in the non-animal portion of our world. You walk outside, you see trees, maybe some fungus growing. Is there some part of the non-animal world that makes you feel more human? Where are you finding your sense of connection, your sense of self, even when you're not interacting with another human or animal?

Joel: What I'm getting at, if I'm getting at anything, is the interconnectedness of everything. For a long time I felt like I could only have really strong connections with humans or with dogs. But in the last few years, I realized I can have just as powerful a connection with a tree, or on my psychedelic journeys — with the cosmos itself, something that has nothing to do with humanity or animals at all.

Charlie: Yeah. One of the reasons I love motorcycle riding, especially with Angela on the back — we have a Honda Goldwing, and I don't mention that as a flex, just for context; it's built for touring, for riding 400 to 600 miles a day — is that we go on these road trips and we live in the Pacific Northwest, which we found out in 2022 just has the most amazing riding roads.

Charlie: I got the bike after my dad passed. We were also launching Momentum, which was an app we had, and the head of growth I hired needed to take a leave of absence right as we were heading into the launch. And oh, by the way, four months later I had a book manuscript due. It was a lot. I was like, I need some road therapy.

Charlie: One of the reasons I love motorcycle riding — especially with Angela on the back — is that your hands are occupied, your attention is occupied. If you're not a motorcycle rider, helmets now have Bluetooth mics so you can talk to your passengers the whole time. And so it's just you, wide open air, traveling for eight to ten hours a day with your wife on the back. Sometimes we'll ride for two hours and not say a word. We're just taking in the terpenes, the Pacific Northwest smell and crispness, the sun, the rivers. That's actually one of the places where I most find myself — because I have to be, and I get to be, fully present. Not messing with a phone, not messing with music. Just the hum of a motorcycle moving through the trees.

Charlie: I was talking to Angela about this yesterday. When we got the Thundercats, one of my reservations was, what about the traveling we'd started doing? I'd been working from campsites during the summers — just holing up for two or three weeks and doing all my work from there. After Petey passed, we went on pilgrimage to the national parks about two weeks later: Joshua Tree, Sequoia, Grand Canyon, Zion — a bunch of cool places in about 21 days. But what I was telling Angela is that life on the road is incompatible with life here in Portland with the Thundercats. And I actually really love both.

Charlie: If I had to put a spiritual or emotional flavor on it — being on the road, being on the motorcycle — a lot of that is awe. Wherever I can find awe. I can find it around Portland too, just not quite like going to Glacier National Park or Yellowstone, or turning a quarter on a motorcycle and having a huge, beautiful gorge open up in front of you. So it's awe versus simple contentedness — which is what we chose with the Thundercats. Physical touch is my primary love language, and now I have Angela, plus three cats bouncing off me all day and cuddle piles at night. Boring? Maybe. But also really simple, really content. I don't need anything more than this. Whenever I can modulate between those two as the seasons allow, as my energy allows — that's where I really find myself these days.

Joel: Maybe you know this about me — I'm definitely a physical touch person as well. I'm looking outside at my driveway right now and there's a two-foot by three-foot A-frame sign I had printed a few months ago. Written on it in big letters: “Free Hugs or Kudos.” Especially in wintertime in Minnesota, it gives me a reason to be outside and interact with neighbors walking by. Yesterday it was 40 degrees Fahrenheit in February and sunny — beautiful — and I had some truly lovely people come by. Great conversations. Janice was like, “Sure, Joel, I'll help start a neighborhood association with you.” TJ from the apartment building over there said, “It's so cool that you do this.”

Charlie: That is the perfect example of being beautifully boring. You're just sitting out there with your A-frame, waiting on people to come by. It's amazing for so many different reasons. Thanks for that illustration of it.

Joel: A picture would be worth a thousand words here, but I only got the words, so that's what we'll stick with. You tell great stories and you pull from so many different traditions — religious, philosophical. I'm a question collector, and I love hearing what kinds of questions people ask themselves or ask each other. Are there any particularly good questions that you find yourself asking lately, or challenging other people with?

Charlie: Yeah. A standard one that's gotten pretty integrated into how I think is: what's the most abundant possibility we can co-create together? It's a question I ask clients, friends — whenever there's a “we're not sure what we're going to do.” I even ask it in places where there's tension and conflict. Just shift the frame: what can we do together? There's a lot packed into that one. “Co-create” means I can't do it alone, I need you with me. “Abundant possibility” means instead of focusing on all the things that might go wrong, let's really think — what can Joel and Charlie do together that neither one could do alone? Let's dream. We might not do it, but we reserve the right to play. And it's helpful even in relationship stuff: that option is still there. That hasn't changed. So that's a good one when I'm really trying to inspire us to be our best versions — and by “us,” I also mean me. Where have I been petty? Where have I been scarcity-minded? Where have I been insecure? It helps me shift from that.

Charlie: Another question I ask a lot is: what would you do if there were no right answers? That one unlocks a lot for people, because we get so rigid about finding the one secret bullet, the one right way to get something done. What would you do if there is no one right way?

Charlie: The third one is: how can this be easy? And the follow-up — are you willing to allow it to be easy? More people struggle with the second part when they're being honest with themselves than with the first. So those are some go-tos: what's the most abundant possibility we can co-create? What would we do if there was no one right answer? And what would we do if it were easy — and will we allow it to be?

Joel: I'm absorbing what you're putting down and feeling at a loss to follow up. Maybe this is an appropriate time to wrap up a little bit — unless there's something you wanted to touch on that we didn't get to, a thread you wanted to pull on?

Charlie: No, but — I say no and then I say yes. Sorry, listener. Sorry, Joel. This is called Surprise Me Joel, right? As I was thinking about this conversation today, I was like, what if we flipped it on the listener? What could you do to surprise yourself today? What would that look like? What would you do? I don't know what that looks like for a lot of people, but since we're surprising each other — maybe, listener, you can surprise yourself too.

Joel: What could you do to surprise yourself? That's a good one. For the folks who don't know you exist yet — and I know before we started recording we talked about how there are still people in this world who don't know the name Charlie Gilkey, which I don't understand how that's possible — for the folks who are like, this Charlie fella seems fun, he says smart things, I want more Charlie in my life, where might people connect with you?

Charlie: ProductiveFlourishing.com — all roads lead there. As we discussed, I'm not really doing social media much, so if you reach out that way it might be a few weeks before I see it. Otherwise, it's charlie@productiveflourishing.com. Those are the best ways to reach me, and then we'll see what fun we can have. Post up in a national park in the United States and wait for me to come through — you might actually see me. If I could figure out a way to do this sanely with a wife and three Thundercats, you would definitely see me out there. Maybe something I'm thinking about for next year, but not this year.

Joel: Right on. Thank you, friend.

Charlie: Thanks for having me.

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Joel: And there you go. That's just one of many, many ways a Surprise Me Joel episode might turn out. You can find links to things we spoke about, takeaways, and a transcript in the show notes at joelzaslofsky.com/smj001.

Joel: Maybe you appreciate this episode or the show in general — consider leaving a review wherever you listen to podcasts, because it helps me stay motivated and gets the show in front of more folks. I'll be back with you again to sling stories, facilitate connections, and whip up experiments to help you make friends with people, possibilities, and ideas.