The Mindful Midlife Crisis

Episode 31--Ride the Wave of Healthy Risk-Taking with John Wessinger

September 08, 2021 Billy & Brian Season 3
The Mindful Midlife Crisis
Episode 31--Ride the Wave of Healthy Risk-Taking with John Wessinger
Show Notes Transcript

In this week's episode, Billy and Brian talk to John Wessinger, author of Ride the Wave: How to Embrace Change and Create a Powerful New Relationship with Risk, about:
--how a surfing vacation gone extremely wrong led understanding the importance of embracing the conditions regardless of prior preparation
--how that surfing experience prepared him for an unexpected realization in his professional life that encouraged him to take more healthy professional risks
--how embracing the conditions, adopting a progression-based mindset, and using risk as a compass has helped him grow as a professional and as a person
--how these three principles helped him redeem himself on the surfboard and in his professional life a year later
--what surfers mean when they talk about "the universal stoke"
--how taking healthy risks have added to his overall satisfaction with his life

Book Offer: Mindful Midlife Crisis listeners can purchase Ride the Wave for 50% off the cover price if you order from  The book has won multiple awards including the Axiom Business Book Awards.  

Like what you heard from John Wessinger?  Contact him at:

Thank you for listening to the Mindful Midlife Crisis!
Questions? Comments? Suggestions? Topics you want us to cover?
"Like" and "Follow" us on Facebook:
The Mindful Midlife Crisis Podcast

Please leave us a 5-Star Review!  Doing so helps other people looking for a podcast like ours find it!

We hope you enjoy this week’s episode!  If this episode resonates with you, please share it with your friends and family.  If you’re really feeling gracious, you can make a donation to Your donations will be used to cover all of our production costs.

If we have money left over after covering our fees, we will make a donation to the
Livin Foundation, which is a non-profit organization whose mission is to promote a positive outlook on life, reduce the stigma associated with depression/mental illness, and ultimately prevent suicide through various activities, events, & outreach.

Support the show

Thank you for taking the time to listen to The Mindful Midlife Crisis podcast. We hope you enjoy this week’s episode. If this episode resonates with you, please share it with your family and friends. We will do our best to put out new content every Wednesday to get you over the midweek hump. If you want episodes to be downloaded automatically to your phone each week, all you need to do is hit the checkmark, Subscribe, Like, or Follow button, depending on what podcast format you’re using. While you’re at it, feel free to leave our show a quick five-star review with a few kind words so more people like you can easily find our show. If you’re really enjoying the show and you want to help us out, feel free to make a donation to You can also access the link in our show notes. We use the money from these donations to pay whatever expenses we incur from producing the show, but, ultimately, we record this show for you so if you keep listening, we’ll keep recording and releasing new episodes each week regardless. If you’d like to contact us or if you have suggestions about what you’d like us to discuss on future episodes, feel free to email us at or follow us on Instagram at @Mindful_Midlife_Crisis. Be sure to check out the show notes for links to the articles and resources we referenced throughout the show. Thanks again for listening. May you feel happy, healthy, and loved. Enjoy the show.


Welcome to The Mindful Midlife Crisis, a podcast for people navigating the complexities and possibilities of life second half. Join your hosts, Billy and Brian, a couple of average dudes who will serve as your armchair life coaches as we share our life experiences, both the good and the bad, in an effort to help us all better understand how we can enjoy and make the most of the life we have left to live in a more meaningful way. Take a deep breath, embrace the present, and journey with us through The Mindful Midlife Crisis.


Billy: Welcome to The Mindful Midlife Crisis. I’m your host, Billy, and, as always, I’m joined by my good friend, Brian on the Bass. Brian, how you doing over there, man?


Brian: I am mind blowing today.


Billy: Oh. What’s blowing your mind?


Brian: You know, just life in general, man. I’m just really happy about everything. 


Billy: Good. Good. You guys have band practice with Generation X Jukebox, Gen X Jukebox.


Brian: We do, we do. That’s going to be a lot of fun. We’re prepping for the video. We’re doing our EPK video in a couple weekends here and that’s what we’re preparing for.


Billy: Very nice. Very nice. What jams are you recording?


Brian: Oh, gosh, we’ve got a really broad cross section of jams that we’re doing for the video, actually, but we’ve got low rap, a little country, a little pop, a little rock, just gives a flavor of the band. 


Billy: Is this band going to be full on ready to go when I come back from Portugal at the end of October?


Brian: Oh, yeah, yeah. Our first gig is at the beginning of October, October 2nd is our first gig right now. 


Billy: Where at?


Brian: Yeah, we’re just doing a private party.


Billy: Very nice. Can we do a private party when I come back? 


Brian: Yeah, sure. 


Billy: Fantastic. I like this. I went to yoga today and it was really hot because at Modo, they keep it about 100 degrees in the room. 


Brian: Wait a minute, so it was hot but it wasn’t hot yoga?


Billy: It was hot yoga. 


Brian: Okay, all right.


Billy: Yeah, so I went to hot yoga today. It was about 100 degrees in the room. I sweat the whole time just as soon as I got in there but it was really refreshing, especially after that conversation that we had with Jill Dahler, I’m like, “All right, I just need to buckle down, I need to go in, I need to do some yoga,” and it felt great and I’m going to try and make it a habit here for the rest of this month, given that I only have a couple of weeks left before I go to Portugal.


Brian: Yeah, you want to be in your best shape when you hit the shores of Portugal. 


Billy: Exactly, because I want to do some paddle boarding off the coast of Portugal and maybe do some surfing. I’ll tell you this, that all you big brawny guys out there who are like, “Oh, why are you doing yoga?” take a class, big guy.


Brian: Yeah. Try Pilates. Pilates sounds like stuff that women traditionally do. Guys, women are tougher than us. It’s hard.


Billy: It was so hard to be in those positions because I’m so used to doing bro exercises but, oh, man, yoga was tough but it felt great. It felt really good. You would think that those exercises that you do in the gym would translate over to yoga. 


Brian: Not at all. 


Billy: Not at all. Not one bit. And, actually, our guest today can absolutely relate to that. Our guest today is John Wessinger. He is the award-winning author of the book Ride the Wave, which is about embracing change and how to explore risks in your personal or professional life. John’s book provides a framework for minimizing risk by using the three principles from surfing to help anyone embrace change, adopt a progression based mindset, and use risk as a compass. In fact, for listeners of this podcast, you can get this book for 50 percent off the cover price. We will put that information in the show notes. Be sure that you check it out. The book has won multiple awards, including the Axiom Business Book Award. We’re very happy to have John Wessinger here. Thanks for being here, John. 


John: Thanks for having me, guys. 


Billy: Yeah, absolutely. So, John, we like to ask our guests what 10 roles they play in their life. So what are the 10 roles that you play in your life?


John: Yeah, so number one is husband. So I am married and my wife is Kate. Second is father. I just had a daughter three months ago. Her name is Waverly. 


Billy: Congratulations. 


John: Thank you.


Billy: Waverly, is there a Chicago connection to this? I think I’ve asked you this before. 


John: We talked about it. So, I originally got the idea from Waverly Place in New York City and there’s a neighborhood that is named Waverly Place in the big city so, yes, but people ask about Chicago all the time when we tell them her name.


Billy: Yeah, just because Waverly Avenue is over there by Wrigley Field so I couldn’t remember, is there a connection there?


Brian: I got to say, that’s much better than my son. I named my son after an action hero. 


Billy: Which one?


Brian: Mason.


Billy: Which action hero?


Brian: Mason Storm from Hard to Kill, Steven Seagal. Yeah.


Billy: Oh, man. These are the beautiful things that we learn.


Brian: That’s where I first got the idea. I’m like, Mason, I like that name. 


Billy: Oh my God. 


Brian: Yeah. Where it came from, that’s honest to God true story. 


Billy: Oh, I love it. I love it. All right, so what other roles do you play, John?


John: Yeah, so cat dad. We have two cats. Clyde and Enzo. I have a brother, Nick, and I’m uncle to his kids. Author-writer, athlete, obviously surfer, former soccer player, team member, I work for a company and I’m part of a marketing team, and then I’m a Tool fan. Hopefully that’s okay to say here. I know that there’s a Pearl Jam fan.


Brian: No. We love Tool. Love Tool.


Billy: Love 90s rock so all good.


John: And movie fan. I really love movies. 


Billy: So before we get into the three roles you’re most looking forward to, you said that you’re a college athlete. So what was your sport? Where did you play?


John: Yeah, so I played college soccer. I played at St. John’s. Soccer was the thing that I was going to do professionally, like I wanted to be a soccer player but I also was interested in board sports like surfing and skateboarding. So I did play a lot of soccer growing up. I played baseball and basketball as well. But I hit that age in I think like middle school where you go to the basketball game and everybody’s a foot taller than you, like the next season or whatever, so I was like, “I’m done with basketball, we’ll focus on a sport where you don’t have to be tall.” Well, you can play soccer. So, yeah, I would say athlete, so soccer was the primary thing and then, obviously, the love for board sports and surfing. 


Billy: And you spent a semester in college over in Italy at one point.


John: I did, yeah. So I played, my first three years I played freshman, sophomore, junior year, and then my senior year I studied abroad so I gave up soccer to basically experience Europe, got to see some games when I was over there but that’s also where my love for Italy came was spending that semester abroad.


Billy: And Americans don’t understand just how big soccer is and I’ve been over in Europe in 2014 and 2018 during the World Cup. It’s a big deal.


John: It’s a big deal.


Billy: It’s like nothing you’ve ever participated in in your life. When I was in Amsterdam, Holland was playing Mexico, and we asked our hotel concierge like, “Where should we go to watch this game?” and she said, “Go down to Museumplein,” and Museumplein is where the Van Gogh Museum is and is it the Rijksmuseum, the Rijksmuseum. There’s a big green space that’s around there and they had three 70-foot-screen TVs and there were about 50,000 to 60,000 people watching that game. And it was a wild party. It was so much fun. And then in 2018, I was in Berlin and right behind Brandenburg Gate, they have 50-foot-screen TVs with picnic tables, all down Unter den Linden, which is right where Brandenburg Gate is. It’s amazing. They set it up. Like you think about Super Bowl parties. Nothing compared. And these are just like random World Cup soccer games. They’re absolutely fantastic. So, did you get to go to Olympic Stadium? Did they play any soccer games at Olympic Stadium?


John: Yeah, they did. So I saw Roma and Lazio to play in Stadio Olimpico and that’s like the main stadium in Rome. And that’s like a derby, it’s like the two home teams, it would be like Yankees and Mets playing each other, and that was crazy. And this is maybe another 90s reference but I don’t know if you guys remember M-80s, they literally set those off in the stadium and throw those around and so those are constantly going off so not only are the fans crazy but you feel like bombs are going off in the stadium while the game is going on so it’s a little nerve wracking.


Billy: Brian is in a band called the M80s and I feel like you need to get a gig at a Rome soccer game some time with M-80s just blowing up all around you guys. 


Brian: I don’t know, that doesn’t sound like such a good idea. I like my music, playing my music when I don’t have the threat of losing digits. It’s just a prerequisite for me.


Billy: All right, I mean, that’s fair. That’s fair. Not as exciting but fair. I’ve seen Pearl Jam in Italy a bunch of times and they’ve all been at soccer stadiums so Olympic Stadium in Rome and then San Siro in Milan and that was huge. You couldn’t believe how big that soccer stadium was. That stadium seats 70,000 plus.


Brian: Wow. 


Billy: It’s enormous. And then I saw them in Trieste and I saw them in Padua, all at soccer stadiums and, man, the Italians love their soccer but they really love their Pearl Jam. They’re bigger Pearl Jam fans in Italy than anywhere else that I’ve been to.


Brian: That’s interesting. Why do you think that is?


Billy: I don’t know. They just love Pearl Jam over there. They go wild for Pearl Jam there. It’s lawless over there during a Pearl Jam show. 


Brian: Wow. 


Billy: It’s crazy. So you’re a big Tool fan.


John: I am.


Billy: So tell us what is it about Tool that you just love? Because I think you’ve named one of your companies after a Tool album. 


John: I did, yeah. At one point, it was Lateralus and I named the company after that album, I just love the album, and I think for me, Tool is, and I’m a Pearl Jam fan, I really got into music during the 90s when a lot of those bands went big so like Radiohead and Soundgarden, those are like kind of the genre that I still listen to today. With Tool, I think it’s just that there’s a little bit of extra effort that you have to put in to listening to them and you can’t listen to a Tool song for the first time and get it and you have to listen to it multiple times and so there’s a little bit of work that goes into understanding that song or connecting to that song. And so, for me, I like that repetition and really kind of growing with a song, if that makes sense, and I’m sure you guys get it. 


Brian: Oh, yeah. I mean, their compositions have grown over time, I’d even say. If you look at their first record, it was a little more pop driven, if you can say that for metal, but then by the time they get to Lateralus, they’re doing those 18 minutes just incredible compositions and I love Tool too. I’ve seen them a bunch of times, and fantastic so I know what you’re talking about. Yeah, I can relate.


Billy: So the lyrics to Lateralus are actually written in a Fibonacci method, and if you don’t know what the Fibonacci method is —


Brian: Golden ratio.


Billy: — it’s where you do one plus one equals two and then isn’t it two plus — or one plus two equals three, or something like, it just keeps adding on to each other, I’m not doing a great job of explaining it. But, lyrically, as you listen to it performed, it’s really interesting how it presents itself throughout that song in their verses. So, yeah, you’re right, you don’t get Tool the first time that you listen to it. So that’s awesome. That’s awesome. I’ve seen Tool a bunch of times in concert, I imagine you have as well.


John: Yes, multiple times, and I actually went to — they did a music clinic where you could pay a little bit extra cash and you got to go in and watch. It was Adam, Justin, and Danny just talk about the songs and do a performance for, there’s maybe 100 people in there, and so that was really cool to hear them talk about polyrhythms and all these things that I don’t necessarily know about with music but having them explain that, you get a better understanding of how they approach their instruments and work together and that sort of thing so it was really cool.


Billy: And those guys are scientific in their approach to playing their instruments.


Brian: They would have to be with compositions like that. 


Billy: Yeah, ’cause they’re working with some wild time signatures in their songs. So, the three roles that you’re most looking forward to, let’s start off with husband. What is it that you’re most looking forward to being a husband in the second half of life?


John: Yeah. So that’s a good question. So, Kate and I have been together for a while, we’ve been married for, I think, three years and, obviously, now we’re starting a family so that relationship keeps evolving and it changes every time you go through one of these new milestones. So, at one point, we’re dating, and then we’re married, and then we’re starting a family. And so we still have that same kind of core element to our relationship that I think make it work. We like planning together and doing things, but it feels like it’s evolving, and now we have this third person in our house and so I’m a husband who’s becoming a father and now we have this other person that we’re managing and making sure that they’re okay and building them into the things that we like to do and what we’re doing. So I think as far as a husband with Kate, I’m looking forward to seeing how that progresses, for sure.


Billy: And the two of you are falling in line with a common trend that’s growing these days of having children later in life. So, how old are you again?


John: Forty. Well, 45. In my 40s, that’s how I typically answer that.


Billy: You’re in your 40s. Brian had his last baby when he was 43. 


John: Okay. 


Brian: Yeah, it’s an adventure. 


John: Yes. 


Billy: So if you need advice about how to be a 40-something parent, Brian’s got it for you. So, what is it then about being a father that you’re most looking forward to? 


John: Yeah. So raising a child, hanging out, having fun. I went for my first solo daddy walk last night with Waverly while Kate was on a Zoom and that was really fun. I was paranoid the whole time. I’m like super protective so like this is the first time I’m leaving the house with a child in the stroller and I’m watching cars, what are people doing, try to be careful. We live in big, scary Minneapolis so try to be mindful of that, but just the interactions that we’re having, even though she’s three months, it’s crazy to see how much they play off of FaceTime and just kind of hanging out. It’s smiling and laughing. So, I’m anticipating this just evolving and growing from there and looking forward to that too with her as well.


Billy: Awesome. And then you also said they’re looking forward to continuing being an author and a writer in the second half of your life so talk about that.


John: Yeah, so I did write my first book and that was a great experience. I loved the process of doing something on my own. I think, for years, I had been soccer player on a team, I worked for companies, you’re on a team, and it was like one thing that I could really do and manage on my own and have 100 percent control over creativity, how I wanted to write, what I wanted to write about, and so, for me, that process was really rewarding. So, as I’m thinking, now that I am 45 and what I’m going to do during the second half of my life, how do I want to spend my time? And if there are things like writing that I can do where you get to manage and control that process and get the enjoyment out of it, I think that that is something that I’m really looking forward to. It’s like, not that I’m comparing myself to any of these people, but Stephen King or like a director kind of honing a craft over time and writing is one of those things that you could do past the age of 45, like I’m kind of done with the board sports. I don’t know, I might have to retire here pretty soon, I could still wake surf every once in a while, but I don’t know how much surfing I’m going to do going forward. I’m limiting my running because my knees are old and I played a lot of soccer. So those things are going to go away eventually so I need to figure out some other thing that I can do to stay passionate about something and have something to look forward to doing every day and so that might be it.


Billy: Yeah. And the book that we’re going to talk about today is your book, Ride the Wave: How to Embrace Change and Create a Powerful New Relationship with Risk and you talk about your love for board sports in there as well. So, we’re going to take a quick break and then when we come back, we’re going to continue talking to John about the three principles to taking risks. Thank you for listening to The Mindful Midlife Crisis. 


Thank you for listening to The Mindful Midlife Crisis. If you’re enjoying what you’ve heard so far, please do us a favor and hit the Subscribe button. Also, giving our show a quick five-star review with a few kind words helps us on our quest to reach the top of the podcast charts. Finally, since you can’t make a mixtape for your friends and loved ones like you used to do, share this podcast with them instead. We hope our experiences resonate with others and inspire people to live their best lives. Thanks again. And now, let’s take a minute to be present with our breath.


If you’re listening somewhere safe and quiet, close your eyes and slowly inhale for four, three, two, one. Hold for seven, six, five, four, three, two, one. Slowly exhale for eight, seven, six, five, four, three, two, one. Let’s do that one more time. Inhale for four, three, two, one. Hold for seven, six, five, four, three, two, one. Slowly exhale for eight, seven, six, five, four, three, two, one. Go ahead and open your eyes. You feel better? We certainly hope so. And now, back to the show.


Billy: Welcome back to The Mindful Midlife Crisis. We are here with John Wessinger and he is here promoting his book, Ride the Wave: How to Embrace Change and Create a Powerful New Relationship with Risk. We’re talking about the importance of taking risks so, John, you start your book off with a surfing analogy. Can you tell us that story and what you learned from that experience?


John: The surfing story was something that had had happened and when I was thinking about writing the book, I was trying to think of a way that I could explain something that happened to me and how it changed me and how I went through a process of growing and learning from that experience. And so this surf story started out as an opportunity for me to basically, like a bucket list item, like I had done everything within board sports that I could possibly do, we’re kind of landlocked here in the state of Minnesota so I had done skateboarding, snowboarding, wake surfing, and done those things kind of in the background for years, and like I mentioned, I played organized sports for years, like soccer, but board sports was this thing that, again, it was kind of a solo thing that I could do on my own that I really liked and enjoyed. And so I said I need to go ocean surfing and experience what this is like because I’ve done everything else. And at that point, I was doing a lot of wake surfing and my brother and I owned a boat together and we would go to the cabin and we would do a lot of wake surfing. So I thought to myself in my head I can wake surf behind a boat, there’s no reason why I can’t translate that and do it in the ocean. And so I planned a trip with Kate where we literally spent a week in LA and we were going to use Wednesday as the day to go to Malibu and I was gonna go to Surfrider Beach and surf and so I’m a super organized person, I put a plan together, I figured out where I’m going to rent a surfboard, how we’re going to get there, where to park. I had sheets of paper detailing everything that we needed to do for this trip.


Brian: Sounds like somebody else I know. 


Billy: Yes, John and I have joked about that.


John: Yes, obsessing over details and trying to figure out where do I need to go? How am I going to do this? And so I had everything on paper planned out and, at that point, this was probably 8 to 10 years ago and I was still in relatively good shape, was working out consistently. I don’t know that I was in surf shape but I felt like with the wake surfing and what I was doing in the gym at that time, I could figure this out. So, we went to LA, we had a couple days just kind of bumming around, and then Wednesday shows up, we’re literally out of our hotel at six in the morning. We’re at the surf shop at 8 a.m. and we’re renting surfboards. And when I talked to the guys at the surf shack, they were like, “What have you done for board sports?” and I explained everything I’ve done and they’re like, “Okay, you got this, piece of cake,” and so they gave me a board that was literally three or four feet long, it was a smaller surfboard, thinking that I had done all these things so this would be a piece of cake for me so I got my board, went down to the water, Kate’s hanging out on the beach, she’s like, “Have a good time. I’ll be here reading,” and literally within 20 minutes of paddling out and getting into the lineup and hanging out in the lineup, I realized this was a huge mistake, I have the wrong equipment, I basically burned out my shoulders paddling out and jockeying through waves and other surfers and was so tired that I was thinking in the back of my head, I’m like I don’t know how I’m going to paddle into a wave, like I am exhausted right now, and so I spent this first part of this day trying to figure out like the basics of surfing, like literally sitting on the board, where do I sit in the lineup, like literally wrecking waves for people who were trying to paddle in, who had obviously been doing this for years and were very serious about surfing and I’m literally the kook from Minnesota who showed up on vacation, too much sunscreen on my face and the wrong equipment and hanging out in the water and so it was a bad experience. It was like the exact opposite of what I expected to happen. And so I didn’t stop there and I spent a lot of time at this first part of the beach where there’s probably three- or four-foot waves and it was super crowded and there’s a spot where there’s a much bigger set of waves that come in and I said, “It’s less crowded and I might have an easier time getting into a bigger wave than I would on some of the smaller ones.” So I went to this other area —


Billy: Wait, with bigger waves?


John: With bigger waves. And my rationale was I have a smaller board and there’s more speed on these waves, this might be an easier way for me to catch a wave. So I went out to the second set and literally got stuck in kind of the impact area of the wave and had to have somebody come and pull me out, put me on my board, and push me into shore. And so I think in the book I talk about Tom Hanks in Castaway, like I literally washed up onto the beach and my wife is standing there and I’m like, okay, so how bad would was that? And there’s 30 to 40 people all in chairs hanging out on the beach. She’s like, “Well, the lifeguard literally got out of her chair and was standing on the beach watching you, so, yeah, it was bad.” So within the first couple of hours, almost drowned on my vacation to Malibu to go surfing and went home with my tail between my legs and we spent the rest of the vacation just like laughing, like my wife was like, “You almost drowned. You almost drowned on vacation. How do you feel about yourself?” So it was a really just unexpected experience. I was planning on surfing, I thought that I was going to be able to do this, and the thing I really thought about afterwards was like that was stupid and there was a lot of risk, like I could have got hurt, I could have got drowned. I mean, there were seals and different things that were swimming around and people were telling me like, “Hey, there’s a seal there, just watch out for sharks,” kind of stuff, like it was not a very smart decision. So I walked away from that experience with just this was like a really stupid thing that I did and I didn’t evaluate the risks that I was putting myself into. I didn’t even think about any of that stuff. And so that got me thinking about how often people do stuff like that and don’t feel like they’re really well planned out but go into situations and things happen that you possibly can’t plan for, unless you’re there and you know the conditions and you know what to expect and had been there. So, that’s where the surf story started and that’s where I started to think more about risk and how I was taking risk or how I thought about risk and how I would plan for risk. I thought it was a universal sentiment that everybody can relate to. Everybody’s had some situation where they screwed up, did something wrong and had a bad experience because of it. 


Billy: And then that serve story became a reality in your professional life so can you talk about that? 


John: Yeah. So right around the same time, I was working for an organization and had been in a relatively stable, same role for a long period of time. And my company was changing, the industry was changing, there was writing on the wall that these jobs weren’t going to exist into the future and so there was a risk for me in continuing to stay and do the same thing that I was always doing professionally and there was fear of how do I change, how do I make a career change? What do I do with myself that’s going to be different? How am I thinking about preparing for the future? And so there was a ton of risk in just standing still and not really having a plan. And then there was also risk in what am I going to do that’s different now, like how do I think about doing something different within my career, and there’s a risk in that that I don’t know that I was ready to explore yet. And so these two things happened within months of each other and so it was a time where I was really trying to think about risk personally, what am I doing here and some of these situations where I’m possibly getting myself into bad situations, and then also professionally, it was like there’s a ton of risk in this professional career that I don’t know that I’ve actually ever thought about. And that was the first time that I really started thinking about how am I taking risk in my career and how am I managing that process? 


Billy: And it’s funny, because, like Brian said, it does sound like me and that you can prepare and you can be over prepared and, yet, something can a lot of times it almost gets in the way because if something does happen that throws you off the routine, then you don’t know how to respond to it. It’s like, “Oh, well wait, I was so stuck in everything had to go lock and step. Otherwise, if it didn’t, now here’s where I am,” and I think when you talk about the assumption that some skills are transferable but they’re not always, like being an athlete on the soccer field doesn’t necessarily mean that you’re going to be able to get up on a surfboard and I have countless examples of where I just assumed that I could walk into a situation because, “Oh, no, I got this,” like even starting the podcast, I taught, I’ve stood in front of people in a classroom, this should be no problem, and it’s safe to say that for the first three months that we were recording episodes, those episodes were sheer dog shit. They were not good and we had to work through those very much. So, from those two experiences, you came away with a whole new perspective on embracing change and taking risk and you compiled those into the three principles. So, talk about those separately. How can we embrace the conditions in order to lead a more fulfilling, risk-filled life? 


John: Yeah. So the first principle is really, and I use the analogy of conditions and being in the ocean, the surf analogy, and so I like to think about this as also change and when you’re in the conditions, it’s constantly changing and there’s always, for surfing, there’s always some dynamic that’s happening, either waves aren’t coming in and you have to sit in the lineup and you have to wait, or there’s a ton of waves, there’s a ton of people, there’s rocks, there’s kelp beds, there’s all these things that you have to navigate in the conditions. And so when I think about that is like the first principle, I think about you have to be out in the conditions regardless of what’s happening to know and understand what’s happening. So, professionally, I had to be out there understanding what’s happening with business? What’s changing? How do I think about my experience and how is it transferable? How would it apply to other situations? Could I get other jobs? And this first one is just about being out there and understanding what’s happening. Like if you want to be an actor, you can’t sit in your house and talk about being an actor, you have to like go do plays, you have to be in theater, you have to have an agent, you have to do things in order to become an actor. And so, for me, this one is really about put yourself out there, get in the conditions, understand what’s happening so that you know what you need to do in order to get better and adapt to situations. 


Billy: In the business world, where were you seeing companies fail in terms of embracing the conditions? Where were they not adapting? 


John: Yeah, and so this was a while ago, right? So the story and kind of the work story are pre when I started my business. So this was a time when, literally, technology was disrupting every industry. So, we were seeing it as sales and marketing people, we were seeing technology get in the way of us doing our job. So, you want to control the narrative as a marketer and market your product or your solution effectively. There is unlimited information out there that any kind of consumer could get that they can pull off the internet and, sometimes, they don’t need you to tell a story about your product or solution or can get information and make their own decision on their own. So what we were finding was that consumers or customers were going on their own journey. They were going out and sourcing their own information, learning on their own and necessarily didn’t want a company to tell them, “You should buy our product or buy our solution.” They were making up their own minds for themselves. So there’s a lot of disruption that was happening, just with technology and websites and information and the people who managed and controlled information, like the companies who are marketing and selling lost that. And so that was a really big change that my organization was going through and so, thinking about yourself as a sales or marketing person, it’s like consumers don’t want to hear from me, what am I going to do in the future? How do I have to adapt now and what jobs are going to be there in the future for me in order to still market and sell products and solutions? It got really congested and competitive. 


Billy: When you talk about embrace the conditions, I imagine what we’re seeing with COVID, people and businesses have had to embrace these conditions because we still don’t know when the end is in sight as cases begin to rise and so how have you embraced these conditions during these times? 


John: It’s a super good question and good example. And the biggest thing for everyone is working from home. So when the pandemic hit and COVID became a reality, that dynamic of working in an office and being a team person and part of a team, that changed. And so I think the biggest thing that has happened is people aren’t in offices anymore and I have 11 Zoom meetings in a day where I am talking to people around the country, I’m talking to people that are in the Twin Cities, are in Minneapolis, everything’s on this new technology platform. So I think the pandemic basically blew up that idea of you have to be at an office in order to work and I think that’s the biggest thing. And so, for me, it wasn’t as challenging because I worked for myself and I had a home office so I literally took all my monitors and my computer from the office and set it up at home and just started working at home so it was an easier transition. But there are people that they need their co-workers in order to get their job done or they liked the fact that they have co-workers and they liked that ability to have a conversation with somebody at work versus trying to hang out with their cat. So that is like the biggest change that has happened. And so I know people that they are no longer employed because of the pandemic and their companies had to cut loose marketing or sales or some of these areas that they have been in and I know people that still haven’t gone back to work yet because of the pandemic. So, that is like an updated example that could probably be in edition two of my book, but that is the biggest market condition or thing that’s happening that people have to embrace and get used to. It’s like you are doing Zoom calls whether you want to or not, you’re working from home whether you want to or not. The pandemic and COVID is in control and they’re going to decide when we go back to concerts, when we eat at restaurants, all of that stuff, and so that’s probably the newest thing that’s happening within business right now is just managing and understanding how do I fit into this massive change that’s happened. 


Billy: And I think that leads perfectly into your second principle, which is developing a progression-based mindset and Carol Dweck would call that a growth mindset in her book Mindset. So, that’s often easier said than done. “Hey, you just gotta have a growth mindset.” So what was your fixed mindset, both in the surf story or even in your professional life and how was it getting in your way and what steps did you take in order to move from that fixed mindset? 


John: I would say, and this is a — progression-based mindset, progression is a surf term, it’s a board sports term, and so to understand that, you have to understand how surfers think about their skills. They think about them in terms of always progressing so if you’re watching a surf competition or a skateboard competition, they always talk about progression and how a rider is progressing and so that means that they’re always moving forward, building new skills, building new capabilities. Progression means you’re on the edge of what’s new versus running with the pack and doing what’s expected and what’s standard. And so I think, for me, I thought of my skills as being static, like I had developed a set of skills, this is who I am as a person, this is what I know, this is what I know how to do, and really thinking about it from a surf perspective. They would never think about their surf skills in that way. So I had to change the way that I was thinking about my business skills, you can apply it to any personal skills or things that you’re — playing the bass, all those things, so you have to really change how you’re thinking about the skills that you have now and where they’re at and how you can move those forward. So, professionally, I was like on a traditional sales route and had really developed business planning skills and presentation skills and building relationships and when I went to work for myself, I really shifted and developed more marketing skills, understanding digital marketing, websites, email marketing, paid media, all those things, and so my shift was more from sales to marketing, but really changing how I wrote and how I built PowerPoint, like all of those things which are maybe more soft skills, it forced me to have to learn how to do those things in order to become a marketer, which is how I changed during this career transition. But, really, that mindset is to be thinking about, I’m in the conditions, I understand that things are dynamic, and I’m seeing up ahead that there’s something new and different that I have to do. What do I need to do in order to prepare myself to catch that bigger wave? Or how am I thinking about making a career change or doing something different? And what skills am I going to need in order to be effective in doing that? 


Billy: Brian, I always feel like you’re ahead of the curve in terms of evolving your business and —


Brian: Oh, yeah, you have to be. I mean, I’m in technology and technology changes so quickly that if you’re not constantly developing new skills, you get left behind. I mean, things, entire protocols in my business get discontinued at a moment’s notice. So a technician can spend, or an engineer can spend five years learning this skill and, all of a sudden, they just change it all. So we have to constantly be learning and evolving in a more progressive-base mindset, yeah. 


Billy: As you’re talking about branding and skill sets and stuff like that, I feel like that’s been one of my biggest areas of struggle because part of the reason why I’m taking this leave is because I want to see if there’s more to Billy than just being an educator, and my dad, God bless him, once told me, “I hope you’re a really good teacher because if you have to do anything else, you will starve to death.”


Brian: Oh, thanks, Dad.


Billy: So part of this is like, okay, what do I need? What do I have to offer? And do I just have my teaching skills to offer? And I’m really struggling with that and I get in a fixed mindset and when I get frustrated with my job, then I start looking for other jobs. But what do I look for? I look for dean positions, I look for educator positions. It’s like why do I want to leave one job that I don’t enjoy for another job that I very well may not enjoy either? So, it really has been difficult for me to transition into a growth mindset professionally, especially because I’ve been doing the same thing for 20-something years. And I wonder how many people out there, not even just professionally, you’ve just been doing a routine or you’ve been the same spouse for 20 years, you’ve been parenting the same way for 20-plus years and that’s who you are now at this point and you fail to recognize that, no, there’s another way to do things. We should always be wanting to learn and we should always be wanting to grow. So, in order to do that, your third principle says that we need to use risk as a compass. What do you mean by that? What does that look like? 


John: If you’re embracing the conditions and you’re adopting a progression-based mindset, risk becomes the thing that helps move you forward with your skills. So you need to take on risk in order to get better and to develop those skills. So, the surfing analogy is that you’re out riding 5- to 10-foot waves, you get bored of that, you need risk in order to get better so you go find bigger waves and that is like the quest within surfing. I think there’s surfers that go out and are more skill based, maybe like a Kelly Slater who is all about style and progression and doing tricks, and then there’s like a Laird Hamilton who’s super aggro and wants to surf the biggest waves. There’s a couple different mindsets there. You can be a Kelly Slater and focus on skill development and progression, but you can also progress in terms of the size of the waves that you surf and there’s a new set of skills that you have to develop there. So the big thing with big wave surfers is they get held down underwater on waves and you have to be able to hold your breath for four minutes. Otherwise, you drown. So you could go out and surf beach break and be Kelly Slater and do these awesome tricks. The second you go to like Nazaré like we were talking about in Portugal where there’s a 75-foot wave, you have to be able to have that skill to hold your breath and get held under for that long. And so that is the craziest thing to think about that you have to be able to hold your breath for four minutes to survive some of these waves but that is like the progression in the risk. So, you could be content, like my wife has essentially done the same job that she’s had since high school and she loves it and I think there’s progression within her job where she gets better at things and she learns and she’s developing her skills, but then there’s also the mindset of, like you’re saying, “I wanna do something completely different and I wanna try to step out of what I’m doing and challenge myself in a new way.” And so, really, seeing that risk is a compass, that is saying, “I want something new. I want a new challenge. I feel complacent in what I’m doing because I can do it on autopilot and I need to re challenge myself.” So you have to seek that risk in order to get to that point. And it’s super scary, because you’re looking for jobs, you’re searching, and you end up landing on things that are familiar but to say, “I’m gonna completely change careers and maybe I can apply those skills in another arena,” but you really have to be comfortable with taking that risk, knowing that you’ve done all these other things to get ready so you’ve gone out and you’ve maybe done some research, you’re starting to build some skills, so the idea is to try to minimize that risk, where if you do take a career change, you’re not going to flounder and you’re not going to fail. It’s going to be an easy progression into this thing versus my surf experience where I literally almost drowned in Malibu. You want to try to plan ahead and think about what you’re going to need in order to make it through that risk. 


Billy: Do you find that one of the biggest barriers to people taking risk and investing in themselves is just making the financial commitment? 


John: Financial commitment, for sure. I think that is probably the biggest one and that was the one thing that I had to really think about when I made my change. And, literally, it came down to, and I thought this deep into it, was if something happens, what happens to my mom and dad? Do I have to live at their house? Is my dad going to have to bail me out financially? Like they were in a position where I was like, “They could take on their son. I could go move in there if something happened.” So I literally thought that deep into it. I would say financial is the biggest one. I think the one risk that, this is an interesting one, is that people, I think they’re really concerned about what someone else is going to think and how am I going to be viewed for trying something new and I think that that was one of the things that I experienced most often was I’m changing, everybody knows me as John, the sales guy or John this, I’m changing that dynamic in the relationship with my people. And some people support and applaud that but then other people make it tough and there’s resistance there because they don’t want you to change. They liked the way that you are and they want to protect you. So they see you taking risk as a threat, not only to yourself but to them too because now you’re a different person. And I would say that that is the hardest one and that’s the one that I struggled with the most, asking permission from people, it was like I felt like I had to ask permission to write a book and it’s like you don’t have to ask for permission, you don’t have to ask permission to start a podcast, you can do these things on your own. And I think that that was a really hard thing for me with risk was negotiating that with myself kind of in my head and trying to say, “You can go do these things, you don’t have to ask people to do it, and If it changes that dynamic with people, then you don’t have to worry about that. That’s on them to figure that out and to sort through it.” So I think financial is like the first obvious one that always comes up. I think that second one is really important and really interesting too. 


Billy: I would tell you that taking this leave and not having any income for the next year, luckily I have money saved up because I am a good planner, I am a good saver, I’m going to be able to do what I got to do with the savings that I have, but it sure would be nice to make a couple bucks here, a couple bucks there, and I’m still trying to figure out part of this podcast, I feel like there’s a bigger purpose for me. I know, Brian, you and I have talked about it. You’re very comfortable in your position here at your company. And, for me, I’m sort of floundering out there like what else is out there for me because I could go back to teaching, like I have that job there waiting for me in a year, but what if there’s something else? And what if I just don’t see it yet? And I think I’m even all the way back yet at principle one where I don’t know that I’ve fully embraced the conditions because I don’t know what I don’t know, it’s one thing that Brian brought up a couple episodes ago that you just don’t know what you don’t know, and I myself feel like I need to get a better assessment of what I bring to the table and then put the effort into creating it and then taking a look around, like, okay, who out there would benefit from a service like this? How do I get it out there? What’s the risk that is involved in it? And how do I use risk as a compass? So, all of these things are really resonating deep with me as I’m navigating through this and I imagine many of you out there have a difficult relationship with risk. So, what we’re going to do is we’re going to take a quick break because I imagine many of you are wondering, did John get back out there and get back on that wave? We’ll come back and tell the rest of that story. Thank you for listening to The Mindful Midlife Crisis. 


Thanks for listening to The Mindful Midlife Crisis. We will do our best to put out new content every Wednesday to help get you over the midweek hump. If you’d like to contact us or if you have suggestions about what you’d like us to discuss, feel free to email us at or follow us on Instagram at @Mindful_Midlife_Crisis. Check out the show notes for links to the articles and resources we reference throughout the show. Oh, and don’t forget to show yourself some love every now and then too. And now, back to the show.


Billy: Welcome back to The Mindful Midlife Crisis. We are here with John Wessinger. He is the author of Ride the Wave. He just got done breaking down to three principles from that book and, John, you got back out there into the ocean and you redeemed yourself. So tell us, how did you redeem yourself? 


John: Yeah, so I actually didn’t start in the ocean, I started on land so I did a lot of training. After the first experience, I realized that I was a horrible swimmer, that I had poor upper body strength and that if I did get held down under a wave, like we talked about, that I would probably drown within a few minutes. So, I spent a lot of time just on like BOSU balls and pretending I was swimming in the ocean and using weights to do those things and just really trying to mimic what I had experienced that first time that I was out. And so recreating swimming motions, working on my balance. There’s a move that you have to do where you pop up on the board. I did all that stuff on dry land first to try to learn how to do it and get the fundamentals down. And then, after that, then we took it to the ocean. And so my wife and I went back to Malibu, so it was a redemption trip, and this time, she went, so we got bigger boards, we brought our own wetsuits. We literally did everything the right way that we missed the first time. 


Billy: For example, what? What are some things that you missed the first time that you did the second time around? 


John: Yeah, so the big one was a surfboard, like I had this short, small board. We had these giant boards that were essentially like paddle boards and so you could float on it. They were super easy to paddle fast with. It was a much easier thing to do when you’re sitting out there in the water and you’re trying to stay afloat. 


Brian: Much more stable, isn’t it?


John: Stable, yes. So we had larger boards. We had wetsuits. I had booties this time. I mean, I literally went out there in a swimsuit the first time and was trying to walk back in on rocks, like we bought our own wetsuits, we both had boots, we knew what to expect this time. And so there was all of this knowledge that we had that I had gained that first time that we applied to the second time in the water. And so I wouldn’t say we were pro surfers after that day but we caught waves. My wife had one where she stood up on and probably had the longest ride of anybody. So, we were able to break it down and figure out how can we just catch waves, like let’s not try to go pro, let’s try to have a good experience and have fun. And so we basically spent a day doing it like we originally had intended and really had a good experience. But it was like dry land training, getting ready, applying some of that knowledge. I actually went to a wave pool to try to surf a couple times in there. So there was a set of things that I tried to do to get ready for the second time, applying the knowledge from the first time.


Brian: So you managed the risk using those tools. 


John: That’s right.


Billy: There you go.


Brian: To tie it back to the book. 


John: So this sounds almost obsessive and persistent that the waves beat you down the first time and a lot of people could have been like, “Well, tried it. I couldn’t do it. It was too hard.” Why were you so persistent? Why did you need to catch that wave? Why wouldn’t you let that wave beat you?


John: That’s a great question. It’s just that feeling of failure and sitting on the beach and just feeling like an idiot. I think that was the thing that I had the hardest time with, that, as a planner, I felt like I had put together a great plan on paper and having it not work out was really frustrating. And so I wanted the opportunity to go back, having learned, and make it right and do the thing that I had originally planned out to do. So there definitely is some obsession there, there’s some compulsive behavior, but there was just a desire to, “I don’t want to go pro but let’s redeem, let’s do something that’s an improvement from the first time that we went out.”


Billy: And then you had a similar redemption story professionally as well. When we had talked earlier, you had talked about when you made a transition that you poured a bunch of money into your new business and it wasn’t working out really well and now you’re really thriving so I imagine that same obsessive persistence lent itself to your success professionally.


John: Yeah. And so the work story that I refer to in the book is making that change and starting a business on my own and running that business for five years and, yes, the first two years, for sure, financially was a big struggle and that was the biggest risk, like we talked about, was that financial risk. I did the book, I built my skills, I tried to do things differently within that business and ended up having success within the business, relatively speaking. I mean, I would have loved to have that business be a billion-dollar business and be the next Elon Musk but, at the end of five years of doing that on my own, I said, “I’ve taken this as far as I can go and I feel satisfied with what I did here. What is my next thing?” And so, for me, I had worked for two huge global organizations, I had worked for myself and started a small business, I had never worked at a venture-backed startup so my next phase out of starting the business was to go work for a small startup. That company got acquired and I’m currently at this company that purchased the startup and it has been like the best thing that has ever happened, like it is a really good path and it was just like when I started my business on my own, I was like, “Why didn’t I think about starting a business years ago?” There’s all these people that start businesses when they’re kids and they sell lemonade, I was out playing soccer and doing sports. It really aligned with who I was as a person and I never knew that I had that in me, that desire to want to start a business. And now that I’m at these startups, it feels like the right thing for right now and it feels like having worked for myself, having built up some of those new skills, feels very natural. And so I feel very satisfied at the end of the day, like I worked really hard, and at night, I can hang out with Kate, hang out with the baby and it’s like I did what I needed to do today and I feel great about it. I don’t feel there’s challenges at my job right now but there’s not the learning curve that there was when I started my first job. And I remember that job being so hard, like it took 18 months to learn the job and to figure things out. My second job was the same way. It probably took another two years to really understand the business. This feels more of like a progression. So I do feel like I’ve minimized my risk and built some skills so that I can start a business on my own, go work for one startup, that one gets acquired, I can still do enough to hang out and stay employed at this new company and so there’s less of this huge switch where it’s like I have to end one and there’s a huge ramping up process to the other one. It feels more of like a natural career progression where I feel like I can manage and control it, which I never would have learned this had I not almost drowned surfing, tried to start my own business, like it took a series of things to get to this point where it’s like, “Okay, I kinda feel like this is the right path right now.”


Brian: I’ve got it. So, if you’re listening out there, all you have to do is almost drown and you will succeed. Does that sound right?


John: Exactly it. 


Brian: Okay, good.


Billy: So what I like is that, after five years, you could have been comfortable, you could have stayed safe, but you pursued another risk. And hearing you now, it sounds like there aren’t the same challenges that you had at the beginning so are you already kind of eyeing another adventure or are you continuing to seek out ways to grow within your company or are you doing both?


John: That’s a fantastic question. So, with the startup, the first one, I was employee 18 and I would say that a lot of people out there would never join a startup unless there’s 100 employees. And so I was very early to that one. I was naïve because I was like, “I just wanna work for a startup and this sounds like a great one and they’re venture backed, they have good people that are supporting the business, and this seems like a risk I’m willing to take,” and, you’re right, I felt satisfied but I was like, “This could be another risk that pays off in a different way and I should do this.” And, again, I went through a process. My brother had worked for a couple of startups. He’s listed as one of the, from the very beginning, one of the roles that I play is brother and we have a close relationship and so hearing him and his experience and the challenge that he took on helped me make my decision. And so I decided startup is another path that I can go down. So I feel really good where I’m at, but you’re right, my risk now is how do I progress inside an organization and how do I seek out new challenges and that is really hard because I joined, I went from being the first marketing hire at a startup and three people to now a team of 50 and so I am now in a much bigger marketing organization and navigating that is a job in itself and trying to get stuff done. So I feel super content right now but, again, my view is to try to figure out how can I stay and how can I progress internally versus leaving.


Billy: So, Brian, I have a curious question for you then. So you are the president of your company. How do you keep that position fresh? How do you continue to build? How do you continue to learn? How do you continue to take risk? Because, I’ll tell you, just being a being a dean for six years, I could have continued to grow but, like you, I just felt like I had done what I could, I didn’t see any more room for growth and, I mean, I could have gone on and gotten my admin license but I knew for a fact I never wanted to be an admin, and the buck stops with you.


Brian: Well, you’re navigating the market, you know what I mean? The market presents challenges. If this product is not selling, you have to be aware of that and pivot to what is selling. Or you’re constantly embracing change in technology, you know what I mean? So you have to. You can’t just sit and expect the market to look like it does today five years from now, which is why you have to hedge your bets in diversifying the company portfolio, whether it be diversifying customers or diversifying product or whatever it may be, but my job is to grow. I don’t get paid unless I grow and make more money for the company. So, by nature, my job is forcing change, really, and I have to be that change leader that leads everybody to believe that the direction the company going is a good idea and all that stuff. 


Billy: And I feel like you have embraced the conditions of the ever-evolving technology market —


Brian: Oh, God, yes. You have to. I’ve been doing this 21 years, 22 years almost now so you just get used to it. Things change. I’ve seen tube TVs come and go. I’ve seen analog to digital. I’ve seen standard definition to high definition, to 4K, all that stuff. So it evolves naturally, we just have to figure out where to position ourselves in that to be profitable.


Billy: So, John, you talk about the universal stoke in the book. Can you explain what you mean by that?


John: Yeah, so stoke is a surf term and that is the feeling of riding a wave successfully, which I didn’t do the first time out, but this is what surfers describe as that feeling of, “I caught a big wave, I went in a barrel, I came out the other side,” and so they talk about stoke as that feeling of success. And so I talk about that in the book as a universal sentiment that everybody has. Everybody has some sort of stoke that they feel and maybe it’s feeling like you’re in the zone or you’re working and you’re at your best and so maybe it’s you’re on stage and you’re playing bass or you’re in a podcast and you feel like you’re really dialed in and you’re having a good conversation. So that I think is what everybody is striving for and that’s the quest, is to feel good about what you’re doing and feel positive, like I described at the end of the day where I come home and I’m like, “I don’t need to do any more work. I gave my all today. I feel completely satisfied. I’m stoked with the work that I did. I’m good for right now.” So having those moments where you feel like it doesn’t feel like work and you’re getting things done, you’re being effective, you want to create an environment or have a job or have a role where you’re constantly in that mode and generating that feeling.


Billy: The last couple of interviews that we have had, I have felt that stoke, like I felt real good about those interviews. So, yeah, that is a great feeling. I always love when we get done and Brian’s like, “That was great,” because, again, going back to love languages, anytime somebody says something nice about something that I do, I get all warm and fuzzy inside. So a lot of what you’re sharing connects directly to what our past guest Dr. Dawn Graham talked about in her book Switchers, especially when it comes to what, for many people, is the ultimate risk, which is switching careers because you’re talking about people’s livelihoods with that. You yourself have switched roles, you have switched jobs, you have switched careers, how have taking these risks added to your overall satisfaction with who and where you are today?


John: Yeah, so I touched on that a little bit and I think, at the end of the day, feeling like I was in control I think is a is a big part of that and so it’s easy to look back now and see that there was a path but when you’re in the middle of it and trying to make those decisions, like you were just talking about your trip and traveling and trying to decide, “Am I a dean or am I not a dean?” and trying to figure those things out and what does the podcast mean and I think you already are on a path and you just don’t know it and maybe five years from now, you look back and you say, “Okay, the podcast was my new point of entry to whatever this new thing is that I did.” And so I would say that looking back, there’s satisfaction in understanding that all those struggles and everything that you went through was part of the path and part of the journey and it’s super hard to realize that and understand it when it’s happening because all you’re focused on is, “This is super risky financially. This is my first year and I’m making no money and nobody wants to talk to me,” so you go through those struggles and, at the time, that’s all you’re focused on and you don’t think about, “This is a new path and this is a different journey,” so I think now, I think about it as, “I’m on this path and there’s gonna be challenges and I should expect those things to happen. If they don’t, it would be weird or I’m not noticing that these things are happening and I should be.” So I’m thinking about these things, looking back and saying, “Okay, I’ve made this decision. I decided to take this route.” Kate and I would always talk about the challenges at the time and she would say, “You wanted this. You decided to do this so you have to deal with the repercussions.” So, right now, when I think about it, I think I made the decision to be on this path and so I’m going to own this and I’m going to manage it the best I can but there’s satisfaction in making that decision and also there’s satisfaction in knowing that there’s some other thing at the end of this. So in another five years, if we did a podcast, how would I look back on my time at this second startup? And so there is going to be a narrative and a story to that whole experience as well and there will be things that I think are positive and there will be things that were challenges, but I think that’s part of it. So I think being satisfied but being reasonable and understanding that you’re not going to be satisfied all the time and that things are going to pop up and they’re going to be challenging but satisfaction comes from having made those decisions and feeling good about making the decision.


Brian: So it sounds like you’re doing a better job of managing your own expectations.


John: 100 percent, and that is like the — so my wife’s in mental health and she’s like, “Your expectations for things are sometimes completely out of whack,” and so there’s a temperament of, “Let’s just see what happens. You’re not gonna sell a million books. You’re not gonna be a professional surfer after your first day.” You’re right, so it’s about managing the expectations of what you have control over and what you can do. And the other thing that I think I really think about now is ruminating and dwelling on those past decisions and building them up into things that are bigger than they actually were. And so it might be more about kind of being present and not thinking about the past. You can evaluate and look back but you shouldn’t judge it and have that impact or influence what you’re going to do next.


Billy: It’s funny how similar you and I are, because tempering expectations and rumination, man, those are the things I do best. Like that’s what I should market is, “You wanna ruminate more? Let me show you how. You wanna have really high unrealistic expectations? I’ll show you how to do it.” That’s what I should be marketing right there. What do you mean you’re not going to sell a million copies? Of course, you’re going to sell a million copies. You are on this show. Kate, you sound like a dream crusher. Just kidding. Just kidding. Kate’s a wonderful, wonderful human being and, John, you are as well. We want to thank you so much for being on our show. Once again, you can go into the show notes and you can buy John’s book, Ride the Wave, 50 percent off the cover price. We’ll put the link in there. John, thank you very much for sharing your story of risk with us. 


John: Thanks for having me. 


Billy: So, for John, for Brian, this is Billy, thank you for listening to The Mindful Midlife Crisis. May you feel happy, healthy, and loved. Take care, friends.