The Great Unlearn with Cal Callahan – EP 33


The Great Unlearn with Cal Callahan

When I quit my job years ago, a lot of people thought I was crazy for doing it.

But why? Was it because I had checked off all the “right” boxes; or because I was making good money and could make even more if I had stayed?

From the moment we’re born, we’re told how to look, how to feel, and who to be. We’re taught to do things a certain way and to follow a certain path. But if we’re not careful, it can prevent us from living in alignment with our true values.

For me, the goal was NOT to make more money, the goal was to buy my time back…

So, quitting my job was the right decision. And of course, the money followed, but if I had listened to what everyone else had told me to do, I would never have achieved the lifestyle freedom that I have today. This is an important lesson that leads to today’s discussion with my friend Cal Callahan.

Cal is the owner of Unlearn Ventures, which is an investment fund and incubator for forward-thinking projects. He’s also the host of The Great Unlearn — a podcast that empowers people to question everything they think they know about life.

Whether it’s spirituality, health, relationships, or fitness, Cal’s superpower is to help others unpack and unlearn preconceived ideas and beliefs, so they can build a better, truer version of themselves.

So, instead of discussing a specific asset class or investing strategies, today’s episode is all about questioning our beliefs. Cal will challenge you to think differently, open your mind, find joy, and approach life with insatiable curiosity — a valuable asset for anyone who wants to live life on their terms, not someone else’s!

Key Takeaways with Cal Callahan

  • Why ROI is not the only metric that matters.
  • What is The Great Unlearn?
  • Understanding your identity and what makes you who you are.
  • The importance of questioning everything you’ve ever learned.
  • The problem with taking someone’s word for it.
  • Why curiosity is the key to learning and growth.
  • Creating a fun and supportive environment for working out.
  • The magic that happens when you open your home and heart to the right people.
  • The big lessons Cal learned from his career in finance.
  • Why chasing that new shiny goal won’t make you any happier.
  • The importance of noticing what actually brings you joy.
  • Quitting a high paying job to pursue a better lifestyle.
  • Striving for progress, not perfection.
  • Fun-makers, fun-haver’s and fun-blockers. 

Clip From the Cal Callahan Interview

Cal Callahan Tweetables

“The Great Unlearn is about being curious and having the courage to question everything.” - @CalCalahanTGU Click To Tweet “The goal was not to make more money, the goal was to buy my time back.” - Justin Donald Click To Tweet


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Read the Full Transcript with Cal Callahan


Justin Donald: Cal, so excited to hang. I’m so glad that we get a chance to connect and it’s been really a fun last number of weeks. We’ve got a chance to hang quite a bit here and I’ve really enjoyed just the direction that our friendship has taken organically and how many people we know in common and just how random meeting up has been at different places, different functions, different events. So glad to have you on the show. 


Cal Callahan: Yeah. Thanks for having me. I agree. It’s kind of what’s been happening. I think you and I can both speak to what’s happening in Austin, that guys like you and I are just finding ourselves in these similar circles and drawn to one another and having conversations that are way deeper than the surface level, kind of small talk conversations. 


Justin Donald: Totally. 


Cal Callahan: And then as we start to learn more about each other, I start to learn where your true genius comes from, which is a space that I’ve been in for 25 years but in such a different way. And so, I’m so excited from the conversations we’ve had and we’ll continue to have to really learn and hone my craft around investing. 


Justin Donald: I love it. And it’s so great that you’re open and willing to learn new things because you have been very successful in your craft of investing. And I’m excited to dive into that on this episode. I think that there’s so much that we can get into. Obviously, on my show, I really love to focus and highlight people and what they do, what their strengths are, what their genius is. I love highlighting lifestyles, investing, and more than anything, I just want to get to the core and the essence of who people are and not be pigeonholed into who I can and can’t interview because of the topic of the podcast or the name of the podcast. And so, I have this desire to bring in anyone that I think is cool that the world should know. And you are so high on that list. It’s funny, I put you down as someone that I definitely wanted to have on my show, and then you reached out and said, “Hey, you want to connect? I’d love to have you on my show.” So, that was really fun. I was going to reach out to you anyway. 


Cal Callahan: Oh, I love it, and thank you. I received that and I’m excited again to kind of share probably a different side of me than I normally get to share, and we talked about this earlier on my podcast but I don’t find many opportunities to talk about that kind of part of my life. You know, it may come up here and there but, yeah, I think in my close circles, there’s a lot of conversations, a lot of questions. There’s a lot of curiosity around a little, “How did you do like you didn’t make your money being a podcast host, did you?” No, I did not. 


Justin Donald: No. It’s how you spend a lot of money. 


Cal Callahan: Yes. I’m still working on getting that into black but I guess I’m not. It’s like just fun, right? 


Justin Donald: It’s fun. To me, it doesn’t even matter. Hey, it’d be great for that to happen but the goal is not profit. The goal is quality conversations with amazing human beings. And if it costs money to produce that, then it costs money to produce that. And that’s a hobby and I love it. 


Cal Callahan: Yeah. And really it’s such a great example of being able to zoom out from the dollars and cents. And whatever I’ve been creating with my podcast in my brand, I’ve spent a lot of money on it but it’s investing in me, in my learning, in the conversations, and the return on that, you can’t quantify it. It’s relationships like this that would have never happened if I didn’t have a podcast. I wouldn’t have 35 guys at my house because no one would have known me to ask me to the first men’s group that got this whole thing. Like none of this would have happened if I hadn’t started the podcast, hadn’t invested into that part of myself without worrying about the tangible return. 


Justin Donald: That’s right. Yeah. Some things I think it’s important that you get a return on your investment but other things, there are ancillary benefits that far outweigh whatever the monetary return is. And I think that podcasting is one of them, especially when it is your passion, my passion to kind of share a message with the world and to bring other perspectives and point of views. And by the way, that’s what I love about your show. In fact, I’d love for you to talk about it because it’s about unlearning all these things that we’ve learned that may not be serving, may not be accurate. Can you share a little bit about kind of the genesis of your podcast? 


Cal Callahan: Yeah. Thank you. You know, the original name for it was Working In and the reason for that is I had this major shift in my life where a lot of it had gone from expending energy to conserving and replenishing my energy. And a lot of that was around these working and practices, whether it was meditation, cold water therapy, walks in nature, just slowing everything down. But 

it didn’t quite capture everything that I was learning. And the idea for the podcast was to take everything that I had been learning as a way to share these people and their ways of learning and their ways of unlearning and the way they questioned our very common belief systems. And so, the name is The Great Unlearn and it’s really about being curious and having the courage, really, and a lot of times having the courage to question everything, everything about the way you’ve lived, your whole belief system. Where did that come from? Was it yours or was it thrust upon you? Were there agreements that you made that you didn’t even know you were making them along the way? All of a sudden, you wake up one day and you’re like, “This is not me. Now, what do I do?” And then just to strip that away, it can be terrifying because, in your mind, that’s your identity, “This is what I’ve known my entire life.” 


I had an event. I was in Las Vegas for the mass shooting back in 2017 in October, and that was a moment that called all of my beliefs into question. A lot of people don’t have that type of experience that shakes the foundation and allows like really cracks that egg open and it’s like there’s nothing else you can do except you can try to put the egg back in the shell, and people do that, or you can walk forward and say, “Okay. Who am I without all of this?” That’s kind of been the journey I’ve been on for probably the last three-plus years is doing that and the podcast was the platform where I could give others permission to question all of it. Now, don’t take my word for it. Listen to my experience, listen to the people I bring on who are questioning it in a way that’s safe, that’s curious, and is open-hearted. When I started to orient my life around people like that, everything changed. 


Justin Donald: That’s so cool. And the reality is there’s a lot we need to unlearn. One of my friends, Phoebe Mroczek, she has a podcast called Unbecoming and it’s very similar in the fact that we’ve become these people but was that by our design, or was that because of who we hung out with and the ideals that we grasped from someone else? And so, there’s a lot of similarities to me in just that whole message. And by the way, this rings true in so many areas. This is health and wellness. This is education. This is certainly financial investing. I mean, it spans to most categories that you would consider. And so, I love that you’re doing this. I love that you’re bringing awareness and just questioning what is. Are these beliefs yours or did you adopt them from your parents or did you adopt them from your peer group? 


Cal Callahan: Yeah. And what we’re seeing today in our world, in everyone’s world, everyone listening here in our own world, if you don’t have the courage to question what’s going on then you’re going to live a life that you will be powerless to. And I think what we found in this community, in particular, is people are beginning to question or have been questioning in a way that’s really curious. They’re not just pushing against whatever is happening. It’s not for the sake of conflict. Like something doesn’t feel right. And so much of that intuition that we’re born with has been armored up because we’ve been told to think a different way, to do a different thing. From a very young age when you didn’t want to go hug your uncle and your mom and dad made you hug your uncle because that was the right thing to do and it’s like, “He creeped me out.” Whatever it is like, how many times do parents thinking they’re doing the right thing, force their kids against their intuition, against their will to do things that they think is for the best? And I think those little things add up and we stop trusting our instincts. And for me, it’s about kind of laying down that armor for people. It’s like what if we led with our intuition, our heart? What would be available to us?


Justin Donald: Yeah. And I think we need to check motives here too because a lot of the groups, companies, agencies, governments, a lot of them, a lot of people think, “Oh, they’re here for my benefit. They’re making decisions that are best for me.” But that’s actually not the truth. They’re making decisions that are best for them or for what they think is people as a whole or based on influence, control, power, et cetera. So, I do think it’s important to question. It doesn’t mean that everything is wrong and everything that’s said is inaccurate but I do think that we need to put on our thinking caps a little bit here and make decisions based on intuition, based on research but not just taking someone’s word for it. It’s the same thing with investing. You know, I’m not going to invest in something just on someone’s word. I’m going to do my own research and I’m going to figure out if that makes sense. I’m going to run it by a lot of people to get their opinion as well to figure out where my blind spots might be. And I think we should do this in all things, not just investing or not just certain compartments of our lives where maybe we found some success. How can we get that to bleed into every compartment? 


Cal Callahan: Yeah. And I think in life, in general, we’re just taught to be right or wrong and it’s so black and white and we don’t come in with that curiosity and really that beginner’s mind like you feel a way that is counter to how I feel like, “Can I just be curious about where that came from and what your experience is with? If you’re just spitting off information that you read somewhere else, honestly, I don’t care. We’re kind of done with the conversation but if you have a direct experience with something, now I’m curious because now you can actually speak from what’s happened in your own life, not from some way that maybe the propaganda machine has gotten the best of you.” It just happened to both of us. I know that. But it’s like being open to not having to be right. In being I guess for that sake, I guess you’re not wrong either but just being okay like, can I just be in the inquiry of this and hold enough space for it to all be there in us for us to not really land on what is exactly the right answer. What’s happened with the pandemic? I wouldn’t want to be a leader in this. You’re not going to get it right. You’re not going to make everyone happy. It doesn’t mean we shouldn’t question the motives. As you said, what is driving certain people in power? What is driving their behavior? What are their special interests? Where’s the money coming from? What is their liability? Oh, they have no liability and they have huge upside on the profits? Oh, that’s interesting. You know, a lot of people don’t know this for certain companies. 


But I think what’s happening now is exposing that and, granted, a lot of people are keeping their head in the sand because it becomes this idea of cognitive dissonance. It’s like there’s no way all this can be true that those ones that are charged to take care of me aren’t really taking care of me. They have other interests. They’re humans. They’re taking care of themselves and their organization and their beliefs about how things should be, not what’s right for the world but with their own beliefs. So, they’re fallible. So, we can question that without saying they’re bad people. They just have had a different experience than us that’s led them down this path. It doesn’t mean we can’t question them. 


Justin Donald: Yeah. And I think that curiosity is the key to all of it. You mentioned it because that’s where learning and growth happen because as a curious person, you’re open to interpretation. You’re open to different ideas. You’re just open versus being closed, being defensive. I just think that curiosity is one of the greatest like places, states of mind, just ways to live life. And I think you do a great job of that and just even in our interactions, you’ve always been curious about all different types of things. And I love that about you. When I reflect on just some of the fun things that we’ve done, I mean, you’ve been really curious about health in general. I mean, you are in incredible shape. The boot camps that you are hosting at your house that I have the luxury and privilege of being able to participate in, they’re epic. I mean, these are some good workouts with incredible men showing up here, 30 men at a time, in many cases just through word of mouth and it’s just powerful. I’m curious how that came to be.


Cal Callahan: That’s such a great question. I’ll see if I can land it for you like for so long, I would say back in ‘08 is when I started training in CrossFit. I did that for a number of years. You know, CrossFit is very much community-based. And so, for a couple of years, I was really into the community and then I built my own gym in my garage and I really got into chasing my own goals, my own personal records, and all that stuff. And I got super into what I was eating, sleeping. I was drinking little to none and I was like on a really good path on some level but it became so intense, my striving for these different goals, which let’s be honest, I’m 49. I was like 42, 43. I want to go to the Olympics. It was all just no one else cared. 


Justin Donald: That’s right. 


Cal Callahan: It doesn’t mean you shouldn’t pursue these things if no one else cares but on some level it’s like, “Dude, why are you doing this?” And I would walk around unknowingly with this energy of just like always kind of like ready for battle. When I started to have this awakening, when things happened in 2017, when I stopped training like I was and I was really taking care of my health and working with somebody who goes deep into your cells to do the work is like you need to slow down on that intense training for a bit. So, my orientation is like, “All right. I’m done doing it.” And so, I stopped working out for probably the better part of a year and I went from probably 200, 205 pounds to 170, and it was all muscle like I was very lean at 205 and I was very lean at 170. 


Justin Donald: I can’t even imagine you with that much more muscle. 


Cal Callahan: I know. Actually, when I look back, it’s very cartoonish. I see pictures of this body. But anyway, as I started to do my inner work, I started to soften on the outside, too. I started to become open-minded, I started to allow in other opinions, other ideas, other ways of being. I started again introduced to a lot of really interesting people here in Austin and through them, other people as well. Again, that’s part of the reason I started the podcast. I’m having these amazing conversations and meeting these amazing people. I don’t want to hoard this information. I need to share this with people because it’s important because it’s changing my life and it may change yours too. So, anyway, I’m just getting back into working out again maybe a couple of years ago and I’m riding the Peloton. Now, you know I have an amazing gym. 


Justin Donald: You do. 


Cal Callahan: Right? 


Justin Donald: It’s incredible. 


Cal Callahan: And for about a year, I was just riding my Peloton in there. I could have been in my bathroom. I made that gym for the Peloton. But something important happened for me during that point. I had this realization that if a year earlier or two years earlier I had considered myself a “peloton guy” and that I would have been having a lot of fun doing it, I would have laughed at myself. But that’s exactly what’s happened. I was just having fun. I enjoyed it. Some of my buddies back in Chicago were doing it so we do competitive stuff but I just enjoyed it. And that started to reorient me around fitness. This can be fun. It’s no longer about just me doing it by myself. I didn’t love training by myself anymore. The Peloton is its own thing but I didn’t love going in riding a workout up on the board in training for an hour or an hour-and-a-half. I used to love that. I didn’t love it anymore and so I wouldn’t do it. And Peyton, my wife, made a comment to me this fall. She said, “You know, have you thought about like working out again? I know how much you loved it,” and it seemed innocent enough, right? It’s like, “I know how much you loved doing it.” I was like, “I’m just not called to it. I don’t really want to.” She followed it up with like, “You look kind of fragile.”


Justin Donald: Whoa. 


Cal Callahan: Yeah. Like, “The f*ck I do,” and I’m thinking, really I’m like I feel so good right now. I feel just like everything just feels really good. Now, mind you, I weighed less than I do now. So, I could understand where it was coming from like, “Is this your sh*t or is it mine? Like, are you wanting me with more muscles or what’s going on there?” But anyway, so maybe she planted the seed in the fall but in November, I was in part of a men’s group and some of the guys had been working out in someone’s garage and they’re like, “Cal, you got the bunker. Can we work out there on Wednesday? Can the guys come over?” I was like, “Yeah.” And from that moment on I think there were six or seven guys on that Wednesday. It’s been open every Wednesday since. And even when I go on vacation, the guys come over. I have a couple of guys who are leading like Steph and Preston and Gary, and they’ll take care of the guys but it’s really about fun. Can we have fun with this? We can work hard or maybe you’re having kind of an off-day and you don’t want to work that hard but you’re going to work together in a group of three. You’re going to have a movement and exercise that you’re going to do for three minutes together. Maybe it’s ball slams. So, you’re all ball slamming together. That’s funny. And then we take a minute rest, then we move on to the next thing. 


You know, it ends up being about an hour workout and you don’t know who you’re going to work out with. You’re going to find some amazing people. And like we’ve talked about, you don’t really know what anybody does and it doesn’t matter. You’re just there for one another. You’re there to share the space, share the energy, share the love, and have fun. 


Justin Donald: It’s awesome. And there are just so many high-powered, successful guys but it’s not about that. People just show up, leave their ego to the side, whatever ego. Many of them don’t even have egos. It’s wonderful. And people just show up and we hang out. And it’s a great way to meet people. It’s a great community. I leave and every day I’m like, “This was a killer workout,” and I don’t know that I would have had this good of a workout on my own. But also, on top of it, I met some cool new guys and it was a blast. It was such a good time. It’s so much more fun to exercise with people and to try to accomplish something or push yourself or you have someone that is able to do something better than you or you watch a technique and you’re like, “Oh, wow, if I just tweak this thing,” like Steph does or whoever. It’s like, “Whoa, this is unbelievable.” And a lot of these guys are in incredible shape, yourself being one of them. I mean, just unbelievable shape. 


Cal Callahan: But it’s not intimidating, right? 


Justin Donald: It’s not. 


Cal Callahan: You walk in there. You don’t know who the new guys, there are the old guys, and one of the things I love it. But I was at a buddy’s house last night for dinner and I met a guy who before he even told me, he eventually told me, he’s like, “I’ve been really looking for my guys here, like my crew.” He’s been here for a little while, and before he even said that, I said, “Dude, we do this thing on Wednesdays and you should come.” It’s just such an easy way to invite someone, drop them into what is being created out there by all of us and they get like, “This is hard.” It’s like, “Hey, come, we’ll go do dinner. We’ll go do this.” It becomes hard when you have a family and you know other things going on. It’s like, “Come over Wednesday,” and I don’t even need to do anything. We’re all doing it together. And you’re going to meet people and you’re going to come back next Wednesday and the next Wednesday. And all of a sudden it just becomes this thing that really has a life of its own. 


Justin Donald: Totally. And it’s no pressure. I mean, sometimes it’s hard like you want to do dinner. You’ve got to coordinate with your wife’s schedule and your schedule and their schedule. It just becomes a whole thing whereas here you can just show up. And by the way, I love it so much. I’m sharing this with you before we started recording. I got a bunch of travel coming up. I’m coming back in town for this event the next two weeks, even though I’m gone and I’m traveling. So, that’s how much I love it and I’m just piling in other stuff on those Wednesdays. One other thing that I’ll say is your home is incredible. It’s one of the nicest homes from like the standpoint of entertaining. By the way, you and Peyton are both great entertainers, great hosts but your home is just so magnetic. There’s just such good energy and it’s really fun like the parties you guys throw and just the things that you do here. You do such a good job of bringing people in and serving them and creating a fun environment. So, I want to pay you that compliment but also I think that your home is an important investment and I wouldn’t look at it as an investment from the standpoint of what’s the return you’re going to make but I would look at it from the standpoint of how does it serve you and how does it make you feel? How do you show up? And as long as it’s not something that basically is putting you in a poor place financially or maybe too much of a reach, I think it can be incredible to have this dream home as you guys have built. 


Cal Callahan: Yeah. Thank you for that compliment. I think the important thing to remember, and it’s something that I’ve experienced, we’ve been in this home for four years, in the beginning, it didn’t quite have that energy and I can’t really speak to what it was that shifted everything, except that maybe it was my own inner work and Peyton’s work and starting to understand that we can have this beautiful home. If it doesn’t have the right love and energy, then it’s not going to be what we want it to be. We have a nice house. It doesn’t have to be this but what are you creating? And one of the things I love to do is bring people together. It makes clear on Wednesdays but also some of the events we’ve had here. I love to use our home as a place for people to gather and to share ideas and to just be in this loving energy together. And you’ve been here. It’s not like a woo-woo loving energy but, I mean, I guess it could get like that. But generally, it’s who are we inviting in? What are the types of events we’re trying to hold here? And being super intentional about all of that. And as we’ve become more clear on who we want to spend our time with, those are just the people that come here and they bring their friends. And it’s almost like you just put it out there, the whole, “You build it, they will come,” that if you just start putting out that energy. And I remember waking up one day in December we had this big party and like a bunch of people that I hadn’t known a couple of months earlier that are just amazing, amazing people. Guys like Mikki Willis and Del Bigtree and guys that I’d seen on podcasts. Now all of a sudden these guys were my brothers in short order because we were doing it the right way. We were just opening our home and our hearts and like, “Hey, whoever is in, you’re welcome.”


Justin Donald: That’s awesome. Well, you can feel it. And I share in many of the same I guess desires and excitement of hosting and bringing people together, I just love good quality, stimulating conversation with people that you could just talk for hours with. And so, you guys do a great job, obviously, with that. I think that what you’ve built here is just so incredibly special. So, I’m curious, how did you get to the place? You said earlier you’re from Chicago. I’m from Chicago. And we are living there at the same time. Didn’t know each other back then. And you used to be a trader and you did very well in that profession. Obviously, there are ups and downs and there are things that you’ve learned and mistakes that you’ve made that added up to you being a smarter, better trader. But I’d love to hear some of your past that helped you get to where you are today because you’re living an incredible life. I would say that most people would look at your life and say, “You have the dream life,” and that didn’t happen on accident. There’s intentionality and things that you’ve done along the way that have helped build this stellar life that you have. 


Cal Callahan: Yeah. Thank you. I would say one of the biggest lessons I learned as a trader and really have carried on through my life is like when something bad happens, if you lose a lot of money on a trade, you have to move on. You need to learn your lesson from that. You can’t dwell on it. And it’s really, really easier said than done but as a trader, you won’t last long. It’s like a relief pitcher. Like, if you can’t forget about the last blow and save you have, you’re not going to be closing very long. And so, it’s like really having that short memory of what just happened, keeping the lessons but moving forward. And I didn’t always do that right. I mean, there’s stuff that I would wear as a trader and certainly in life but as I’ve just really tried to stay like when you can stay present and not worry about things that you’ve done wrong or you felt that you’ve done wrong or you’re striving to get to the next thing. And all that striving is just missing out on what’s happening right now. With the striving is generally this idea that right now, I’m not enough. What I have right now, there’s not a sense of contentment. Things aren’t okay. And I think if people really check in with that, if they really just quiet their mind, they sit with it and they look around and like, “In this moment like I’m actually pretty good.” It doesn’t mean I don’t want to achieve more things but I think we spend an inordinate amount of time in that space of projecting the future and trying to reach these I don’t know if they’re goals or what they are for people but it just takes us out of the beauty of like what’s happening in this very moment. 


Justin Donald: Yeah. That’s powerful. And when I think about some of the best decisions I’ve ever made, it’s because I’ve been present. I haven’t been focused on the future. I haven’t been focused on the past but it’s really getting clear today and what today looks like and the steps you can take today to have the tomorrow that you want but it all stems from today. So, you just got back from a trip to Cabo and we were chatting because it’s one of the places that you’ve been going for years. Same with me. I mean, it is my favorite place in Mexico. It’s one of my favorite places that we frequent. And I just got back from a trip a few weeks ago with a bunch of buddies. So, yeah, I’d love to know. I mean, you live life. There’s no doubt about it. You are life first. And I have so many other questions I want to ask about that because I know you’re very intentional but what are your thoughts around building this ideal lifestyle? Because you have it. You’ve done it. And I’m curious what it takes from your standpoint. 


Cal Callahan: Well, we have to understand that we have choices. Again, a lot of what I learned through my own work and having these conversations on my podcast is you don’t need to do it the way everybody else did it or told you how it’s supposed to be done. And I’ve really lived my life that way. I wouldn’t even necessarily say it was intentional. It’s just how I was wired or it’s just what felt right to me. Like, I don’t f*cking care what anybody else thinks like I’m going to go do this. I’ll take this risk because it feels right and like I’ll see what happens. And sometimes it’s like it happened with some drugs like maybe I was a little too risky but it also happened with my job and trading. It was like, “Guys don’t leave trading at 41 as a partner living in a great city like Chicago, da, da, da, da.” I was like I don’t care like I don’t love it anymore and I don’t want to live in Chicago anymore. I want to go someplace warm. I want to try something new. I want to do something different. And I think it’s just questioning where are your belief is coming from and can you orient your life around joy and what brings you joy? Can you get clear on that? Don’t feel like you need to get clear on it in a day. Just start to pay attention. Start to pay attention to the things that don’t bring you joy. Do less of those if you can. If you can’t, figure out a way that you can. There’s always a way around these things and the more you fill your life with things that bring you joy and remove the things that are really constricting to you, then everything just starts to flow, and you just know your yes and you know your no and you start to have your boundaries. And for me, that’s been like a big part of my learning over the last couple of years is like everything can be fun. 


Justin Donald: Yeah. That’s awesome. I mean, you live that. You exude that. So, I think that that’s great. You can tell that you’re very present and that’s just who you are. I think it’s important to recognize, though, you are in a position where you are making incredible income. You would have continued to make incredible income had you stayed there but you had clarity on what you wanted. And it reminds me of when I left an opportunity where I had built a business underneath the umbrella of another organization. And I remember people saying, “Hey, why would you leave such a great income? Like you’re crazy. You have more lifestyle, more flexibility than anyone else that’s doing this role. And why would you leave it? Like, I get that you have enough passive income that you don’t need it but you could double up on what you’re making.” And it’s so funny to me because it’s so hard sometimes to get through to people because the goal was not and is not to make more money. The goal was to buy my time back. The goal was to live this life that I had envisioned, which I had enough money for it. I didn’t need more money. And so, I love that you can make that choice because it’s not an easy one. When all of your friends are telling you you’re crazy and when it’s the thing that you know and for how long you’ve been doing it, I mean, one of the only things that you knew professionally, that’s a hard change because you’re stepping out into uncertainty. 


You don’t know what’s next. You don’t know how much you’re going to make or was this a fluke or are you ever going to see that type of income again or have that type of position or have that type of let’s even call it assumed authority. So, you’re taking a step into the unknown and you did it. You did it knowing that all this may not continue. And I’d love to kind of hear more your thoughts on that. 


Cal Callahan: Yeah. And just to be clear, it was actually in a weird kind of period of trading where a firm was not making a lot of money. So, there was that added sense of like, “I don’t even know why I have all my money at risk because I don’t feel, I don’t see it anymore. I’m looking at this investment like, “This is a bad investment.” So, really kind of had a different lens on it. Had all this money at risk. And this was eight years ago, I have friends who are still trading. And to be fair, I was in a much better financial situation. I was a partner but they’re still there. And so, my question is, yeah, like you can stay and in your case, you can double up, but at what cost? At what cost? And I don’t think many people are given the tools to look at their time and understand that is that one resource. I was spending all my time learning about fitness and coaching and I was going to become a coach and that doesn’t pay very well, at least in my opinion, what I had seen and like I can make decent money. I’ll never, ever come close to the money I was making as a trader but I was okay with that. I wanted to connect with people in a different way. I wanted to get away from this thing that was just not serving me anymore and move towards the things that were lighting me up that was really alive for me, that I was spending all my free time learning about and having experiences with. 


And so, I think it’s just, yeah, like tuning in and going against the norm and not caring what anybody thinks. This is your life. You care what your partner thinks, sure, but this is your life. And I don’t think people give themselves enough credit to take on that responsibility. They think they need to act in ways that everybody else will find acceptable. Meanwhile, they’re just making, A, they’re making assumptions about how everybody will feel. They don’t really know. And then if these people are voicing their opinions, I don’t really care. That’s not the feedback I need. I’ll ask for feedback on an investment but this is my life. And I know that this time for me to move on and to find out whatever else is out there because there’s so much out there. In 18 years as a trader, I didn’t know what else I could do except maybe coach people in fitness because I was really into it and I had done some stuff around it. But beyond that, I had no idea. I didn’t care. Like, I just need something new. 


Justin Donald: Yeah, I love it. You said and I think this is so powerful that it didn’t serve you anymore. And I think it’s great to have that recognition because there are certain stages in your life where things serve you really well and you should keep doing them while they’re serving you. But if you’re truly in touch with who you are and what you want, you’ll recognize when things aren’t serving you and you’ll make the choice even though it may be a tough choice. It may be moving away from relationships that you value or the thing that you know really well but that’s where great change happens. You learn and you grow as you get uncomfortable. And when you get out of your comfort zone, that’s when some of the best education comes to play. And I think that you are really blessed in the fact that you had a fantastic mentor that really taught you the business and took you under his wing as a trader but he didn’t do it like everyone else. You know, most people would grind 80, 90, 100 hours a week and we know some of the other, I mean, I read a book that kind of highlighted all of the life of a trader, a lot of traders, and it’s just incorrect. I mean, some of the stories are just you wonder like how can this really happen? But I’m thinking, in your case, what a gift to have someone that actually said family first so that you could pour into your wife, pour into your kids, and make decisions that were best for your family, not just financially, not just from a standpoint of moving up the ladder. I think that’s incredible. 


Cal Callahan: Yeah. And I didn’t maybe know how kind of odd that was to find someone in that industry that was like that. My partner, Will Hobert, who had hired me, was very much a family-first guy and in that business, it’s rare. I don’t know many others in the business but we all grew up in that way. You know, coming in our early 20s, that’s all we knew. We didn’t always get it right. I wasn’t always a great husband and a great dad but there was some tension around it for me, underlying tension that I know Will’s doing it differently. Okay. So, what’s going on here with me? And that’s just my own sh*t to work out, right, but to have that kind of north star there to show you like this is what it means to put your partner first or to love your partner or to be there for your kids and to be at this recital and to be at this game and to do all those things that was really encouraged and really in some ways kind of demanded upon us, you know? So, it was a real kind of rarity to find that in the business and, yes, so grateful. I mean, who knows if I got hired by someone else who had a completely different way of being like how that would have ended up for me. 


Justin Donald: Right. It’s like your podcast. You may not have recognized for a long period of time what you need to unlearn from the role and the mentorship that going down a path that you weren’t in alignment with would create. 


Cal Callahan: Yeah. And it’s just like even though I didn’t quite embody the concepts that Will was sharing with all of us, as I started to figure it out, I had those lessons, I had those reps is like, “Oh, this is the right way to do it.” So, even though there weren’t maybe a lot of other areas of my life that were showing me that growing up, he was certainly a beacon for that for me. 


Justin Donald: Yeah. And you had mentioned before we were hanging out, you hosted an incredible get-together here with a bunch of amazing people. And you are sharing that even when you moved here, it wasn’t as picturesque as it looks today that there were some challenges with the home and what ended up happening just where you lived and having to move. And it looks so nice from the outside but sometimes people don’t know the struggle that it takes to get to the point where it looks really nice. 


Cal Callahan: Yes. What do they say? Like the overnight success that took 10 years and it’s like, yeah, it’s amazing to offer to be able to kind of host and offer this space for people but it wasn’t pretty. And like building this house, there was a lot of tension. There was a builder who wasn’t doing his job and so we had to find a new builder and then, unfortunately, that builder passed away. And there was just a lot of complications just from the building of the house. And then once we moved in, I would say that Peyton and I weren’t necessarily in a great position together and that had its own challenges. And here I am thinking we’re finally in this house after three-and-a-half years of renting and the first year, we rented a nice place that cost a lot of money and I said, “I don’t know how much longer we’re going to be in a rental. I ain’t paying that again. So, find us something.” And I may have even said like, “Find us like the cheapest thing you can find,” and I think she took me at my word and we found something that was less than half the price. And when we moved out two-and-a-half years later, they tore it down. So, like finally, so I went from a tear down to this beautiful home and I’m like, “Okay. Great. We’re here. We’re good,” and we weren’t good. And I was looking around at the house like it wasn’t exactly like I thought it was going to be. It wasn’t perfect. And I had to start to let go of what I thought perfection was and I started to understand all the tension I was feeling with the house not being perfect, all the little things that weren’t quite right. They were causing me distress. 


And I wasn’t going to do anything about it. If something was really wrong, I would have the builder come and fix it but it was just like this general sense that I had this ideal version and here I am, I spent all this money in this house, and I’m not happy with it and our relationship, and it was all this stuff like came together. And then October 2017 hit and that changed everything for me. I did my first plant medicine ceremony not long after that, and it was the first time I had deep gratitude for this house, for everything that it provided for me and that was the moment that shifted for me. And I would say it hasn’t necessarily been smooth sailing since that day. My wife and I have gone through our challenges but we’re in a great place today, and as you can feel when you walk in this home. And we love that and we’d love to kind of show up in the community that way. 


Justin Donald: Yeah. Well, a relationship with a partner spouse, it’s ever-changing. It’s a work of art but it’s a constant work and people that just let it happen will soon realize that things don’t function as well as they do when you’re really intentional and put energy into creating a space where you’re loving your spouse in the way that they receive love best. And often that it involves being intentional because usually, it’s not in the way that you receive love. So, there are a lot of things that I find myself doing with my wife where I’m like, “I don’t receive love this way,” but I need to give love this way, even though it’s not my nature and even though it’s not even always comfortable but I know that she’s going to feel that and receive that. And it’s interesting, you talked about perfection, the house, the relationship, the whatever, and I feel like as achievers, it’s really hard to not go after perfection, even though perfection is the most elusive thing in the world like it doesn’t exist. And so, we noticed and, by the way, my wife and I, this is something that we talk about all the time and we feel like we embody that like there are things in our past that move us towards wanting to be perfect, wanting to be the perfect parent, wanting to be the perfect spouse, wanting to be the perfect investor, businessman, whatever it is, and we saw that showing up in our daughter. And we’re like, “Whoa, this doesn’t work.” And so, we have adopted this saying that, “It’s about progress, not perfection.” And so, that’s what we say all the time and by the way, we share it with our daughter. It’s more for us than for her and hopefully, she learns along the way. But that’s it. It’s just about progress because you can feel great about progress. But there is no end. The perfection end doesn’t exist. It’s elusive. It’s a mirage. It’s like it’s not there. 


Cal Callahan: Well, I think that’s the important point is there feels like there’s then this endpoint, which is the perfection. And I think in my work over the last few years of this inner work, I’ve just had this knowing like, yeah, there’s no end to this. It’s just being on the journey. I’m not trying to become this thing that I say, “There, I did it.” I’m working through different things that help me become kind of more conscious of what’s going on and to grow but I finally let go that there’s any like way that I’m going to perfect meditation or being in the cold water. Whatever it is, I let go of it and I just try to be in that experience, to try to be in the journey, in the process of it versus aiming for I’ve got to be the best, I’ve got to nail this, I’ve got to get this right. And I don’t know that I necessarily had this perfection piece like I’ve got to get this right. And I think with inner work what has taught me is that there’s no kind of getting it right. It’s just like being in it. You’re going to learn what you need to learn by just being in it, being active, being present in the process, whatever that is for you. 


Justin Donald: Yeah. Who you become along the way on the journey each step of the way, I think that’s an incredible way to look at it. And if you look at life that way, my job isn’t to be the resident expert. My job is to just get a little bit better each day. That’s a whole different place than the ego that can take form because you think you’re the best at something, I’d rather not be the best at anything ever and always be this student eager to learn and feel like I don’t know so much about the world and so much about different areas. I mean, that’s one of the things we talked about this before. I love going to conferences where I don’t know anything. I like being the most novice person in the room because that is a fun place. It keeps me curious. It also helps me to relate to people that maybe they don’t understand how to invest or maybe they don’t understand how to get into shape or how to strengthen their relationship with their spouse. And instead of being a position where you would ever want to roll your eyes, you’re in a service position. Let’s lock arms and do this one step at a time. 


Cal Callahan: Yeah. I do love that. It comes back to that kind of beginner’s mind and we’re just not taught in school to be curious. We just aren’t. It’s like, “Hey, remember these answers. Memorize them real good and you can do great on the test,” and that’s one thing that I would say over the last year that I’ve really tried to show up for my kids in a different way to just like let go of all these ideas about what I thought how they were supposed to grow up and who are they? What are they interested in? The more I anchored into that, the relationship I have with my kids, each of them kind of individually just kind of blows my mind because I’ve just created space for them to be who they are, and without judgment but just with curiosity. And when I don’t understand something and maybe it’s a little scary, I ask them. And if I don’t ask them or if I ask them in a way that feels judgmental or if they say something and I get triggered, they’re not going to trust me. If I can’t hold that for them, they’re going to go to someone who can. And it’s probably going to be someone not of my choosing. 


Justin Donald: That’s exactly right. You want to be the first stop and create that space. I’ve also found like we’ve talked a lot about curiosity today. I actually am going to take it one step further and say I think a lot of kids get punished for being curious, right? It’s like, “I got a question about this.” “No. This is not what we’re talking about. We’re on this subject.” And I have memories of that and I’m just thankful that I never let that kind of dissuade my curiosity but it’s true. Kids are so curious about everything. And then somehow as we grow up, we lose all that curiosity like we become these adults that either think we know everything or don’t have a desire to know more kind of stuck in our lane versus being curious even today about the things that you want to learn. Part of the reason I wanted to take a year off in 2018 is because I wanted to figure out where I wanted to be curious. I just wanted to let my mind roam and just figure out what it was that I wanted to do. And I feel like that was one of the most healing years of my life that served me incredibly well. It served my family incredibly well. And we got a chance to travel all over the world that year and it was a blast. It ended up gone to like 12 or 13 different countries and just had a great time but it was out of the space of wanting to figure out the next step but not feeling like I have to. 


Cal Callahan: Yes. That’s it. And again, it’s all learned. You know, this is the stuff that as kids, as you mentioned, yes, they’re by and large punished for the curiosity. Too many questions is enough. You know, you’re being a nuisance, so it’s not welcomed. And then we get into the real world and we’re rewarded for having information, I wouldn’t say not for innovation ideas certainly have their place but generally known things and just those seem to reward financially and those are the things that people are drawn to. That’s what I was drawn to. Trading is like I get two plus two equals four and I can do a little bit with that. So, I think where our whole society, unfortunately, is steeped in that culture. And it’s in what we’re finding as we get older is, oh, actually, there’s a lot in there to be curious. They let go of the having to be right and wrong and, wow, I’m actually learning. Because once I think I know something, I’m done learning. Right? I don’t have energy for it. 


Justin Donald: You shut off. 


Cal Callahan: But if I’m open to it, I might learn one little thing about something that could really serve me well. And then I’m also opened up to what your thoughts are, what your feelings are, what your experiences are, which now we have a different connection. But if I come in with all my ideas and my beliefs and what do I have to do with those? Well, I get to defend them. I could be nice about it but you start stepping on them, I’m going to start defending them, and then all of a sudden we’re not having a conversation anymore. We’re having a little bit of a battle of words here. And I think, again, the best thing we can do is continue to have these conversations, continue to question things that maybe aren’t always questioned, and to show up for our kids in a way that allows them to be just super curious and no matter how f*cking weird or wild or just doesn’t make sense just to allow for it. Because, again, if we respond in a way even if our words say something, they’re going to read our energy. And so, just be mindful that they’re relying on us and if it’s not us, they’re going to find somewhere to feel safe. 


Justin Donald: That’s right. Yeah. I mean, such true words and we want the default to be with us. By the way, anyone that is important in our world, we want to have that influence. We want this to be the first place that they go. We want our home to be the place that they want to hang out. We want for us to be the advice that they seek and I just think that that’s powerful. And staying curious is going to do it, one of the things that you’ve mentioned fun and joy, and when I think about you. So, I think about the world and people and where they fit into these different categories. And I haven’t talked about this on my podcast but I kind of look at people in three different categories, fun makers, fun havers, and fun blockers. And if you really pay attention, I feel like people kind of show up that way and I’m always like kind of assessing where I want to spend time. And I love spending time with fun makers and I love spending time with fun havers too. And then fun blockers tend to really kind of be a parasite to my energy but I also feel like I need to be the person that can show up to try to help shift their energy. But you have been a true fun maker in my life and it’s been great and I love being in your ecosystem of amazing people. And I’m so thankful that we’ve gotten a chance to connect. I’d love for you to share where our listeners can find you online. 


Cal Callahan: Awesome. Thank you. Thank you for that. And I’ve really enjoyed the past couple of months that we’ve gotten to get to know each other. And I think I share this with you before but my wife absolutely adores you. She says, “His energy.” She’s like super-tuned into energy. She’s like, “His energy is so sweet and loving and, oh, just love him.” 


Justin Donald: That’s so nice. Thank you for sharing that. 


Cal Callahan: She doesn’t really remember a lot of my friends’ names. She always remembers you. 


Justin Donald: Oh, it’s nice. She’s awesome. You’ve done so well. 


Cal Callahan: Thank you. Thank you. I’ve tried to mess it up a few times. You know, I’m on Instagram, Cal.Callahan. Not super active on there. Definitely, tune in if you want to see what we’re doing on Wednesdays. We’ll post about that but really, just the podcast, The Great Unlearn. You find it on Apple and Spotify and wherever else. So, thank you. 


Justin Donald: That’s great. And thank you for opening up your home. This is fun. I rarely get a chance to record episodes in another friend’s studio. Your studio is incredible. I love just everything about it. It’s inspiring. It’s comfortable, it’s cool. And I can see how you have so many deep and wonderful intimate conversations in here. And it’s funny because this is the place that we always tend to eventually hang out at some point. Right? 


Cal Callahan: My friend, Boyd, dubbed it The Unlearn Layer. 


Justin Donald: That’s catchy. 


Cal Callahan: Doesn’t it just feel like a layer in here, right? 


Justin Donald: That’s so cool. 


Cal Callahan: It’s got a vibe. 


Justin Donald: I love it. Well, I’d love to leave my audience with what I think is the most important thing that they can do. So, for those of you listening, for those of you watching, be sure to take one step towards action today, moving in the direction of financial freedom and building a life by design, not by default. And I just challenge you whatever that step is, take one step. It can be a small step. It can be literally a conversation with someone. It can be reaching out to someone via email. It can be connecting in some way, shape, or form and getting out of your comfort zone. I think any time you get out of your comfort zone, you’re making a step towards progress and towards growth. So, thanks for tuning in and we’ll see you next week.


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