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SPI 769: New Job, New You with Barrett Brooks

Very few people work the same job their whole career anymore. Even so, many of us still perceive having to change careers as a kind of failure. But what if a new role is actually an opportunity to learn more about ourselves? What if exploring our options is the key to growth and finding our ideal path?

This is what I’ll discuss today with my returning guest, Barrett Brooks. It’s been almost a decade since our last chat in episode 147, and a lot has happened. In fact, Barrett has had to leave the position he was in at the time and reinvent himself several times to uncover the best use of his knowledge and talents.

Listen in on this inspiring session because we highlight the real ups and downs of entrepreneurship and provide a fresh perspective on career experimentation!

I can’t wait to share this with you because Barrett’s wisdom on becoming a better person, leader, and employee is incredibly valuable — so much so that we’ve hired him as a consultant at SPI to help us learn about each other and work better as a team!

Don’t miss out on this discussion. Tune in and enjoy!

Today’s Guest

Barrett Brooks

I believe business can be the most powerful force for good under the right leadership. I’ve dedicated my career to helping people reach their potential and apply that potential to solving hard, but important societal problems.

I believe that servant leadership based in altruism and paired with a high standard of excellence is the key to building a better world. I write, podcast, and serve as an executive coach in order to help leaders of companies make an impact with their careers and use business as a force for good.

I’m a husband and father of two young boys. I am most at peace when I’m in nature and have made it a goal to advocate for and protect ecosystems, biodiversity, and the future of our planet’s health in all that I do.

You’ll Learn


SPI 769: New Job, New You with Barrett Brooks

Barrett Brooks: Once I said, Okay, what is my work to do? Like, what is my little piece of making the world a better place? That felt much healthier than, like, how do I solve every problem everywhere? And then when I realized I can work hard, but that rest is equally important and if I start there and value that in addition to working hard, that creates a balance that I can sustain over time. So those created the conditions for me to say like, alright, let’s go play, let’s go explore, let’s find what the path is from here.

Pat Flynn: One of the unique things about this particular podcast is it’s been around for a very long time, 15 years now almost, and as a result of that, we have a unique advantage of being able to go back into time to uncover a person’s journey through years and where they have ended up. And we’re going to go on one of those journeys today with a guest who was once on the show nine years ago, nearly a decade ago.

His name is Barrett Brooks. Back then, when he came on the show, he was with two other gentlemen, Chase Reeves and Corbett Barr. They together made up a company called Fizzle, and that was an online digital education company. Barrett had been removed from that position. And had gone through this journey of self discovery and we’re going to talk a lot about what that actually means because I think a lot of us are on that journey or have been through that journey and it’s nice to hear a story of not just figuring it out right away, but also learning a lot about oneself along the way.

All the way to recently, we actually hired Barrett at SPI, not, not as an employee, but as a consultant to help us through an assessment that helped us discover more about ourselves as employees and as humans and individuals so that we could work better together as a team. We do talk a little bit about assessments and the validity of things like that to like strength finders and the one that he’s involved with.

But we talk more about his journey and the ins and outs of that through parenthood, through internships, through experimentation, and I think this is gonna be a really inspirational episode. For those of you who might be going through career changes, especially. And if you happen to know somebody who’s going through a career change or you yourself are thinking of one, well, this is definitely for you, but even if not, this will be a great story because Barrett’s a great friend of the brand and you might recognize him or, or maybe I’ve heard of him before.

It’s just a great reality. And we do talk about some things at the end, which involve the importance of masterminds and getting together with people in this busy day and age. So we talked with Cal Newport a couple episodes ago about slowing down and you’ll see moments of that in this episode through Barrett’s journey and how vital and how important it’s been to, in fact, while trying to find something, slow down.

So here we go. This is Barrett Brooks. Enjoy.

Announcer: You’re listening to the Smart Passive Income Podcast, a proud member of the Entrepreneur Podcast Network, a show that’s all about working hard now, so you can sit back and reap the benefits later. And now your host. He’s recorded over 2, 000 interviews in his lifetime, and he’s not done yet. Pat Flynn.

Pat Flynn: Barrett Brooks, welcome back to the Smart Passive Income podcast, my friend. Thanks for being here.

Barrett Brooks: Thanks for having me, Pat. Nine years later, I think.

Pat Flynn: Nine years, almost a decade. And the last time you were on the show, you were with a few people. In fact, you were with Chase Reeves and Corbett Barr from Fizzle.

You were at Fizzle. You were helping them and creating content with them. And you’ve since gone on to do several other things. And I’d love to kind of maybe start with where we left off. I mean, you were at Fizzle for a while and then you decided to, or something happened and you moved on from there to an incredible position somewhere.

Might you be able to kind of paint inside those lines for us a little bit?

Barrett Brooks: Yeah. Yeah. So the Fizzle days, I think a lot of what we were going through at the time was like behind the scenes anyways, was what do we want to do with this company? Do we want to grow it? Do we just want to kind of enjoy it? So there was a lot of internal conversation going on and I was at a point in my career where I really wanted to grow a company, like that was the focus for me.

So I pressed pretty hard. It was like my job was growth and I wanted to create a system for it and move through it as fast as we could. And that was in conflict mostly with Chase, I think at the time where he really wanted to have a more creative, like, enjoy my day, do what comes to me, be a creator, which obviously I totally respect and like loved him for that.

So ultimately those things just didn’t click. And in the end, Corbin and Chase sat me down and they said, Hey, it’s time for you to move on. Today’s going to be your last day. You know, we love you. We’ll do anything we can to help set you up for success, but this isn’t working anymore. That was a pivotal day in my life, for sure.

Pat Flynn: I bet. I mean, they wanted to just kind of chill. You wanted to grow. Was that kind of unexpected? Or were there signs or hints that, you know, something like that would have, would happen?

Barrett Brooks: Well, looking back and having gone through everything I’ve gone through since then, managing a lot of people, growing teams, it’s like, yeah, of course I should have expected that something like that would happen.

But did I? I did not. It was a surprise to me. And I was super caught off guard and really stressed actually at that moment in time. I mean, you’ve been through being fired in your career or laid off. So it’s just a hard moment where it’s like, where’s the money going to come from?

Pat Flynn: So what was your next move? I mean, how do you rebound from that?

Barrett Brooks: Well, the first thing I did was I set up a coaching business. I had been coaching on the side for a while. A lot of our customers at Fizzle would reach out and say like, Hey, do you work one on one at all? I would keep a couple of people here and there just to stay fresh and see other businesses from the inside.

And so I went pretty hard at that. I grew my coaching business to like eight or nine clients pretty quickly. And that took off some of the like weight of the money. And then I was having two conversations. One was with a friend about potentially partnering with him to buy an existing software company that everyone in this space would know.

I’m not going to name it cause it’s just not helpful in that kind of situation, but we almost bought a software company that I was going to be CEO of. So that was one path. And then the other path was I talked to Nathan Berry, the CEO of ConvertKit, about teaming up with him. And he had actually reached out about six months prior to me being fired and was like, Hey, why don’t you come lead customer success for us?

And I was like, no, no, we got a good thing going on. You know, I’m focused. And so I called him and I was like, Hey buddy, I’m available. And so we ended up having a long conversation, a series of long conversations. And I joined that team kind of in a special projects role at first, cause they didn’t really have a role open.

And then that grew into leading marketing and growth. And then from there, that grew into me becoming COO for three and a half years and kind of running the whole company.

Pat Flynn: Yeah, and that’s where you and I got really close because as an advisor to ConvertKit, I mean, we had regular meetings and we’d talk about the company and where it was going.

And that was a really fun, it almost felt like even though ConvertKit had been around for a while at that time, relatively speaking, it still felt like, a little bit of startupy, a little bit of like, let’s grow this thing. And did that kind of scratch the itch for you? And so maybe the Fizzle thing was a blessing in disguise in that regard.

Barrett Brooks: Definitely did. I mean, it gave me so many opportunities, like so much of my fascination from the first business that I started back in 2011 was on how do you build great company culture? How do you recruit people that fit that culture? How do you build high performing teams? And so ConvertKit gave me this like, you know, moderately high stakes sandbox to try these ideas out. What does it look like to build culture? What does it look like to hire great people? And so it definitely scratched that itch I think we grew from when I got there, we were just under 3 million in revenue. And when I left five years later, we were just under 30.

So we 10 X the company basically. And the five years I was there.

Pat Flynn: That’s incredible. What might you say is the difference, the biggest difference between working in a small group with like Corbett and Chase and how things worked there versus in a company with 50 ish people and feeling like there’s a lot more at stake, how do you, as the operator, In those companies, manage people.

What’s the difference between the small company and the big company?

Barrett Brooks: Well, I think Fizzle was probably doing somewhere in the neighborhood of a half million dollars of revenue when I was there. So there’s a world where that company could have become as big as ConvertKit. You know, there’s no reason that it couldn’t.

And so it was really more about intent, but in terms of operating, I mean, it’s really like you go from doing everything yourself. I mean, I was like in the nitty gritty every day from answering customer emails to writing blog posts to doing the SEO research, just, you know, it’s an entrepreneur to in a big company, you have to think much more in systems.

I kind of think of it in two phases. It’s like, growing a company, that’s a startup where you intend to hire a lot of people you experiment, you run lots of experiments, what works, what works, what works, and then when you hit on something, you build it into a system. And that’s entrepreneurship in general, but especially when you’re trying to get high growth.

You’ve got to test a lot of things, find what works as fast as possible, and then turn that into a repeatable system over and over and over. And so your job a lot of times is to hire people who can do one or the other. They can run the experiments or they can be more like a little mini operator and their piece of the business and run that thing hyper efficiently. Because we know it works well.

Pat Flynn: Then in that stage, you are now managing managers, if you will, or directors even and imagine that at some point you have to make really tough decisions about people that you didn’t have to before, for example, firing people or letting people go. Did you actively have to do that?

And what was that like? Having to do that for the first time, even from the position of somebody who had once been fired. I mean, did that change how you approach that? And was that still hard?

Barrett Brooks: Oh, it’s so hard. It’s one. I think it’s the hardest thing in all of business, aside from shutting your company down.

So I think shutting your company down and firing people are the two hardest things that I’ve had to do in business. And for me, firing people should be the last resort. I think it’s one of those things where you should be like, my intent is always to, Hey, where are you going as an employee? Like, where do you want to go in your career?

Let me help you get there and let’s make sure that this role fits where you’re trying to go and what trajectory you’re on and that I understand how it fits on that. And then I want to help manage you from a skills and both hard and soft skill development standpoint so that you can actually be on that trajectory long term.

And then we have goals, obviously, right? As a company, it’s like you have to both, you want to develop towards your path, but also we need you to perform and like hit our goals as a company. So being really, really clear about what that means. You know, what are our goals? What is your role in that? What do we expect of you?

What are the metrics we’re going to evaluate you on? And then if those things start to diverge, there can be two reasons for that. One is the person is not capable of doing that job and they might be better suited to another one. And the other is they just don’t want to do the job. They’ve outgrown it. It’s not what they want. It’s not interesting to them anymore. So in the best case scenario, you can have that conversation consciously. You can say, Hey. It seems like maybe this role is not the best fit for you anymore. Are you seeing that like what’s going on for you? And make it into a collaborative conversation about where they want to go with their career so that it can be more of a conscious ending, a proactive ending, if that’s what needs to happen, but I think a lot of times we’re so worried about as entrepreneurs, we’re worried about achieving our goals, the headache of hiring, the loyalty to the person, the love of the person, maybe if like they really matter to us and a lot of our small companies, that we forget that they’re a human with goals, and it might be best for them to move on. And so instead, on one side or the other, we just hang on and hang on and hang on until it gets so bad that we have to let someone go. So my goal is always, like, make firing the last thing, and I think a lot of what allows that to happen is to have the courage to have the conversation of like, hey, this seems like it’s not good for you anymore. How’s that land with you?

Pat Flynn: I mean, imagine if that approach was taken with you back in the day when you were surprised and sort of the rug got pulled out from under you. If conversations were had about your goals as an entrepreneur might have become very clear not just to them, but also to you that maybe Fizzle wasn’t the right thing.

And you know, I know You all are still friends and stuff, which is good, but it doesn’t always work out that way. And I think that’s what a lot of us are afraid of as entrepreneurs. Can you speak to, before we move on to kind of where you are now, speak to the entrepreneur listening to this, who is afraid of hiring because they’re afraid of firing.

Barrett Brooks: Okay. So this comes from the work that I do now, but one of the things that I know to be true now is that all of our past painful experiences that we carry with us everywhere we go affect how we show up every day as entrepreneurs in the same way that whatever you went through as a child affects maybe your marriage or your personal relationships.

Those same kind of habits and patterns show up in your business and with the people who work for you. One of the patterns that I see is that often entrepreneurs ended up entrepreneurs because of some combination of painful experiences along the way. Bad managers, getting fired, getting laid off, whatever.

And often not wanting to hire because they don’t want to fire is rooted in that pain. So the first thing I would say is, really looking at that inside of yourself and understanding where it comes from and coming to terms with it, maybe working with a therapist or coach to kind of understand it better so that it’s not controlling you would be a big step. But then the next one is just to say, look, the more courage you have to approach people as human beings who work for you with their own goals and families and values and everything else, and the more willing you are to have intentional conversations along the way, the less painful it has to be over time.

And if you want to reach your potential as an entrepreneur, you’re probably going to need help to get there. There’s the saying that I’ve come to, which is the idea that the cost of joy is grief. And there’s a similar parallel here, which is that the cost of joyful team might be the disappointment of occasionally having to let someone go.

Like you get the upside by embracing the downside. They can’t exist without each other. And so some of it is just coming to terms with that and realizing like, Hey, if I want to do everything I want to do here, I have to risk the fact that I might have to fire someone one day and that’s going to be a hard day and that’s okay.

Pat Flynn: Yeah, it’s pretty rare for a company to grow from the ground up and scale without making those tough decisions and experiencing a little bit of that team grief, if you will, I think that would be unheard of, in fact. It’s tough and that’s part of the game and it’s a learning experience and you’re not going to get it right the first time.

And you learn as you go, just like we do when we date, just like we do when we try to find our career, all, all those things. So I appreciate the sentiment and the honest conversation and you know, I think because you’ve gone through your own personal experiences and have managed a large teams, you are very well qualified to do what it is you do now.

And I’d love for you to share a little bit about kind of the role that you’ve taken amongst the business world these days.

Barrett Brooks: Yeah. I mean, you know, speaking of like intentional conversations, I ended up leaving ConvertKit through one of those intentional conversations and what Nathan and I found was that we valued different things for the future of the company.

There was a day when Nathan kind of said like, Hey, I’ve realized I compromise on the thing I value most and running this company and. I want to revert back to more of that intent. And when I heard that from him, I realized that conflicted with what I wanted. And I said, you know what, man, I respect that.

And I want what I want you to have, what you want in running this company. And if that’s the case, I think it’s time for me to leap. And I said, that’s not like an ultimatum. I’m not trying to create leverage. I’m not, I don’t even have another job I would go do. I’m just letting you know, like, sit with it, make sure that’s what you think.

And if you come back in a week or two and you know, for sure, that’s the case, let’s start making a plan for me to leave. So we ended up making like a six month departure plan where it was really intentional. I documented everything I did as the COO running the company. We slowly rolled out the communications to the team.

I took a sabbatical for a month to make sure that I wasn’t just like burnt out and needed a little time away. You know, we got to have like a really thoughtful departure and that felt amazing to be able to cater to the team’s needs that way and make sure we were being purposeful about it. So that was how I started this journey to end up where I am.

Which took me like 18 months. I mean, looking back, I realized I got to a point of really deep burnout. I was depressed at the time. And I wasn’t able to see it. My wife actually had to call it out at me. And that was really what started to increase my awareness of like, Hey, maybe my values and what we’re doing here are misaligned.

Pat Flynn: What were the symptoms that she was noticing?

Barrett Brooks: Oh, so much. I mean, the biggest one was just how little energy I had for my family. And how irritable I was every day after I got done with work. And, you know, finally she sat me down and she was like, look, this isn’t working. I need you to either go to therapy, get a, you know, work with your coach, whatever you need to do to get okay with what’s going on at work.

Number one. Two, I need you to quit and go do something else. Or three, we can’t be married anymore. And it wasn’t like I’m going to divorce you, but it was like she was trying to make the point that this doesn’t work this way. You being irritable, not present and all of that, like it’s not working. So let’s figure something else out.

And obviously when you sit down with your life partner and they say to you, it’s gotten so bad. I don’t recognize you and we can’t be together. If you can’t figure this out, it’s like, Oh, okay. I got to do something. So what did you do? Well, that led to seeing it more clearly, which is the value of feedback like that, right?

Sometimes we’re just in it. We can’t see it.

Pat Flynn: You’re out of automatic mode at that point, right? It’s like you, you kind of zoom out and you’re like, holy crap. I see it now.

Barrett Brooks: Yeah, exactly. And you know, as entrepreneurs, and I’ve always thought of myself as an entrepreneur, even when I’m occupying a role, you know, I wasn’t like the founder or owner, full owner of ConvertKit. But I was an owner and I was running a team. So I thought of myself as an entrepreneur. Building businesses is hard. You know, sometimes it’s just like, Oh, well, this must just be what it’s like. It’s just hard. But sometimes we get confused with this idea of like grit.

And how we’re supposed to power through the hard stuff, which is true. And when it crosses over into an unhealthy amount of almost like self flagellation or torture or like, you know, whatever it is that, that tilts it over into that bad place in our minds. So, I left in August 2021. And I felt lost, honestly, I felt like I didn’t know what I was going to do next.

Thankfully, we had made enough money where we knew I could take kind of a year to figure it out, which was a huge privilege and I was very grateful for. And I had no plan about a week later. My plan was I just needed to sit still for a while. And about a week later, my mentor and friend, Seth Godin, who I’m sure everyone who listens to your show know, or probably has heard of, I worked for him back in 2013 and he emailed me and said, Hey, I’ve got this idea for a project. I want to make a fact based book about climate change for everyone who wants to know more about it but is scared to wade into, like, the culture wars of it and just wants the facts. And I said, Oh, that’s amazing because the only hint of an inkling I had about what I might want to do is I wanted to potentially work at a startup that was combating climate change.

Like that was maybe a direction I wanted to go, but, you know, I’ve worked in the creator economy for a decade and so it’s like, well, how do I make that transition? And this felt like the perfect way to do that. Build a little bit of a reputation, get my knowledge up, have something fun to work on with a mentor.

So I ended up working on that for six months, basically full time as a volunteer. It was an all volunteer project. We made this book called The Carbon Almanac. It went from idea to the publisher in six months. And it’s a 300 page anthology of all of the facts based in data with citations about what’s going on in our natural world and how we might be able to fix it. That allowed me in some ways not to sit with what was going on with me and just jump into something else.

Which was both a blessing and a curse in its own way.

Pat Flynn: I mean, we could dive in to that for sure. The book is amazing. I have one. Thank you so much for the copy, by the way. And I think more people need to, to see it. So I would imagine it’s under Seth’s name on Amazon and other places in case people are curious about that.

Barrett Brooks: Yeah. Yep. You can find it any, anywhere books are sold as they say.

Pat Flynn: Yeah. Carbon Alamanac. Nice. And then from there, I know you have now kind of gone back to your roots in coaching. And you’ve actually helped us at SPI, the team SPI, we, we hired you to help us with understanding more about who we are as employees and really as humans and people so that we could better work together.

Does it feel like at this point that you are landing in the space that you want to land on and kind of your life’s work at this point?

Barrett Brooks: Yeah, I think so. The Carbon Almanac gave me the space to begin thinking intentionally about how did I want to approach that period of time that I had available to me to figure out what came next?

I developed a perspective of, okay, I’m going to run a series of experiments to find out what I might want to do. And it ended up being three, six month chunks that then led me to go back to my roots in coaching. So I made the Carbon Almanac. I went to work with my friends here in Portland who run a coffee company that has five stores and they were looking to grow from there.

So I did six months with them as their COO. So much fun. I would probably still be doing it today, if I hadn’t gotten used to making the kind of money you make in startups. Coffee and startup software, startups just have drastically different pay scales. So I left that due to money. And then I went back into startups at a climate tech startup, building these massive, basically they wanted to transform the energy system in the world by using the ocean’s power.

They’ve just come out of stealth. That’s at And so this was this like deep tech hardware startup. And I went back there to see, Hey, maybe a different environment would work better for me. And I saw a lot of the same patterns coming up of like frustration and irritation. And I wasn’t even working that hard.

So it, it wasn’t that. And the realization I had was I kept looking for a leader that I could work for that I would believe it, you know, that I could like really be led by. After I reflected on it more with my coach, I realized, Oh, I’m looking for someone who can lead me better than I feel like I can lead others.

And I’m having a hard time finding it. I think I’ve been looking for me. And that realization in my mind was like, ah, I need to be an entrepreneur again. Like, that’s what I’ve been looking for, but I’ve been scared to admit it because that comes with responsibility, financial responsibility, the risk, taking the leap.

I thought about it and I said, all right, I could start a startup. I could go out on my own, be a coach. And becoming a coach again felt like the easiest first step to getting back to being an entrepreneur. It’s like, I know the business model. I know I’m great at it. I know who my clients would be. Whereas starting a startup is this whole other bigger thing.

So the way I talked about it with my coach is this is going to be a fourth career experiment. I’m going to find out, do I want to be a coach again? And this was last March, so March 2023. And I said, I’m going to get some clients. I’m going to see what I think. And we’ll go from there. And I had this great hesitation about coaching because in the world of coaching, coaching can mean almost anything. Because it can mean almost anything there are some people who are not very good at what they do, and I think they take advantage of people. And so sometimes coaching gets a bad rap because of that. And it certainly had a bad rap in my mind. And so there was this big mental hurdle I needed to get over of, like, I don’t know if I can own the title of coach and be good with that.

And the thing that allowed me to unlock that was thinking about the coach I had been working with for five years from a firm called Reboot. They work primarily with startup founders and leadership teams. And what I realized was he was probably the second most important person in my life, next to my wife during that period of time and that I had relied on him for all of these big decisions and he had been an incredible professional, extremely talented, very, very well versed in a wide range of skills and methods of helping people work through what they’re going through.

And I was like, okay, I’ll just be like him because he’s great. And I don’t have to think about all the people that aren’t great. I’ll just be that kind of coach. So it’s been a year now and I held it loosely and I said, all right, if I love it, maybe I’ll do it forever. If I don’t love it, I can go start another company.

I can go join a company. I have options. And I would say a year in, I’m more convinced that this is one of the best uses of my skills than ever. And it gives me the freedom to do things like work on podcasts that I’m starting right now that’ll be out by the time this interview comes out, write more consistently, you know, so it just means a lot of needs all at once.

And I’ve been loving the work.

Pat Flynn: That’s amazing, man. Well, I’m proud of you for for finding yourself. You know, I’ve been a friend of yours for a very long time and from the sidelines have seen the ups and downs and also the journey that you’ve been on to find yourself in this way. And I appreciate the honesty and the vulnerability talking about trying things.

You know, I am 41 now. I’m an old man. And we’re When I grew up, you get one job and you just stick with it, right? And like longevity in the job means you were good at it. And if you left, that means you failed. And I think that’s why when I got laid off in 08, that was a even maybe bigger moment of depression for me than maybe it had to be because I was taught you just have one job and you stick with it.

So the fact that you are experimenting, career experimentation. I’d love to talk about that and maybe unpack that a little bit because did you feel like because you hadn’t found yourself yet that you were failing? Or how do you stay in that mind of, no, this isn’t it yet, but I’ll find it. And how do you learn between each of the different experiments?

Barrett Brooks: Okay, so the first thing I should name is the wonderful thing about software startups is if they work, you can make a lot of money doing it. And we did not make retirement money, but we made enough money where if it sits in an account for 30 years between now and when, if we retired at a normal, you know, they’re like stereotypical age, we would have a very modest retirement, but we would be okay. And so what that did for us was it gave us this margin of, I still have to earn money to pay our bills, but it’s not like we’re grinding it out, you know? And so that’s the first thing that unlocked more freedom and it would be totally false if I didn’t name that as a huge unlock for me.

But there were two big habits I had from long ago that I had to work through in therapy to get to the point where I could embrace this approach. The first was I have always felt like If I work hard enough, people will see me as a good person and I will get rewarded for that. And the way that that manifested itself in my life was just like grinding, work as hard as I can for as long as I can until I’m so exhausted that I can’t do it anymore.

And that was no longer serving me because there is a great value to hard work and doing it intentionally. But when it is with the intent of filling a hole of do people think I’m good and do they love me? You actually can’t fill it with hard work. You have to fill that from the inside out. So that was the first thing I had to work through.

The second thing I had to work through was throughout my life. I have also carried kind of like the weight of the world on my shoulders. It’s like I take everyone else’s problems and I make them mine. And I try and solve them for them from a healthy state of mind. That’s a beautiful thing. It comes from a place of service and wanting to care for people and take care of them.

But from an unhealthy place, again, if I’m trying to fill a hole that has to be filled, starting inside. It becomes this, like, I take on every burden of the world and treat it as if it’s mine. And so I had to let go of the idea that, like, I was gonna solve the world’s problems, and I had to realize how egotistical that is to think that, like, any one person could do that.

And so that was a lot of the, like, deep background work that then once I said, okay, what is my work to do? Like, what is my little piece of making the world a better place? That felt much healthier than, like, how do I solve every problem everywhere? And then when I realized I can work hard, but that rest is equally important and taking care of myself as woo woo or lame as it sounds like, legitimately loving myself, if I start there and value that in addition to working hard, that creates a balance that I can sustain over time. So those created the conditions for me to say like, alright, let’s go play, let’s go explore, let’s find what the path is from here.

Pat Flynn: Did you have guidance to help you discover those things about yourself around the time?

Was that a, was that a therapist or a coach? And I want you to talk a little bit about that because I think a lot of us are afraid of having those kinds of conversations about ourselves. And can you speak to how important that is?

Barrett Brooks: Oh my gosh. Yes. I’m in a writing class right now. This is related to the question.

I’ll answer it directly in a minute, but I’m in a writing class right now. My wife introduced me to it. It’s run by a creator and a writer named Ruthie Ackerman. She used to be a New York Times columnist and now she runs a writers collective. She mostly serves women. It’s not intended to only serve women, but that’s just who she ends up attracting.

So I’m in this class, it’s a year long class, and it’s like me and a half dozen women, and I feel so privileged to be in this space because I get to gain so much wisdom from people who are mostly older than me with more life experience and just a different perspective on the world. And the goal that I have in that class is I want to write a memoir about this process so that when my boys hit young adulthood, you know, they’re mid twenties or whatever, when you start asking these questions about where did I come from and how did my parents screw me up and whatever else, they can see like, Oh, my dad went through that.

So it’s okay. Like I can go through it. And I want them to feel like they can come to me. And tell me the things that were hurtful, first of all, and I will apologize. And secondly, that we can talk about this stuff because I think it’s so, I want to break what you just said. I want to break that pattern in the world of these are scary things to talk about, I better hide it away. Because I think that causes way too much pain for people. So then to answer the question directly, I had two critical people in my life. One was a therapist who I started seeing who practices a therapy modality called internal family systems. And the idea of that is that when we experience a lot of pain growing up.

We kind of like freeze a little version of ourselves at a certain age and time and that person stays inside of us might be eight, might be five, might be 12 and anytime that we’re going through hard things as an adult, we end up reverting back to that little emotional being and then we develop these protective parts of us that try and fend off pain in the world from hurting this little little person inside of us.

I know that that sounds a little out there, but the modality basically allows you to identify these parts of you to speak directly to them, to release them from the old patterns and habits that they’ve been using to protect you so that you as the adult can essentially soothe the younger you when you’re going through hard things.

So that was the first thing was therapy and that modality. And then the second thing was my coach who I had been working with for five years, Andy Christinger. He’s the head of coaching at Reboot. just a remarkable and kind human being. And so between those two things, therapy helped me uncover and understand what was going on inside of me, and coaching helped me apply that to, and where do I want to go in my career based on that.

Pat Flynn: Incredible. I think we should normalize therapy and not talk about it like it’s a band aid, but it’s healthy. It’s a conversation. It’s another perspective, which we often need. And I know that beyond those places, you are very much a believer of masterminds and you know, something we’ve talked about on the show before, but tell me a little bit about that, any masterminds that you might be a part of and how vital they have been for your growth as well before we get into some more tactical stuff shortly.

Barrett Brooks: I kind of think of like, who are the key relationships in life? So there’s family, obviously, there’s the extended family, there’s our close inner circle of friends who are, who might be local and they’re just kind of the people that you’re social with and can count on.

And then outside of that, there’s this kind of like professional peer group, maybe aspirant peers as one way they’re referred to, who are people doing the kinds of things that you really look up to and respect and that you can learn from. So masterminds for me, number one, have been critical to all of my growth over time.

And repeatedly over the years, if we go back even before the last time I was on the show, so I don’t know, I’ve been doing masterminds for probably 12 years now. Repeatedly, I’ve had breakthroughs. Either in business or in my mindset at these sessions, because you get this outside perspective from other people who are in it with you. You know, not like in your business, but they are in their business. And so, you know, it’s coming from a place of like, I see what you’re going through because I might have experienced something similar. So the two groups that have been critical one, we had for a long time and it’s kind of fallen off as everyone’s gotten more successful was group of Nathan Barry, Caleb Wozniak, James Clear, Sean McCabe, Ryan Delk.

And there might’ve been one or two other people. And so we all knew each other when we were literally nobody. We were the opposite of somebody at the time we were nerd. We had no style. We weren’t culture. We didn’t know anything about entrepreneurship. Like we were trying to figure everything out. And now I bet many people in the audience will be like, Oh, wow, I know some of those names, you know, Nathan Barry, the CEO of ConvertKit, James Clear, holy moly, yeah, James Clear, best selling author of all of 2023.

And when you’re part of a group like that, where everyone is challenging themselves and growing and doing work that matters to them, you get this arc where you get to see the full journey, you know? And I think sometimes people think, I need to like mentors who have already done it. And yes, you do, but that’s different from peers who are doing it as you both grow together.

And there’s so much reward in like having been friends with any of these folks before they did all the things they’ve done because it’s not like, oh, now I want to be your friend because you’re successful. It’s no, I was your friend before, regardless of what you did, and now I’m just happy for you. So the group I go to now is run by a guy named Sean Blanc.

He’s got an incredible online business. If you’ve never heard of him, you should look him up. And he runs a retreat in Breckenridge, Colorado every year. And it’s a little bit of a amorphous group. There’s kind of like a core group of folks who come every year. And then there’s a few folks who come in and out kind of mix things up.

And that has become my kind of annual ritual of going to the mountains of Colorado, having deep conversations, connecting with these folks and, and learning from them. And so I guess to answer the question, it’s like, how did that come about? Well, first I drove the like, let’s do retreats together thing initially, and then that became a shared habit that we all look forward to.

And now Sean is the driver of the one that I’m a part of now, and I make the effort to set that time aside and make sure that I get there so that I can have the experiences. And that’s the cost, right? It’s like, you got to be willing to put the time and energy in to make it happen.

Pat Flynn: For sure. I mean, commitment is required from all parties for the group to work, and I wouldn’t be where I’m at today without the two masterminds that I’m a part of.

I’ve been a part of them each for almost a decade, and they’re less in person, more ritualistic Mondays and Wednesdays, respectively, that I have, and I make the time for them. I would not be where I’m at. And there’s a giant list of names, but I’m not going to go into that right now, but you know who you are.

I appreciate that. It’s always a good reminder. And as we kind of finish up here, I think it would be remiss to not speak to the work that you’re doing now with relation to the Highlands Ability Battery, which is something that I don’t know if a lot of people have heard of before, but I think we’ll understand.

I’ll let you describe it in just a second, but it’s along the same lines as a lot of these assessments that we have that whether you’re a CEO or maybe you are an employee, you take a test to discover more about yourself and your abilities. And there’s a million of these things, right? And there’s even ones that are outside of business that we might be familiar with, like the Enneagram.

I mean, categorizing and understanding more about ourselves is important, but it’s almost become cliche or even kind of just like, Oh, another one of these things. And I’d love to hear your stance and your position on how important is it to take a test or understand yourself in a way that makes sense. Is through a lens of of data and understanding so that we we can become better versions of ourselves so that our teams could become more meshed with each other.

Talk about a little bit about how you got into this and kind of why is it so important? We’ll go from there. I have some follow ups, but I’d love to know kind of how you got into this first hand.

Barrett Brooks: Okay, so from a coaching perspective, it’s like. I want to develop a set of tools and training and methods that I can use to help people unlock their potential and then grow their businesses from that place.

So I am willing to explore anything that I think will help entrepreneurs grow their businesses. And be better leaders, like be the kinds of leaders we all wish we could have worked for earlier in our careers. So within that, one set of tools are assessments. And I don’t believe that any one assessment is the end all be all.

I think that there are many assessments that give helpful data. And I think the degree to which an assessment is useful is the degree to which it gives you a new insight about yourself. And whether it’s a data driven assessment or it’s more of like a spiritual kind of background like the Enneagram, if you learn something about yourself and are able to make meaning of that and apply it to your work, that makes it useful.

What I like about the Highlands Ability Battery in particular is, number one, it’s one of the most intense and rigorous assessments that I’ve found. It takes about two and a half hours to complete. Many assessments are like, how are you, they ask you questions, self assessment questions, basically. It’s like, what are you like at a party?

And then you tell it, you know, one of the answers. And so the problem with that is it’s relying on you to already know what you’re like. Sometimes that’s the exact problem we’re trying to solve. So how the Highlands is different in that way is that it’s a series of what are called work samples that are not dissimilar to things like you might do prepping for the LSAT or brain games or things like that.

And what it’s meant to assess are there are these different patterns in the way that our brains work where we naturally develop a set of talents early in life, you know, similar to the timeline of our personality developing. Your talent, your natural abilities are kind of set by about the age of 13 to 15, somewhere in there.

And then your brain operates that way basically for the rest of your life. Then they don’t change that much over time. And so the Highlands Company has done long term studies to show people are pretty consistent in their scoring. I like that data richness of the fact that they have shown over time it stays consistent.

Because things StrengthsFinder once every five years. It’s changed a lot over the years. And then what it gives you is it tells you For example, what is your natural time horizon? Do you think in, you know, the next year of a chunk? Do you think in one to five year chunks or do you think long term, you know, five plus years?

And then based on that, how should you be supplementing your natural way of thinking with better planning to account for your weaknesses there? Or how adept are you at manipulating the physical world or working in the physical world? And how important is that for your brain? And there’s a work sample on that.

And so that helps you understand, like, if you’re really frustrated doing digital work all the time, it might be because you have a very high natural ability towards working with physical objects. And so that will help you either by developing hobbies or moving your business that way, be more satisfied with work.

So that’s the kind of thing you get out of it.

Pat Flynn: I can attest to just how rigorous this thing is. It kind of gave me a little PTSD as far as tests that I remember taking for, you know, AP tests and whatnot, but the results were worth the effort. We learned a lot about each other as a team. I learned a lot about myself and I do like how it kind of gets to the root level of who you are versus just how would you act in a certain situation?

Because how I would act, in a certain situation in 2010, when I was first starting out is different than, you know, I’ve changed as a person, my brain is like you said, the same so I can be able to understand more about what I’m planning to do and how that fits into who I am based on that, which is really neat and, you know, discovering these things about others is really interesting as well and it allows me to better understand how to communicate with them.

It’s similar in how the Enneagram has helped me in my marriage with, with April, my wife. And you know, that’s been an important part in a common language that we now have together. So as a leader of groups of people like Team SPI is somebody who has given us this assessment. How do you as a coach begin to make connections and what are some of the most interesting, if not valuable things that one can uncover when we understand these things about ourselves?

Barrett Brooks: So the reason I got certified in this assessment was it’s a great input to the beginning of coaching work with someone. It’s kind of a perfect place to start because it gives me and them solid data that we can work from. And then we can go supplement that with things like doing a 360 degree review from their team to hear how they show up at work in relationship and yada yada.

But the big thing that this type of data gives you is how am I naturally wired and therefore, how should I design my work as a leader or as a CEO or as a solo creator? Like what should I do myself versus what should I outsource? What should I rely on my team for versus what should I take ownership of?

How should I structure my days in terms of things like interacting with the physical world or being in a relationship versus working on really in depth like expert level problems? But most importantly, it allows you to see how your natural way of seeing the world, how your brain works might be the exact opposite of someone that works for you.

And that doesn’t mean that you can’t work together. It might actually mean you’re a great fit to work together, but you might have to work really hard to communicate effectively with each other. So when you have different brains that work super differently, that can be very complimentary. It actually might mean you have all your bases covered when you’re running a company.

But how that might be coming out is frustration at each other. It’s like, why are you so hard to work with? And when you realize the answer is like, oh, your brain’s just wired differently. Great. So how do we deal with that? That’s a completely different problem from like, why are you so frustrating to work with?

And so that’s the biggest thing I see at Unlock is once you figure out how you want to structure your work based on it, now you can figure out how to be in better relationship with the people who work for you and lead them better. As a result of knowing these things about each other.

Pat Flynn: Yeah. I mean, that, that’s absolutely huge and it betters the company.

It betters the individuals working within the company. You know, a lot of times we need to, in order to figure things out, we need to go back to the root of, of who we are. I love that. If anybody listening is curious about the Highlands Ability Battery test, do you have a suggestion on where they might get started or how to go about doing that, you know, exploring that.

Barrett Brooks: The Highlands website is And that kit that just kind of gives you like an overview of the assessment, the research behind it, you know, all of that kind of thing. And then they only deliver the assessment through certified consultants. So you could come through me or they have a whole directory on their site where you could find someone close to you.

If you want her to be in person or someone with a background that matches what you’re looking for.

Pat Flynn: Nice. Cool, man. We’ll put those links in the show notes and to finish up, I want to ask you, what does the Deschutes river mean to you?

Barrett Brooks: Speaking of masterminds, actually. I realized a couple, you know, in the pandemic, like many people around the world, I was already feeling a little lonely here in Portland, which is a common experience, especially for men as they age. Men, as compared to women tend to become more and more isolated as we get older. And Portland is a beautiful place to live, but it’s also not the most entrepreneurial place in a lot of ways. Like I’ve had a hard time finding peers here. And many of my best friends, like I talked about earlier, all over the country.

So, I wanted a way to more consistently connect with some of those friends around the country that aren’t in the masterminds with me and get outside. So I started fly fishing a few years ago and the Deschutes river is a massive river that feeds into the Columbia, which is the river that runs in between Oregon and Washington.

And as I’ve had kids, it’s like harder to get out for full days to do anything, golf, fishing, whatever. It’s just like hard. So I reached out to about 10 friends and I said, Hey, I have this idea. I want to do a three day, two night guided fly fishing trip on the Deschutes river. And I was wondering if you might be interested in that.

And a lot of people were like, well, I’ve never fly fish in my life, but I found this guy shop that I’ve been working with for years now when I go out and they’re incredible teachers, it’s like, you can be a total noob and they will show you everything you need to know and you’ll be catching fish day one.

So that alleviated that for everyone. And basically now for the past two years, this will be the third in 2024. I’ve had six to eight guys come to Portland. We drive down to Bend, Oregon together. We have a great dinner and then we go out and we raft and camp and fish for two nights, three days. No cell service, no, nothing.

We’re just out there in the wild. And it is like, I come back so refreshed and just. at peace with myself from the combination of being without technology in the natural world and with friends I deeply value having great conversation. It’s another example of like the value of putting effort in to bring people together and have meaningful experiences together, for me at least.

It just, it makes my life infinitely better.

Pat Flynn: Yeah. I mean, the last couple of years I’ve also rediscovered fishing in my life and it’s not fly fishing, although I love fly fishing and I hope to go again at some point and maybe we can at one point go together, but the space to just be. And not worry. And you know, I know that when I’m fishing in particular, I get in sort of a, of a, of a zone where nothing matters.

Nothing else matters. And I’m just free. And it’s so like, I wish that for everybody else to find your version of what Barrett just talked about or what I just talked about. And it’s been so key for me to stay sane as I continue to grow different companies and create and get out there. And I I wish I had discovered that sooner, so I just wanted to bring that up because I know that’s very important to you and to your growth, and it has been for for me as well, so I appreciate that, and you know, maybe one day we can, we can, we can get on a river together because that’d be a lot of fun.

Barrett Brooks: Yeah, we’ll have to for sure. I just want to plus one that what you said. It’s like when there’s a fish on the line. You’re not thinking about anything you’re anxious or worried about. You’re thinking about that fish. And there’s something about just the motion and the experience of being fully engrossed in something that takes you out of all of those day to day worries.

Your mind is still working in the background. You know, I come back with such clarity on everything that was worrying me before I left. And so, you know, you don’t have to fish. If it’s hiking or even just doing a silent retreat or meditation or whatever it is, finding something that just fully engrosses you so you can check out a little bit.

Yeah, I wish that for everyone too. Yeah.

Pat Flynn: Amen. Bear, it’s been great to catch up. Thank you so much for this and proud of you and I’m looking forward to just following along and being a part of the journey with you. So I appreciate you my friend. Thanks for what you do.

Barrett Brooks: Yeah, likewise Pat. Thanks for having me.

Pat Flynn: Where can people go to follow you and find more of you?

Barrett Brooks: Yeah, well, when this episode comes out, my new podcast will be out, still working on the name for it, but so the best way to find out about new episodes and also to get my Saturday newsletter on becoming the leader that you are capable of being The opt in right at the top will get you both the podcast and my newsletter, and that’s the best place to find me.

Pat Flynn: Nice man. Cheers. Have an awesome one. so much.

Barrett Brooks: Yeah, you too.

Pat Flynn: All right. I hope you enjoyed that conversation with our good friend Barrett Brooks. As he said, he’s got a new podcast and at the time of this recording, at least it is not known what the name of it is, but please check out these show notes at so that you can go and find that and learn more and subscribe over there. So thank you so much, Barrett. I appreciate you.

Thank you for listening. And I hope a lot of the things we talked about today, which probably was across a number of different topics. I think that especially the slowing down and finding other people to connect with and to even unplug a little bit, that is a common theme I see with a lot of entrepreneurs, not just in the discovery phase, but in the after having discovered phase to be able to continue to have renewed creative energy as we go. And again, I’m pointing back to a previous episode with Cal Newport in 765. That might be the next best episode to listen to. We talk in that episode about productivity and redefining what that actually means and working more slowly and avoiding burnout, which is important for all of us.

So go ahead and listen to that next. If not, definitely go ahead and obviously subscribe to Barrett’s new podcast. And thank you. So maybe you can self reflect on the things we talked about today, and I appreciate you and I look forward to serving you in the next episodes here. Hit that subscribe button if you haven’t already, if you enjoy the show, and I look forward to serving you in the next one.

Cheers, everybody.

Thank you so much for listening to the Smart Passive Income podcast at I’m your host, Pat Flynn. Sound editing by Duncan Brown. Our senior producer is David Grabowski, and our executive producer is Matt Gartland. The Smart Passive Income Podcast is a production of SPI Media, and a proud member of the Entrepreneur Podcast Network. Catch you next week!

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