Creating a Beautiful Future with Barrett Brooks

[00:00:00] Introduction


[00:00:00] This is Grief and Pizza, a podcast exploring the highs and lows at the intersection of business and emotional well being. In this episode, we spoke with Barrett Brooks about how acknowledging and integrating past pain is essential for personal growth and success.

[00:00:11] So Barrett, it's great to have you on the podcast. Uh, we met in the summer at, uh, Sean Blanc's retreat and in the short period of time that Um, we've known you, I've come to think of you this very clear communicator and very courageous person. And so today I'm really excited to learn more about the work that you're doing with that in mind.

[00:00:33] Um, cause I think, you know, I know who you are as a person, but I don't actually know much about the work that you're doing. Um, so just the way that you show up in the world has been really inspiring and some of the advice that you gave us at the retreat. Was actually quite impactful in the way that in the decision making that we made towards the end of this year, we had to make some really tough decisions and your directness and the way that you communicate with such compassion was really helpful, um, in us moving [00:01:00] forward.

[00:01:00] So I'm really stoked to talk to you today. So Barrett Brooks, uh, former COO at ConvertKit and now executive coach. Um, maybe you'd like to introduce yourself here. Yeah, well, deeply honored by that, uh, really, really kind intro, um, I can't think of better ways to be described, uh, would rather be described in those ways as, you know, thoughtful and, and, uh, I don't know, something like authentic.

[00:01:24] I think you said, um, then accomplished. So, uh, thank you for that. Um, yeah, I'm Barrett. Uh, I am an executive coach. Uh, used to be a startup executive, um, at ConvertKit and a couple other companies that I worked at over time. Um, As a person, I am a dad of two young boys. My wife and I have been together for going on 15 years now.

[00:01:47] And I live in Portland, Oregon. And I would say I feel most at peace and at home in nature. I have a really deep passion for protecting our natural world. And a lot of the work that I do in the [00:02:00] world is in an effort to help protect what we have. And also to try and inspire people to tackle hard and important problems and what they choose to work on in business, especially, um, I think that business can be one of the most powerful forces for good in the world, but it takes really courageous leadership to make that true.

[00:02:20] And I really want to hold up role models and examples of people who use business that way, both through my coaching work and through my writing and my podcasting and my other efforts, um, to try and create. Another definition of success beyond just building the next unicorn or, you know, financial measures that we typically use.

[00:02:42] So maybe that we'll use that as a jumping off point. Yeah. I'm curious if that sort of passion may be on the nature side, like has that always been there or was there sort of a, a turning point for you or like, what were some of the breadcrumbs that led for that to become part of your big mission? Yeah.

[00:02:59] Uh, it's such a [00:03:00] thoughtful question. I think a lot about origins, uh, and threads to pull on like this, both for my clients and for myself. And the best explanation I have on this Well, number one is that it's just still deeply rooted in our biology. I mean, we haven't really evolved beyond this as just a species, um, not to get overly philosophical right off the bat, but, um, I think some of it's just hardwired into us still that we're very connected to the natural world and we haven't fully figured out how to replicate that attachment and the way we build architecture and the way we build communities and cities.

[00:03:33] Um, so that's there, but from an early age, my parents just got us outside a lot. Uh, I hated a lot of it. I mean, we went on a lot of hikes and like boring camping trips, what felt like boring camping trips at the time. And now as a parent, it's completely transformed my relationship to that because that formed the basis for wanting to do those things and loving it.

[00:03:56] And, um, and wanting my boys to do that with us too, and wanting [00:04:00] them to enjoy it. Uh, I'll also just add that we watched so much Discovery Channel and like Nat Geo and all that kind of thing growing up. Um, If it wasn't sports on the TV, it was nature shows. And I think that just had a deep psychological embedding in my, in my mind that stuck around.

[00:04:20] And so, you know, you can get all kinds of arguments for why we should protect the natural world. You know, maybe there's cures for cancer out there. Maybe, uh, humanity will die without it. Um, you know, whatever it ranges. My argument is that nature is just beautiful. The natural world is just beautiful. And I think that that alone, we don't allow ourselves to make that kind of argument enough in society that just like beauty is enough to want to protect something and we can build all these logical reasons for why that should be true and like why we should do it.

[00:04:54] But I think that can be enough just to say it's beautiful and therefore we should protect it. It's so [00:05:00] funny how we don't appreciate that stuff when we're kids, right? Like the going outside and all the stuff that, in retrospect, we wish we'd appreciated more. It's almost, it's, it's too bad. I'm curious how your kids are maybe dealing with that now.

[00:05:11] And you're like, no, trust me, we want to be outside. Like, are you having to, to deal with that from your own kids in the way that maybe you resisted? It's funny because, you know, if you give them an option, you can have your tablet or you can go outside. They'll say, I want my tablet. But if you were a scientist studying their behavior and you looked at them on a tablet and immediately afterwards, and you looked at how they behave outside and immediately afterwards, they're both much more, they're maybe equally engaged in each when they're outside, when they're on a tablet.

[00:05:41] But the after effects are so drastically different. I mean just completely dysregulated, don't know what's going on with their emotions after being on a tablet versus after we're on a hike or something like that at peace. Calm, engaged, connected, um, and I'm not saying that means it's [00:06:00] always better, obviously, for them to be outside.

[00:06:02] Like, technology is a beautiful thing, but I do find it fascinating that just from a evidence based perspective, anecdotal, of course, to my family, like, they love it and they're much more at peace after having spent time outdoors.

[00:06:17] The brokenness of the natural world and organizations

[00:06:17] How does that, um, in your work, you talk a little bit on your website about the importance of Biodiversity in, in business.

[00:06:25] Like, do you see any corollaries or parallels in that, in, in leadership that, you know, if we're, if we're out of, out of touch with our more based nature and, and, you know, how, how could we bring more of that feeling of connection to nature in the work? Um, do you, do you see any correspondence there or? Yeah.

[00:06:45] Oh man, there's so many directions we can go here. Um, absolutely. You know, I think the. The brokenness of our natural world that we have created is reflected in the brokenness in our [00:07:00] organizations and in our relationship, in our personal relationships. I mean, we could go whichever direction with that. And I think all of it is rooted in pain and trying to meet our needs.

[00:07:11] Um, And fundamentally, if you have unmet needs, you know, the lower down Maslow's hierarchy you go, the more you're willing to sacrifice almost anything else to meet them. And I think in society, even when we have met those baseline needs, we often operate from a mental place of acting as if we're still trying to meet those needs.

[00:07:32] I mean, you can have millionaires, billionaires still acting as if they're trying to never be poor again. Um, And not necessarily intentionally, just through their actions, if you look at them. So, I mean, I would say that our organizations end up broken in a similar way to the way nature gets broken because of old pain and the way that we don't process through it and grieve it and move beyond it.

[00:07:55] Um, and then we inflicted on the people around us. We inflicted [00:08:00] on often the people who love us the most. Um, some of whom are colleagues and some of whom are the people who work with us and for us. If, uh, if I may, Barrett, I love how you shared your mission on Twitter. Um, if I could just read this out.

[00:08:16] Help people acknowledge and integrate their pain from their past, so they can realize their potential and use it to make the world a better place. First of all, I just think it's a beautiful articulation of your mission. Um, obviously you're passionate about this. How do we take the pain from our past and Again, whether it's working through it, whether it's acknowledging it, noticing like why we're driven to make decisions out of fear, something that we're avoiding or something that we're seeking.

[00:08:44] Um, so seeing this at a leadership level, I imagine it's pretty interesting because as a coach, you're probably somewhat. like a business therapist, right? Like you're seeing a lot of people's junk and kind of how it's influencing what they're putting out into the world. So I would [00:09:00] just love to maybe dig into that a little bit, maybe how that became your mission and even how this shows up for leaders over and over again.

[00:09:07] I'm curious how many leaders actually are in therapy and working through that stuff. Like, I'm just really curious, kind of what you're seeing as an executive coach and kind of what's most interesting for you in this space. Yeah. Yeah. Uh, let me answer the last part first. Um, it was interesting because I, I wrote that mission and the vision I shared with it on the plane home from the retreat where we met.

[00:09:31] Um, and it was just kind of like stream of consciousness. I felt like I had a lot of clarity that retreat was a big kind of turning point for me last year. Um, and I see. pain every day in working with clients. I see pain showing up at work every day. And so let me just caveat this straight. Let me give my caveat.

[00:09:55] I am not a trained psychologist or therapist, and I think there's a really, really important [00:10:00] difference between coaching and therapy. And I think great coaches know that, acknowledge it, work with that, are intentional about it. Um, And I, my ambition is to be a great coach and to be able to draw that line.

[00:10:12] I'm also very fascinated in my own journey through therapy and coaching alongside each other and how they interrelate. So what I tell all my clients is it would be ideal if every person I worked with was both in therapy and working with me. And the reason I say that is the shit's gonna come up. Like it comes up at work because for founders and creators, especially Your entity that you are building, whether it's just a newsletter or it's like a team is an attachment.

[00:10:46] It's like a, an attachment relationship, which in therapy speak is like your parents growing up or whoever's taking care of you, your partner in life as you grow older. And I really believe that for entrepreneurs, your company is like another [00:11:00] attachment relationship. And so every pain, trauma, hardship, Old pattern that's no longer serving you mostly shows up first in your attachment relationships.

[00:11:13] And, you know, now that seems obvious to me, like, of course, the patterns are playing out at work because for founders it's that personal. Um, but I don't think that's always visible to everyone. And I'm not sure every founder wants to work on it. I do think most of the people that end up coming to me want to work on it.

[00:11:31] They're like, I've hit a limit. My patterns won't let me get past this anymore. And so I have to figure something out. And when I find, when I work with people who are in therapy, what I notice is often the things they're learning about themselves in therapy directly apply to how they're showing up at work.

[00:11:49] And so we get to work with what they're taking away from therapy in a work context. I'm not trying to, I think it's really important. Like I don't have the training to help [00:12:00] you process a trauma. That can be really dangerous, right? But if you have processed a trauma and you now recognize patterns from that that have showed up at work, that's really fruitful ground for coaching.

[00:12:12] And I just think there's a nuanced difference there between tackling it at the base level and then talking about how it applies at work. Appreciate that distinction, for sure.

[00:12:22] Finding inner and outer alignment

[00:12:22] Yeah, I'm curious about another tweet that you wrote this morning, actually. You were talking about being focused on Inner and outer alignment this year, uh, and in the past that you felt that this was more of a seeking type relationship with that, and that now you feel like it's actually really become embodied.

[00:12:42] Um, I'm curious what, what's changed for you. Uh, what do you think the key was to feeling? Cause it, it, I think you also mentioned how people keep noticing that, wow, this guy seems really. Really aligned, really confident, and you know, is there something that you can point to or what you've [00:13:00] been working on that you feel has been helpful in that regard?

[00:13:03] Yeah. Well, I mean, I'm really lucky and thankful to have the resources I have to invest in these things, so let me say that first. Um, but I would say it's kind of a trio of things. One is my wife and I have done marriage counseling from the day we got married and we felt like it's a wellness practice for us, not a like, let's wait till it's broken and then seek it out, which is okay too, because sometimes you just end up there.

[00:13:30] Um, so that's been a huge tool, uh, alongside that we each do individual therapy and my therapist works in a modality called internal family systems. Um, there's a, if someone wants to look into it, there's a great book by the, uh, person who came up with it named Richard Schwartz, uh, that's called No Bad Parts.

[00:13:53] And, um, whole idea is that basically we all have inner children that get kind of frozen at a point in time [00:14:00] based on pain that we experienced growing up in our attachment relationships. Um, I guess theoretically it would be possible that some people don't, don't have that, but mostly we all do. And in times of.

[00:14:12] Triggering, uh, where we are triggered, we return to that little person, basically the state that that little person was at. And so this form of therapy helps you dissect all of the parts of yourself that you build to protect that little person. And these are kind of like rep representative of the patterns that you have in your life.

[00:14:31] So beginning to go to that form of therapy was an end of 2022 thing for me that opened all of these doors. To integrating new patterns for old patterns that I knew were there, but I couldn't figure out how to get out of. So this just happened to be the modality that allowed me to kind of move through it rather than just being able to see it and not figure out what to do with it.

[00:14:58] Um, and then the last was just, I worked with a [00:15:00] coach for five years who I love. His name is Andy Christinger at a firm called Reboot. Um, their founder has written a couple of wonderful books and they have a great podcast for anyone interested in this stuff. Um, by the same name reboot and he created the space for me to create change in myself relative to my work and helped me through a very long arc of transition that began with realizing, uh, in my old role as a COO that I was, I had recreated conditions at work that allowed me to constantly live in old pain.

[00:15:39] And. That was why I left that job was I could not be in that job and get better Like it where where get better is not like improve my performance, but like feel better inside So that was kind of the beginning of this arc I think was leaving that job and then going on this kind of walkabout over a couple of years [00:16:00] Using all these resources to help me kind of unpack it and then put myself back together

[00:16:05] Patterns from childhood and their influence

[00:16:05] Are you willing to share any of those maybe Yeah Like specific patterns or like, I didn't like that or, or, you know, uh, I imagine your coach helped you kind of hone in on them or notice them and maybe the therapist helped you with that too.

[00:16:18] But like, are you able to or willing to share some of the ones that have been big for you? I just wrote about this in kind of summary the other day as I was writing my review for myself of the last year. Um, so one of them was, uh, my father was an incredible, um, Servant leader and that he showed us his love, but he was not very able to communicate his love to us.

[00:16:44] And he was the stay at home partner and my parents partnership. And so he took care of my brother and I growing up. Um, and he also had a lot of repressed emotion, a lot of anger, and I learned to be super hyper vigilant, um, super [00:17:00] hyper, just hyper vigilant, uh, in response to that, because it was always kind of unknown what would spark anger.

[00:17:06] And in that process, I learned to repress my own emotion in favor of kind of having feelers out all the time for what is everyone else going through right now? And how do I head off anything that might go wrong? This is incredibly useful for things like coaching and leading because I'm hyper aware of what other people are experiencing.

[00:17:29] I can see their emotions. I can see the impact of my actions and the impact of other leaders actions on their people. But there is a negative pattern in there, which is if you, or if I remain hypervigilant and continue to negate my own experience and my own feelings in that process, I become resentful, frustrated and repressed myself.

[00:17:54] Right? And that's the great irony. And so that was a big pattern that I had to work through. [00:18:00] Was beginning to acknowledge my emotions and learn that there's a difference between caring for people and Trying to head off their emotions before they can communicate them So that was a big that's yeah, that's a huge one like Learning not to manage other people's emotions as a way to almost manage your own, to not feel the discomfort of, yeah, that's.

[00:18:25] And it's ultimately a safety thing, right? Like it's a safety inclination for if someone else's emotions are dangerous, then I better take care of them so that they don't become dangerous to me. Yes. So that was a big one. Um, another one is that, uh, so my mom was a breadwinner, incredibly performance driven person, like high achiever, managed sales teams, always met our quotas, that kind of person.

[00:18:48] And we joke now, like we, my mom, I have this great appreciation for, like she can have these conversations and recognize what was good about how she [00:19:00] herself as a mom and also maybe where she fell short and like we can talk about it, which is an incredible gift. Um, so we joke now that mom was kind of more of a coach than a mom in a lot of ways.

[00:19:11] It was like very, at least for me, my brother has a very different personality. Um, You know, I had a lot of talents and like I was able to do things relatively easily at the beginning at school or in sports. And my mom was just so performance driven that it was like, here are the 12 ways you could get better after today's game.

[00:19:31] And we very rarely celebrated or like really took the time to look at prior achievement up to now and appreciate it. So, one might expect that out of that comes a great inner critic who is never satisfied with anything. And, um, so a pattern is that I am constantly striving for perfection and to get everything right before anyone can give me any feedback.

[00:19:58] And so I'm trying to have [00:20:00] all my ducks in a row all the time, no matter what, so that no one catches me doing something wrong before I do. Um, that can lead to a big sensitivity to criticism and shying away from over. From putting myself in situations where expectations are high and I might let someone down and the major negative way that showed up for me is I had this upper limit where if I got to the point where I actually was doing well on something, my audience was growing, my writing was getting traction, the company was growing, whatever.

[00:20:31] Now it goes from, can he do it to everyone expects him to do it. And that's harder to maintain. And so there was like performance anxiety almost, where I would sabotage myself or slow down or disappear. Um, so that one I'd say I'm still like actively working with and playing with and reforming habits around.

[00:20:49] So there's probably four or five like that, that were really present for me, that I've had to, or gotten the opportunity to just change and transform and learn their beauty and learn their shadow [00:21:00] side and have a different relationship to them. Incredible, incredible level of self awareness and willingness to confront those, those parts of us.

[00:21:10] Like, I know doing that work is not always easy and, you know, kudos to you for looking at the hard parts. Thank you. Yeah. Yeah. I'm very thankful for it. It's, uh, you know, maybe because of some of these patterns, I've always had a tendency to look inward and to try and understand myself. And I think that's been a gift.

[00:21:31] In the process, because I'm already kind of there, but now instead of getting anxious about what I see, it's like I have the tools to be able to work with it. Interesting. Yeah. Yeah, I'm curious how you're, and this is a bit more of a personal question, but how the dynamics of noticing like the mom's the breadwinner, dad the stay at home, um, how that may have shaped or influenced your own relationship with your partner now, and then I'm sure you're even confronting aspects of that, being a father, just kind of curious if, uh, If [00:22:00] that's been an influence for you or in kind of how you see your own dynamic with your partner.

[00:22:05] Huge. Um, I think I default to a belief that women are extremely capable leaders and business people because my mother was. Um, and you know, I am a white guy who kind of meets the stereotype of tech exec in terms of background and all of that. Um, But I found, I find that I'm, I often feel out of place and conversations with other stereotypical tech exec type people because of my background in that way.

[00:22:35] Um, it's like I default to thinking that a woman is going to want to have a career, is going to want to drive earnings in the family, may not want to be the one who stays at home, that there's going to be, um, equal or maybe even lopsided division of labor at home. Towards the male in the relationship. And so there's a lot of things like that where like I [00:23:00] hold myself to a standard of I expect to do half of the like, you know, underappreciated labor at home.

[00:23:06] I don't think I always live up to that. Um, but that's my inner expectation of myself. I don't think I would have that if my mom were like a stereotypical stay at home mom. Um, I thought a lot about this in my schooling as well. I went to school in Atlanta. There was a very kind of forward looking, uh, integration program for students in underserved schools as measured by performance outcomes, having the option to, um, go across the county to school.

[00:23:36] So, what that ended up looking like in practicality was often black students, sometimes, uh, Latino students. Getting on a bus, riding an hour to the north part of the county where I lived and going to what were previously majority white schools. And because of that, we had about a 50 50 population between white students and non white students.

[00:23:58] All my teammates on, [00:24:00] on basketball teams and baseball teams, like 80 percent of them were black. Uh, many of my fellow students in classes were black and Latino. And so So again, it's just like that conditioning piece of what are your defaults? And so my defaults are half the people around you are not going to be like you from the same background and put the same skin color and income level and whatever else.

[00:24:24] Um, so anyways, all that's like a very long way of saying, I think that shows up in kind of everything that I expect and do both at work and in my personal life. And I also feel quite out of place because I look like that would not be the case. Um, but I feel out of place with people who think like what I look like.

[00:24:48] If that makes sense. That makes sense, yeah. So it's just a weird thing. Um, that I'm also very grateful for. I mean like I would not trade anything in the world for my mom having taught me everything she taught me [00:25:00] about leadership. I think I have an inherently more Empathetic, connected, human oriented approach to leadership because my mom was the one who taught me to lead.

[00:25:10] That's so, so interesting, too, because I think Ben had a pretty, you know, independent mom. It was pretty adventurous and do, like, very much, you know, carves her own path and goes on her own vacations and does her own thing. And I think that's a big reason why there's, like, a lot of respect, like, mutual admiration and respect for us both being the, You know, independent creators that we are, and so I'm always, you know, grateful.

[00:25:35] Kudos to the, to the mums that, uh, you know, help shape, uh. Trailblazers, you know. Yeah, absolutely, absolutely. Yeah, I'm grateful for it. It's um, it's a complex thing, you know, I think, I think my, my view on it is kind of what my view is on most things. It's like, I don't think there's a right model. There's not a right gender based model.

[00:25:57] I think that there are partnerships where [00:26:00] people should make conscious agreements with one another about what's good for each of them. And as long as everyone's in, in there acting from their agency, it's like, great. That works for you. Amazing. And that just happened to be the one, the agreement that I came from.

[00:26:14] Transitioning to coaching

[00:26:14] I'm curious, uh, To kind of pivot a little bit how you think about your work Given that you've you kind of shifted to a new type of work or maybe you were doing coaching before but you know now thinking Of yourself as a coach and really thinking about your capacity and how many people you can work with and I don't know How much the people that you work with when you're kind of taking on Other people's problems a little bit or you're having to really hold space for people like that's a special skill set I'm curious how you think about and divide your time from day to day And how you think about what your capacity is for holding space for other people versus your own ideas that you're really craving to bring forward Yeah, I was really worried about that trade off when I started this In fact, I think I did it I tried almost everything [00:27:00] not To do this path And part of that was just I had a mental barrier on the idea of coaching in general like I had a Default negative perception of coaching Even though well the thing that allowed me to get over it was realizing my coach had been so instrumental to my growth So professional so well trained And I was like, okay, so there are some coaches in the world who are full of it.

[00:27:26] Like they're, they're doing a great disservice to people. And my coach and their firm has figured out a way to train themselves and be that represents what I would like to be. And so that was like the mental hurdle I had to get over first of all. But the next worry I had was, will I feel stifled by not building myself by like being in the seat of, you know, It's not, you're not even really an advisor, just like holding space rather than being the person building something really concerned about that.

[00:27:57] And I'm a year in now [00:28:00] and I'm, it's just like, that doesn't even cross my mind. Um, which is just fascinating. Who knew? I, I didn't know I needed data to back it up one way or the other. So. I don't worry about that as much now. However, I did structure things with that in mind, where I coach on Tuesdays and Thursdays.

[00:28:20] I have eight coaching slots a week. There are four slots per Tuesday and four slots per Thursday, two in the morning, lunch break where I can pick up my kid from preschool, two in the afternoon. Those are the ones available. If you can't do it during that time, I can't coach you. Good boundaries. And so Monday, Wednesday, Friday are then available for my own creative work for.

[00:28:41] Um, business development for volunteering family time and that division has seemed to work. Okay, uh, I didn't have the most creative output in the world last year, but that was because I was growing my practice and making sure I had enough clients where, you know, I needed to take care of income first, basically.

[00:28:59] So now this [00:29:00] year, I feel like I've got enough clients and room where I can work my business development system that I always work. Which is not complicated, just basic outreach and relationship building, um, and make room for creative work, which is really why I love the executive coaching model. It's like I can have as many as 16 clients that comes out to somewhere between, depending on the pricing of individuals and whether they're at a nonprofit or whatever, uh, 35 to 50 grand a month.

[00:29:30] And then with the rest of my time, I can do whatever I want. And I identify as a writer, as a creative person, and I just happen to have a valuable coaching skill set and background now that provides a great business model for that. So I'm living more into that this year as well, of kind of creating that room to make stuff, which feels good.

[00:29:50] Coaching's influence on writing

[00:29:50] How much does the, the calls that you have, the coaching that you're doing throughout the week influence what you're writing about? Like how, I guess, different is your, [00:30:00] you know. Here's what I'm noticing through my executive coaching, or like, how separate are those things for you? Well, I'll answer. I remember there was a second part of your question before, and it.

[00:30:10] Plays into this as well. How do I hold space for the people that I'm working with? I've, I feel like I've been able to have good boundaries in terms of not like taking it home with me, not feeling like it's my job to solve for anyone. Um, And that took a lot of work. I mean, I think in the past I'd be thinking constantly, like, how do I solve this for this person?

[00:30:32] That's not my job. My job is to be with them as they figure out how to solve things for themselves. And ideally to work myself out of a job so that they don't need me anymore. They just have the tools. Um, so the next question was about, um, will remind me. Oh, just that, um, I'm curious if you are writing about kind of what's coming up in those sessions.

[00:30:56] Yeah. Um, yes, definitely. Uh, I try to separate [00:31:00] it by at least a little bit and I don't know if I've ever written a tweet, LinkedIn post. Newsletter, anything else about a session that wasn't also about another client? So it's very rare that problems are unique, that unique, right? The specifics, you know, might be unique, like the specific scenarios someone finds themselves in, but the patterns are common.

[00:31:26] Um, and so I always, I always describe it to clients that like there's the long arc of growth and then there's the little arcs of growth that add up over time. And really the little arcs are like working with different patterns in some ways of behavior. It's like, Oh, here's a pattern that's holding me back and let me work on that.

[00:31:42] And now let me work on the next one that adds up over time to where they want to get to. If they're ready, you know, if they're ready in their inner world to do that. Um, and I, I write about both. I write about the long arc [00:32:00] and I write about the little arcs and I will admit that. I mean, there are times when I'm writing from a place of past pain, you know, it's like I'm writing towards an old boss or an old partner or an old whatever, because now I can see the brokenness with such clarity from the seat that I sit in.

[00:32:21] Um, and then there are times where I'm writing from a place of deep compassion for the common challenges that I see entrepreneurs facing. Um, I think a little bit of that fire is healthy. Too much of it is probably not very good. Yeah. I'm curious how much you are aware in the moment that you're kind of coming from a, yeah, yeah, I think there are times.

[00:32:45] Yeah. There are times when I think like, okay, now remember the whole audience you're talking to look to you for compassion, right? Your audience is not whoever created the pain. Um, And in [00:33:00] fact, they didn't even create the pain. I created the pain in response to whatever they were doing. And I think that's an important distinction too.

[00:33:06] Um, so

[00:33:10] you were going to ask something though, Ben, I cut you off. Ben, did you have something you were going to ask around that?

[00:33:13] How would you coach yourself?

[00:33:13] It was, uh, it was kind of related, you know, in terms of executive Barrett, former executive Barrett. How, like, how would you. How would you coach yourself or how did you wish you were coached at the time when you were an executive?

[00:33:27] Sounds like you got a lot of good stuff from your coach But you know in terms of the way that you would approach somebody like yourself, what would that look like now? I think I Mean, I think my coach did a great job. First of all, I think he He was probably Default more patient with me than I am when I can see someone is In a situation that's not serving them anymore, or they have thought patterns that aren't serving them related to their situation.

[00:33:55] So, I mean, some of it would be [00:34:00] probably going right at making sure I had clarity on the dynamics at play. Um, And how they were triggering old patterns for me. Um, I don't know. I don't know that I would have been ready for that though. I think in some ways, probably the amount of space it took was the amount of space it took.

[00:34:24] Maybe I could have been led along a little bit faster, but I think my coach showed great discipline and letting me arrive there on my own and not being artificially pushed to, to arrive at some conclusion. Um, But now I mean I can just see the pattern so clearly. It's interesting, like I talked to him about that, like how interesting it probably was for him to so clearly be able to see the patterns.

[00:34:48] And just to need to wait. It's like look at the turn, it's shaky. Gently. Some of the job is just being okay. Being okay that in their own time each person will, [00:35:00] will arrive at, um, an understanding. And, and by doing it on their own time it will be much more meaningful than you pointing it out to them. I was going to ask if you thought there were questions he, you almost wish he'd asked that maybe would have helped you maybe notice some of those dynamics earlier or just did it just need to happen at the pace that it happened?

[00:35:22] Like how do you notice the dynamics at play? Yeah, so what's interesting is, is I actually, what I wish for is that he had been with me a year and a half earlier than when we begun our work. We began our work, um, because that was when the conditions were established that set me up for where I ended up. Um, so just to tell the story really quickly, um, I'm going to grab my chair real quick.

[00:35:53] Navigating joining and leaving ConvertKit

[00:35:53] Here, gather a chair. Come around the fire. Gathering around the fire. So I, I [00:36:00] joined ConvertKit. Nathan Berry, the CEO of ConvertKit. Dear friend of mine for a long time, um, we were in a mastermind group together and, um, I got fired at my job at a company called fizzle because I was irritating the living hell out of one of the co founders by being very, very like outcome driven performance.

[00:36:23] I want my job was marketing. My job was to grow the company. I wanted to go to the company and I wanted us to make it really big. Um. Some of that was healthy. Some of that was unhealthy, but in my view, the thing that makes companies big is repeatable systems. People's systems aren't very fun. They're very like boring in a lot of ways.

[00:36:44] And for creative people, if you say, I'm going to put you in a box and that box is the system and we need to run the system. They're like, get away from me. Why do we hire this guy? Yeah, exactly. I can see that pattern. And the CEO was caught in [00:37:00] between the two of us where he wanted the company to grow, but he was in partnership with this other person.

[00:37:05] And so effectively, I forced him into a situation where he had to choose. You're not going to choose the person who's not your business partner. Um, so, you know, from that angle, I have a very healthy relationship to all of that now. And like, I'm very close to both of them. So anyways, Nathan brought me into ConvertKit on the back end of me being fired from that prior job.

[00:37:25] Um, but he wanted that drive. He wanted all the things that I said weren't working before. He's like, yes, come help me grow this company. So I led marketing there for a while. And then I decided that the conditions were not working for me, that I needed to leave in order to, for my career to continue to grow in the way I want it to, for me to be okay.

[00:37:43] So I took a job with a mentor in New York. He was going to pay me like almost twice what I was making at convert kit. We got out of our lease in Portland. Signed a lease in New York. Everything was in motion. I told Nathan I was leaving ConvertKit. Um, I've [00:38:00] told this story on a podcast with Nathan, so this will, none of this will be a surprise to him.

[00:38:03] Uh, we cried together. He came back 48 hours later and said, Hey, what if you stay here as COO and we'll do a whole thing. I'll give you ownership and increase your salary and blah, blah, blah. And I was like, okay. I don't know. That sounds very stressful. I'm moving my life. I've already agreed, you know, I don't know.

[00:38:21] You'd already made the plans and checked out mentally. Yeah. I ended up staying obviously, cause that's how you introduced me was the COO of ConvertKit. Um, but the number one mistake I made was the same mistake I made at the prior company, which was we agreed to something, but there was not a contract in place yet.

[00:38:42] And so there was a set amount of ownership I was going to have by percentage of shares outstanding. We knew those would be partially time based, partially performance based and a number of other things. I now have a strongly held view that it is [00:39:00] the CEO's job to put a contract in front of a person that is agreeing to work for you.

[00:39:07] But it is that person's job not to agree to work for you until they get the contract. So my flaw was, I agreed to a thing, I started acting on that thing, and I did that before I had a contract. And I got rid of the leverage. And it wasn't intended to be leverage, right? But like, in that situation, the incentive for the leader to get a contract in front of you is the other thing that you're going to go do if they don't do that.

[00:39:31] So, a year went by and there was no contract. That's a bad situation to be in. I deeply regret putting myself in that situation because even if the person you're negotiating with wants to do what's good for both of you, all incentive, all leverage is gone and in a negotiation without leverage, you're not negotiating.

[00:39:52] You're agreeing to whatever the other person says. So I think that situation [00:40:00] created the conditions that would end up leading to me leaving that company. And if I could do that over again, or I think I would have done it differently had I had a coach alongside me at that moment, but I didn't. So that's my very long winded story and answer about, you know, if I could have my coach do something differently, it's like I would have a magically appear 18 months earlier and help me work through that so that I can have clear boundaries and operate from patterns that I wasn't ready to operate from yet.

[00:40:30] I think that's a place where he could have stepped in and said, look. There's the long arc of development. There's a small arc here that's like very practical that I want to make sure that you're protected in. Yeah, that the first situation you mentioned where there's that like very outcome driven I want to solve these problems feels a bit related to that like as an ops person You're like I see all the fires and I see where all the problems are and I can imagine there was probably some Some similarity.

[00:40:54] Oh, yeah Yeah Yeah I'm [00:41:00] also kind of curious, maybe when were the first inklings while you were working there that you're like, Ooh, okay, this is either the patterns are showing up, or you're realizing that something wasn't aligned with the kind of work that you wanted to be doing? Well, I mean, the core of the core of what I was challenged by was, Nathan and I had incompatible Um, desires for how big the company was going to grow in staffing and neither one of us was right.

[00:41:31] They were just incompatible. It's like if you married someone who, who didn't want to have kids and you wanted to have kids and you knew that going in, then you're like, well, what the hell? You know, you're wrong, but it just isn't working. Yeah. Chose the wrong partner. Um, so for me, this might not come as a surprise given the work that I do.

[00:41:48] It's like I view. Leadership as my core competency, like that's what I want to be great at. That's what I want to help others be great at and to lead. You have to have team. [00:42:00] Um, and because of all of the brokenness I see in organizational cultures, it's like, I viewed my work as create great culture that makes people want to show up, that, that gives them an environment where they can thrive and do the best work of their careers.

[00:42:15] And so part of the purpose of the organization was to create great jobs. Like that's part of what we were doing there as leaders. Um, you know, not like artificially, I don't think you should ever grow a team beyond the needs of the organization, but I did feel like that's part of what we're doing here. I think for Nathan, he comes from more of a school of thought, uh, that he's spoken to in different cases.

[00:42:39] Like he's talked about, he started the company with a kind of. Limit hard limit on how many people you wanted to have. You want to have 50 people or less on the team. And that was driven by this idea that like Instagram grew to billions of dollars in value with 12 people on the team. And there's examples of this throughout time.

[00:42:56] Um, and I just don't value that. I mean, that's just the bottom line. [00:43:00] I don't value it in that way. And so we had a lot of conflict over that thing. I think without really naming it, you know, it's like we were dancing around it and trying to figure out solutions that would work for both of us. And just ultimately it wasn't aligned.

[00:43:12] Um, And that's okay was the thing that I wasn't able to say at the time. It was like, it was more like, and that's not okay. And, and we're gonna, you know, figure out how to make it work. Um, and I think once we got honest with ourselves that that was at the base, it was a lot easier to be like, Oh, well, you know, what's great is we can both continue to live great lives and not work together.

[00:43:40] And how did you navigate that? Because I know like you'd worked there for a while and you had a deep friendship there. And like, I know, untangling these kind of relationships is like, it's really hard to leave well. And I'm just kind of curious how you guys managed to navigate that through the complexity of that new ego, letting go of things.

[00:43:59] How did [00:44:00] you get through it? Did you guys have a coach or someone that was helping you work through the, the mess of that? Yeah. Yeah. We did a lot of joint coaching, you know, but we each had our coaches. They were both at the same firm. We did joint coaching with them working through all of that. Um, but there was just a day where Nathan said, you know, uh, we've made some compromises on the size of the team that we have here.

[00:44:22] And I, I think I regret those compromises. I think I'd like to try and keep a team small. Um, I have, this was over two years ago, so I have no idea how his perspective may have changed since then. I want to make sure to leave room for that. And I said, okay. If that's the case, I totally respect it, and I know that my time here is coming to a close.

[00:44:42] And so I just want you to think on it for another week. And if you come back and you say, yes, I'm definitely sure that I want to kind of level out the number of people for a period of time, then I think we should make a plan for me to depart. Um, and he came back and he said, yeah, that's what's important to me right now.

[00:44:56] And I said, okay, let's make the plan. And I think that was [00:45:00] March or something like that. 2021. I left at the end of August. It was about a six month transition. Um. In the middle of that, I took a month of sabbatical to make sure it wasn't just like burnout or that I needed space or whatever. And so we told the executive team I was leaving before my month off and left it open with them.

[00:45:20] He might come back and we might say, this is okay. But the default plan is he's leaving. And I came back and I knew even more then that I needed to leave because I had the space to really reflect on. What was and wasn't good for me in the situation. Um, and then we wrapped up, we communicated it to the team.

[00:45:40] I kind of handled all of the communication structure and offboarding, documentation of everything that I did and blah, blah, blah. So I think I left well, which is quite different from the person to person relationship between he and I, you know, leaving the organization well and managing the complexity of the [00:46:00] Friendship, beyond that, very different things.

[00:46:03] So challenging, yeah. I think we're still figuring that out. I still have a lot of pain. He probably still has a lot of pain related to that. Um, and I wrote in my review, I said, I, and the person that's paying the biggest cost for carrying that pain is me. But it's just not ready to move through, you know?

[00:46:19] And I'm okay with that. It's like, it'll move through when it moves through.

[00:46:24] The cost of joy is grief

[00:46:24] I'd love to I'd love to ask you, I feel like this is a decent segue here, about, um, like leaving well in the sense of, um, sometimes I think we don't, when we, when we set aside projects, we, or we see them as failures, or we see like this didn't work out, or I'm still dealing with this, like, I don't think we necessarily take the time to, to grieve the, the change and the change of identity through that.

[00:46:49] And so I know that a lot of the things that you talk about is is working through these emotions and i'm curious like actually I think we both lost our dogs right around the same time [00:47:00] last year and we had talked offline a little bit about The grieving process for that and you know losing a pet that's been with you for so long and stuff And i'm curious about your your relationship with grief and like how how has grief enabled you to feel more joy What are the benefits of?

[00:47:17] Figuring out how to let that move through you and really, you know, that embodied emotion. Yeah. Uh, it's one of my favorite topics and it's one that probably five years ago, definitely 10 years ago, I couldn't even have, I couldn't even have like broached it. Yeah. Sadness is one of those bad emotions.

[00:47:36] Sadness and anger were the two that I was best at repressing. Um, and when I repressed them, they came out as anxiety. It's like, well, can't feel those. So instead I'll get anxious and like, look for stuff in the world that I should be worried about. Um, of course not consciously. Right. So now what I've learned is that crying, [00:48:00] sadness, fear, anger, these are just like base level human experiences.

[00:48:05] Um, one of the things I keep, uh, right next to my desk for anytime I'm having a coaching session is this, um, Emotion sensation wheel, which for audio listeners, they won't see it, but it's like, it's got all the base emotions. And then all of the descriptors that can come out of that for the nuance of the emotions that we experience, because so often we just have like three words we use, um, you know, it's like happy, sad, angry.

[00:48:29] Those are like the ones we know. And there's so much more nuance of the emotional spectrum than that. So I've grown a lot of appreciation for that fact. Having come from a place that's more kind of traditional masculinity of like repress everything Stoicism in the unhealthy sense not the like classical acknowledge emotions Move through them despite that Like the don't acknowledge emotions and act like nothing's going on kind of stoicism, you know [00:49:00] So I view that as I'm very proud of that transformation of being able to access it to begin with.

[00:49:05] And I think it's a really hard arc of growth for people who come from that kind of background, which is a lot of people, uh, because generationally it just wasn't really a thing if you go back 123 generations. Um, so the relationship between grief and joy, uh, is something I'm very passionate about.

[00:49:26] Probably. At least a chapter in a book that I'm working on will be called The Cost of Joy is Grief. I just firmly believe that The Cost of Joy is Grief. Because you can't actually When you don't acknowledge either end of the spectrum, a lot of people won't acknowledge joy because they're scared. They're scared that they might lose it.

[00:49:49] Uh, they're scared of grief. And when you cut either end off, it's like when you're unwilling to grieve, you can't access joy. When you cut off joy, you can't access grief. And so you get this narrow emotional bandwidth. [00:50:00] That's where I lived for a long time. And when I finally figured out how to grieve, it was thanks to my coach.

[00:50:06] Actually, he really helped me learn how to grieve. There's this wonderful book called, um, the wild edge of sorrow. That's about grief that helped me learn how to. Use ritual and thoughtfulness to process as things are happening. Well, I had a lifetime of shit I needed to go back and grieve. I mean, that was a big part of this growth arc.

[00:50:29] I had to like empty the well, you know. It's like, damn, there's a lot down here. Um, but to come back to the, the dog thing. So Hank, Hank was our black lab. He had been with us for, um. 14 years. I got him my second last year of college, uh, or last year, whatever in college lived at the fraternity house for his first year or something like that.

[00:50:53] God knows what that dog saw did a, um, [00:51:00] and so he was our, he was our like Marley. Um, he, he was, he entered my life a month before my wife did. And, uh, You know, he had cancer. It was a tumor in his mouth. It was very visible. It was, we waited too long, which every dog owner that I've ever talked to basically says the same things.

[00:51:18] You just can't see it. You know, you can't see it happening, um, in an objective way, I should say. So we had him euthanized in our backyard. It was. Beautiful. And I feel like it was literally at the first moment in my life where I could fully process grief appropriately as it was happening. I had just gotten done, like, digging out the well, you know, of backlog.

[00:51:47] And I was so grateful. That I could grieve properly because I could experience so much joy and presence and just thoughtfulness in his final days and the days [00:52:00] after it and just allow myself to cry and be with it instead of like what I used to do, which would be repressed and then get like panic attack inducing anxious.

[00:52:13] Um, so anyways, that was, that was that experience. And I just think, you know. There is no formula for learning to do it. Mm hmm, but like If I was gonna give someone an exercise there's a Okay, so the woo woo ness of coaching I just like is so hard for me because I both Can hear it before it comes out and I just can't say anything other than that.

[00:52:39] It works sometimes. So anyways One of the postures I really love is a hand over the heart and a hand over the gut Center You know, just standing with yourself, you know, ideally with yourself, especially if this is the first time you're doing it and I always When someone's going through this and coaching with me for the first time I say, okay hand over the heart and I want you [00:53:00] to imagine That there's a string growing either out of your finger or out of your heart Towards the opposite, you know from your heart towards your finger from your finger towards your heart and that you are Developing a direct attachment as if it is an electrical wire and I just want you to Um, allow whatever flows through that string to flow and just describe to me if you want or keep it to yourself what comes up.

[00:53:26] And so often what comes up is pain because that's where it lives. It lives in our body when we can't express it lives in our body somewhere. And we often associate that with the heart. It's like where our deepest, most, um, personal feelings live. And just that exercise and writing down what's coming up for you is probably a starting point for exploration with the therapist or with yourself to say, okay, I might need to cry about this.

[00:53:54] I might need to yell about this. I might need to do any number of things to help process it. But as you go through [00:54:00] it, the thing I love about the Wild Edge of Sorrow book is it has all of these examples of ritual that conclusively allow you to act out an ending. And By acting out an ending, it gives closure to something that is otherwise ephemeral.

[00:54:16] It's, it's, a dog's soul lives in the ether, you know? It's like all dogs go to heaven, where does it go?

[00:54:25] Whereas rituals, like for us, the ritual was the euthanasia and having him cremated, and then we bought a statue and put it right next to where we cremated him. Or, uh, sorry, right next euthanized in our backyard. Um, And there was a processing that came along with that and on the day we like put the statue out there, I just sat out there and cried at the base of it for a long time.

[00:54:50] I couldn't have done that five years ago. I just didn't have it in me. I didn't know how to cry. It sounds ridiculous. You know, I just didn't know how to cry. So [00:55:00] for a lot of people, a lot of men, especially, I don't want to limit it to just men, but a lot of men, especially, you just got to learn how to cry.

[00:55:06] Um, because that's a part of grief. It's kind of uncanny how similar the experience is. I don't know if, Ben, you're comfortable sharing any of your experience. Oh, yeah. Yeah. I mean, our dog, our dog Mochi was also 14, uh, was, came, has lived with me for, uh, I say, I like to say this a lot, two wives in two countries because, uh, I adopted her when she was eight when I lived in the U.

[00:55:32] S. and now I'm in, in, uh, Canada. And yeah, like the, I do feel that that sense of the polarities there where, like, I was definitely living in the middle because when I started feeling this level of grief and anguish, like, for the loss was, like, I Couldn't understand it. It made no sense. It was like I've never actually felt this emotion before and It just gave me this renewed appreciation like, you know, like I [00:56:00] almost see it more as like rather than a polarity but more like a Circle where like you get over to one other side and you can kind of peek around the edge to see the other side a little bit so you're so the thing of like it Giving me a renewed appreciation for my capacity to love a creature and people and things like that And I also we also experienced the same the same rituals where we got Mochi cremated I put her in these little put her in these little vials and jars that I put all over the house So anytime I catch one out of my eye, it's like this reminder.

[00:56:33] It's the The momenti mori thing, you know, always think about death and reflect on that. And yeah, I took one of her when we went to japan for a month recently and I took her around with me and you know It felt like this kind of Like completion ritual in a way, you know, she was uh, we adopted her from a breeder outside of seattle That had a partner in japan So she had come over from japan and then like I was like almost like returning with her to [00:57:00] To make this like ritual complete.

[00:57:02] Yeah All that stuff just really helped unlock, unlock things and cry about the stuff and and Having this like beginning and end kind of you know, the circle is complete kind of thing felt really good. Yeah. Yeah Yeah, the the other tool Just seems so obvious now that I started using this here was writing I'm just writing about the emotion of it and the grief of it.

[00:57:28] I My uncle died this year my my dad's brother and that was his Last relative from his family of origin. And so my dad's kind of alone now and that made me really emotional. It gave me a lot of grief, not just for the loss of my uncle, who I wasn't very close to, but for my dad and his experience of what that must be like.

[00:57:48] And writing on the plane home was just such a powerful. It was, I didn't have anything else to do, and I think it was the first plane ride I was by myself, number [00:58:00] one, and I just cried the whole way home, basically, while writing about, uh, who my uncle was, what he meant, what his life must have been like, what it means for my dad to be alone now.

[00:58:10] Um, I think you have, you kind of have two options with those emotions. You either let them move through you or they live in you. Um, and I, it's. really toxic to let them live in you without moving through. Um, you know, the version that lives in you after you let them move through is very different from the version that exists if you don't let them move at all.

[00:58:35] It's a great, I think great framing of that to understand. Yeah. It feels different after you've, it's like the, you know, our last guest Joe Hudson talking about, it's really the resistance to emotions that hurts. Yes. It's not like the sadness itself hurts. It's actually like trying to resist that feeling that actually causes us the most pain.

[00:58:54] Yeah. And I think the, the most unhealthy expressions of them, you know? Yeah. [00:59:00] To say I am angry can be said just like that. I'm feeling angry. You just said it hurt me, I'm hurt. Um, but what we more often get is being yelled at or someone acting it out, slamming a door, you know? And it's saying the same thing, but the release from naming it is so much, for me anyways, it's been so much healthier and in some ways easier than just having to act it out and let it find its way out of me in some other way.

[00:59:34] Power of memoirs

[00:59:34] You mentioned I don't know if it was on Twitter or threads, but something about how you felt that reading memoirs was, you know, so much more powerful than, um, various personal development books. And I was thinking to myself, like, A question I would have for you is, what's the title of your memoir, or what are the breadcrumbs and themes that would show up in your memoir, and is what you're writing a memoir, or is it something different?

[00:59:58] Yeah, uh, [01:00:00] I am, so I'm in a class with a teacher, a woman named Ruthie Ackerman, former New York Times columnist and an author herself. My wife introduced me to her. She runs a year long class to write your book, which is personal writing focus, mostly memoir. Um, if you'd asked me, so I gave a TEDx talk in 2013 or something like that.

[01:00:23] And if you'd asked me who my idol was for writing, it was like some combination of Dan Pink, Adam Grant, you know, Malcolm Gladwell, like very data driven, everything cited and anecdotes and data and blah, blah, blah. And I think I try, I basically tried to mimic Dan Pink and giving that talk is why I bring that up, which is amusing looking back, you know, um, Um, if you had asked that version of me, would you ever imagine yourself writing a memoir?

[01:00:52] I'd be like, come on, what a ridiculous thing to do. Like maybe if, maybe after I'm president of the United States or something, [01:01:00] um, and now I think it's just reflective of my emotional growth. It's like, there are no one size fits all solutions for anything. It just doesn't work that way. Um, even hammering a nail, there's a hundred ways to hammer a nail.

[01:01:17] You know, but that, that nuance gets lost in social media and in how to, and, and self help and all of that. And there's nothing wrong with it because methods can work for different people. And I think there's a lot of like truth and beauty and people's pursuit of methodology. Um, but I think a reflection of my own growth is that I now know that no one methodology is going to solve my problems.

[01:01:44] And I can read stuff that gives me a methodology with an openness to learning something. But to think that applying that is going to finally make me feel the way I want to feel is just a fool's errand. Um, and so out of that [01:02:00] has come a new appreciation for the beauty of story, for helping people make their own meaning rather than making meaning for them.

[01:02:10] And I think it's a big reflection of the core practice of coaching is like, If I'm making meaning for you as my client, I am really I don't know if I'm allowed to cuss But you can bleep it out later. I'm really fucking my job up Because I'm robbing you I'm robbing you of the opportunity to make your own meaning and on some level every system robs you of the opportunity to make your own meaning I Don't think that's necessarily completely bad I think for A long time, I needed other people's systems to help me get where I've gotten, to be able to have the possibility to process through stuff.

[01:02:49] But at this point in my journey, I gained so much from making my own meaning of other people's stories. And someone basically asked me, it's like, I can't read memoir, [01:03:00] like it seems self indulgent and ridiculous, so can you help me understand your point better? And I gave him a few examples. I said, I look over here because these are my bookshelves and I always love being able to look at everything I've read here.

[01:03:11] Um, so memoirs I've read in the past year, I read a book, uh, Paul Newman, uh, memoir that's like posthumously compiled by his children, I think. And that one was just pure, that's like the celebrity style where he was famous. You know, he was before really, I, he came before really, I appreciated that his like work, um, I was too young to appreciate him as he was doing his work, I guess, is another way of saying it.

[01:03:39] So I read that just from a personal interest standpoint, but then I read one called, uh, Deep Creek. And that was about this author and writer who purchased a ranch in the high country of the Colorado mountains and lived there alone for a lot of years. You know, she had partners on and off, but like. That was the place she carved out for herself as her safe [01:04:00] place, and it was about nature, and climate change, and trauma, and like, parents, and, you know, all the things we do to heal.

[01:04:07] It was beautiful. It was like the intersection of a lot of things I needed to see and read. And then I read one called, um, You Can Make This Place Beautiful. It's right here. I just happened to order it, and it was used. And I didn't know whether I would even like it, but two people had recommended it to me, my wife and the teacher of that class, and I opened it up, and it was signed, and it is by far my favorite book I read last year.

[01:04:36] Wow. It is a book about, presumably, getting divorced and trying to heal from it. I'm not divorced. I don't plan to get divorced, but, and it wasn't, I wasn't reading it because I planned to get divorced. I was reading it because it was recommended to me as a beautiful exploration of what it means to grieve the loss of something.

[01:04:58] [01:05:00] And what I took away from that book was actually that it's a book about healing ourselves. And then Using that healing power to then go do something good, you know, it's like how to be a parent, how to lead, how to heal from hard shit that happens to all of us. And it's just so beautifully written and formatted in such an unexpected way.

[01:05:23] I couldn't have gotten that from like, I can't get that from someone telling me how to heal. You know, it was by reading her experience. In her writing style that then allowed me to say, here's what this means for me right now in this moment in time. So to me, that's what memoir is. And if I were going to name a memoir, it would be a line from Deep Creek, the book I mentioned earlier, which I think you all have heard me say.

[01:05:48] Uh, I would call it an unbearably beautiful future. And the reason why is, I've always said I'm like, I'm an optimist. But I think, in a [01:06:00] way, my optimism Was rooted in trying to avoid negativity, trying to avoid negative feelings, trying to avoid sadness and grief and everything else. And there's this thing that happened to me when I started learning to actually feel grief, which was like, now everything can be even better.

[01:06:21] Like this is even better. I can like fully experience sadness. I can have had something, a relationship, a job, uh, whatever. That I love so much that I have to cry to process through what it means to lose it. And that's where that line comes from in the book. She's talking about realizing that you can heal enough for the future to be so unimaginably different from today that it's almost like I don't want to touch it.

[01:06:52] Like a hot stove. I love that idea. It's so reflective of where I've landed, I think. [01:07:00] Current place Maybe and who knows what that'll be like in a year and ten years and everything else. I Love that and I think that's maybe a beautiful way to to wrap up the conversation and just

[01:07:13] A beautiful future

[01:07:13] What is the sort of beautiful future that you are imagining and even just kind of what's next for you?

[01:07:18] Like what are you most excited about right now? Yeah Well, I mean, the most beautiful future I could imagine is a future where everyone has the access to resources to process through their own, their old pain and integrate it to live just a fuller, healthier, holer, holer is not a word, but you know, holer life where they can operate from a place of alignment with themselves.

[01:07:46] Um, because I think that would eliminate it. A lot of the pain we inflict, you know, when we are able to heal our own pain. I know it's not fully possible, but I think it's worth working towards. [01:08:00] Um, and I've come to believe that coaching is an incredible tool when taken seriously and when treated with the proper care for helping, for being a part of what helps people get there.

[01:08:14] Uh, it's also inherently unscalable. I mean. There's like maybe not a less scalable profession

[01:08:23] And I love that about it because I get to have such deep deep impact on each person But I also know I'd like to reach a lot more people So I am taking this writing class. I'm gonna write a memoir and the only purpose I'm giving that memoir is to give my two boys the permission to do all of the exploration of their pain that they need to do when they reach the point when they're ready And then I will be there for it for whatever they need in that process.

[01:08:50] Um, and I want to share my story in such a way that makes them feel totally safe to do whatever they need to do to feel whole. [01:09:00] Um, and I hope and think that maybe that might help other people too, but I'm only, I'm only setting out with that purpose. And then the other thing I'm doing is I'm making my own podcast right now.

[01:09:09] That'll come out sometime near when this comes out. Um, And that was largely inspired, I mean, that was the topic of my hot seat when we were together in Breckenridge, what is my podcast going to be? And that session basically gave me permission to make my podcast whatever I want it to be, that my coaching earns my living so that I can make my creative work whatever I want it to be.

[01:09:31] And the triangulation that I've been giving as kind of like guideposts is I'd like it to occupy a space somewhere in the middle of Uh, Krista Tippett's On Being, which is just like an absolute classic of the podcasting and radio genre. Tim Ferriss show, which has some things I hate and has some things I love.

[01:09:51] And then a show called 80, 000 Hours, which is a show from the effective altruism movement about, um, the most high impact careers [01:10:00] you can take on from like a Data driven perspective, it's annoyingly nerdy. And so I don't want it to be any of those things, but if it was some mix of a little bit of all those things, I think that would be really awesome.

[01:10:11] Um, and I'm interviewing what I'm calling high impact leaders who are, or leaders, thinkers, and artists who I think are working to, um, build a better world and some concrete way, and that doesn't have to mean they're building nuclear power plants, but it might. It might mean that they're writing books like You Can Make This Place Beautiful that are helping people heal and learn about themselves.

[01:10:37] It's gorgeous. Beautiful. Yeah, it's really beautiful. Looking forward to being a subscriber and a fan of yours for the next decade or so. Absolutely. Thanks, y'all. Yeah, where can people find, uh, I guess more about you or your work? What's the best medium for people to explore your writing? Yeah, the best, absolute best medium to stay in touch is, um, by subscribing at [01:11:00] barrettbrooks.

[01:11:00] com. Um, classic email call to action there. Um, I'm sending a Saturday newsletter this year, and then I'll send emails for my podcast, and I try not to do much more than that. And, uh, and then Twitter is probably where I'm most active, although I've been picking up on LinkedIn too for I don't know, some people really hate LinkedIn, but if you like LinkedIn, I'm there as well.

[01:11:24] And that's Barrett A. Brooks on any social platform. You can find me. Awesome. Amazing, Barrett. Thank you for just being so, so you, just so open, so vulnerable, so thoughtful in the way that you show up. It's truly inspiring to us. Writing down all the book. I'm like, okay, it's time to check out memoirs, which is something I might not have even thought of doing until I saw your writing and I thought, what a beautiful way to learn more deeply about those lessons than frameworks.

[01:11:55] Like, I'm just really grateful for that little, little note. Yeah, [01:12:00] there's a place for both. Yeah, yeah. Well, thanks, y'all. I'm so grateful for you having me on. And I'm really grateful you're making the show. I think it'll be important for everyone who ends up listening. Thanks so much. Amazing. Thanks so much Barrett.

Creators and Guests

Benjamin Borowski
Benjamin Borowski
Notion warlock at, Systems at, volunteer firefighter, hacker, DJ
Marie Poulin
Marie Poulin
Taming work/life chaos with Notion • Leading • Online Courses • ADHD • Permaculture
Creating a Beautiful Future with Barrett Brooks
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