David speaks with Barrett Brooks, a writer and executive coach specialising in guiding mission-driven founders and creators through emotional and strategic barriers to business growth. His writing focuses on leaders and companies tackling critical societal issues such as climate change, biodiversity, education, food systems, healthcare, and circular products. Previously, he was the managing editor of The Carbon Almanac (a bestselling book on climate change led by Seth Godin), COO at Good Coffee, and COO at ConvertKit.
They talked about:
🧩 How past experiences cause startup misalignment
⚠️ The negative side of self-imposed challenges
⚖️ The tension between achievement and fulfilment
🥊 The inner battle behind our external pursuits
🧳 The burden of generational trauma
🌱 The transformative power of mentorship
This is just one part of a longer conversation, and it's the third part. You can listen to the earlier episode here:
Part 1: 🎙️ Purpose, Passion, and Perseverance with Barrett Brooks (Episode 109)
Part 2: 🎙️ The Diary of a $30M COO with Barrett Brooks (Episode 112)
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🎧 Listen on Spotify:
📹 Watch on Youtube:
📄 Show notes:
[00:00] Introduction
[02:10] Why job choices matter for startup collaboration
[05:32] When intentions align but outcomes don't
[07:00] Lessons in growth and resilience from ConvertKit
[10:13] The role of operations and data in a business success
[12:16] The challenge of over-responsibility
[14:10] How internal competition drives us
[17:12] Balancing ambition and the fear of missing out
[19:51] No achievement can replace self-love
[22:04] How writing became Barrett’s path to self-acceptance
[23:56] Work smarter, not harder
[25:37] Finding the courage to be who you are
[27:32] The hidden impact of generational trauma
[30:00] The strength in connection and acceptance
[31:26] What Barrett learned from his key relationships
[34:23] Lessons in love and leadership
🗣 Mentioned in the show:
ConvertKit | https://bit.ly/convertkit-de
Nathan Barry | https://nathanbarry.com/
Google | https://about.google/our-story/
SpiderMan | https://en.wikipedia.org/wiki/Spider-Man
Peter Parker | https://www.marvel.com/characters/spider-man-peter-parker
It Didn't Start With You | https://amzn.to/3WU7iJe
Mark Wolynn | https://markwolynn.com/
The Wild Edge of Sorrow | https://amzn.to/3YCJWJI
Francis Weller | https://www.francisweller.net/
Andy Crissinger | https://www.reboot.io/team/andy-crissinger/
Reboot | https://www.reboot.org/
Seth Godin | https://theknowledge.io/freestyle/
👤 Connect with Barrett:
Website: https://barrettbrooks.com/
Twitter: https://twitter.com/BarrettABrooks
Good Work with Barrett Brooks: https://www.goodworkshow.com/
👨🏾💻 About David Elikwu:
David Elikwu FRSA is a serial entrepreneur, strategist, and writer. David is the founder of The Knowledge, a platform helping people think deeper and work smarter.
🐣 Twitter: @Delikwu / @itstheknowledge
🌐 Website: https://www.davidelikwu.com
📽️ Youtube: https://www.youtube.com/davidelikwu
📸 Instagram: https://www.instagram.com/delikwu/
🕺 TikTok: https://www.tiktok.com/@delikwu
🎙️ Podcast: http://plnk.to/theknowledge
📖 Free Book: https://pro.theknowledge.io/frames
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🖥️ Decision Hacker: http://www.decisionhacker.io/
Decision Hacker will help you hack your default patterns and become an intentional architect of your life. You’ll learn everything you need to transform your decisions, your habits, and your outcomes.
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🎞️ Descript: https://bit.ly/descript-de
📨 Convertkit: https://bit.ly/convertkit-de
🔰 NordVPN: https://bit.ly/nordvpn-de
💹 Nutmeg: http://bit.ly/nutmegde
🎧 Audible: https://bit.ly/audiblede
📜 Full transcript:
Barrett Brooks: There is something in my psyche that wants to say, all right, let me collect all the problems and I'll take care of them for everyone. Let me take care of all the world's sadness and all the world's pain and all the world's negativity. I'll take it all on so that everyone else can be okay.
That is a very bad thing for every, not just for me, for everyone else around me when I do that in an inappropriate way.
And so that was the hard part that I really could not see accurately at the time that I was taking on stuff that in some cases I couldn't solve. And in other cases, it wasn't my job to solve.
This week I'm sharing the third part of my conversation with Barrett Brooks, who is an executive coach, and also a business writer. Barrett has had a really interesting background, most notably being the chief operating officer at ConvertKit where he helped them to scale from 3 million to over 30 million in ARR and also being the COO of companies like Good Coffee.
So in this episode, you're going to hear Barrett and I talking a lot more about the personal side of business. We talk about the internal struggle of leadership and why achievement isn't enough to feel whole.
We talk about our writing practices and the risk that comes with writing authentically, and some of the hidden costs that come with overcommitment. Finally, we talk about the gift of healing from the past. And also more specifically, I talk to Barrett about some of the key relationships that he'd had at various points in his career.
So his relationship with his partner, with mentors, with coaches, and asked for the lessons that he learned from each of those different types of relationships. So you're going to hear a lot about the impact of mentorship and support on your personal development as a business leader and also as a individual person as well.
So you can get the full show notes, the transcript and read my newsletter at theknowledge.io and you can find Barrett online on Twitter @BarrettABrooks his website is Barrett Brooks. He also has an awesome podcast, Good work with Barrett Brooks, which you should definitely check out.
And if you love this episode, please do share it with a friend. And don't forget to leave a review wherever you listen to podcasts because it helps us a ton to find other listeners just like you.
David Elikwu: Okay, you make a really interesting point, which has made me think a lot about the relationship that I had with my co founder as well. And he's, he's a dear friend, you know, someone that I love dearly. And, you know, we've talked a lot about very similar things, I would say. And it's funny, even just with the last part that you were saying, it resonated a lot. This idea of, yeah, like, you know, how people develop, you can't always track it based on the nature of your relationship and the point that just came to mind just as you were sharing that it just, and I don't know if I'd necessarily thought about it in the same way, but yeah, like it just hit me that we had decided.
So I'd been kind of, consulting slash working with the business for a while before I eventually joined full time. And so we'd been talking about it, talking about it. And funnily enough, at the time that I joined the startup that I mentioned, I actually had three really good job offers.
One of them was actually to be a director of growth at some other business, like a startup that was doing quite well. Another job was to be like an intrapreneur at an insurance company. So it was weird, like not necessarily what I would want to do, but the job itself seemed like an amazing job. I think the business had originally started as a general insurance company. And so they had developed to a few million doing that. And then the part, the segment of their general business that took off was purely doing pet insurance. So they'd become a pet insurance company, but they actually had a mini business within the business that was all this old stuff, because they still have all these recurring premiums from when they were doing general insurance. So they wanted someone to come in and kind of own that small little part of the business. And that would have been cool. You'd be like a mini CEO of like, a few million a year business, et cetera.
So I had that on the table and then I had the opportunity with the startup that I did join, which was, Hey, you know, this is a startup with a lot of potential, great opportunity. They've just raised this round. They need some people to come in and be part of the like strategic or operational backbone and to scale to the next few levels. And it did go on to become a unicorn, which was great. But when I was considering those options, I spoke with the guy that became my co founder, my friend about these opportunities. And we weren't just talking about what would be best for me personally. We were also talking about it through the lens of, Hey, eventually he wants me to come and join this startup full time. And that is also what I want and which job would actually give me the best skills to be able to then come in and join this business. And so that was interesting for two reasons, because I said in that business for a few years. It's interesting that, okay, we kind of made that decision together. Like the job that I took was the best job, not just for me in terms of my development, but was specifically would give me the best possible skills to them, maybe come and do this down the line. But also kind of in the vein of what you mentioned, it's interesting how I learned so much in that journey of going and doing this other thing that by the time I now come back and say, okay, cool, let's go. Here's how I think we should do things. And I'm trying to implement a lot of the things that I've just implemented in this other business. It then can create some friction or it doesn't necessarily work in the same way. I'm like, Hey, you know, we need to have this CRM. We need to run this in this way, you know, and I'm just trying to port over a lot of these things that I've learned. Now there's actually a bit of a disconnect because we were previously aligned now and now there's some misalignment.
And again, doesn't necessarily affect our relationship. We still have a great relationship, but it's interesting how those things can happen as well.
Barrett Brooks: It's just fascinating how the variables change over time, you know? And, and even if we think, okay, if we had gone back and done it differently, would it have turned out differently? And it's like, maybe, maybe not. Maybe there would have been a different set of things that come up, right?
I think ultimately what did not work for me that I had to leave to go answer for myself was there was a, an internal view that I had of myself, or maybe just like hopes that I had for myself or what I believe my potential was in terms of being able to lead. And there was what I felt Nathan's view of me was intentional or not intentional. And they felt out of alignment with each other. I felt that my view and my hopes were higher than or maybe that we were behaving, then our system of behavior was allowing me to realize at the time, even though I think his aspirations for me were similar to my own. And so there's this interesting thing in relationships, right?
Where like our declared intent can sometimes be the same, but our behaviors might prevent that from coming true sometimes for reasons unknown to ourselves, for deeply psychological reasons from our past tied to fears or hopes or other things that are going on. And so even when you think you're aligned, there can still be forces at play that cause those things to get out of alignment or not to come together in the right way to make it work out.
And I think there are elements of that, that are still a mystery to both of us. We're not quite sure exactly why it didn't work. We just know it didn't. Relationships are complicated in that way.
David Elikwu: Okay. I'd love to know two more quick things about convertkit separate from your relationship with Nathan. One is, is there anything that you recall a particular, it could be a challenge or, or something that you did or had to figure out how to do that unlocked a step function in growth or development in some way. I know you've written about some culture stuff before. I don't know if it's really, it's a culture or perhaps just related to general operation of, okay, here's something that we had to figure out to unlock this next level of growth.
And then I'm also interested in for you as a person, again, outside of the relationship part that you mentioned, you mentioned the term failing upwards before, right? The trajectory definitely feels like up, but I know that the reality is that there's loads of ups and downs.
And so I'd be interested to know for you personally, what might have been the hardest thing to get through during that time as well.
Barrett Brooks: Okay. I mean, yes, we learned so much. There are so many things that we unlocked. I don't know that this directly led to revenue growth, but it created the conditions for the rest of the team to generate revenue growth. So the three categories of problems I would say we like really nailed.
One is, financial knowledge and planning for the business. So how do you budget account for project for revenue and all of the expenses that are going to come in? I think that the system that I came into and the system that was there when I left worlds apart, and they were going to need to reinvent it again for the next stage of scale. So like, that's almost always true when you have a rapidly growing business, but I think that our financial knowledge and planning was much better then it had been, and we still had a really hard time accurately predicting revenue going forward. So like we would budget for what we wanted to do, but we couldn't always tie all the variables together to say, yep, that's what we're going to hit. And so that was the next level of maturity that I think that they'd been working on building from what I understand and see from the outside.
The second category of things was creating an equitable and motivating compensation structure and we put in place a few things that were very effective. We have a standardized salary system that we put in place at convertkit. We have a equity award system that's in place there now, and we have a profit sharing system that's in place there.
All of those things did not exist before I took over as COO. And obviously there was a huge team that worked on all those different things. It was not just me. I was just kind of like, helping coordinate and spur the team on.
Those things are still in place and are very effective. We talked about some of the pitfalls of them on that podcast I mentioned, but largely they have done the job they set out to do.
And then lastly was putting in place a hiring and recruiting system. So hiring is like this famously challenging thing to get right. And I think that we went from what most startups at that stage do, which is like, somewhat structure, but also somewhat haphazard hiring that like, depending on the manager that might be doing it or the role we're doing it for might be completely different to a much more standard. Here's the flow of the process. Here's the communications around it to candidates. Here's how we go recruit people proactively. Here's how we seek people inbound and then how we funnel them all through the process so that we get the right outcomes for roles that we need to fill. I think that process was like infinitely more mature when I left than when I joined.
And those are a lot of the core of what operations is, you know, it's like people, finance, legal challenges. I led the data team as well. So we had a whole data process that we put in place around. This gets a little bit nerdy, but basically putting in the infrastructure on the backend so that you have access to the appropriate data that you know what it is, you know where to find it, you know how to warehouse it so that it can be accessed without affecting performance of the application, for example, for reporting. And then that you're able to have it structured into reports in such a way that your everyday person within the company can use it. So there was a lot, a lot of that kind of thing that went on behind the scenes too.
And all of that type of stuff creates the conditions for a company to continue to be able to scale beyond a certain size, because you can kind of have like brute force growth methods up to a certain point. And then you need really smart data and information to inform continued investment in the business.
And if you don't know what's working at a certain scale, there's no way you're going to continue to grow because you're just going to be throwing things at the wall. And the more you do that with the more money that's at stake, you know, when you've got a $10 Million marketing budget, for example, you can lose a lot of money really fast if you're not sure what's going on behind the scenes.
So those are the kinds of things that we worked on that made me a lot more confident that I'm fairly certain with like, let's call it 90% confidence that I could have led through 150 or 200 people before I hit my like, okay, now we're really operating with a new set of things here that I have no idea how to do. I might've been able to figure them out, but I don't think I can credibly say I would be a very good COO for a 250 person company. I don't know. So, you know, kind of to your point that I think there are these stage gates where maybe it's 10 people, 50 people, 150 people, you know, somewhere in the like 350 to 500 and then beyond that, yeah, I agree with you. You're kind of a corporation, whether you're a public company or not.
So that was that end of things. And then you asked me the second question, which was what was hardest, right?
What was hardest for me was the inner doubt and harshness that I experienced with myself. The internalizing questions, whether they were coming from a co worker who was angry that I got the job that I got and they didn't. Whether they were coming from a customer who assumed ill intent on our part or the incompetence on our part by not having the product work the way they wanted it to, whether it was someone giving us feedback about the way that we were leading internally that was affecting them negatively.
I think I internalized basically every negative thing coming at us because Nathan and I very much operated as co leaders of this company. I took it personally. I took it as if it was my burden to solve every one of those things. I've done a lot of work internally since then to figure out how to right size my responsibility. Like, how to determine what really is my work in a given moment in time. Versus this, like, almost arrogant or egotistical tendency to say, here are all of the problems in the world. They are all my responsibility. Like there is something in my psyche that wants to say, all right, let me collect all the problems and I'll take care of them for everyone. Let me take care of all the world's sadness and all the world's pain and all the world's negativity. I'll take it all on so that everyone else can be okay.
That is a very bad thing for every, not just for me, for everyone else around me when I do that in an inappropriate way.
And so that was the hard part that I really could not see accurately at the time that I was taking on stuff that in some cases I couldn't solve. And in other cases, it wasn't my job to solve.
And I think now I have a much healthier relationship between what's my job and what's your job. Like if we are in relationship with one another, what do you need to take responsibility for? And what do I need to take responsibility for? And how can we be honest with each other about that?
David Elikwu: I think that probably ties decently to the other thing you mentioned before about this idea of kind of chasing the edge, and I'm interested in the extent to which that might be synonymous with ambition. I'm not sure if it 100% is in the way that you're describing it, but I'm thinking for myself that there's a lot of that that I definitely experienced. And I think a lot of it comes from for me, anyway, and you can explain the extent to which to you might be different.
I have like a deep sense of internal competition and they often leads me not in the right direction, sometimes it's fantastic. And the only reason I managed to get things done is just because I just won't let something go if I internally challenged myself to do something, then I kind of have to do that thing.
And sometimes that can be great because that gives me drive. It gives me ambition and it gives me a lot of other things. It can also not be good because there are times where I would just doggedly do something, just for the sake of doing it.
An immediate example that comes to mind, even though I think it worked out, I mean, it was fine. I enjoyed it, in retrospect. Is I did a walk, I think it was like 81 kilometers in a day, a few years ago. And it's funny because that was something that, yeah, I know. I think it's actually harder than even as I say it, it was genuinely one of the worst things I've ever done in my life. I think I was walking for about 17 or 18 hours straight and you can't really stop because if you stop, my feet would hurt too much. And to make it even worse, I only gave myself a month to prepare. And I did it in the middle of the summer. And obviously this just sounds silly. And I was doing it completely myself, it wasn't part of some organized thing. And you say, Oh, why would I do that? And I will say, Oh, I was raising some money from charity. Is that the reason I did it? Not really. Like that's the excuse that I had to put in place to give myself the justification for doing it. And I did want to raise the money for charity. And I'm glad that I did that. But the idea just came to my mind one day. I think I heard the recommendation of, you know, someone says, Oh, you have to do 10,000 steps. And I was just like, Oh, what if you did a hundred thousand steps? And then I converted and calculated like, what that would actually be. And it's basically like two back to back marathons. And I was like, Oh, you know, what if I did that? And I think I Googled and I couldn't actually find anyone that had done it in one day actually walking, I'd seen some examples of some people where they did some bits on the treadmill. They did some bits walking and then, and they took breaks in between. They were doing lots of different things, but I couldn't find anyone that had actually just done it in one go.
And I asked a friend who was a doctor and I asked for their thoughts before I, you know, said out loud that I'm going to do this thing a month from now. And they basically said, no, don't do that. Cause I think at the time I'd only walked, the most I'd walked was about 14K. So I'd walked 14 K and even that felt hard that took like a few hours and they were like, yeah, no. I'd already said in my head that I wanted to do this thing. And even if no one else knew, I could not imagine giving up. If I had given up, or if I had just said, Oh, actually I'm not going to do it. And it was for any reason other than there's something stopping me from doing it. I don't know. It just felt like it would have haunted me. So I just knew I had to do it.
The first week, I think I did 20K for the first time. And then the week after I did 30K for the first time, the week after I did 50K for the first time. And then the last week I did the full 81K. So the last week, like the ground I was covering, I'd never actually walked there before. Like I've never, I've never even been there. I was just doing it for the first time.
So anyway, all of that is just to explain that sometimes this drive that I have can lead me to do irrational things, but I'm just interested in the tension that exists for you when you talk about that edge because I know the more common example, at least for me, was leaving law. I had decided I wanted to work in corporate law. I wanted to work in finance and banking law, that is exactly what I wanted to do. That's exactly what I did. I worked at the dream firm that I always wanted to work at. Like everything, I was doing the thing, but when I came in, I had this ambition of, Oh, I wanted to make partner, right. And so obviously I went on this journey where I figured out actually, you know, I want to leave and I want to do something else, but in my head, I kind of had to substitute partner for, Oh, I just want it to be a competent executive. Like I had to recreate or redefine what that goal was to give myself permission just to leave that thing. But it's interesting that even since then leaving and going and doing other things, there's a sense in which if I haven't achieved the maximum thing, if I haven't done whatever I thought was the edge of what I could possibly do. It feels like I'm leaving something on the table. And then even now, as I'm kind of, you know, running my own business or, you know, for now I'm not working full time on anything else, there's a part of me in the back of my head that's like, do I need to get another job so I can tick this off like I don't know if you've played any video games, but like there's this star I haven't collected, which is getting to the very top of an organization. If I haven't done that, I haven't achieved that thing. I don't know, I can't just die and, you know, and go off and do something else, like I have to do that thing.
So yeah, I'm interested in how that resonates with you in the context of what you just mentioned.
Barrett Brooks: Yeah, it resonates a lot. I mean on the video game thing, I'm a completionist. If I have not done every single challenge in the video game, then I haven't done it right. And that's why I don't play a lot of video games because I get obsessed. But in life there are two ways, I'll, I'll answer this to frameworks that I've come to.
One is, why am I wanting to do this thing to begin with? Whatever it is. Climb Mount Everest, become the CEO of a company, go zero to one in a startup because, you know, I joined at 3 million and so like, I haven't done zero to one or whatever. And one version of that for me is, I'm trying to do it to prove something to this like undefinable other. And in fact, what that undefinable other is, is this feeling of an unfillable hole. I didn't realize this for a long time, but this is unfillable hole in my soul that I was trying to fill with all of these other things. And that unfillable hole was this sense of like, I am worthy. I'm enough as I am. I am a good person or the inverse of I am not in fact a piece of shit. I am not in fact unworthy of love. And so there was this hole that I didn't realize only I could fill, only I from inside of myself, I could fill with I am loved. I am worthy of being loved. I am not a piece of shit. In fact, and by proof, in addition to in fact. And it took me a long time to realize that's the thing that I was trying to do with a lot of my achievements, with a lot of my pursuits, with a lot of my declarations was to fill that hole that no one else could fill, no achievement could fill, no finish line could fill. And I still have to work on that actively, still actively have to notice when I'm trying to do it again, because it happens all the time.
But I think today from my seat now, I'm more convinced than ever that in fact, I am not a piece of shit, that that's an old message that I don't know where it came from. And it's not mine to carry anymore. And I can't carry the burdens of the world. It's just not possible for one person to do that. And so if I'm trying to achieve something to fill that hole, it's not going to work, it's just not going to work. But if I'm trying to achieve something, because I want to find out if I'm capable, I'm genuinely interested and motivated towards it.
I genuinely care. It's probably worthwhile. I genuinely want to write a book. I think it will challenge me in productive ways. I think that it will force me to embrace my own story in a way that it doesn't when I'm like a book editor or packager, which I've done. Then I don't have to own it in the same way. Whereas if I put my name on that cover, it's mine. I think that'll be good for me. I want to do that even if no one ever reads it and I want to hold a physical copy of it for myself. Now, if I'm going to do it, I might as well try and put it in front of people because I think it will be valuable to other people who can relate.
And so there's another piece of this, which is, I think there are times when I have done things that are deeply important to me, but I have sabotaged their success because I'm scared of how they'll be received. And so I don't put the effort into marketing it. I don't put the effort into putting it in front of people. I don't ask for help. Because that circles back around to, if I think I'm a piece of shit. And I genuinely care about this thing and I put it in front of people, they might tell me I'm a piece of shit. It might affirm the very thing I'm scared is true. And so I had to fix that first before I could begin putting actual effort into allowing a thing to reach people that can benefit from it. That's true of the podcast I make now, that'll be true of the book that I'm writing, that's true of any number of projects that actually matter to me is there's a different risk profile to it, which is they reflect me. And if someone doesn't like them, an old me would interpret that as, I knew there was something wrong with me. And current me is like, well, that's my story, man. I don't know what to tell you.
So that's a little bit on finish lines. And then there's this other old story I had to let go of that I still find myself caught in, even like this weekend, I had to notice it, which is hard equals good. If I'm working hard, that means I'm probably being a better person.
And that's not always true. That's sometimes true. If you are on a mission trip to build homes for people in need. The harder you work, the more homes go up in the week you have available. It is true. The harder you work, the more good you're doing. There's still a limit that everyone hits that you should be aware of, right. But that's true. But if, as we were talking about before we started recording, if I can serve a wonderful client base by coaching eight hours a week in my business, four hours on Tuesdays and four hours on Thursdays, and that provides financially for my family. And I do great work on behalf of those clients to serve them well, I don't know that it adds much more to my life to be coaching five days a week. In fact, it begins to detract from my life because now I don't get to write. I don't get to podcast. I don't get to do the things that are really important to me as an entrepreneur and creative person. And there's an old version of me that might've tried to fill as many hours as possible with coaching. But that version of hard doesn't make me better as a person. It might not make me better as a coach, might actually make me worse as a coach.
And so when I'm doing hard things now, I really have to question myself. Is it because this serves my growth? Like, am I reading a book that is intellectually challenging to me to understand because it will help me learn something I want to know, or am I doing a hard thing because I think it's going to prove that I'm a good person? Or I think that will allow me to embrace what I earn as a result of that and that is something else.
And so those are kind of, for me in my psychology and my unique, like all the things that shape me, those are the things that I have to be aware of. And I think everyone has a version of that, right?
David Elikwu: One thing that came to mind, just with what you were saying now, I wonder if, did you have to go through any process with your identity coming out of the last wall you were in being the COO, now to work on by yourself, okay.
Because I think the specific word that you mentioned that was making me think this was also when you were mentioning, you know, the idea of like self sabotage, right. And I actually, I think in your conversation with Nathan, I also heard you talk about this idea of like taking your seat, right. And, okay, there's this thing that you're meant to be doing, but there's some work that you need to be able to do to accept that.
And I think the analogy that came to my mind was in Spider Man, I think it was Spider Man two when, you know, Peter Parker quits being Spider Man because it's hard. And sometimes you're not actually ready to like there is a thing that you know that you need to do an identity of the person that you know that you need to become, at least for this phase of your life. But there is still a process that you have to go through to be ready to do it. You can't just put on the outfit and then, Oh, now you're this person. Actually, no, like, even though he'd already put on the outfit, there was some inner work. There was a process that he had to go through to finally be fully ready to put it on with the correct sense of intentionality that allowed him then to perform at his best when he put the suit back on.
Barrett Brooks: Yes, I have. I did not know this on the front end, so maybe others can benefit now from me being able to reflect back, but here were the phases I had to go through.
The first thing was I had to acknowledge that I was not okay, I was not in a good place when I left ConvertKit personally. My wife was a person who was able to reflect that to me in a way I could finally see. So I had to have someone hold the mirror up and say, you're not okay. And It was like, damn, I'm not okay, huh?
Step two was I had to understand and release the burdens of my upbringing and of my parents. So that number one, I could have a new relationship to them. And number two, so that I could be free of things I was carrying that weren't serving me and weren't serving them.
So there was a whole process of understanding my parents in a new way and how they were shaped by their parents and what burdens that created for them. And what of those burdens got passed down to me just because of who I am? Like, what did I take on that was actually my dads? What did I take on that was actually my moms? And the book that most helped with that was It Didn't Start With You by Mark Wolin. And it's kind of about ancestral pain and trauma and how that gets passed down and like, what we take on as ours that isn't actually ours to own or live out.
And I realized that I had internalized a lot of things I got from my dad as my own. And in fact, they were a result, I think, of his relationship to his mother. And the fact that she did not love him very well, to the day that she died, she did not love him very well, even though he loved her deeply. And so I had to let go of pain from the past of directly from my parents, and then indirectly from their experiences with their ancestors.
So that was the next phase. I recognize how woo woo some of this sounds, I'm just telling you what worked for me. So, you know, it is what it is at this point.
Once I let go of the past, then I had to realize what I was still carrying that really was mine, for example, I was sexually abused as a child by a relative and I decided that it was important for me to heal from that before we had our first son so that I would not bring any of that into my relationship with him. And I went through a very long process of therapy, eventually I confronted the person who did that to me and sat down with them and had a coffee and talk directly about it and then integrated all of the learnings and came back a lot more whole to myself in a way that like now I can talk about it. It's just part of what I experienced, you know, it's just part of what made me who I am. So there were things like that, you know, that's the most drastic, but there were things just normal, everyday stuff of like messages I internalize in ways I was living, patterns I was living that weren't serving me anymore.
But I had to let go of the past before I could deal with all of that, which was in the present and what was actually affecting me that was mine. So dealing with all of that, and then that opened up the ability after doing all of that opened up the ability to begin to acknowledge my real gifts of like, who I really am, what I'm really uniquely capable of, like how great I am at my best to really like, there is great vulnerability and admitting to yourself when you really are exceptional at something. That's been the last phase of this journey has been really acknowledging to myself like I'm exceptional and in these ways, you know, not in every way in these ways.
Further, that there are people around me who see me as exceptional in those ways and actively want to help me. It's not a burden to them for me to ask for help. There are people in my life who want to help me succeed. That was another big breakthrough of like acknowledging the resources I have. And the last big one was like acknowledging that my marriage is that.
Like my wife has been here every step of the way and I didn't even see the ways in which she was trying to support me because I just couldn't receive it. And so there's this, there's been this like process of coming to wholeness on what I have, on what I am gifted at, on the resources I have available to me and accepting that all of that has been the process to allow me then to like claim space again to like, take my seat as you put it and as I put it.
And the last thing I'll mention is an important part of kind of like, coming to terms with both the past and letting go of that and also the present and what I needed to heal in myself was learning to grieve properly, like really fully grieve losses. And the book that most helped me with that was called The wild edge of sorrow by Francis Weller. Wonderful book. And all of these, I'll just say like literally every book that I've mentioned so far other than Seth's books came from my coach and mentor, Andy Christinger, who is the head of coaching at organization called Reboot. Just a wonderful source of wisdom and new territory for me. And then that's obviously led to me discovering a bunch of other stuff.
But it all started with, with him really influencing that in me.
David Elikwu: Okay, wow. That last part that you added is going to make me feel a bit prescient and I'm glad because the final question I wanted to ask you is literally about the four relationships that we've talked about in our conversation. Your wife as your partner working with Nathan Barry as both as a friend, but also as a co founder and then a mentor and Seth Godin and also your coach, Andy Christinger at Reboot.
It's a two part question. One is, it strikes me that all these people have had, you know, some deep impact on your life, but it strikes me that these are all people that you chose. Well, at least you chose to interact with them in the context that you did. And so the first part of the question is like, what you've learned about choosing those kinds of people in all of those different capacities for each one, like what was important about that process? And then two, maybe just what the biggest thing that you've learned from, from each of them is? Either directly from them or just through the process of your relationship with them.
Barrett Brooks: The number one thing that I think I've learned about selecting is that almost every person I've ever met is drawn to certain types of people. Certain books, certain YouTubers, podcasters, journalists, like musicians, we're all drawn towards people.
And some of those people are accessible to us directly, some of them aren't, but just learning to notice who you're drawn towards and what the trends in those people are, what they represent to you, writing down the qualities that make you drawn to them is really informative. So that's the first thing that I've learned about selecting is just like, we all have an inner knowing that's drawing us towards people.
And making that a little bit more explicit, defining why so that we can seek out more of those people. I think is really valuable.
The second thing I'll say about attracting or being in relationship with people is putting yourself in the position to do that. I mean, I was very intimidated to apply to work with Seth Godin the first time. I assumed I would not get picked. I was still living a story about myself that was, I did not deserve to be picked, but for whatever reason, I've always been willing to at least try. Probably because getting said no to affirms that story. You know, if you try and you get said no to it affirms a story. Now, I believe that when I put myself in the like hat, you know, to get your name pulled out one way or the other is an essential element of connection.
You have to attempt or you're already assuming the no, if you don't attempt, you've already assumed the no, and you've already internalized the story that implies. Putting your name in the hat opens you up a lot more vulnerably, because now you might get an actual no, which might affirm the story. But the other thing that can happen is you can get a yes, and now you have to live this whole other version of the story, which is like, oh, my God, I'm the kind of person they say yes to. David's the kind of person, Barrett wants to come out of a two hour conversation with. That sounds awesome. Well, what does that mean about you? You know, and with me, it might not mean that much, but like with other people that you really look up to that, like, you really been seeking out for a long time. That might really change your view of yourself.
So you got to put yourself in the game. You got to ask to be in relationship in some way if you're drawn to someone. Obviously in healthy ways while respecting people's boundaries and all of that. So that's what I've learned about selecting and seeking people out.
And maybe I'll say one word about each of them. Nicole, my wife, I've learned how to be loved from her. I've learned how to be loved by her. I don't think I really understood how to be loved, how to accept it. From Nathan, I've learned the value of an intelligent, caring, sparring partner, like really someone who's willing to debate with you, to push you, to challenge your ideas and thinking and to be challenged in their thinking, I think it's exceedingly rare to have intellectual sparring partners in life, and he's been that for me. From Seth, I've learned what it feels like to be led by a person you admire, respect, and who treats you as if you are capable, he has taught me more than anyone in my life other than maybe my mom about how to lead well through example, not just through his writing or words. I think him and my mom in terms of living, you know, people that I've met. And then Andy, my coach, I think he taught me how to just receive support, like how to be held by someone in my completeness and my wholeness to be like, lifted up and believed in and, you know, treated as if I am already good and that he is just helping me come to realize that on my own. I've said before that he was the second most important person in my life behind my wife throughout the period at ConvertKit and after, as I left, because of the way that he just held me in high regard, regardless of what I was going through or what I was experiencing.
David Elikwu: Okay. Amazing. Barrett, thanks so much for being so vulnerable. Thanks for sharing so openly. It's been incredible to have you. It's been a really great conversation.
Barrett Brooks: Likewise. Thank you so much for having me, David.
David Elikwu: Thank you so much for tuning in. Please do stay tuned for more. Don't forget to rate, review and subscribe. It really helps the podcast and follow me on Twitter feel free to shoot me any thoughts. See you next time.
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