Barrett Brooks is an executive coach, writer, and CEO of Presence-Based Coaching. He works primarily with seven-figure creator-founders, helping them grow their companies without losing themselves in the process. Previously, he served as COO of Kit, where he helped scale the company from $3M to $30M in annual recurring revenue. He is also the host of Good Work and writer of the weekly newsletter Little Leadership Lessons.
1) You have worked closely with a lot of fast-moving creators and operators. In your experience, when growth outpaces self-awareness, what tends to break first? And after having a front-row seat to so many different founder journeys as a coach, what have you had to change your mind about when it comes to leadership, motivation, and what people actually want?
What breaks first, practically speaking, are the relationships. The way it starts to show up is the creator-entrepreneur not maintaining their creative habit. Then it becomes resentment or blame, or ways of misplacing that angst as “my team’s not performing.”
What I’m usually observing is that it’s a leadership capacity issue, and the team and the company have outgrown the creator. The creator ends up resenting the whole system because they got into it as a creative person. That was their initial drive. What they ultimately realize is that along the way, they began chasing the ability to keep being a creative person while earning more money. The way you have to do that is pretty circuitous, and it takes a while until you can get back to just being the creative person. There’s a certain amount of scale that has to happen to increase your income as a creator initially.
The paradox is that to reach the scale where you can be the creative person again, you first have to become a CEO. You’re managing a team, and the creative person is thinking, “I don’t want to be a CEO; I want to remain a creative person.” That’s what ultimately breaks things apart.
So, there are two paths I see people go down. One is that they become conscious of this dynamic and say, “Okay, I actually don’t want a team. I’m going to go back to the original scale of the thing that allows me just to be creative, and whatever I earn, I earn.” (Justin Welsh is an example of someone who consciously made this choice.)
There’s another version of this where they’re not aware of it, and it just keeps playing out. What that ends up looking like is a lot of turnover, a lot of internal conflict on the team, and usually, revenue stalls out. Either they get so fed up with it that they shut it down, or so many people leave that they’re like, “I don’t even know what to do now.” It’s now a culture issue. Who wants to work for someone who actively resents them?
The thing that solves for it is this active choice between, do I want to build the CEO skill set, or do I want to be okay with less revenue, but more creative time?
There’s maybe a middle ground, which is, can I hire a great operator? However, what I usually find is that when the founder-creator tries to get around this whole dynamic by outsourcing team management, the conflict is concentrated in one relationship rather than across the whole team. Then they have to worry about the replaceability of that person because all of that energy is getting directed at the operator. It usually ends up looking a lot like the same patterns that attachment relationships have, marriages, and things like that, in terms of how the pattern plays out.
For me, regarding what’s changed, it’s interesting because I come out at the opposite end. I am a creative person. I enjoy writing. I enjoy podcasting. I enjoy all of that. But I love teams. I genuinely enjoy the building of culture and the active creation of community. But I also wanted to get back to having a team when I left ConvertKit, so I worked really hard to earn the right to have one. My growth came from learning leadership practices that are highly effective at unlocking significant future potential.
Yet, for some of my clients, that’s not their motivation. Their actual motivation is to be as free, independent, and creative as possible, and everything else is just window dressing. That mental model doesn’t work for me, so I had to start studying things like a scientist. In my work as a coach, I had to ask questions like, “What is the actual motivation here? How can I help them make a much more active choice between these paths available to them, and not get in the way of the fact that they just want to do whatever it is they want to do?” Otherwise, I’d be applying my framework or my value system to their decisions. As a coach, that simply doesn’t work. I had to get used to that. And, not just understand it, but get all the way to compassion for it. Otherwise, if I’m thinking, “Okay, I understand you, but I don’t think you’re right,” I’m still not effective.
Getting all the way to compassion allowed me to say, “Okay, I’m actually totally free of this.” For a long time, it was personal because I had experience as the C-level executive, creator, and founder, and I deeply care about teams. I was taking some of that baggage into client relationships and almost advocating for my client’s team. But, instead, I needed to be the advocate for my client, that’s the work of a coach, and I had to do my own processing so I could get there.
2) Why do you think so many smart, capable people can give great advice to others, but still struggle to apply it in their own lives? And in your view, what’s the difference between coaching that helps someone perform better and coaching that helps someone live better?
Why is it that we can see in others what we can’t see in ourselves? The first thing is that we are subject to our own experience in a way that we’re not subject to someone else’s. I can observe you doing things, but I’m not in it. You’re in it. I’m in my own experience. The most base-level answer to this is that we have to build the skill set to truly see and feel before we can make change in ourselves. We have emotional reactions to the things we’re subject to, and these emotions influence our behavior, thoughts, and sensations.
So, this is the value of coaching. This is the value of therapy. This is the value of friendship and community. Other people can say, “Hey, did you notice?” And you’re like, “Well, no, I didn’t.” But now, next time, maybe you have a better chance of noticing, because your level of awareness was raised, which helps you understand that’s the thing you should look for.
To the second part of your question, there’s a spectrum in coaching, from performance to developmental. For instance, it’s not like I’m this or I’m that when it comes to coaching. I wouldn’t get paid what I do for coaching if I didn’t have an eye toward business growth and/or some form of ROI. It’s got to at least be experiential for the founder, if it’s not financial. And, there’s always a performance outcome of some kind. There are results that happen from all behavior. It’s really a theory question about what gets you there and what sustains it.
I think performance coaching can find some shortcuts. Not that it’s intentionally trying to find shortcuts, but there’s more available to you in terms of frameworks. For instance, if you’re trying to improve your batting average performance, it doesn’t matter how your dad yelling at you growing up affects your experience in the batter’s box. It matters whether you get a hit.
A developmental coach would say, “How do we work with not even understanding the history of all of this, but understanding how that shows up for you right now, and all of the ways in which that’s affecting your life?” Then, “How can we start to detach from that and create new behavioral outcomes that you can sustain over time? How can we re-pattern around this so that it can serve you in many different areas of life?”
I believe that for a human’s overall development, that’s a better approach because it offers more benefits. But that might take five years, and if you’re in a contract year, you’re not looking for a five-year solution. You’re looking for a tomorrow solution. There are a lot of these little psychological hacks you can use to essentially suppress and repress things that are getting in your way in the short term, so that you can get a short-term outcome. I don’t think that’s right or wrong. It’s just not going to fix the underlying issue.
That’s why I think a lot of athletes struggle after leaving athletics. They’ve still got all the same issues, but it’s not a short-term window they’re looking at anymore. They’re looking at a long-term developmental window, and none of the tactical skills they’ve learned previously now apply. They have to start back from square one, and I think that’s a lot of what drives their struggles.
Of course, there’s a real loss, and there’s a real transition that happens aside from this, but I also think they need all-new tools to perform in a new environment. At the broadest level, tools that can be applied across multiple domains, whereas performance coaching has a level of specificity that accomplishes a particular goal.
3) How do you think about coaching identity-level change, not just helping someone improve a skill, but helping them become a different kind of person? What have you learned about the relationship between inner state and outer execution, and how much of lasting change is really state management?
Let’s take the identity thing first.
I can be a little allergic to turning my thinking into frameworks for whatever reason. But I’m beginning to develop an increasing level of conviction that identity-level change requires something like this process: If you were to map your life on two dimensions, time scale and emotional valence (positive and negative) throughout your life, you’d see that you have core memories in your memory for a reason, as well as some repressed memories that also shaped you. Repressed memories aren’t as common. To start with, it’s really a question of what the emotional arc of your life looks like. If you were to plot all of your core memories, what would that look like in terms of emotional valence over time? I think this is kind of step one. What is the longitudinal view on the experiences that have most shaped you?
Then there’s a process of seeing how each of those things represents a story that shows up as behavior, thoughts, emotions, and somatic experience today. You show up in the world based on the things that have shaped you. You show up in the world a certain way, and that gets you so far. Then one day you wake up and say, “Okay, maybe I’ve gotten really far. Also, I haven’t really told anyone this, but it’s kind of killing me inside.” This is usually when people come to me and say, “It worked. But, also, I can’t do it like this anymore.” I think the first condition is someone realizing that everyone outside of me might think this has been very effective, but I need someone to know it’s not going to keep working because I actually feel like I’m at a breaking point. Reaching this type of breaking point has to happen for an openness to identity-level change to occur. You become aware of how you’re showing up, and then you say, “All right, what do I need to grieve, process, say out loud, and move on from?”
What I find for most people, generally speaking, is that there’s a backlog of grief for the way things have been. There’s grief for the things that were hard and haven’t been acknowledged, because acknowledging hardness doesn’t exactly equal survival. We have a low tolerance for this type of work, especially in Western society.
So people have to go through this backlog of grief and process it, and the way they do so varies from person to person. Once one gets through that backlog, you’re kind of back to even. Then you say, “All right, I’ve grieved everything that was difficult about getting here. I’ve acknowledged all of the great ways that my habits were serving me. Now, how do I want to go forward, and what is the actual outcome I want?”
It might be, I do want to get to 10 million dollars. I’m going to be willing to do some hard things I don’t enjoy as a CEO, but I’m not going to do them in the old broken ways, with my old relational patterns and my old emotional patterns. I’m going to choose not to take suffering on myself, but instead to actively hire people who can take the burden on for me, or whatever the thing is.
I think it’s essentially this: What has shaped you, and how is that no longer working for you enough for you to realize it, raise your hand, and say, I need help? Then you ask, “What’s hard?” You process through that backlog, and you move on and say, here’s how I want to be going forward.
That’s going to take some retraining. For instance, when someone is upset with you. Rather than collapsing and saying, “Okay, I’ll do what you want,” you’re going to stand your ground and say, “Okay, I hear you. What you’re asking for doesn’t work for me. Here’s another way we can get to a solution. Does that work for you?” Then you learn to embrace the cost of that decision. But that’s better than collapsing and suffering because you weren’t willing to stand your ground on a thing that mattered.
Changing those little behavioral loops becomes the identity change over time. You go from thinking my job in a relationship is to acquiesce and collapse to realizing you have an equal role to play and every right to ask for things, too. Now you have a whole new reality you can lean into.
Essentially, you shift from implicit to conscious trade-offs. Everything’s hard. There’s nothing worth doing that’s not hard. But if you’re making implicit trade-offs, that’s usually suffering. If you’re making explicit trade-offs and knowing that you always have a choice, that’s growth.
So, the state we’re managing is suffering versus growth, and the outcomes might still be growth in either case: growth of revenue, growth of team, growth of whatever. But I think the internal experience changes once you realize you are actively choosing the pain of a growing team, or losing money for a year, or whatever it might be, because it’s in service of this bigger thing that you want over here. Once people embrace that, their whole experience changes, even though the circumstances remain fundamentally the same.
4) You’re aware that I think a lot about enjoyment as a driver of adherence. Do you think leaders underestimate the role of energy, aliveness, and enjoyment in doing meaningful work well? You and I both care about how people do hard things in a way they can sustain, so where do you think hustle is overrated, and what should replace it?
First of all, there’s no inherent value in suffering. I just don’t believe that.
Suffering can yield things that you value. But there’s no inherent value in suffering, and I think at some point we started to get that backwards. That’s the thing with hustle culture. We forgot that the point isn’t to be always on and busting ass nonstop. The point is that you had some way you were trying to improve your experience of life.
When the whole point becomes proving that you are hustling, proving that you’re working hard, or proving that you’re suffering more than the next person, my experience is that it’s a form of brokenness. It’s essentially playing a status game where the status is measured by how much suffering you’re willing to endure, which seems silly to me.
There’s enough suffering in the world. You’re going to experience suffering through externalities, the biggest of which is that we’re all going to die. So why would we place an inherent value on suffering as its own thing? It doesn’t make any sense.
What’s the point then? The point, I think, is experiencing what we’re capable of. That’s a different lens on what can look like the same thing. What we are capable of could be in any domain. I actually don’t care what domain. But, to be fully alive, you should have some domain where you’re trying to find out how good you can be. Good can be measured however you want.
How you present yourself as a father or mother can be a perfectly wonderful organizing force for your life. I think there are a lot of people talking about hustle culture who would say, no, that’s not what I’m talking about. I’m talking about going to achieve a ‘thing.’ I would argue that what more could you achieve than being a present parent to a child who is going to develop into a whole person? It’s a whole life you’re affecting.
Assuming that is the organizing force, number one, you have to recognize the risk you’re placing in any one identity, because that identity can be taken from you in any number of ways. But if you do that consciously, I think it’s okay, which is the whole non-attachment idea that gets popularized in Buddhism and other mindfulness practices.
If you have a domain where you’re trying to be great (however you define great), then you can have meaningful bouts of suffering that are in service of that effort. In our parent example, doing bedtime every night can be a form of suffering with a certain three-year-old, for example. But if the practice in the middle of that is asking, “How can I experience this in a way that is not just gritting through it?” You remember your experience as a kid: Go to sleep! If you don’t go to sleep on this timetable, we’ll be angry with you. If you keep going, we will eventually spank you, and then you’ll stop asking us to help you fall asleep.
What’s the opposite of that? It’s saying something like, “I’ll be here no matter what you do to me right now, because I am a capable adult, and you’re a child with less emotional capacity to regulate. You’ll know that you are infinitely safe with me.” If that’s my mission, my child yelling at me has basically no bearing, except as an opportunity to practice.
The joy part of that is holding my son once he’s asleep and realizing that tonight, my son was dysregulated, and I rose to the challenge. He will experience safety because of that. I’m not saying that every moment of it was joyful, but the amount of meaning I get from it is nearly infinite. It’s like I won that day in that situation. It doesn’t get all the way to joy, but I think if you can access joy, joy is not opposed to achievement. Somewhere along the way, in the way we started valuing suffering, we started assuming that joy means you’re not going to achieve anything in this life. Why?
5) For someone who wants an immediate taste of the benefits of being more present, what are a few small, repeatable practices they could start experimenting with right away?
The simplest one is: take a walk.
Your only job on the walk, your only assignment, is to do nothing other than be on the walk. Really radical idea, leave your phone at home. You don’t have to do it for long. Take a five-minute walk around your neighborhood.
We need to make it goal-oriented for a moment because people are so goal-oriented. While you’re on the walk, your assignment is to notice five things, one thing per minute, in your environment.
That is as simple as I can make it, because it’s five minutes. I promise you, you have no excuse. Your only job is not to take anything with you. Don’t do anything else other than walk and notice one thing for a minute. Your brain is capable of noticing hundreds of things per minute, so it’s really a pretty easy assignment.
I think what you learn over time is how many things you just blow past because of whatever’s going on in your head, or whatever task list is on your mind.
The reality is, if you’re taking a walk, even if it’s just from your office building to your car, or walking your dog, or wherever, what is the relative value to you of, for example, scrolling Instagram while your dog poops versus noticing a cardinal on a tree branch? What is the value you get from each? And if you were making a conscious choice, what would you wish for yourself?
I have an assumed answer. Maybe I’m wrong; maybe you really do want to scroll Instagram, and that’s fine. But I assume that most people would say, “Well, it’s probably really nice to look up at the blue sky and think, wow, it’s a really beautiful day today. I’m really grateful for this.” Rather than looking at whatever workout someone did, or whatever some random person had for dinner, or whatever.
I’m not saying you have to be that way all the time, but I think if you can take a five-minute walk, then you can, over time, learn to do a hundred different versions of that.
Something I’ve started doing is, every time I go speak somewhere and I’m away from home for two nights, I intentionally go eat alone on one of those nights.
My challenge to myself is to have a meal at a nice restaurant that I would enjoy even if I were with friends. I don’t look at my phone. I don’t take a book. I don’t listen to anything. I just sit there and experience the meal, have a glass of wine, and think, “Wow, look at how many things I could miss right now.” You’re just watching people, acknowledging the environment, seeing how service is being delivered, thinking your own thoughts.
I used to be extraordinarily anxious about eating alone. Now I savor it. It’s this wonderful exercise, even in noticing. I’ll have moments where I think, I wonder how many people think I’m weird. I’m alone, I’m having a glass of wine, I don’t have anything on my table, especially before the food comes, because then there’s really nothing to do. I’ll think, “I wonder if anyone wonders why I’m alone?”
A younger version of me would have been embarrassed by this. Now I think, “What a privilege, to be aware enough to say I’m choosing this for myself.” We probably miss 80 percent of the moments in our lives that could be special in some way because we’re so caught up in where we’re not.
