[Transcript] Clearer Thinking Episode 250: Getting a handle on your goals and big life changes (with Tee Barnett)

[Transcript is AI-generated with light edits. May contain errors.]

JOSH: Hello and welcome to Clearer Thinking with Spencer Greenberg, the podcast about ideas that matter. I'm Josh Castle, the producer of the podcast, and I'm so glad you've joined us today. In this episode, Spencer speaks with Tee Barnett about how shifting values can affect personal development, harnessing modernity, and beauty and aliveness.

SPENCER: Tee, welcome.

TEE: Thanks, Spencer. I'm really happy to be here.

SPENCER: You spend a lot of time working with people to help them be more productive, more efficient, and more effective at achieving their goals. What do you see as one of the biggest leverage points to helping people in that way?

TEE: I have a deep respect for the fact that there's no objective answer to this, but in my mind, the answer is consistently seeking and conjuring inspiration to lead a better life. Now I'm anticipating a bunch of "wait-a-minutes" from people who have their own preferred forms of development, practitioners who have their specialties, people who are just skeptical of that claim in general. But if you really think about it, for many of us, the greatest realized gains in cases come from the infusion of creative inspiration. It's that perception shift. It's that different way of seeing things. It's that trying something out and getting more information, and that being a thing that changes how you think about how the world works or how you identify with it. So when I say imagination, I'm not talking about pure fantasy. I'm talking more about imbuing a lot of your efforts with an imagination that leads to actualization, manifestation, whatever you want to call it, bringing what is imagined about the world into doing better and leading a better life, maintaining the motivation to pursue and figuring out the craft and skill of continually bringing that to your life and your work. I think that's the highest leverage thing that leaders can try to tap into. And I don't mean for this to sound like a thing that's only meant for leaders. I think that this is really something that is applicable more generally to virtually everybody. So as it relates to my work, I'm a self-styled personal strategist, which is a variant of life coaching, you could say, but in my mind, with my clients, that's consistently what we're really doing, in many cases, even when we're talking about very specific things or very idiosyncratic aspects of themselves. It's a thing that I think I'm always trying to help guide them towards. When you think about it, none of this is new, strictly speaking. I think the spirit of my coaching is continental philosophy mixed with American pragmatism. There are different therapeutic methods I tend to lean on, really like coherence therapy. And part of that patchwork is me trying to reach for inspiration in terms of making sense of the world myself, but also making sense of it in a way that I can try to help pass along to others or help others discover. But yeah, I guess the sense in which it's new is that it's a new phenomenon that's an outgrowth of our modern society and the needs and desires of people who are born into the society. So think in previous societies, a lot of the way it was structured, the needs that people had, the ways those were fulfilled, the other roles that helped fulfill those needs, those things kind of filled whatever requirements of people that coaching does. Now, I don't think that delegitimates coaching. It just is a commentary about how our society is and what people need right now, people that they need to lean on. But also I think there's really something in that commentary for us to pay attention to, both as coaches and as people who are looking for something, who are looking and seeking things. That's not to say that it's totally absent in society. Some of the stuff can be recreated if you turn your attention towards things, things like wanting mentorship, wanting community, placing your awareness on that and adjusting a lot of your efforts to attain those things can make it so that you actually can find it. I don't always think coaching is the answer, as maybe some of the previous things I was saying kind of alluded to. There's an industry of coaching and self-improvement and personal development that would lead you to believe that's the case. There are individual practitioners that are trying to make a living, trying to sell you things. I don't think that's true. I think people need to meet the right influences at the right times. I think what's important is holding a disposition that allows you to come into contact with the right things at the right times, but it doesn't need to come from a coach at all. In fact, I think having a consistent coaching relationship at the same frequency, or therapy relationship at the same frequency for a really long time, doesn't necessarily matter much to the natural ebb and flow of people's needs and paths of development. In short, I think giving yourself the opportunity to continuously meet what's ahead of you with creativity and inspiration and hopefully newfound agency is a high leverage point for pretty much everybody.

SPENCER: How do you think about who should consider seeing a coach, and when is the right time to see a coach?

TEE: I get asked this a lot when people are thinking about whether they'd like to work with me. If in your past you've ever had somebody that you've worked with or worked alongside, and you found that the kind of dialectical process, or a process of bouncing things back and forth and building concepts — rubber ducking is another word for this — has led to more formulated thoughts or crisper thoughts, or has opened you up to new ideas. You've seen pieces of other people's maps, and you wanted to bring that into your map, then you'd likely be a good candidate for coaching. A lot of it depends on fit. A lot of it depends on the type of thing that you're going to a potential coach for. Sometimes it's straight advice or knowledge transfer, which I think a lot of people think about as coaching, like, "Oh, I'm a CEO, I'm a former founder, and I exited, and now I'm going to tell you my secrets," and so on. But there are a lot of different relations and orientations that coaches can have to people. Sometimes it's like having a thought partner. Sometimes it's like going on a safari and having a skilled guide walking alongside you and pointing things out in your mind and your emotions that can be important. The most ideal time, in many cases, is when people are undergoing some kind of transition. That can be incoming, reactive times of crisis, like a slow-burning type of burnout situation, or positive things, where you receive a promotion, you get new responsibilities, a new stage of life is unfolding, you're about to have children, you're about to enter a new milestone, whatever. Sometimes it's not just purely in reaction to what's going on in your life. It can be that people are stuck or in a rut, or they're thinking they're on top of things, and they're thinking, "How can I be a better leader? How can I be a better father? How can I be a better partner? How can I improve my experience in some way?" Coaching can certainly help you with that.

SPENCER: Coaching sometimes gets a bad rap because it's so non-standardized, and also does it require sort of an official proof that you know what you're talking about. If you go to a therapist, at least you know they've been licensed. How do you think about what makes a good coach or someone who actually is trustworthy?

TEE: I think about this a lot because I don't like being associated with the bulk of the industry in a lot of ways, and I have a lot of philosophical and methodological bones to pick with people out there. There are the get-rich-quick coaches, there are the shamanic woo ones. Those can be okay; it really depends. I think attempts at standardizing this kind of thing are really tricky because fundamentally, a lot of what coaches are helping with are questions of perception and deep emotional schema and constructs, which are notoriously difficult to get a grip on, even in the fields of expertise where people could just tell you. I think it's easier to be an expert in neuroscience and be able to relay facts about the mind in some cases, although I think that gets pretty blurry, and there are points of contention there, versus being a psychoanalyst. Psychoanalysis, mid-20th century or something, really did try to make this into much more of a hard science and predictably found it quite difficult. The ways they tried to make it into a hard science were actually counterproductive for the patients in the industry. But that's a whole thing. I think about it in terms of trustworthiness. It's really nice if you're trying to consider a coach embedded within a trusted network. If there are a lot of overlapping signals that this person is helpful to people you trust and care about, and those people are willing to relay the referrals and recommendations and their experience, that can be through testimonials, what they say, or different artifacts of how they have tested their coaching and what the effects are. There has to be a collage of indicators that can give you a sense of what is good about this, instead of trying to quantify something that's notoriously difficult to quantify, like exploring the individual psychology of a person. I'm not sure if some of the guests that you've had on this show would agree. I would like to give a quick shout-out to Scott Miller, who you had on episode 70. I did a coaching training program where we had a cohort of nine coaches, and I modeled some of it somewhat off of therapy training programs, and Scott Miller has had a lot to say in that regard, so I appreciated his work.

SPENCER: A lot of interesting ideas about what makes a coach or therapist effective, and what's kind of in common between effective people to help you. I think I tend to be pretty optimistic on coaching. The reason is because the base case seems pretty good. By the base case, I mean that I think most people could benefit from one hour or an hour and a half a week reflecting on their life. At the very lowest level, if a coach just gets you to spend that much time a week reflecting on your life, that already seems good. Then you add on top of that, "Okay, let's say the person's empathetic, and the person has a lot of experiences that they can draw on to point things out to you that could be useful." That's even better than just spending that time reflecting. You can bring all the coaching skills on top of that that are just gravy, and they can make it even better. To me, it seems like the base case is already pretty strong for the value. A really good coach hopefully could do a lot more than that, but already you're starting with something that's probably beneficial to most people.

TEE: I think that's right. I'm really interested in this because I think this could be an interesting challenge for your audience. How did you come to believe that reflection is an important part of your process and your life? Some people just don't think that's the case. They've never reflected very much. They do, but it's in a very localized way. "I'm a researcher, and I only reflect on this field and these papers." Reflecting on the whole of your life, or reflecting on parts of your life, I'm curious how you came to believe that that would be useful.

SPENCER: I tend to think of reflection as being useful in two very broad ways. One is in terms of your goals. Oftentimes we don't spend that much time reflecting on what our goals are and what our current approach is. Can we try to get there in a more effective way? Maybe our goals are not that well aligned with our values, and we want to tweak them to make them better aligned with our values or to better match our skills and interests. Periodically reflecting on your goals can have really big benefits because it's sort of like, imagine you're on a long adventure, and then you realize you're heading to the wrong place. You know how much time you wasted going in the wrong direction. That's a very broad useful purpose of reflection. The second one I think about is automaticity. So much of what we do in our life is because we've always done it, or it's a routine, or it's a default or a habit. Reflection can help break us out of that and make us realize, "Oh, wait, maybe some of our behaviors are not healthy. Maybe there are certain people we want to spend more time with or less time with, or they're having a good effect on us or a bad effect. Maybe we want to start doing certain healthy behaviors that we've never done before, and that's going to have a really good long-term benefit." I think reflection can be really powerful, both for long-term trajectory stuff and also for breaking out of automaticity.

TEE: I agree. If someone asked me to give one line of what my coaching is trying to do, it's trying to give people creative inspiration to lead better lives. A lot of that is not just about flourishing. You might hear hand-wavy things from other people in the industry about flourishing or about becoming better versions of themselves. I think that's all good. I like to flourish. I think flourishing is fun and nice. A lot of what I'm responding to with people is in response to the modern condition, the condition of modernity. There are great things about the modern world, but there are also distinct challenges that come with the modern workplace, for example. When you talk about automation or automaticity, a really simple concept from coherence therapy is that your strategy is not fitting the context in a lot of cases. You could be settled into a strategy, and a transition happens. That's why coaching is very good in transitions. You find yourself in a different context where the behaviors you were exhibiting before may have been good for the previous environment and may have made a lot of sense and been coherent — coherence is another term related to this — maybe you were existing in a shark tank, in a consulting firm. You couldn't trust anybody, and then you switch over to a nonprofit. This is a live case I've encountered with someone. You're treating people with suspicion still, as if you're working in this shark tank. Your mind is still emotionally trained to function the same way. You move to a nonprofit, and everyone's trying to be more collaborative and be on the same team. You have this person who still struggles to trust people. That's an example of the automaticity, as you're saying. It's easy to recognize that when I say it here, just kind of pointing it out on the meta. But it's really tough when you're in your own experience, living your life, trying things in some of these new or newish environments, or sometimes the environments have shifted a little bit. What worked before, what was healthy before, what made sense before, no longer makes sense. Those are some of the things that you can address with coaching.

SPENCER: You mentioned the conditions of modernity. What are those conditions that you're helping people grapple with?

TEE: Yeah, I love that. I love that question. Burnout is a term that's pretty hot in some of the circles that we run in. I think burnout is a distinctly modern condition for certain reasons, but there are also ways that people instrumentalize themselves. They treat themselves as a resource, not just for the company. They don't just let companies treat them that way, but they also treat themselves that way. Then there are more macro things like degradation of the environment, which I think is a uniquely modern issue. Degradation of the environment, because capitalism needs to continue to grow, and it often is at the expense of trying to exploit natural resources, which is the foundation of a lot of the Calvinist, puritanical work ethic. We can get into a lot of that stuff, which is very interesting, but I'm not anti-capitalist by any means. A lot of my coaching is, "Okay. So you have these modern conditions, and some of them are amazing, like this ability to have scalable media. You can have your voice go out to hundreds, thousands, millions of people that can be used for good. But there are also bad things that come with the scale, and so on and so forth." What are the ways that you can harness modernity to live the life that you want to live? That's a thing that we're constantly in the background trying to do where we have all this material abundance, for example, in the modern age. Most of us white-collar workers, people listening to this show, I would imagine, and yet, we're working more hours than ever. We're hassled, we're harried, we're not sure whether we can have children if we want that, and our financial futures are uncertain. All of this is interesting. I think a lot of the people who predicted how capitalism would go eventually thought there would be a lot more abundance than psychologically there seems to be now. There's a lot of material abundance that's misallocated, yes, but there's a lot. I think it's surprising how deprived people feel, how much of an energy deficit a lot of people are running around with, how much people wish that they could still be doing when, in fact, we have so many machines that are making our lives easier. What accounts for that is some of the mystery of modernity.

SPENCER: Do you think it has to do with a changing structure of social environments where, a hundred thousand years ago, we'd be a small tribal group with maybe 50 people or 100 people, each playing a role in this little community?

TEE: It's really hard to say. I think it's probably a confluence of things, but what you brought up makes a lot of sense to me. In that setting, you have norms and a moral fabric and a social fabric where people know what their roles are, how things work, and how the actions they take will play out in a lot of cases. I think that was a lot more predictable for a lot more of human history than now. You have globalism, the fraying of social ties, and institutions of trust in these institutions and so on and so forth. It's no wonder that in this modern setting, with a lot of stuff fraying or being pluralistic or piecemeal, which, again, in some ways, is great, you get some liberation from oppressive structures of previous times. But also with that liberation comes what's next, and so people come to coaching. It's a marker of people not having enough indicators out there to make sense of what to do. That makes something like coaching and therapy valuable. On the one hand, it's great to do what I'm doing. I have fun. I love helping people. I think it's meaningful. On the other hand, I really wish it wasn't the case that people need to build their own internal sense of what to do, how to be thinking about things, and how to think about meaning, because there's just so little out there at this point or it's conflicting, and it's really hard to make sense of it. That's another reason why people come to coaching and therapy.

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SPENCER: You mentioned people treat themselves as a resource. Could you explain that a little bit more? What does that really mean, and why do people do that?

TEE: There's a way of not being clear on the experience you want to have or the value that you can create, which makes a lot more sense for a younger person, for example, who hasn't explored a lot of the world and how it works and what they can provide to it. In the case where you're just sort of trying to serve or fit into a role in order to get a job or to fulfill some function within a wider set of functions in an organization, a lot of the Western work psyche is still kind of tethered or predicated on the five days a week, 40 hours a week type of thing. A lot of people are equivocating whether they're doing a good job with how much effort they're putting in, how many hours they're there. It doesn't really help that a lot of the expectations of organizations are based on this type of thing as well. You're starting to quantify things that, in some sense, especially when it comes to knowledge workers, it's tough to actually quantify well. A lot of it can also be performative, where a manager might think that a person being present for a certain amount of time is a proper way to fulfill the job. When you start to think of people in that way, and when people start to believe in that kind of thing, they start to try to fit themselves into a more quantified way of thinking about the world and sort of be an instrument, trying to fit into that conception of what it means to fulfill the role. It's kind of like being a component, or something like a sufficient component, and that is difficult on people. I think it divorces them a lot from their own internal experience. It has them override ways that their body is uncomfortable, that their mind is uncomfortable with what's going on. Maybe increasingly over time, they're made to go through a lot of sprints in their corporate life and so on. It's no wonder that there's chronic turnover, a lot of burnout out there, and a lot of issues because people are trying to reach some kind of quantifiable standard or instrumental standard for themselves that maybe their own experience doesn't respond well to.

SPENCER: Other than treating yourself as a resource, what do you see as other major causes of burnout? Well,

TEE: A predictable answer is a crisis of meaning, but maybe a less predictable answer, a novel twist on this, is a clash of virtues or clash of principles. There are a lot of people who are in a role, and there's a way of thinking about how to do the role that is good. To do good work, "What does it mean to do good work?" is a question we confront a lot. For example, I had a client who really loved to be seen as being on top of things. When something was requested, they wanted to jump in and do that thing right away and always be present on Slack, always wanting to be responsive. The problem was that they got promoted because they were doing so well. But then, as you get promoted, you're responsible for things beyond just being present and being responsive, being their version of "on top of things." You need to build a vision, manage people, and do a bunch of other stuff that requires reflection and different strategies. This was really hard on them because they were trying to be the equivalent amount of "on top of things," but also these other virtues of the role or goals that they had for the role that came up as a necessity of fulfilling it well. Those were clashing. When you try to hold it all together while they're clashing, instead of taking a look at each one, trying to redefine them, for example, trying to see how they fit together or how they don't, then it's a lot more work. It's a lot more work that's kind of like trying to batten down the hatches or button down an internal state of conflict and dissonance. If you're so divided against yourself for a long time and you're overextending to try and hit the pinnacle of multiple competing virtues, that's really difficult energetically, but it's also really difficult internally. I think that's one reason for burnout, definitely.

SPENCER: Are there any other reasons for burnout you would point to?

TEE: A really difficult thing for people is measuring themselves against an abstract ideal. In the circles that you and I kind of run in or are familiar with, a lot of this is called replaceability. There are other concepts associated with it, like imposter syndrome and so on. But essentially, it's the idea that there's always going to be a person better than you at something. You could just go out and pluck a random person on earth, and they would be a better fit. There are a lot of problems with this thought experiment and how it haunts people. I think a lot of it erodes people's ability to build confidence in what they're doing, and in fact, they could contextually be a very, very good or the best person for what they're doing. What I mean contextually is that there are a lot of trade-offs associated with going to find the best person, or maybe that's not possible. You don't have the resources, whatever, so you're actually the best fit, contextually speaking, which I think actually matters. But in terms of burnout, it erodes your confidence, and you're trying to overextend once again, trying to hit these conceptions of what the best person would be able to do. A lot of times it's just more. A lot of times people are just told to do more, do better. I have this endless list of emails, this endless list of tasks, and I'm thinking about how a person who's better at this role, especially if you're a person who cares about doing good in the world, would want the best person in that role. Oftentimes these people are bothered by this, but there's an endless list of things. So they're just going to do as much as they can all the time. They're going to overextend and keep trying to get better at that. Maybe if they keep trying to do that, they will get better at it, and they'll just get better at doing more, and they'll just always do more. That's sort of an unconscious, implicit logic that a lot of people follow. The issue is that it's a lot all the time; it's hard to sustain. But also, there's an added component of maybe you don't like this type of work, and this is a sort of listening to your own internal experience type of piece here. A lot of people match themselves to roles based on what's viable for them economically, what the organization needs, or what their skill set might be, but they really don't actually like this stuff. It's kind of deadening. It's like being chained to a computer, as a lot of people have said to me, and it forces them to be in this hunched-over posture all day. Whatever the case may be, even if you have all these rational reasons for why you ought to be in the role, in terms of on-paper fit and stuff like that, it doesn't necessarily translate into what your body, mind, and spirit are really responding to and enjoying. That gulf can be bridged by doing the job sustainably, taking your time, not working too many hours, and trying to find stuff within that job you really enjoy focusing on. There's a lot of stuff. It's the people who, on paper, a lot of stuff looks good. Maybe, in fact, they are doing good in the company. But their body and mind are not necessarily always on board for this. On top of that, they're really pushing themselves, really pushing to keep doing more, to keep up with sprints, to keep up with deadlines, and your body is going — if anything, in my experience, it's true here — your body is going to catch up with you; it's going to call it quits. I've worked with people who have been burned out, and they couldn't work literally for six months to a year. They couldn't look at a computer screen without getting sick. This stuff really happens. Paying attention to all of these things through a coach can be helpful for this.

SPENCER: When you're working with a client in that situation, what's your approach to helping them get to a better place?

TEE: I trace their ontology. That's very jargonistic, but basically I spend a lot of time trying to get a sense of how people think the world works and what they feel their identity is. What are the stories they tell themselves about all this stuff? Hermeneutics is a word for this. How do they interpret everything that's going on? I think why that matters is because the sort of misappropriation of energy, the misallocation of effort and resources to be mistaken for so long "mistaken" to be expending energy or spirit in ways that are counter to maybe a better way to do that, which you could find, ultimately can be very bad for people. For example, to make it less abstract, what does it mean to do a good job? We can return to that question. A lot of people haven't thought about that beyond, "I'm briefly talking about it with my manager. I know the duties of the role, and then there's going to be some biannual or annual performance review where I hope it goes well, and we talk about how much progress we made on projects and so on." But really, when I get into this with people, what does it mean to do a good job, even from the standpoint of just external expectations of what it means to do a good job? Just guessing and throwing a bunch of energy at some of the stuff that's loosely been touched on is not very strategic. One of the most illuminating questions that I ask people is, what do you think your manager would respond to? What does the company actually want from you? What are outputs that would not just be satisfactory or meet expectations, but would exceed them? What would be surprising? Things like that. I think that pushes people into more creative territory in terms of what they could be doing. In a lot of cases, it could end up leading to less work. Because you're not just trying to throw all of your energy and effort at vaguely what you think is doing a good job, but you're coming up with an ethos on what it means to do a good job in that role, and you're trying to target specific operations and actions repeatedly in a very concerted and intentional way, such that you hope that will push the dial much more than just broad effort. That tends to be a thing that works a lot in terms of what does it mean to do a good job? When it comes to internally speaking, what does it mean to do a good job? This is where a lot of the exploration really hasn't happened for a ton of people. It can be really illuminating to get a sense of what it means to do a good job, not just in the current role, but also over the lifetime of your work. What does work mean to you if you're trying to set up a learning project for several years or decades, and you want to become a certain kind of person, or you want to acquire a certain facility with a certain kind of knowledge? What does it mean to do a good job? It should almost certainly include your internal standard for a lot of this stuff. A lot of times, people find their internal standard for how to do a good job is actually way higher than the external standard. Once they crystallize it and start aiming for it, they'll be like, "Oh, wow. I really fell short of my internal standard, but my manager is raving about the good job I've been doing." That can be really disorienting in and of itself, but that all presumes a certain orientation to work, in terms of taking pride in it, trying to be more aligned with it, and so on. I recognize some people are not in that position, but that's a different discussion.

SPENCER: When it comes to people's internal standards being very high, is that a healthy thing or an unhealthy thing? You could see it both ways. A high internal standard could mean you're striving to be excellent according to your own lights, but on the other hand, that could put a great deal of pressure on yourself, and even if you're excelling in your role according to everyone else, you might still feel like you're constantly falling short because it's unrealistic.

TEE: Yeah, that's a great point. A lot of it is about how you relate to the outside world. A lot of it is what you're internalizing in that sense, and what your reaction is to not reaching the quote, unquote high standard. Maybe high isn't even the right word, because in some ways, that's quantified. There's a caliber, potentially, or a feel, or a quality to that thing where a "high standard" could be part of that. One of the many properties to describe the type of work that you want to produce, but it's double-edged. One of the things I don't like about a lot of coaching or therapy is trying to make people feel better, and sometimes that's at the expense of being functional. Sometimes it's at the expense of moving towards or achieving higher-order virtues or values. Basically, trying to always get people to go hard, sometimes not be functional, sometimes take it easy, is the routine prescription for a lot of this stuff. If you're really clear on the kind of standard you want to hold for yourself and your work or your hobbies or your family life, sometimes it can be exacting, and sometimes you can endorse that it is exacting and that it takes something out of you. But maybe you have a higher-order ideal that that's what I'm shooting for. We have to be careful about that because you can take that way too far, and it can be purely sacrificial. You lose a lot there, and that can also lead to burnout. Part of the trickiness, but also the beauty of all of this stuff, is understanding how to hold it. Maybe I do have this high internal standard. How can I get a sense of these trade-offs? Maybe I can square all of this by saying, "Okay, well, maybe I'm going to have this really high standard for my work output for this duration of time." It can be phased. During this phase, I'll ease up, and I'll focus on my family and recover, because that may take a lot out of me, and then I'll go back again. Some of these higher-order forces of life and nature matter a lot, which is your own personal rhythms, seasonality, phases, momentum. All of this stuff matters a ton. That's a thing I'm building into my next project, and why I think coaching by itself isn't sufficient a lot of times. The right touch at that time isn't, quite frankly, it isn't to just release the gas. Sometimes you need help in getting through a crunch time or a crunch period, which is going to make your life markedly better in some way or contribute to a value that you care about. You need help getting through that. Maybe you need help for how to plan after that and so on. You figure this out with a lot of trial and error and reflection and making sense of what just happened. The more you do a thing like that, the more you figure out how to hold or how to orient towards things like strong internal standards and not let them get away from you and grind you up.

SPENCER: Could you give an example of working with a client? Will you help them figure this out, either a real example or just a hypothetical that's sort of typical of people you work with? Will you help them understand their own internal standards and also help them understand the timing of when to apply the different standards, I suppose?

TEE: Yeah, great question. So I'll take one that is modeled off of a client that I have. This person had done a handful of roles that increasingly became more like leadership, increasingly took on more responsibility, up until the point we started working together. They had done therapy before, but a lot of coaching can be very applied to introspection. It's sort of like, what are you facing now? Tracing the ontology, looking at beliefs, looking at unconscious, semi-conscious thoughts about things, how they're playing out now, how they could change, and so on. You can have gone through therapy and not done this. So, it was uncovered throughout the session that they had this vague sense of, I am ambitious, and my default is to climb the ladder. I like to push myself really hard in service of climbing the ladder and being ambitious. I'm kind of oversimplifying some of their deeper beliefs here, but that was the gist of it. It was the driving thing for a lot of the questions before them, in terms of, what role should I take next? Should I vie for that promotion? This came from a deeper sense that it's good to climb the ladder for various reasons, like I can have more influence, I can have more resources, I can do more good in the world with that, and so on. It was eventually presented to them that there was this role that was definitely a step up for them, but it was a very different role. By that time, we had been working together for a while, and they had gotten into a real groove with the current role that they were in. We had built up a bunch of, what does it mean to do a good job? What are you building towards? This person was thinking, "Okay, I'm really good in this domain of what I do." We can call it grant making. I'm really great at grant making. This is not the actual person's domain. We started to chart what it looks like to do a good job for yourself in grant making. What do you think your managers are looking for? What do you think serves the organization really well? After about a year of really getting into that strategic thinking and reflecting, getting things wrong, getting things right, just trying to interpret what's going on, they hit this groove. Eventually, this other role opened up that was not grant making, and they were conflicted because it was like, "Well, I really want to take this role because I have this deeper driver to ascend the ladder and just be more important and do more important things for the world," but it conflicted with other virtues they had, or principles and feelings they had, values you could say, around their own work that they had cultivated for about a year, including the importance of having it be sustainable, the importance of connecting with the people around them, the importance of feeling like they're building long-term, really valuable skills that they can take wherever. If they were grant making at a different foundation, they were cultivating this deeper knowledge that would be impressive to anyone and was good for themselves too. They saw this growth in knowledge and understanding. They were really trying to figure out questions of grant making for the purpose of understanding reality better, to make grants to make life better, instead of just covering their bases or doing what was sufficient or impressive to others. This other role would have been, like I said, a big step up, but it wouldn't have been at all in line with what they had been accumulating skill and experience-wise. Their notions of what it meant to do a good job, and the subsequent realization that they really loved the current role, and that they had found a way of connecting more meaningfully to it, and in fact, being way more impressive at it than they could have ever thought by way of building their interior landscape, connecting with themselves personally, thinking about how to do that really well according to themselves. Obviously, that paid off dividends externally. It became much clearer that just trying to ascend for the sake of ascending might not be a good idea for various reasons. One of those reasons is, if you're really divorced from how to do a role well, how to do good work, especially because it's maybe an alien role, you might be doing a bunch of work you don't like. You might be pressed for more hours, which is often the case with more responsibility and ascending. You may be putting yourself in a compromising position, especially if you don't have any means of reflecting on it, or a coach or support network of some kind. That's one way that becoming clear on these kinds of things was really helpful for them, not only in the current role but also in a potential future one that they were looking to take.

SPENCER: You mentioned that the stories we tell ourselves can be key to making progress. What are other kinds of stories you see people tell themselves that you work on with them that you think can be big leverage points?

TEE: A really simple one is stories that people tell themselves about maintaining peace, or what good coordination looks like on their teams. Oftentimes, there's a certain reactiveness; they'll inherit, they'll come into a role, and it's sort of like, this is how the culture works. This is how you're supposed to respond to things. They look around and see how everybody else is setting up their day and responding to things and being present. They tell themselves, okay, the way to do it is to fit into everybody else's work stream and so on. That can be true. It can be varying degrees of true, or it can be way off. A lot of people are just sort of doing the automaticity; they're just doing a workday, and they haven't really strategically planned it out or been intentional about what exactly they're trying to do, or the goals they're trying to hit. A lot of people, just in how they progress through their day, will be like, "All right, I open my computer and I go straight to my inbox. It's good to get through those emails first, and then I'm going to be on Slack, I'm going to answer some messages, and then I'm going to take lunch when other people do, and I'll go back to work." This gets even trickier for remote people who are trying to fit into a culture and a typical way of working when they're on a different continent, sometimes in a different state, or different country. A thing I often do with people is help them get a sense of, "How would you ideally like to be working in this role? How would you like to feel? If you could have it all your own way, and you're the king of this company, or the absolute boss, what would that look like?" In some cases, people are the executive directors or CEOs, or they're senior-level enough that they can shape their own schedule. A lot of people don't have a sense of how their energy works, or the best times to do strategic thinking, the best times to take meetings, and all that stuff. That's sort of step number one. We work through that, and a lot of times that can look very different than if you just had some stories in your mind about fitting in and responding to how the organization typically works. If the stories are more like, "I'm going to figure out ways that are okay with other people for me to work at the best times, whatever I'm going to work with them on, what work product we want, and the quality and things like that, have these discussions." That can really reshape your day-to-day actions quite a bit. Some of the stories we tell ourselves around how to make that happen are, "I could never ask for this sort of thing. This is too much. It would be weird to try and shift all these meetings. It would be strange to have this conversation. This person above me, and they would be offended if I requested a different time." These are all stories that can get in the way meaningfully. They're not necessarily explicit stories, but they're sort of unconscious stories and beliefs, ways we chain together our notions of the world on which we operate. We may never even think to ask our boss to have a call at a different time of day. There's an elegant way to do that and an inelegant way. If you were to rearrange your schedule meaningfully, you'd be a far more productive, efficient, or effective person because you are channeling so much more of your energy in the right way.

SPENCER: Do you think it's common that people come into their new jobs carrying over a lot of assumptions that they learned at prior jobs, and that this leads to them acting in a way that's maybe not appropriate for the new workplace, or at least not optimal for the new workplace?

TEE: Absolutely. I'm curious. So you're an entrepreneur, but I'm curious if you've had that experience.

SPENCER: I have not.

TEE: Okay, yeah, it's really common. It's common even, and especially for entrepreneurs that go into a workplace with other people, where they're not the one founding something. And vice versa, where people that worked a corporate gig are now founding stuff. They have legacy notions about how to do everything. A big territory of my coaching is also, I happen to work with a lot of people that are in really progressive companies in terms of, "Your time is your time. You figure out how to use it. What we really care about is the work output." I know I've been talking a lot about how most people don't have a handle on that kind of thing, and that's really important to explore. But actually, among the kind of companies and people that I work with, these companies are actually pretty good at asking for this sort of thing and thinking of it that way. But that presents a different challenge, especially for the people that are only recently out of university, for example, or have been working a nine to five job for a very long time, and now they've taken this opportunity where, again, there's this transition, you have more responsibility. Leadership is like, however you get this done, get it done. If you need to work these hours, or have this many meetings, we'll leave all that up to you. You figure that out for the most part, beyond these one or two essential meetings. It's a very free-form environment where people don't have a sense, like I said, of their own energetic patterns or rhythms, what they know, what they don't know, how many meetings to have, how to run those. There's just so much that's really difficult to figure out from first principles. But also, even if you came from an environment where it was pretty standardized, it could be that none of that applies in this new environment, or very little of it. If you tried to transplant some of the nine to five ways of working into this new role where you have a lot more leeway, it may work, you may get decent results, or it could just be a really bad fit for the environment. A lot of people who come to this kind of coaching are starting to realize that just transplanting or transposing my notions of how to work don't work here. That's often a go-to because it's safe for people, but you quickly learn that that may not be the best way to go about doing things.

SPENCER: Other than merely trying to be aware that the assumptions from your prior jobs may not apply at a new job, what other advice would you have when someone's transitioning to a totally new place?

TEE: Awareness is a really great first step. Sometimes it's sufficient for people to cause an emotional or perceptual or perspectival shift to take different actions subsequently. So that's great. I think awareness is the first step. You mentioned the importance of reflectivity, why it mattered to you. I hope everybody listening to this episode can really give some form of reflection, reflectivity, even building a kind of apparatus, like reviews of different kinds, a real try. I think that's important. But sitting and spending time making sense and wading through these emotions, particularly the emotionality, I'd say is critical. You have your perception of what's going on, but it also makes you feel a certain way, and then internally, you're responding to what's going on around you according to the best that you know how. We can only really do the best with what we can with what we're given, and that's sort of like our current emotional profiles. The question is, is our current emotional profile sufficient for ever-increasing responsibility, or sufficient for the moment? Is the most truncated way to say that, but is the current way that we handle things always going to be the best way to handle things, or always going to be the most advantageous or strategic? I think I would pose, if I were to challenge a person who didn't think this type of work is important, that would be how I would frame a type of challenge, which is I think it's a pretty bold claim to say that you have all of the emotional tools, all of the intellectual tools that you need for any incoming situation, and that any examination of how you do things or how you interpret things isn't all that valuable or important. I'd be incredibly skeptical of something like that. That's one of the bones that I have to pick philosophically with people who are less into this kind of thing. But that would be what I'd recommend. It's like, you say an hour and a half a week, or even less every two weeks, is a typical cadence. How do I feel about certain things will almost certainly, if you are really going into it and spending time on it, especially with someone who's pretty skilled, lead to different outcomes and actions, different actions that will lead to different outcomes. Consolidating those over a number of weeks, months, years, decades could be a huge difference between doing things a native way.

SPENCER: If I try to embody the perspective of someone who's skeptical of coaching, I doubt that they think that they have every emotional tool or every intellectual tool that they need to optimize their life. My guess is just that they're more skeptical that another person is going to be able to give them those tools, rather than that they would work through it on their own.

TEE: Yeah, a more charitable interpretation of that would be, as you said, or the person thinks that the process is going to be too slow and that they could do it themselves. These are other things I've heard, and I think that's fair. I don't advocate for coaching in every context and for every person, and different psychological profiles respond really differently to this type of thing. There are people who give it a really good go, an earnest try, and for some reason, a lot of what the coaching is just doesn't stick. For them, it just doesn't work. It gets lost somehow. It's very slippery. Then for other people, you can work with them for very little time, and they have this introspective process that is very powerful and shifts a lot of their perspective and subsequent actions. I don't think there's a clear answer in terms of a universal approach. I'm just very skeptical when a person hasn't tried it and is saying it's not worth trying. To me, that is a strange position.

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SPENCER: I think some people don't like the idea of self-improvement in general, this kind of focus on optimizing your life, whether it's reading a book or working with a coach. I think there are just some people like that. I know some like that.

TEE: I love that too. I'm actually very sympathetic to that. I am probably currently in a phase where I'm not trying to improve myself. But the point of my coaching that I mentioned, being creative inspiration to improve your life, sometimes a function of coaching can be inspiring, thinking of different ways to enjoy life and exist in life, emergent stuff that can come up in a session that reminds you of ways that you used to be and used to live, and the kind of joy that you want to recapture, the fun activities, the type of person you want to aspire to be. I don't know if it's all "improvement-oriented" or efficiency or optimizing type stuff. It depends on the coach. Obviously, some of them are explicitly about those types of things. But at least when it comes to my coaching, a lot of what improves life is actually these bursts of the sublime, the creative, the beautiful, the aesthetic that is also still worth it, and quite worth it in a lot of cases.

SPENCER: How did you get to that point where now you're in a phase where you're not trying to prove yourself?

TEE: This is going to reveal a bit of my epistemics, but a lot of it has to do with letting things come to me and kind of responding to momentum and signs out there that I see and trying to catch waves. Basically, it's a lot more kinesthetic oriented, and I think that's definitely a privilege of my station in life and progression through my career. I think in a lot of cases, you just sort of need to work hard from the bottom as a 20-something or a teenager. You just kind of have to, although sometimes not, it really depends. This is what the box modern society often puts that age of person in. So, you know, that's a different discussion. But in my current position, it actually pays a lot more to be attentive to relationships and people and invitations. Walk through open doors. Notice doors that are a little bit ajar. Pay attention to my gut feeling and my intuitions about what would be good and who would be good to work with. If I shut out a lot of that stuff and just tried to optimize in certain directions or be efficient in certain directions, I actually think that would overall be way less effective. I would have my head down, my awareness collapsed, and I would be climbing a ladder in the kind of Tim Ferriss speak that I don't want to be climbing. I need to be connecting dots a little bit differently at this point. There are some cases, like when we launched this new project called Super Cycle, which is a community platform for personal and professional development. When we launched that, I'm going to have to run a much tighter ship with myself in terms of discipline and getting all of that together and putting the structure up. So there's going to be a phase where I go back to learning and relearning, learning what it means to be more disciplined and efficient and so on and so forth. And that's why I say I think it is a matter of phases in one's career and how you hold that stuff.

SPENCER: So it sounds like you think that it's best to have a certain focus at one time, that you shouldn't be all the time trying to improve yourself and also look for opportunities and also do other things at the same time. But rather, you should be cycling back and forth between priorities.

TEE: I think so. In a lot of people's cases, I think the quality of attention that's required for these different phases and types of focus, as you say, is really different. And there's a transitional, interruptive cost to them, for sure. In addition to what you're saying, occasional scrutinization of the focus, of the goal, of the direction, and that's a thing I really hit hard, the word occasional, because I often work with people who are constantly reassessing their path. These are people who want to do really big, impactful things for good in the world, and there's a lot of differing opinions about how to do all of that, and they're just constantly reassessing, and it really undercuts their ability to work hard, even day to day, because it's kind of like an overarching existential angst about, Am I doing the right thing right now, which can permeate your productivity pretty seriously. So that's why I think any questions of productivity need to go often, need to go really, really deep in terms of, "Why am I doing this? What am I working towards? How appropriate is it? How am I holding this set of motivations?" Because the meta of it, the macro of it, can also really destabilize.

SPENCER: Before we wrap up. I know that you often work with leaders or managers. What are the sort of challenges that you think are in particular common among that kind of person, and how do you help them through those?

TEE: I have a few, and maybe you can ask me about one or more of them. One is when is it actually worth investing in yourself in this way, in terms of trying to develop yourself personally, develop your inner sense of what's a good idea, your decision making, things like that. There are positions, lower positions where working hard, fulfilling the duties that your managers put ahead of you, is the way to go, and too much trying to be strategic about it may not be the best course of action. I'm not saying it isn't. I think injecting intentionality and strategy into most things at most times is a really good idea, but sometimes it's not. But then people are leaders, and they ascend, and there's a question of is reflectivity of a certain kind and intentionality getting to know myself more and my preferences, building out all of these quote, unquote soft skills, when is this going to be really valuable? This is a tough question that a lot of leaders face. I think a lot of people aren't tracking what I call a personal energy economy, so they don't have a great sense of when it is best for them to do what kind of work, or across what moods to do what kind of work. I think if people really got to know themselves a lot more in their bodies and how that translates into output, this is the thing that faces leaders a lot, because they're stretched, and they're often doing a lot. It feels like too much, and so they're really just trying to keep up, and that can often be divorced from the best ways of utilizing their minds and bodies. Virtue and value clash, as I mentioned before. There are a lot of ways we may want to do a role, even if we've thought a lot about internally, the type of person we want to be, what hard work looks like, what good work looks like. There's still going to be some clashing between those things. I think people struggle with that. Number four, appreciating the power of context and subjective experience. I think a lot of people are bringing abstractions or walking around with abstractions or ideals that don't serve them. If there was a lot more focus on the local context and what's happening right now in their experience of it, they might have a lot more creative solutions that come to them. One concrete example of when it is worth investing in yourself is people who just step into management or leadership, but even people who've been there for a really long time, they don't know how to clear out time to strategically think, or they don't see the value in that. In virtually all cases where I've worked with people who take that seriously as a result of the coaching and get some scaffolding there in terms of different questions that they could ask themselves, inquiries, or prompts, it really does pay off, because it's strategic thinking about pragmatic, practical things. More often than not, when you spend a half hour, an hour, multiple hours, sometimes a week, doing this, you will come to some creative understanding of how to do this differently or better or in a way that accords better with the situation.

SPENCER: Why do you think people don't spend that much time strategically thinking about what they're doing?

TEE: It's hard. I think some of it is we were brought up in an educational system that really didn't emphasize this kind of thing. My personal experience was none of that, really, plus no education about my emotions or any of that. I'm not sure if that matches yours, but most people wouldn't think to. As a kid or as a person growing up, you really don't need to do that in a lot of cases. A lot of stuff is laid out before you, and the tracks are obvious and clear, so you're not really pushed into a free-form environment where that type of allocation of attention and energy is something that you need to do. Maybe sports would be an exception to that, or some kind of outside clubs, I'm not sure, but I think that's often the case, and people are busy. I empathize with that a lot. You can get by and be a pretty good leader, pretty good manager, pretty good anything, by staying on top of stuff, working hard, really trying at it. A lot of this strategic thinking and taking time to reassess your whole perspective and orientation on a lot of stuff is actually going to be a thing that accelerates your ability to function well in these situations, in ways that's really unusual for a lot of people. It's hard to just have that come to you naturally.

SPENCER: Something that I struggle with, and I think a lot of people do, is that often there's very tangible stuff in front of you that you need to do. It's on your to-do list, and then there's this intangible stuff with no deadlines, with sort of more ambiguous aspects, like thinking about your overarching strategy, or how you're managing people, and how you could do it better. Because that stuff doesn't have deadlines, because it's abstract, it's not that clear how to begin on it. Nobody's demanding that you do it. It's easy to just push it to the side.

TEE: Yeah, I think this is a perennial issue, especially for people who are put in newer positions of management and leadership, or they've been doing, as you say, a lot of the things in front of them, and a lot of time has slipped by, and then they've realized that they need to be more strategic, maybe because the landscape shifted and the organization's in trouble, or something's gone stale, or whatever the case may be. There are a lot of different ways to approach this, and I think doing them all to some degree in concert is a really good idea. One, reconnecting with the importance of doing that longer-term strategic thinking. Some of it is about how it feels good to you, or how you want to shape this whole thing, or how your views on where everything is going and how everything looks have changed over time, maybe if you've been doing this for a while. But there are smaller-scale experiments you can run, which I think are really important for coaching. Coaching is a bit different than therapy in many cases, where it's good to run experiments and get these feedback loops where you try stuff, then you come back, you talk about how it went, and you adjust. Maybe it went well, great. Maybe you adjust and try it again. Maybe it didn't work. What happened there? There are a lot of interpretations and feedback loops that I think span this process. You could do a feedback loop like, let's say you have a quarterly review for evaluations for your staff, or whatever. If you did that in a bit more of a strategic way in terms of how the reviews are done, maybe you improve the process a bit. Maybe you put a lot more thought into some of these reviews, and just see how that affects the near term. That can actually build evidence in your mind for how this type of thinking can be really important for the medium and longer term. There are smaller feedback loop experiments, which, yes, they're not like, "I'm going to clear my inbox today. I'm going to kill off this Asana task or whatever. But they're things that you can find out in a few days, or in a week, or in a quarter, and depending on how that goes, that can really build your motivation to want to do the longer-term thing as well.

SPENCER: The final thing I want to ask you about is when you're working with a client and they really have a huge change for the better, like something really big, a dramatic positive shift. What do you think usually causes that? What's your mental model of what's going on in those really big shifts?

TEE: Well, some people might call this memory reconsolidation, but I think it's a deep emotional learning, essentially, where they may have come to some perspectival shift, and that has caused them to see the world much differently in a way that maybe all the listening audience has experienced, just like an idea, a framework, or whatever. It just illuminates, and when you have something that can lock a lot of information into a way that makes sense, it just clicks for you. That's quite an experience. It's pretty incredible. Emotional learning can also be like, I have a hunch about what happened. If I tried something differently, if I relate to it, I tried it out in real life, and in fact, I was rewarded with what happened and what came to me. That can be just incredible. I was super afraid to bring up this set of things with this person because I thought that it would just lead to conflict and tension. Then you go through a coaching session, and there's a concept that's raised, like, "Well, sometimes getting through tension can actually bring you closer and can actually reveal so much more about what's going on, and maybe increase alignment between you two by quite a bit because you get to understand the other person's perspective," and so on. Then they have that conversation, and lo and behold, it turns out that way. That's pretty shocking because it's like living in a different world. You imagine decades of walking around thinking that if you bring up certain things to people, it will be bad for you, and then you try something else, and the world is different in a really meaningful way to you. That's huge. It's beautiful, and I think that's what a lot of those look like.

SPENCER: Do you have another example where maybe you've had one of these shifts, or one of your clients had one of these big shifts, just so we can get a clear feeling of what that looks like?

TEE: Okay, I'll do a really potentially vulnerable and revealing one, and one more common one. So one common example is I did time tracking for a long time with an employer, and the employer would see the time, and that's what we agreed on. It was sort of like quantifying the time worked, and so on and so forth. I moved on to a different place where I was in charge, and I kept tracking my time. I had basically internalized that doing a good job was putting in X amount of hours and clear focus, according to the time that I quantified and was tracking. There was a time in my life where I just couldn't put in that many hours for whatever reason. I was sad, or I was going through a tough time, I was going through health issues, or there were personal things happening. I forgot what it was, but I couldn't put in those hours, and I felt so shameful and guilty about it because this was my own project, and I wasn't putting in these tracked hours in the way that I had previously. I worked with a coach on this, and we found that I was internalizing a lot of moral concepts related to fulfilling these tracked hours, and that nobody was watching me, nobody was looking at it, nobody was judging me. I didn't know how those tracked hours would translate into my actual outcomes. I was just chaining myself to that type of thing, and then realized I didn't need to do that. In some ways, quantifying and tracking time isn't necessarily going to lead to the outcomes you want, and sustaining yourself over the longer term, maybe redoubling your efforts, labor, or really good quality energy and thinking put into what I was doing mattered more. All these things kind of came after that, so that was huge for me. Now I can have a day where maybe it's not my strongest in terms of the amount of time I'm putting in, but if I have a really great idea, or I reach out to a person, and that leads to a big thing, I'm tracking that as a really big, important outcome. I'm trying not to let myself off the hook too much by never working, but paying attention to ways that there are these non-linear, surprisingly huge things that can occur that are just really small, like having an idea in the shower, versus demanding that you grind away for a set amount of time. The second one, really quickly, is I had a deep, fundamental personal realization that I was actually uncertain about being an atheist. From my late teens to early 20s, I was a pretty irritating and insufferable new atheist, a la Christopher Hitchens, Richard Dawkins, and Daniel Dennett. I held this sort of metaphysics of the universe being dead. It's just the big bang, it's expanding, nothing beyond that. It's all empty space and atoms and so on. Going through some coaching, there was a nihilism that was creeping in for me that came with that. It's not always the case, but it was for me, and that was making things really hard. It was tough to actually care about stuff. Then I had a session where I realized my true position is that I genuinely don't know; life is bizarre and weird, and waking up in this world is strange. I think some things are more plausible than others, but I am genuinely uncertain. This had a crazy effect; it was kind of destabilizing, but it made me feel like the world could be much more alive than it was. I think that potential aliveness is something that I've carried into the present day, where I make allowance for the way I can relate to things that new atheists would have scoffed at and ridiculed, and it has made my life better. So those are two things.

SPENCER: Final question for you, what do you want the listener to remember from this conversation?

TEE: The thing I'd really like listeners to take from this interview is some sense that your life could be enhanced dramatically by inspiration. In ways that you've felt particularly inspired or creative, or really in tune with things that are going on, you can take actions to try and recapture that again. You can reanimate these parts of yourself that feel like you understand the world better, or that it's all making more sense, or you can move through it more smoothly and elegantly. That is a feeling for many people; that's why you're alive. It's what makes life worth living. In some cases, recapturing a feeling like that can come from coaching, and I've seen it happen a lot, but I don't think it's exclusively going to come from coaching. If you're in a life or a situation where everything's kind of become iconized, where everything is routine, everything is reactive, or it's just a rut, that's fine, and that can be good. But there have probably been moments in your life when you've gotten this burst of energy from seeing things very differently and stuff coming together. I think there's so much more of that in store for you if you try, just simply try to pursue it. There are a lot of different ways to try to pursue that, but I think trying to do it will greatly enrich your life and the lives of those around you. I certainly think it's worth striving for because ultimately that will make the world a much better place, but also for you to live in.

SPENCER: Tee, Thank you for coming on.

TEE: Thank you, Spencer, it was fun. I really appreciate it.

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