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Exit Paradox Podcast Episode Summary: Rick Eigenbrod - “Post-Exit Death is Inevitable”
Episode Overview In this episode of the Exit Paradox podcast, host Anastasia Koroleva interviews Rick Eigenbrod, a clinical psychologist and esteemed thinker in the post-exit entrepreneurial landscape. Eigenbrod discusses the inevitable psychological transformation that entrepreneurs experience after exiting their businesses, particularly the concept of a “death” of their former identity followed by a “rebirth.” He provides insights into coping mechanisms, the addictive nature of dopamine, and the importance of redefining purpose and fulfillment in life after a business sale.
Key Concepts
- The Paradox of Success
- Death and Rebirth: Eigenbrod emphasizes that after selling a business, entrepreneurs undergo a psychological “death” of their previous identity as a business leader, which is followed by a necessary rebirth into a new self.
- Focusing Illusion: This term describes how entrepreneurs often focus on the idealized version of success, neglecting the complexities and challenges that accompany it.
- Identity Loss and Reconstruction
- Loss of Structure: Entrepreneurs lose the organizational frameworks that their businesses provided, leading to feelings of emptiness.
- New Beginnings: Taking time to redefine one’s identity and purpose is crucial post-exit. Eigenbrod advocates for stepping back to evaluate what truly matters in life now that traditional business structures have dissolved.
- Dopamine Addiction
- Understanding Dopamine: The thrill and satisfaction derived from business achievements can create a dependency on the dopamine rush associated with entrepreneurial success.
- Awareness and Recovery: Recognizing this addiction is the first step to recovery; entrepreneurs must learn to find joy and fulfillment outside of their previous business environments.
- The Role of Support and Legitimization
- Support Groups: Eigenbrod highlights the importance of finding peers who understand the unique struggles of post-exit life. Sharing experiences can help normalize feelings of confusion and loss.
- Legitimizing Experiences: Feeling frustrated or lost after a successful exit is common, and acknowledging these struggles is essential for healing.
Practical Tools and Exercises
- Reconnecting with Curiosity and Playfulness
- Rediscovering Interests: Entrepreneurs are encouraged to engage with activities that spark their natural curiosity, moving away from business-related pressures.
- Journaling and Reflection
- Self-Inquiry: Eigenbrod recommends keeping a record of personal feelings and thoughts to track changes in identity and purpose.
- Embracing the Mosaic Life
- Constructing a New Life Framework: Eigenbrod suggests viewing life as a mosaic, where various tiles represent different aspects of life (e.g., family, hobbies, philanthropy) rather than focusing on one large goal.
Societal and Personal Impacts
- Social Pressure to Succeed: There is a societal expectation that exited entrepreneurs should be happy and fulfilled post-sale, which often leads to feelings of shame if they experience anything less.
- Leaving People Behind: As individuals grow and change, they may find that some relationships become strained or feel unsatisfying, necessitating difficult choices.
Conclusion Eigenbrod’s insights provide valuable frameworks for navigating the often tumultuous journey of life after a business exit. He emphasizes the importance of understanding and accepting the psychological changes that occur, and the necessity of finding new sources of fulfillment and identity. The conversation concludes with a hopeful note about the potential for growth and happiness in the post-exit phase as long as individuals are willing to embrace the journey.
Final Thoughts from Rick Eigenbrod
- Legacy of Giving: Eigenbrod expresses a desire to be remembered as someone who contributed positively to the lives of others and encourages listeners to reflect on their own journeys and identities.
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This episode is a poignant reminder of the complex emotional landscape entrepreneurs navigate after selling their businesses, and the importance of community, reflection, and rediscovery in forging a path forward.
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Transcript
Automatic transcript. May contain errors.0:00You've just given me a sequence I have never thought about. inkling intention action. The paradox is when you get what you want, it is both price and prize. And we are much more focused on the prize than we are on the prize. Rick Eigenbrod is a deeply respected thinker in the post-exit world, a clinical psychologist and co-author of the classic Yale paper, What's Next? The Entrepreneur's Epilogue. He spent years guiding founders through life after the exit as an executive coach. In this conversation, we get into why Rick believes a death of who we used to be and a subsequent rebirth are inevitable post-exit, and how resisting these changes only adds to the struggle.
0:48Rick generously shares the tools and exercises he's found most effective in navigating this transformative process. We also explore the grip of dopamine addiction, the healing power of legitimizing post-success frustration, simple ways to reconnect with our natural curiosity and playfulness, and the bittersweet reality of leaving some people behind as we experience exponential personal growth.
1:20Hello, Rick. Hi. Thank you for inviting me to join us. Very important conversation. So, Rick, I am very excited. It's a very special interview for me because you're quite a celebrity in the post-exit founder world as one of the authors of this incredible paper called What's Next? The Entrepreneur's Epilogue and the Paradox of Success. And I've seen and heard so many people being very grateful for you and your co-authors for that paper, because in there you offer this four-step framework for how to think about the post-exit maze, which is a very confusing and complex situation for most of us. and today what I'd love us to do if you don't mind is talk about some of the hottest issues for the post-exit community to see how your framework can help us get through them so if you don't mind I'd like to ask you to talk a little bit about yourself and your experience and your work with Exit Founders because that paper is not the only thing you do for the community First off, thank you for that.
2:41To hear that is so satisfying to make a contribution, you know, that this is a contribution. One of my intentions or my core intention has been, I want to make a difference with people who are going to make a difference. and this audience, right, they already have. And the question is, what are they going to do with all the resources that they've gathered? And I just don't mean financial. And what they can do in the world is just going to be amazing. And so the thought that I might be able to make a difference with people who make a difference, that's my intention. and to hear you say, oh, I think your intention in some way has been realized is very satisfying.
3:31So thank you for that. Glad I came already. Let me give you a very quick sense about how I came to this subject. And I should say, I didn't come to it. It slammed into me. It's really the experience. um it's uh my background i started out as a pretty straightforward clinical psychologist i have a phd in clinical psychology and basically worked in that clinical area forever um got a call and ended up uh leading uh groups of ceos for what's now called vistage um and that really was a transition into working more and more in what i would think is organizational psychology. And if you work with people who are building, one of the things that happens is it will get built.
4:31And so I think the seminal or the critical event, if you will, that introduced me to this set of issues came with a call from a colleague who was running a Vistage group. And he said, one of our members has benefited from all our wisdom, sold his company. And of course, what we did is we kicked him out because we're not about arriving. We're about striving. And he's having a really tough time. Would you be willing to talk with him? And of course, I was having no idea what I could offer. So that was really the start. The name of that article includes the paradox of success. And clearly, thinking of an exit as a paradox is something you and I have in common.
5:24What does it mean for you? Let's come at it this way. Here's a question I ask to potential clients. What did you hope to buy with the sale? I love the question. it's it's a bit more difficult for them to answer than one might expect basically it comes down to money and freedom would you agree yeah absolutely absolutely and and those are connected in some way they think and therein lies a bit of a problem is that they think money buys freedom and you know what i've learned is yeah money matters but you can't always count on it. And you have to understand what it buys and what it doesn't. Yeah. And so let's say for the sake of our conversation, that at a high level, it buys money and freedom.
6:23Now I would ask you that question. Is the money and the freedom in your experience, both personal and your work, is the money and the freedom the price or the prize? An excellent question. I don't think it is the prize because we, even though we think it's the prize, we very quickly post-exit realize that it's not the end, it's the means to the end. Both of these things enable us to achieve things, but without more actions, about more work, about more learning, we are not getting what we are actually after. And part of the reason is because we don't even know what we are after right after the success.
7:05And I think that's the paradox. The paradox is when you get what you want, it is both price and prize. And we are much more focused, for reasons we might talk about, we are much more focused on the price than we are on the price. So, for example, when you sell your company, is it an ending or is it a beginning? Is it an exit or is it an entry? I love this. I went to a Jesuit high school in New Orleans, so I had six years of Latin. And I stumbled into the word success, and it has two meanings. One has to do with accomplishment. The other one has to do with, well, we'll, sorry, we'll edit that out.
8:01Um, the other one has to do in the meaning has to do with that, which is to follow. Okay. And so I think that the, for lots and lots of good reason, the attention of the entrepreneur is, is on the ending, not the beginning. and so there's this paradox that they run into which is i counted on getting one and i got both and so one of the questions for us is one of the things that i got curious about is why aren't we better prepared for that paradox yeah because i guess we are we are running fast to get what we think is the prize. And so few of us actually experienced it. And those who did experience it don't talk about it as much.
8:57It's one of the reasons why I started this podcast, by the way, because I wanted people to hear what it means to be on the other side of success and whether happily thereafter actually happens. And if it does, how it happens. Well, I think you've hit on the answer to the question why are we not prepared? Why don't we understand this?
9:25There's a term, I think, that covers it that I use often. It's called a focusing illusion.
9:35It's like the arrival fallacy. A focusing illusion is a picture we paint for ourselves, if you will. And that picture is incredibly compelling. And what makes it compelling is not just within it, but what it leaves out. Right. So we're painting a picture for ourselves all along with the help of the investment bankers of a picture of happily ever after.
10:10and so when the reality hits when we really experience the paradox we are really not prepared
10:23and you said something very important for a long time you couldn't talk about it well part of it is no one to talk to and another part is that we think that we cannot possibly complain about any problems because we know the society thinks that we've succeeded and we should be happy and we feel it it's wrong to complain in our situation we should be grateful so we shut up and people and other people unfortunately miss the opportunity to learn from our experience to see that just getting to an exit is not necessarily the ultimate way to achieve true fulfillment. There's so much in what you just said.
11:15Probably this came to me a dozen years ago. Like there wasn't any groups like we have now. Now there are many, many groups that that one can be a part of. And those groups to me have two benefits. The first benefit is they can be consultants to each other. But secondly, in a more subtle way, they are legitimating, they have a legitimating function. That is what you're experiencing, they say to the members in so many words, what you're experiencing is natural, normal, predictable. yeah and if we see it as an opportunity um it is if we see it as such it's an opportunity but i think you know when i first stumbled on this people the the people i interviewed for the research very much felt like they had failed at success no it's absolutely so the the criticism that was in the dismissiveness.
12:22By the way, I did it. It took me a while to realize, oh, that's great data. So when I first talked to this gentleman, he told me about what he was going through and he eventually put an ad in the Wall Street Journal, LA Wall Street Journal, and it read like this, sold my company, find myself with lots of cash, but depressed and unable to find a new rhythm in life. If you're experiencing anything, write me, P.O. Box, whatever, Wall Street Journal, LA. But it took a while for him to do that. The natural inclination is to reach out, anybody out there like me. But I will tell you, when I first had the phone call with him, and this is a little embarrassing, but it was great data eventually, here was my reaction.
13:05You sold your company, you have lots of cash, and you're depressed. Really? If I had your problem, I'd have no problem. I would be a much more worthy recipient of this largest than you. And here was a subtle, I think a subtle piece that I learned from myself and eventually could see out there. Here, I was bordering my life for a piece of the pie. And this guy had a Costco-sized pie. And this is what he's experiencing. It was deeply, deeply disturbing. And so I think that with evolution, we now have, what shall we say, we now have you. We can have these conversations. They're legitimate. And that's huge.
14:05Because we don't want people to feel like I've failed at success. Yeah. And there's another aspect of this which matters for me personally a lot. It's just thinking that these people who are some of the most capable people in our society who actually prove the ability to create value, which is great enough for somebody to want to buy their business. So these people get stuck in psychological issues for sometimes for decades, sometimes for the rest of their lives. Oftentimes they actually miss the opportunity to create more value out of all this incredible experience they have just because they're confused and lonely and very sad.
14:49And lots of them end up, I interview people here who went through a decade of substance addiction just because they were so confused and they couldn't find any better way of approaching it. So it is actually not just an issue for exited founders themselves. I think it's a huge issue for our society to ignore these people and just think that their concerns are not legitimate just because they have money. And another point from my own experience, like you, when I exited my first business 13 years ago, there were no organizations to support us. And what happened to me personally is that I actually didn't even connect my problems with the exit.
15:34I so did not have the connection in my head that I started blaming myself. I started blaming my spouse, my friends, everybody else around me for how I felt. But most importantly, myself, I felt something was terribly wrong with me because I should feel very differently. And I ended up in years of kind of self-sabotage, actually, just because I thought something was wrong with me. So for me, doing what I'm doing now and also seeing all these organizations supporting the community is just so invigorating and gives me hope for not just them, but also the society at large. It's a really powerful thought.
16:22I think we've really crossed the bar in some important way. If you go back and really think about how profound this challenge is, the challenge of choice, right? If you really think about the layers involved in that and how we are unprepared to think about it. I mean, basically, when you sell your company, what you are getting in return, and you want it to some extent, but you want it like you're focusing illusion laid it out for you. It's the end of life as you know it. And so you have this blank sheet of paper. You haven't had a blank sheet of paper in how long? A long time. And I love the quote from Hemingway.
17:12He said it takes more courage to face the blank sheet of paper than it does the bull in the ring. It's very scary. And so let's go back to this notion about it's the end of life as you know it. I did it. Now what? The challenge of choice. Right. The paradoxes. Gain comes with loss. right so the first choice i think is how do we think about it well i didn't have any structure at the time so it took me quite a while of going through mistakes and trial and error and what and now when i look back i realize that lots of my decisions were just ways to escape that blank sheet of paper and ways to escape the pain and confusion.
18:06For example, I jumped into another business very soon after my exit just because running a business actually was my comfort zone. But I didn't see it like that at the time. At the time, I told myself that, oh, I have this entrepreneurial each. That's who I am. I need to be doing that. It actually took me a couple of years to hit another wall when I realized I'm actually no longer motivated to build a startup. And I couldn't rationalize it fully because I was very lucky with that second company in the sense that I could see the early traction and I could see the product market fit. And everything I knew about startups, I could tick the boxes to say, yes, we should go ahead.
18:50And at the same time, deep in my heart, I had to admit that I had no desire of building this thing. And this is when I started thinking, oh, my God, something's so wrong with me. What's going on? Of course, now, you know, many years later, I realized that it was perfectly normal for me to no longer have the motivation I had before. I had no motivation for more accomplishment, for more money, for more success. all I wanted was to actually focus on my little kids and figure out who I am and what I actually really do. But I felt very guilty about it. I felt that I was failing as an entrepreneur because I didn't want to work, but I wanted to spend time with my kids.
19:33And that's very sad. It shouldn't be happening. People should have better guidance in these situations. Yeah. And that's why I think what you're doing, what I try to contribute, has such a subtle value to it in terms of the legitimating function, the legitimating aspect. So let me take what you just said, and it may be helpful to take what you said about your own experience and put it within the framework of, let's say, either the book or the Yale White Paper. Let's go back to end of life as you know it. The first place that this disruption takes place is in structure. You used to have a company, and now you don't.
20:19You can't sell your company and have a company. Think about all the frameworks that running and building a company provides structurally. Not just the obvious ones, but what time you get up in the morning, who you talk to, what you talk about. The rhythms of staff meetings and annual events, it goes on and on. They're striving structures. And all of a sudden, you have lost all of that. And that's what the gentleman, he's given me permission to say his name, Wes, that I first talked to. That's what he meant. The rhythms and routines are a subtle structure. So if nothing else, the sense of wow, this challenge is really hard.
21:13It's significant. It's uncomfortable and it's unfamiliar. So structure goes. You can't sell a company and have it. Meaning goes. Satisfaction is the death of desire. all that juice you used to get that sense of purpose um that was associated yeah with building that structure gone yeah right let me give you an example of how meaning goes and it also has a bit of identity um one of my clients had a company that um they were smallish and they really loved going after the big distributors. They were a small distributor. And one day he said to me, you know, we're so successful. We're not the little guy anymore.
22:14We loved having the sense of purpose of being gorillas, like GU, right? Like we were gorillas going after the big guy. And now we are the gorilla.
22:32Isn't that great? That whole sense of meaning left with their success. And also, that's an example of the loss of identity. You can't sell a company and have a company. You can't be the person who runs a company and haven't sold it. That whole sense of who am I now is up for grabs, for renewal, for refinement, for modernization. And that's one of the opportunities. And I remember one of the women I interviewed saying, I always wondered who lived in those big houses. And now I know it's me. The disruption takes place at the three of the most important parts of our lives. So what do you do? How do you respond?
23:37Well, I think you said one of the ways, which is I know I had a fried chicken franchise, so I'm going to start a hamburger franchise. Start with structure. And derive from that as meaning and identity. but there's no vitality in it often. So what I encourage people to do is to see if you can avoid the inclination to deal with this discomfort by trying to fill the hole with what created it. Yeah, that's what I learned the hard way. It's definitely true. So let me check back with you. I've just done a little sermonette. I want to come back to, you said something about having to step back and really sort of begin with, well, wait a minute.
24:30Who am I now? What's true about me now that didn't used to be true? What's not true about me now anymore that used to be, right? Talk about that. Can you talk a little bit about that experience? Yeah, for me, it all started with my changed motivation. So the most obvious thing for me was that I was no longer driven by what I was driven by before. And that triggered a lot of self-doubt and kind of sadness, really. Totally. this idea of what's wrong with me. But then over time, and it did take quite a lot of time, I started accepting. I actually ended up closing that first business, and I think it was very important because I felt intuitively, very strongly at some point, that I needed to create space.
25:26I needed to give myself permission to not have a structure for a while, not build a business, but experience something else. I traveled, I focused on my kids, I did all these other things. And I think it was, it was absolutely critically important. I'm very happy I did that. Even though the decision was, was not entirely rational from the outside, lots of people couldn't understand why I would do that. But it was very clear. So anyway, that was sort of what I did. And then after motivation, the next big question for me was, what do I truly want? Like, if I can do anything at all in the world, and I tried running a business, I know I shouldn't go in that direction, a second business.
26:15So what is it I want? And, you know, I now call it, you know, freedom paradox, because we have this freedom, but we don't actually know what we want. and that's again without some guidance feels like something's wrong with you and there's also if when I try to be rational about it and I had a list of like kind of a bucket list of what I wanted to do I had to admit that lots of these things I wasn't quite motivated to do and there were so many options I ended up in decision paralysis I was like, okay, how do I prioritize all of that? And that's an interesting push into self-discovery because then you have to ask yourself what it is that truly matters for me.
27:04What you have shared is essentially the model that we tried to capture from people's experience like yours. is everything I know, everything that ended up being in the Yale article in the book and in my work really comes from listening to the experience of people and trying to make sense of it. People said, why'd you write the book? You know, people write, generally write books for an audience. I had an audience of one. Me. I wrote the book so I could know and understand what I thought. I had all this information. And so can I come back for a second to what you said? The typical, we grow up with, and I'm going to use shorthand here.
27:58We grow up following a model that is built around the grand narrative of success. It is structure, which provides meaning and identity. At some point, you say to yourself, I could repeat myself, but there's no vitality. Some part of my tummy goes, I can't do that. What you naturally did is step back and started with identity. Gosh, I used to be the woman who, and now I'm the woman that. I didn't used to be that, and now I am. And that led to a question about that woman, that person, who I am now, who am I now, led you automatically to the next stage, which is meaning, which is what matters to me now.
28:57And then lastly, the structure. And you said it, so I'm just putting in the word. What forms of expression will I find, build, create? to express identity and meaning refreshed. That process of I'm not this and I used to be that, I used to be that and I'm not, et cetera, those are the two driving force dynamics of human development. They're called integration and differentiation. So what I discovered is this is an amazing opportunity, a vehicle for their own individual someone's individual development and you just gave a very personal example of that no i absolutely agree with you uh over time i realized that an exit is actually the true opportunity of a lifetime because this is the opportunity to make this huge leap in in in your development but also in spiritual development in any kind of development and get and build the life we truly want so we finally have all the resources we just need to have a direction and we need to have to give ourselves a permission to do that and to appreciate the opportunity because i almost squandered that opportunity with that first business.
30:26If I stayed in there, which would require some discipline, if I stayed in there, or if I brought investors in or hired someone, I basically would have missed the opportunity to grow tremendously. And be where I am today, which is a much happier place than it was before or immediately after my exit. You know, you raise an important issue that I also ran into. there are people who are um like you know it's time to go but they can't why because they have some instinctive sense that there's a blank sheet of paper that they're going to have to face let me give you a quick story in the interviews i did i was sitting on Cape Cod with this gentleman in his third home or whatever.
31:22And we were talking, and I said, so which would like to be successful? He said, kind of quietly, he said, well, I always wanted to be a business mogul, and now I am one. And I went, wow, that must be fantastic. And he got very quiet. And he looked out on the water, and he said, I'm like one of those sharks out there. And I said, really? Oh, oh, I get it. You're the apex predator. And he said, no, I have to keep swimming or I'll die. It's what I call done but not finished. If we took another way, another lens for looking at this, and we use, say, Joseph Campbell's work with the hero's journey, we know it has three parts.
32:19The call, separation, you go into the wilderness and face the demon, you win some boon, and you bring it back for others. Here is someone who would not respond to the call. And in the model, he would be called King Holfast, who becomes a danger to himself and others. And so I like to think, yes, it was heroic what you did.
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32:55Now, another hero's journey begins. Yeah, there is an interesting trap there, which is a financial trap. At some point, I got very interested to see what is the most financially dangerous pitfall post-exit, because I started meeting more and more people who wasted so much money in the few years after the exit. And I found that actually that is starting a new business without realizing that, as you said, there is no vitality to it. Then invest in your own money into it because we don't want to bring in investors, even though we know it's easier to raise money, but we have this sort of pride. We actually want to this time around use our own money for our new venture.
33:48And then what happens when this crisis hits you that you actually no longer want to do business, you already have invested so much that you cannot stop. So you start throwing good money after bad and you get really stuck in that. And I've seen these stories again and again. And what happens is that years later, people waste so much money. They feel so horrible about the whole experience. And they end up in a much worse place than where they started. And on top of it, this is when they really don't want to talk about it. Because then it's really embarrassing. Because they also have this idea that everybody expected them to keep being successful.
34:29And they failed. And this is the saddest situation ever for entrepreneurs. Well, and I think that you may know these statistics better than I, but I think I remember reading that the probability of success of a second business is actually quite small, quite low. But I think that that's a great example. If you don't know how to think about where you are, you try to solve the problem with what created it. And there's nobody to stop you or say, wait, slow down. Right. And and so there's a whole area, as you know, of this experience, the paradox of money. You know, what's the role of money when you get it?
35:23what do you want money to buy you?
35:29And, you know, we could probably have a whole conversation about that. You've seen it over and over. I mean, people with incredible wealth who every day get on a computer to see how their portfolio is doing. You know, I've noticed an interesting evolution in how we think about money in myself and many other exited founders who exited more than a decade ago. And the evolution goes like this. After we've gone through this initial excitement about wealth and shopping sprees and all of that, we discovered that the meaning of wealth is in giving us safety, so we don't need to worry about it. So wealth properly managed can be a beautiful liberating force, which allows us to stop worrying about money, achieve that financial contentment, and then go after things that are not necessarily about chasing money.
36:28This is the first step in the evolution. Then later people realize that the meaning of wealth is also in sustaining years of this life, which is stress-free, self-discovery. It actually enables us to explore without being rushed. And then the final ultimate meaning of wealth, which I found and other people discovered as well, when you find that real purpose in a very selfless, very spiritual sense of the word, when you find what it is you can contribute to the world and get fulfillment out of it. When this happens, then suddenly your wealth, not necessarily suddenly, but gradually, your wealth becomes leverage for that purpose.
37:16And then it's a completely different meaning of wealth, and it's a very different motivation in managing that wealth. It's no longer about just getting more, but it's actually about how I can enable giving more. Let me comment on a couple of things you said. I mean, that's so rich, what you're offering your experience. And it hits a couple of things I've run into over and over and over again. What does money buy? For me, I've known money buys safety. It doesn't always buy security. Because I've seen people who are completely safe by any objective standards and who are incredibly insecure. So money by safety can't be by security.
38:07So that's one thing. I noticed something that's really important I want to point out. Notice how, I noticed how, you tell me if I'm noticing correctly, how over time the questions you ask yourself changed. When you first exited, you had a certain set of questions. Yeah. And over time, they changed. They got refined. They got more, they came more out of not fear and anxiety and pressure and social pressure and expectations and the tyranny of the shoulds. They came out of this emerging woman. And a dear friend of mine who I quote regularly, his name is Pat Murray. He said, progress is measured by trading in your old questions for a set of better ones.
39:01And John O'Donohue, the Irish poet and writer, said, questions hold the lanterns that light the way. And I think what you just said is your questions, as they changed, they got better in some way. more about coming out of you and something authentic. And they lift the way for you into what's true for you now. And so I think that notion about sort of honoring the questions, letting the questions emerge is really important and you illustrated that. Thank you for that. You know, one thing that I think about a lot these days is on the one hand, I feel so grateful that I had a chance to go through that challenge and that personal growth.
40:04At the same time, I'm thinking our life on this planet is very limited. Is there a way for people to go through this amazing journey, but without getting unnecessarily stuck in wrong places. So this is my question for you because you've seen and studied so deeply. Okay. Where do you think people get stuck most often and why? And I'm going to refer, I think it's the refusal of the call. They just refused to go on a journey that they're being invited on.
40:43Secondly, thank you, I hadn't thought about it in these terms. What I've been aware of lately, of what gets them stuck, is using the mental models, mindsets, attitudes, and resources that got them here. Building a company requires certain attitudes, mindsets, et cetera, et cetera, expertise, et cetera. Facing the blank sheet of paper is a totally different task. And so you get this, what I'm going to call negative transfer of learning. They try and apply that expertise, those mindsets, to a completely different task. Can I give you some examples? Please.
41:36So I have a list here. I'm going to refer to it. And this is new for me to have come up with this. Brute force effort. Brute force effort is no good with the task of now what? In a blank sheet of paper. Impatience. It's not, it's not, it's going to be counterproductive. And what I loved about a part of what was my colleagues in the Yale article offered was a timetable. And often when I talk to people initially, they are so impatient. They want answers really fast. They want to solve this problem. They want to beat it into submission. You know, and it's like, if that's where you are, this is not going to be a good fit because I know what it's going to take.
42:31and so this impatience stands in contrast to the timetable in the Yale article which is two years and I think you said that was about right for you right next, next, next it's great when you're running a company productivity is the key metric I remember one of my early clients and he tells a story about this. He said, Rick, I'm doing this, I'm doing that, and I'm doing the other, but I don't feel productive. And out of my mouth without realizing it came this response. If you try and measure by productivity, it will get in your way. So using these skill sets, the need for control, competitiveness, the need for speed, the need for dopamine, all those things.
43:28They will get in your way because the nature of this task is really different. And that's why I think people, it's one of the reasons people have such a difficult time. Rick, given that you're a clinical psychologist and I don't have those ever on my podcast, can I pick one of those issues you just highlighted? And that's the dopamine addiction. Can you please help me understand from your professional perspective how that works and why people get stuck? And most importantly, how to overcome that addiction, which serves us very well while we're building the business, but does not serve us in that post-exit stage.
44:17If you're an entrepreneur building a company, particularly a company that's growing quickly, there's so much juice, right? And the juice can keep you going through amazing fatigue and all kinds of stuff. And so I think it is, again, it may be helpful to say and think about it, is the need for a dopamine hit is the same as a need for a hit for anything else. And we have to deal with it like we would an alcohol addiction, a drug addiction or something else. You know, those models, I think, can help us. But I think it all begins with awareness. I don't think, you know, my experience in working with some of these folks or listening to some of these folks when I talk to groups, I don't think they're aware of the extent to which the juice has them.
45:18And so I think talking about this, beginning with awareness, what is the role? To have a conversation like, let's talk about dopamine. How do you know when you're getting a hit? How do you know when you need a hit? Where do you go for it? To have this conversation, this exploratory conversation, so that you, in a sense, fatten your awareness about it. And as a colleague of mine said, don't try and change what you don't understand. So I think it starts with an acknowledgment that it's no different dynamically, physiologically, from any other addiction. And the starting place is to just notice the role of dopamine and to search for it in my life.
46:14Now I can start making interventions in small places. So once you recognize the addiction, and I have to say, in my experience, lots of post-exit founders do, there is an interesting dynamic here, which I notice quite a bit. people feel it but then they don't want to let that addiction go even even rationally because they're very scared that once it's gone they'll be very they'll be incapable like one of my friends actually uh described it as as a fear of death he says i absolutely understand but if i let go of this addiction, I'll be dead. It's not me. I'm an entrepreneur. I should keep going.
47:00That's my essence. And I refuse to stop. What would you tell that person? This entrepreneurship has them. This life has them. They don't have this life. So it really touches your heart. I would say you're right. You, as you know, you is going to die. Now, let's talk about what that means, what the anxiety pulls up, where the fear comes from. I wouldn't try and say to them, no, no, you're not going to die. You're not going to physically die. You can feel that way as addicts do. But I think what they're saying in a most profound way, it is the death of the person as I know me. It is the death of my familiar desire.
47:51and where does that leave me? And now that's the next exploration. When I work with folks early on, I give them some homework. And one of the things I ask them to do is to keep a running kind of record of their response to this question. what's it like to be me now the second thing i ask them to do is to pay attention to the sense about it's the teacher it's two t charts it's differentiation and integration what used to be true and now it's not what's true now that didn't used to be and again it's it's an awareness exercise but i wouldn't try and talk them out of the notion that you're onto something there.
48:44Natural, normal, predictable. How would you encourage people to go through this death and rebirth? Like what can help them be less scared to go through it? I think one has to just acknowledge they're not ready. They're not ready to go through this. You know, it's part of what I try and assess when I get a call from somebody is a sense of readiness. You know, and the truth is some people are not. And I can feel like crazy for them. I can want to give them a pep talk. I can want to do all kinds of things. But if it's not there, it's not there. And they have to feel worse. Is it possible to go through this transition in your experience and your professional opinion?
49:37without going through death? Can it be smoother? No. And should it be smoother? No, I think you cannot go through this without experiencing some death. The death of who I used to be. The death of the structures that gave my life a sense of stability. But part of what you need is companionship. Planionship, part of what you need is comfort, part of what you need is validation. And that's what these folks are starting to get in the groups. Oh, you're going through that too. Wow. Yeah. But I think it begins with acknowledging that's the nature of the challenge that comes with now what. and you are unprepared, generally in two ways.
50:35The focusing illusion didn't set you up to expect it. All of our narratives end with some version of they lived happily ever after. So we are ill-served. Secondly, yeah, you're going to leave some things behind. actually, here's an example. I think, I ran into this. I think you have to leave certain people behind. Absolutely. You have to. And that's one of the most painful parts of the exercise, isn't it?
51:18Yeah. They can't go with you. If they can't go with you, you got to leave them behind. And you will do anything because you're now, you know, this rich person. You will do anything to kind of reassure them that, you know, no, just because I'm rich and famous now, I'm not that, you know. And you'll try so hard and they can't go with you. You have to leave them behind. And so to experience sadness, loss, uncertainty, that's going into the woods. that's going Stephen Sondheim's play essentially says we go into the woods after we got the golden fleece we go into the woods where most of the fairy tales end that's where the real journey begins, into the dark wood and so I don't think you can take that away from people because they know what their experience is and we know what their experience is now.
52:24We've experienced this ourselves in many different ways. Do you find, Rick, in your experience, that this readiness has to do with age? I think age is a variable. The kind of map that we have historically takes us out in a striving mode to where we are, where we quote unquote retire. It was binary. It was pretty clear. It took a lifetime in Levinson's work, Seasons of a Man's Life. It took a lifetime to build the structures and then you retire. What about a 35-year-old entrepreneur who sold two businesses for a billion dollars each? It's much harder. That really is a dimension because you take the notion of this binary retirement out.
53:34And now you're looking at sequences, stages. right one of the things that folks I work with really wrestle with is answering the question what are you doing now
53:52and if you're 65 or so you can use the word retirement which by the way I think is a terrible term here's an example you're on a plane first class of course you're sitting next to somebody and this is a very American thing I've heard is Europeans don't do this. Americans. So what do you do? And you say, well, I'm building this company and we're doing this stuff. And all of a sudden you're in London because you had a fabulous conversation. Okay. He says, so what do you do? Oh, just about anything I want because I sold my company. Oh, good for you. Congratulations. Up goes the paper. Of course. And so, yes, the answer is, I think, for younger folks.
54:40And it's going to come more and more with what somebody called the democratization of success. And I think with AI helping us, it will be happening even faster, for sure. And the problems, you know, I think our philosophy, psychology, ethics are not keeping up with the speed at which science develops and technology develops. And for me, they really aren't. The biggest problems right now is actually to close that gap as soon as we can, because there will be even more of this kind of suffering we are talking about right now. And people are even less prepared for it, because with the help of AI, we'll have even younger folks having the problem of identity structure and meaning and not being prepared for it.
55:33Absolutely. But I'm very curious, Rick, from a practical standpoint. So you have a client, 35, sold two companies for over a billion age, sits on that plane in the first class. What do you tell them or recommend that they say to avoid feeling, you know, alienated and lonely in the society? I actually put together a checklist. if I could get to you before the sale. It's called checking in before you check out. I love it. Selling a business is so focused, right? But it would get far enough up, you know, back into before this event, which is all-encompassing, and begin the process of being aware of, you know, what really the complexity on the other side of, in a sense, trying to crash into the focusing illusion, reminding them of what this sale really is buying, helping them understand what life on the other side looks like.
56:50So if I had that, I'd do it.
56:57But in terms of afterwards, they're very different in terms of where they are and how much they're struggling and where they're struggling. So I just try and meet them there. One of the things that I certainly I try and bring to the table is a sense about what's getting in the way, what's getting them stuck. And can I reach into that dam and pull that one stick? They will be told by everybody around them, you need a new goal, and they don't mean a smaller one. You need a new hill to climb, and they don't mean a smaller one. I invite them to experiment with the notion of changing scale. So I give them two things in that area.
57:51One is an image. The image is, instead of looking at one big thing to replace that structure, one structure, I give them the image of a mosaic. And that mosaic has these beautiful tiles. Each one is gorgeous. And if you look at it, there's some coherence to it. and I call it the mosaic life. You can keep constructing it. So I give them a different kind of image. The second thing is I invite them to think about, and that image does it, change scale. Can you find things that in the experience of them, in the moment, have amazing engagement, energy, vitality, satisfaction? And they begin to be able to see those things that they couldn't before.
58:49And any one of those smaller things can take them somewhere else. Here's one of my favorite stories, very quickly. A guy down here in Silicon Valley was in this situation and he was taking his kid to school and there was no crossing guard and everybody was saying, God, Jim, you got nothing to do. Why don't you become a crossing guard? So he did. And he said, this was so amazing. I met people. I had conversations. I felt like I was doing something. Fast forward, out of all that, he became the mayor of the town. True story. So I think those two things can be helpful initially. And the third one is follow vitality.
59:32I think it's brilliant. And I think it's definitely a great guidance to find, you know, how to think about life again. But if we go back to a much more superficial problem, but still very important, how do we best describe to others where we are in a way that is not alienating? One of my clients had a great word for it. He called it cover. He said we need cover. And it was brilliant. I said, what do you mean by cover? He said, you know, it's what you tell everybody else and yourself you're doing while you're trying to figure out what you're doing. And I think whatever it is you say to people has to fit the two criteria that you just said.
1:00:30It has to be authentic.
1:00:36And because people are going to, what's going to satisfy them is the sense about this is true. So if you start with what's true for them, you can work your way into the language you're going to use. The other thing I think here that I've discovered is what you say depends on who it is that's asking the question. For some people, you can just flat out tell them the truth. You know, I'm out here with the gift of a blank sheet of paper trying to figure out what I want to put on it. With some people, you can tell them that. With some people, you can be playful. I've done this myself. I say, well, I'm at the point in my life, they asked, are you retired now?
1:01:28Little gray, light gray. And I have this playful thing that I do cautiously, selectively, where I say, well, at the point in my life where I serve at my pleasure, then pause for effect, and I'll do some version of this. Honey, can you remind me what my pleasure is?
1:01:54And for the right person, they will laugh as you did, and they will get it.
1:02:03and so I think it's a process of beginning with what's your situation what's true about it how will you describe that in a couple of three ways depending on the audience and they can usually come up with something as a matter of fact I just did that with someone and they were really satisfied with it. It was just great to see him go, okay, I'm not afraid to walk the streets of New York now. And if you're in New York, you're going to get that question. Absolutely. So Rick, say somebody went through a rebirth, and they see this beautiful mosaic of life and they follow what feels right. They're in touch with their vitality.
1:02:54They overcome addiction to dopamine and adrenaline and they still feel they really want to start another business and go back in the game. What would you tell these people? Go ahead. But first you got to tell me why.
1:03:18okay tell me why where's that coming from where's that coming from um okay if the answer is because i i'm now ready to contribute and i think this will give me purpose and it's something that I love doing? In that case, go for it. What would you watch for to say, maybe not? What would be those red flags for you to think, oh no, that's not the right path? Yeah. Oh, Anastasia, that's a fabulous question. I look for what I call anklings.
1:04:10They're little pinholes of light that people get. And inklings have these three characteristics. And I'll try and say a bit about these. Truth, vitality, and fear. but as I sit with them, I listen like crazy to, is what they're telling me true? Oh, I really want to go back and do this. Does it feel like it's true? And if you listen carefully to them, not just with your ears but with your tummy, you can have a sense about this is true. and it's coming from and attached to something authentic. It's not a palliative. So is it true you really want to start a company? You can feel people's energy, can't you?
1:05:10You can do this for yourself. You talk to people and you notice it in yourself. People notice it in me. God, you're really fired up about that. Oh, right, I am. So I look at truth, vitality, and here's the real thing. I look at fear. I'll look for fear. Why fear? Because if there's no fear, it means that they're not, the fear generally, if it's true, it's got vitality and fear associated with it. In some way, this inkling, if it's followed, will push them up against some developmental frontier. And I used to think the fear, oh, yeah, you're right, you could lose this, that would happen. I used to think, well, in that case, don't do it.
1:06:03No, that's what they think. So I'm looking for those three things as I'm listening to them. um i'm listening for the sense of this is the thing to do versus i don't know what else to do rick can we dig into the fear a little bit more because i'm trying to understand i'm not sure i fully understand it so for example when i when i started a business then i closed it and then And I looked back and I thought that that decision to start the business was largely driven by fears. And it was a whole cocktail of fears. One of them was FOMO because I saw all these other people, you know, running, doing great next big thing.
1:06:52There was a fear of failure and also, you know, public failure. People seeing that I was a one trick pony and I couldn't do another business. there was also, you know, there were lots of fears there, right? And now you're telling me that actually you want to have a fear when you are starting a business for the right reason. So can you help me understand that? Right. I mean, if you start a new business, there's risk, et cetera, et cetera. But if they say, I want to start a new business and it's really scary, then I want to talk about the nature of the fear. If the nature of the fear comes up with things like, I'm doing it because I, you know, something along the lines of what you said.
1:07:44I'm doing it for fear of living in shame. I'm doing it for fear of other people's, what do you call it, evaluation. I'm doing it for fear that I have these things that I should do and I'm fearful if I don't do it. Those are the things you really look for. To start a business and have fear that's legitimate, but to have fear that comes out of some undeveloped part of you, that's kind of what I'm looking at. That's the fear I'm looking at. If I go and do this, I'm really afraid that I won't get, you know, I'm doing it because if I don't do it, I won't get other people's approval. That's the developmental piece.
1:08:37So discerning what's connected to some realistic risk and what's connected to some psychological barrier or limiter is a part of the conversation. What about a fear that I'll be not capable? I don't have the skills. I won't be good enough at this. Which bucket would you put that fear in? If you say, well, this is really new territory and it's a new industry, I'll go, well, hell, you should be scared. So that would be a good fear. You would want that fear. Yeah. Right. All right. And if it's a fear of being left out while the rest of the ecosystem is developing, then it's a different kind of fear.
1:09:29So you're left out of the ecosystem. So what? So you're not in a gang anymore. So what? You can kind of bet where you're going to track that back to. In that brilliant paper of yours for Yale School of Management, you were talking about the challenge of transitioning in the mindset from being an entrepreneur to becoming an investor. But you highlight the risk of a completely different mindset that an investor would need comparing to entrepreneur. So I would love you to share a bit more of your experience, how you saw people struggle with it and what you found helpful in that transition. It's one of the paths people go down, right?
1:10:20You make a bunch of money. What are you going to do with it? Well, you can watch it. You can make it bigger for reasons you don't know, but bigger is better. That's what you've always heard. So it gives you something to do in the morning and blah, blah, blah. And the other, another path, you know, starting another business and another path is to become an investor. Private equity, private investing, et cetera. That's, that's not unusual at all. The question is, that's a structure. What purpose does it serve? tell me why you would think about doing that right it's a structure it's okay it's not illegitimate but tell me why you would want to do that okay and that's really important because it leads to this One of the things that I think people get confused is what's the purview of ownership and what's the purview of management?
1:11:33Those are very different. The roles are different. The responsibilities are different. The activities are different. The nature of the engagement is different. And people who are used to having their hand on the wheel are tempted as investors, owners, to get involved in management. Their role is in the purview of governance. So you say, what's the purview of governance? What's the role? What's the duties? What's the responsibility? What's the territory for, I'm going to call it governance, ownership, right? Governance represents owners. And watch for where they want to move into management, to the purview of management.
1:12:25Now, it's done all the time. I get it. But, you know, it's like, again, why are you getting involved over there? you know is it because they need you or is it because you you can see how they could do it better and so keeping that boundary between you know your sort of nose in and your your thumb out is a real challenge I think for people who are doers the most common thing post-exit founders crave in my experience is the sense of purpose and most people I talk to actually admit that they didn't think about business as something that gives them a sense of purpose until they lost it they only realized it was this the the source of the sense of purpose so my question to you is what do you think generally for humans is the source of this sense of purpose and why we crave it so badly after we sell the business?
1:13:33And of course, the most important bit is how do we recreate it outside of a business structure? I use the word meaning. I use the word matter. purpose is purpose is big purpose is um has this encompassing quality to it but a search for purpose becomes really hard um it's kind of elusive etc but i realize in my conversations with people i'm using the term matters what matters to you now that they can answer and and that mattering certainly has some element of purpose to it doesn't it what matters to me now is to make a difference with people who make a difference was that a purpose oh okay so i think in some way if we changed what i've done without being conscious of it till these conversations, conversations of fertile ground for emergence, including awareness, thanks to you.
1:14:46I don't even use the word purpose. Yeah, it sounds like you would replace the question with another question. It's always, always very helpful. You would basically, somebody asks you, how do I find my purpose? And you would say, what matters to you today? Can we just put that aside? That's a biggie. Talk to me about what matters to you now, now being an important thing. And it comes out of who they are now, right? Right. Mattering really is a is a is something that the identity, the sense of self selects. So I can have a much more I can invite them and me into a much more manageable arena by talking about tell me what matters to you now.
1:15:39And how do you know what what tells you it matters? and what do you do with the mattering? It just makes things, it seems to me to make things more navigable. I think it's very helpful. I really like it. But Rick, just to clarify, does that mean that you prefer that people don't think about the direction in which they should develop? You've raised another issue that I think is maybe in the Yale article. this notion about two ways of knowing and two ways of going, which I stole from Robert Irwin, the artist. How you know is how you go. And what I think in general, there are two ways of knowing and two ways of going.
1:16:30One way is what I call destination. And that's what we're used to. I'm going to get a degree. I'm going to get a PhD. I'm going to go work here. I'm going to build a company. Destination. And that's when you set another big goal. I'm going to start another company, for example. That's destination. There's another way of going, which is you use the term direction. I'm headed off in a direction of. And it's this. Yeah, it may be that thing out there that says that we might call purpose. Or I'm going to move in a direction of living according to what matters. to me um i'm gonna i'm gonna move in a direction of following the vitality and as it pops up in my life even if it surprises me uh and there's sort of two metrics for those in in generally in direction i mean sorry in destination um it's the metric is closer further In direction, the metric is more of or less of.
1:17:40How would you connect that to the sense of fulfillment? Like if I tell you, why don't I feel this deep, lasting satisfaction with my life? Like where should it be coming from? What am I missing? Help me isolate the problem. The person who is the entrepreneur in everything they build, everything that got them there, they suck at fulfillment. So true. They suck. My line to one of my clients is, you suck at savoring. They literally don't know what fulfillment feels like. They don't slow down enough to savor. One of my clients, we were talking, he said, well, I got to go. Okay, fine. I'm getting bored and blah, blah, blah, blah, blah.
1:18:35And by the way, he's wonderful. I love this guy. He said, blah, blah, blah. I'm getting bored. So I guess I'll go walk the dog. And before I could stop myself, I said, don't go walk the dog. Go walk like the dog. The dog's never bored. You can take the dog down the same street, and they are incredibly happy. They are incredibly fulfilled. They haven't a grand time. So go walk like the dog. We have to learn to walk like the dog. And I said, what's the name of your dog? And he goes, Mojo. And I said, oh, okay, I get it, like juice. And he said, no, it stands for more joy. go walk with more joy and that's a developmental learning yeah to be satisfied to um savor um to um to feel uh you know we're so we it's back to dopamine happiness forget those things you know it's like can you feel a sense of peacefulness contentment satisfaction and it doesn't take great big things to give it to you if you are capable of taking it then i guess instead of dopamine we get serotonin and that at that point right Because nature in its infinite wisdom gave us the right biochemistry to have that feeling.
1:20:18It's just that we are not given it a chance oftentimes to let us experience the beauty of contentment and this serotonin instead of dopamine feeling. Brilliant. Brilliantly said. and I think it fits with this notion of change in scale to some extent. I have two wonderful stories. I'll tell you real quickly. One is I was in this group of CEOs, and one of the guys was complaining about selling his company, and before they threw him out, you know, blah, blah, blah. I don't know what to do. And one of the guys said, and I don't think you can do this anymore, but one of the guys said, well, you need to come with me.
1:21:02And the guy goes, do what? And he said, come with me. I'm going to the hospital and I'm going to go hold a baby. You go, what? Yeah, this hospital has, you know, lots of babies that have mothers that can't care for them. The staff can't. We know how important it is in brain development and et cetera, et cetera, for these babies to be held. So they have people like me who volunteer to come in and hold a baby. And the guy so looked at me, he said, he said, if you want to experience pure being, hold a baby.
1:21:38we can almost feel in ourselves being in the present, slowing down, sinking in when we hold a baby.
1:21:55Entrepreneurs who are looking at the next, the next, the next, the juice, the juice, the juice. That's such a different experience for us. And the other quick story is, somebody said what are you going to do this for vacation he said you know I'm into photography I think I'm going to and I have this incredible backyard I think I'm going to photograph my backyard I said oh that's well that's interesting okay so fast forward to the end of the summer and he said so how'd your summer go he said it was amazing oh my god I took so many photographs I just saw things I never saw it was I just my wife had to call me in and come to dinner and he goes oh well that's fantastic so what are you going to do next summer he said the other hey that's brilliant i love it isn't that a great story it's so beautiful um rick i am afraid we do have to wrap up even though i absolutely hate doing it and i hope maybe we can have another interview soon so I can get a bit more of your wisdom.
1:23:01But there is one question I always ask everyone at the end of an interview, and I want to ask you as well. How do you want to be remembered?
1:23:14Oh, as a man for others. That's so beautiful. Thank you so much. Jesuit High School, New Orleans. Here's where my mind's taking me now in this work, which is, it's been a gift, this work, because it's layers and layers and layers. I think we're providing now for this very unique subpopulation. the question coming to my mind is we understand the dynamics now of arrival excuse me in ways we never have i'm beginning to see this dynamic expressed all over the place i can't not see it remember i said your awareness fattens. Just to give you an example, in the same month, I got a call from an ex-Navy SEAL and an ex-British Special Forces guy, both of whom were coming out and both of whom were experiencing exactly these dynamics.
1:24:35yeah where else is there where where else in the world do we see this and what could be offered that's where my curiosity is taking me yeah i i know exactly what you're talking about because i see these parallels all the time as well i talk to people for example who are athletes and their career has peaked in their 20s, and then they wonder what to do next, and they've arrived and they're exploring their options. It's not that different from what Exeter founders experienced in its essence. We do have very particular, very different kind of fears and issues, but overall, it's also part of the arrival fallacy for sure.
1:25:24It certainly has the complexity of age as you raise. So, oh, that's interesting. What do we know about that? What can we learn about that? If we went out and talked to people, which is what I did early on. I mean, in companies, company goes public. Does that end life as they knew it? You better believe it. what's disrupted structure meaning identity um if you read the if you read the book um by the gentleman who uh ed cadmall about what happened at pixar after they they made their their first they proved you could make a first a full-length uh animated uh uh movie and he's saying what am I'm going to do, make cartoons for the rest of my life?
1:26:15And he found something, a direction to move in. What was that? He said, I realized my role and what excites me is how to enhance, protect,
1:26:34create, enhance, protect, et cetera, creativity, which is at the heart of our business. So he puts all his attention on that. That's a direction. Making movies is the destination. I love that you use the word intention because I think it's our intention that actually gives us feelings. So, for example, if our intent is to serve others rather than grab more resource for ourselves, then we do get a different kind of satisfaction than we get from the sense of achievement. Right. And if our intention is to walk like a dog, as you described, or to slow down and look at the flower, then we get yet another feeling, which is that feeling of being calm and happy and content.
1:27:23So for me, the discovery of the power in a way of intent, because this is something we can control, is probably the biggest help that I got in my journey. Because it gives this beautiful sense of, you know, autonomy and control in a very good way, in a very good sense, right? Yeah, in a good and best way. but controlling my own energy, right? Yeah. Because intent allows you to change your focus and that allows you to direct your energy where you want it to go. You've just given me a sequence I have never thought about. Inkling, intention, action. I can't wait for us to continue the conversation when you give me your feedback on that with all your professional and personal wisdom.
1:28:17I would very much love that, Rick. It was such a fantastic conversation. And again, I just hope we can continue. I can keep going for hours and days talking to you. Anastasia, selfishly, I would be delighted. And I thank you again for this incredible conversation. Thank you so much, Rick. I have this thing. I grew up in New Orleans. and I use this often, which is if you grew up in New Orleans, speaking of what matters, we have this kind of worldview, this screen, and it's like, well, if we're not going to have a good time, why would we do that? So this is a wonderful time. Thank you. Thank you, Rick.
1:29:08And again, I don't want to let you go, but I have to. so let's do it again already we made i made lots of exceptions with this interview first of all you're my first person who is not an exited founder on my podcast ever it's my longest interview ever and it's the first time when i'm absolutely determined to have a sequel
1:29:33well so it's nice to join it's nice to join you on the frontier thanks we'll be talking
From the publisher
Rick Eigenbrod is a deeply respected thinker in the post-exit world. A clinical psychologist and co-author of the classic Yale paper What’s Next: The Entrepreneur’s Epilogue, he’s spent years guiding founders through life after the exit as an executive coach. In this conversation, we get into why Rick believes a “death of who we used to be” and a subsequent "re-birth" are inevitable post-exit, and how resisting these changes only adds to the struggle. Rick generously shares the tools and exercises he’s found most effective in navigating this transformative process. We also explore the grip of dopamine addiction, the healing power of legitimizing post-success frustration, simple ways to reconnect with our natural curiosity and playfulness, and the bittersweet reality of leaving some people behind as we experience exponential personal growth. _____________________________________________________ TIME STAMPS: 00:00:00: Introduction 00:00:21: The paradox of success 00:00:43: Rick's background and contributions 00:01:04: Discussion on post-exit rebirth and struggles 00:01:12: Exploring dopamine addiction and post-success frustrations 00:02:30: Exploring the post-exit maze 00:02:45: Rick's background and experience with exited founders 00:04:47: Rick's critical event with Vistage group 00:06:09: The price and prize of money and freedom 00:07:52: Reflections on the dual meaning of success 00:08:53: Grappling with post-exit paradox 00:09:41: The "focusing illusion" and the arrival fallacy 00:11:12: The societal pressure to be happy post-exit 00:12:01: Support groups and legitimating experiences 00:13:08: Initial reactions and reflections on the post-exit reality 00:14:31: The societal issue of ignoring exited founders 00:15:33: The lack of support and self-blame post-exit 00:18:00: Escaping the blank sheet of paper 00:19:07: Dealing with loss of motivation 00:20:38: The challenge of striving without a company 00:22:21: Stories of loss of identity and success paradox 00:23:02: The impact on identity and structure post-exit 00:24:29: Avoiding the inclination to fill the void with the same elements 00:25:32: Closing the first business 00:26:18: Question of true desires and freedom paradox 00:27:19: Attempt to create a model from experiences 00:29:06: Journey from identity to meaning and structure 00:30:02: Revisiting personal development opportunities 00:33:16: Financial dangers post-exit 00:35:30: Paradox of money and its role 00:36:09: Evolution of the meaning of wealth 00:41:03: Refusal of the call and negative transfer of learning 00:44:10: Dopamine addiction as an obstacle 00:47:00: Fear of losing entrepreneurial identity 00:49:00: Navigating the journey of death and rebirth in personal growth 00:51:13: Leaving people behind during personal growth 00:52:29: Real journeys begin where fairy tales end 00:54:08: Redefining retirement and societal expectations 00:56:03: Advising young successful entrepreneurs 00:57:23: Identifying and addressing emotional struggles post-sale 00:58:46: Embracing a Mosaic Life 01:00:00: Communicating personal transitions to others 01:03:07: Returning to business after personal growth 01:05:00: Listening for truth, vitality, and fear in decisions 01:07:32: Distinguishing between legitimate fears and psychological barriers 01:09:08: Discernment of skill-related fears in new ventures 01:10:14: Transitioning from entrepreneur to investor 01:13:20: Rediscovering a sense of purpose post-exit 01:14:00: The search for meaning and what matters now 01:16:22: Two ways of knowing and going: Destination vs Direction 01:17:57: Understanding fulfillment and satisfaction 01:19:20: The importance of savoring moments 01:21:00: Stories about finding fulfillment 01:23:26: Legacy question 01:24:00: Discussion about dynamics of arrival 01:27:00: The role of intention in satisfaction




