How Past Success Can Cost You Your Future: The Identity Trap | (#112) Beyond Success: Psychology & Philosophy for Achievers, with David Tian, Ph.D.

Welcome to the Beyond Success Podcast: Psychology and Philosophy for Achievers on the Bigger Questions Behind What You’re Building, and I’m your host, David Tian.

Imagine a founder who has spent the last 10 years, maybe 15, 20 years, building a company. He’s used to having people depending on his decisions, his judgment, and he’s used to taking responsibility for a lot of people and for a lot of important decisions, and one of those decisions was to sell the company. He wanted the sale, and he spent quite a lot of time going back and forth negotiating the terms so that they ended up in the way that he was pleased with.

He got what he asked for and he should be happy, and now, after the sale has gone through, he still keeps checking his messages and checking in on his former team. He’s not used to them making the big decisions without consulting him first, so he goes and finds reasons to offer more advice to them that they didn’t ask for. [00:57.1]

Now, when he was considering selling, he had a lot of other plans, other things he wanted to do with his life, but all of those have now receded after the sale and he begins planning another company. Now, starting a new company might be an excellent decision objectively, but he needs to distinguish wanting to build a new company from needing to remain a founder of a company so that he’s not neurotically stuck in another state of dissatisfaction.

Now consider another example. Imagine the heir of a multi-generational business, a multi-generational family enterprise, who is now considering selling that enterprise. This is a set of businesses that his grandfather established and that his father expanded, and that he has spent many years trying to preserve. His family office presents to him a credible case for considering a sale. They have a great offer on the table, and he and his family office advisors cannot think of any rational reasons not to sell. [02:01.2]

He understands all of the commercial arguments and he says that he’s intellectually convinced, but he repeatedly postpones the decision and drags it out. You see, in his mind, selling would make him the generation that sold. He can examine all the financial consequences from a kind of cold, clear, logical, objective perspective, but the main emotional obstacle is that this would somehow mean that he has failed his father and grandfather.

In the first case, the founder fears losing the one role that he has known for decades and that he created, and in the other case, the son, the grandson, fears failing the responsibility he has inherited. Both of them experience a change in circumstances as if it’s a threat to their self-worth, to their identities. [02:57.5]

This same difficulty, the same dynamic psychologically, arises when you’re unprepared as a parent for your children to become fully independent from you or when your career ends, or when a long relationship you’ve been in changes or ends in some way. Even more so than the circumstances changing, what you experience is an existential threat to your identity, which makes it very difficult for you to adapt to the new circumstances.

In this episode, I’m going to show you how to distinguish a worthwhile commitment from a stuck, ossified definition of yourself that you feel neurotically compelled to defend, even when the circumstances or the context has changed under you.

Understanding and getting clarity on that distinction determines or limits whether you can make the right decisions going forward in your life or whether you can take in uncomfortable truths or facts instead of being in denial of them, and whether you can create a life that flourishes under the new context or the new circumstances, a life that you have never lived before with a role or identity that you’ve never taken on before. [04:10.3]

You can lose decades of your life trying to prove that you’re still the person that you were a long time ago and still trying to force-fit the “you” from a long time ago into new circumstances that need a different shape of you. Being stuck in an old identity ends up becoming the reason you can’t grow or evolve in the new circumstances or the new context, the new level that you find yourself in.

So, what we’re looking at here is how to evolve your understanding of yourself so that it’s spacious and capacious enough and inflexible enough to accommodate learning new information, new facts about yourself or the world, to adapt to changed values, newly improved or clarified or sharpened values that you’ve come to, as well as new ambition, new dreams, new wants for yourself. [05:02.3]

I’ve been throwing around the word “identity” so far quite casually here, and let’s examine it a bit more closely to get a better, sharper definition of it. Identity is what you adopt as an understanding of yourself and your role in the world through repeated experiences.

Let’s say you become good at something, and then other people recognize it and give you recognition for being good at that, and then, pretty soon, you organize, you prioritize your days, your career around that something. Those experiences give you, over time, a familiar account of who you are. They tell you who you are and you uncritically imbibe them. You just adopt them and accept them, because it does lead to something positive. You’re good at that thing. However, over time, that account of who you are can become very restrictive when you now treat it as a requirement for deserving respect, belonging, or satisfaction from yourself and from others. [06:04.8]

Now let’s look at how this applies to the first example, the post-exit founder. In creating his startup, in scaling it into a big enterprise, a big business, he needed to be decisive, to be persistent, to be independent, and that helped him build the company. After selling the company, though, he finds it very difficult to spend much time doing anything that doesn’t require those qualities of decisiveness, persistence, and independence.

So, what ends up happening is mere learning for its own sake without monetizing it or having a plan to monetize it seems indulgent to him, and he quickly loses interest and becomes like he has to scratch that neurotic itch for monetizing, for turning into a business. Asking for help feels uncomfortable to him because that’s not part of that package that helped him build the company. [06:57.3]

A period without any impressive project that impresses other people feels like evidence to him that he has lost his edge, he has lost his ambition. His newfound freedom post exit ends up being spoiled by and governed by standards from a previous phase of his life, and as a result, he’s stuck in this box limiting him from the next evolution, the next stage of growth for him.

Now take the second example of the heir of the family enterprise, who is now the family principal and he is contemplating the sale that his advisors advise him on, that the rest of his family is supportive of, a sale that would, as a result, bring more security, more stability for the family funds. When he was given the leadership for the family business, he was used to taking responsibility that brought trust and brought him a sense of belonging, and for many years, he saw preserving the family enterprise as evidence that he was a worthy successor for his father and grandfather that he so admired and respected. [08:04.7]

As the head principal of the family fund was used to relatives depending on his decisions and increasingly depending on his decisions over time, and this new proposal to sell or to sell a portion of the business and thereby share authority with others outside the family ended up feeling like a challenge to his own value within the family, so his judgment was compromised in a way. Right?

He sincerely cared about everyone affected by the sale and how much they wanted and recommended the sale, while also needing the existing arrangement to stay put in order to reassure himself of his own value and his own place in the family as a worthy successor.

So, let’s look at this defensive pattern, this defensive sequence. What happens is you get used to seeing yourself as a particular role or in a particular way, and then you encounter some information or some facts that contradict your old familiar account that you’re so used to. [09:08.4]

You interpret this contradiction as a threat to who you are, so you end up defending your own identity, your own old account of who you are, without or before you can examine the new information or the new facts objectively. Then what happens over time as you continue to do that is that the other people around you discover and learn which topics or subjects or facts provoke this identity-level threat in you and they end up holding back and withhold what they really think. [09:43.6]

They might not bring to you the information that’s so crucial for your judgment because they don’t think you can handle it, and you end up, over time, receiving less and less of the useful information that you need to challenge your reality and to adapt to the new reality. You end up living in denial and the people who are supposed to be bringing you the information about this new reality withhold it.

Even worse, over time, is that you become more and more certain that you understand and see the situation objectively, when, in fact, you’ve gone further and further away from the new reality, the new circumstances or contexts that have changed. [10:20.0]

Now, this is not to criticize or look down on the old identity. The old identity got you where you were and brought you whatever success you’ve gotten up to this point, and those old roles probably brought you or involved genuine skill and brought you connection, and involved sacrifice and brought you satisfaction. You genuinely enjoyed that daily involvement with the nitty-gritty of the business, and losing that as a result of the sale can bring reasonable grief.

It makes sense. Being needed may have become your most dependable reassurance that you matter, and then being a dutiful, responsible heir or leader may have become your most dependable reassurance that you belong. So, that old identity was very useful and served an important role. [11:09.5]

However, when the circumstances change, when the context changes, a rigid, fixed identity prevents you from developing a better, more accurate understanding of your business, your family, your achievements, and what should really deserve the rest of your life, what you should really be focused on for the next decades of your life. You can spend years learning how to become more effective at the old thing while refusing to learn anything new that would allow you to flourish or excel in the new changed context or circumstances.

In the ancient Chinese philosophical text, the Zhuangzi, there’s an excellent illustration of this principle. This is from the gourd story, as it’s called, in the first chapter. There’s a man named Huizi and he grows these enormous gourds. Gourds are large fruits from the plant family and thousands of years ago they were used as containers. They were hollowed out and they’re kind of in the sort of vase-like shape. [12:13.0]

Now, Huazi was growing these enormous gourds, and because he couldn’t see a way that they could serve the usual familiar purposes for gourds that he expected, he ended up just destroying them. He said, “These gourds are too big to be used for the normal, in the normal ways that we use gourds,” and Zhuangzi suggests he could have used these enormous gourds to float on rivers and lakes like boats.

So, Huizi’s conclusion that those enormous chords are useless depends on the uses that he used to use them for, the ones that he could, in his little box of his mind, imagine, but because the use for these were outside of the box of his mind, he couldn’t see a use for them, so he destroyed them. [12:59.5]

Now apply this principle to the concept of your identity. You can dismiss a worthwhile possibility simply because it doesn’t obviously satisfy a familiar test or fall into any of the familiar categories, or can’t be forced into the conventional boxes—so, you end up ignoring it or destroying it, or just going back to the old way that things are done, and you miss an amazing innovation, an amazing opportunity for something new and improved.

Even worse, you end up being stuck with the old gourds when the new use for them has completely changed. The context or the circumstances in the greater environments or the market has changed and moved on.

Again, let’s return to that first example of the founder, the post-exit founder. If he makes the mistake of Huizi, he ends up evaluating every possibility, every new dream or new interest, by whether it resembles his old successful business. [13:58.0]

He might try to study history or cultivate friendships, or become more involved in nonprofits or philanthropy, or family life or start a family, but all of these don’t look like and feel like what he has known the past two decades or so in building that startup and business. So, then it seems so foreign, feels so foreign to him that he rejects it, because it’s so hard and difficult to justify under the old standards by which he measured whether something was worthwhile in pursuing or not.

Now, he might actually genuinely prefer starting a new business. That might genuinely be objectively good for him, but judging whether it is or not, his judgment is compromised. If every other activity must defend itself by the old commercial standards, then he hasn’t given any of those alternatives a fair and objective hearing. Even as he’s thinking about or trying out new possibilities, he keeps asking these new possibilities. To produce a business plan first. [15:02.3]

Now let’s look at the second example of the family principal. As he grew up, he learned that contribution through some kind of formal responsibility in the family enterprise was the most honorable so that when he discovers a new interest in a different field or a new way of contributing to the family that hasn’t been done before or brought up before, he might unconsciously reject it too early before giving it a fair chance, because it’s too unlike the previous generation’s achievement, and as a result, it feels secondary or less than.

So, then he would lose out on identifying his true potential, his gifts, his real abilities that may be substantial, but because his definition of what a worthy successor looks like is too narrow, those new abilities, the new talents, the new gifts can’t fit inside that box. As a result, he doesn’t give them a fair chance. They don’t grow. They don’t flourish, and he can’t even, in many cases, even recognize them. [16:07.6]

The solution is to hold your identity lightly, to keep it flexible—and what this means in practice is having the freedom to experiment, to learn new things that might contradict what you believed and held before, to reevaluate your values and come to new values based on new thinking or new information, letting new things matter to you.

You can enjoy an activity and get good at it and play with it, experiment with it, before deciding whether it should deserve a permanent place in your life. You can contribute without turning that contribution necessarily into an ossified identity or role or title. You can become interested and try out something that your earlier Self would have dismissed and never even given a chance. [16:57.7]

Sometimes, the real problem isn’t more effort or more motivation. It’s knowing the right direction. A lot of people listening to this podcast are capable and driven. Things still look fine on paper, but life still feels strangely flat. When that happens, more advice usually isn’t the answer. Clarity is.

I’ve put together a short assessment that takes about two minutes. It’s simply a way to see which area deserves your attention most right now, whether that’s relationships, decision-making, or how pressure is being handled day to day. Based on your responses, you’ll be sent a short set of master classes related to that area.

If that sounds useful, you can find it at DTPhD.com/quiz. That’s “dtphd.com/quiz.”

Now, it’s important to avoid replacing one fixed identity with another fixed identity, so the post-exit founder shouldn’t immediately become or try to become a celebrated philanthropist. The family principal doesn’t need to find an equally prestigious role or status before changing the old one. [18:04.8]

In one of the original Chinese classics from thousands of years ago, the Book of Changes, which belongs to the broad Chinese philosophical tradition, both encompassing Confucian and Daoist interpretations, the Book of Changes argues that good judgment requires attention to what’s happening now, especially when the circumstances or context of what’s happening now is changing. When it calls for a response, a new response that’s unlike the one that you’re proud of having mastered, unlike the one that you are familiar with, comfortable with, it’s even more important to pay attention to this, to adapt to what is needed and necessary now.

Your past experience or your past identity should help you understand the present to recognize when these are genuine changes in reality or the circumstances, but they shouldn’t require the present to resemble the past in order for you to act effectively, to be able to effectively adapt to the changing circumstances. [19:08.4]

It’s also important, as you are coming to understand the reality over time, that not all situations require you to change. Some situations require persistence in the old ways. Other situations require waiting and seeing, or refusing to change, especially refusing to just follow trends, and it might mean preserving a tradition or bringing back an old tradition.

So, holding an identity lightly actually makes those responses also possible and available. You don’t have to keep changing merely to prove that you’re adaptable, so merely changing your identity to being adaptable shouldn’t force you to adapt when you’ve deemed that the circumstances or context doesn’t require it. Otherwise, you’d be committing the same logical error, but now with this new set of qualities of flexibility and adaptability. Hold lightly even to those qualities. [20:05.3]

Now, the circumstances and the context that matter the most in coming to decide whether any kind of change is required is learning. Learning can change what you believe is worth wanting and what your values are and what your principles are.

Now, it’s important to distinguish between just getting information, hearing it, taking it in, getting a report, okay, and accepting this information. It’s important to distinguish just that accepting of the information from allowing it to educate you, allowing it to change your self-concept or your values. You can learn a fact or and acknowledge a fact while refusing to reconsider its implications and its consequences, and what it would mean for your old values or your old ways of doing things or your old identity. [20:58.1]

True, real learning becomes consequential when it changes your interpretation or your priorities, or your understanding of responsibility or your values, or what you believe mattered most to you. To be open to learning new things requires being open to discovering that you had false beliefs or an imperfect way of understanding things in the past, or an imperfect identity that is coming to this breaking point now as reality is shifting.

Here’s an example from family offices. Maybe as that heir learns more about his family’s history and digs deeper into it, maybe discovers a relative’s experience of the toxic expectations that affected that relative’s life that was left out of the traditional, conventional, or the usual family narrative. Or maybe someone that he regarded as uncommitted and checked out or betraying the family may have experienced years of being unheard, rejected, isolated, exiled from the family. [22:05.3]

Maybe he discovers that a relative whose contribution received little attention from the louder people, the more dominant people in the family in the past, might have discovered that this person has actually made important sacrifices that should now be honored.

These discoveries can change what this heir or this principal regards as fair participation or gratitude, or responsible stewardship. So, your values, your identity, your beliefs need enough openness to improve as your understanding improves, as your learning continues and grows.

It’s important to point out that a new view isn’t better simply because it’s new. It’s got to be true, right? It’s got to be objectively true. Examine whether the new account of reality accounts for more evidence, more of the evidence that you’ve discovered, or represents other people more accurately or withstands better serious objections. [23:06.5]

But after a fair and objective—as much as you can be—examination of the new information and allowing it and its consequences and implications to affect your current reality, how you see yourself in the world, how you see your enterprise, your business, it may require, then, a new vision. A new vision may naturally be born in your mind as a result of taking in and wrestling with, and allowing to affect you, this new information or these new values.

It may then, because it’s a new vision, require you to become someone you haven’t yet learned how to be, and new knowledge, new experiences can make you want something that you hadn’t previously even imagined. You may discover a new or different ambition, or a relationship now that has taken over your heart and your mind that you want to invest in rather than spending all of your time maybe making a new business, or a new kind of contribution that you want to make to the family or to the world. [24:11.0]

Achieving that vision now requires changes in how you relate or decide, in how you spend your time, and how you see yourself and your relationship to the world. You can sincerely want a new life while remaining attached to being someone whose habits make that life difficult to create. You can get stuck in the old ways while still wanting this new way, but being too wedded in the old way, stuck in the walls of the box, doesn’t allow you to grow outside the box or to think outside the box, and therefore limit your evolution, your growth, your development.

Take as an example the case of the post-exit founder and something that has come up with many of my clients, wanting marriage and children after the exit, but now being thrust into a whole new category or area of thinking and being that feel very foreign. [25:07.1]

It’s not like doing a startup again or that business world. Now it’s the world of relating to people very different from himself, to relating to his own emotions and the emotions of others that feel overwhelming sometimes and feel out of hand sometimes. This is someone who has prioritized and built his life around choosing his own priorities that he has decided for himself and then solving these business problems efficiently.

So, he approaches his personal life in the same way that he approaches business problems, and it doesn’t work very well. Now there’s this messy thing called emotional connection and being equal partners with someone who is very different with different energies, a different personality, and now he wants a lasting lifelong partnership, relationship, and to build a family. Once you bring kids into it, it’s a whole other thing. It introduces a lot more chaos that he’s not used to, that doesn’t belong in the business efficiency. [26:04.7]

That life, now, that he wants or says he wants asks him, requires him to remain interested when this conversation is uncomfortable emotionally. It requires him to consider another person’s needs sometimes above his own, and to be dependable to another person without being able to control every outcome or without being able to control the other person. You can’t just fire your kids and replace them.

If he keeps defining himself as someone who is in that old role, in that old identity as a founder of companies and that’s it, who therefore doesn’t need anyone in that emotional way, closeness, connection, emotional authenticity with others and love will repeatedly feel like a threat, an existential threat to who he is, which makes it very difficult for him to make that adjustment into this new realm of being. [26:58.0]

But as he learns to listen more deeply, more actively, as he learns to open up without and not give in to his fear with courage, learns to ask for help when something feels uncomfortable or beyond his competence or experience, and when he’s able to share in the decision making with someone who is very different, coming from a very different place, those responses become, over time, more and more natural. He becomes someone whose ordinary way of living supports this new family life that he wants. 

So, our identities evolve through repeated conduct. You don’t need to feel fully ready to change yourself before beginning this process. In fact, you won’t ever feel fully ready, and you’ve got to just take that step and begin to change how you behave and how you think, and how you respond to the new circumstances. [27:55.2]

Over time, the repetition develops skill as you adapt to the feedback you’re getting from the world or from other people. As you change over time, your expectations for things, for reality, for how other people will treat you, for how life is supposed to feel, will give you, over time, a new experience of yourself, and other people respond to your new identity, which allows new and different relationships to develop.

Over time, achieving that vision will follow more naturally from how you consistently behave and think and feel, how you consistently live, and it’s important to reiterate this requires persistence over time, participation in practice and training over time. It’s not just a one-off thing and it’s not just changing the hat. It is an identity, something that will develop over time as you step more fully into it and repeatedly reinforce it. [28:54.6]

Again, keep that vision open to further learning, adaptation, and improvement. Okay, so serious commitment to something doesn’t require pretending that you already understand everything that that goal involves. Your experience as you step more fully into this new identity improves the vision itself. You want to make sure that you don’t make that new identity another ossified, calcified definition that you must defend at all costs, so let learning change how you live. 

So, if you want a step-by-step, how-to action steps kind of thing, I’ll give you five action steps. Okay, so we begin with I guess this is the pre-step: choose one actual decision or one new vision that you want to take on, experiment, and try out. This could be another business venture. It could be a family transition. It could be a new relationship or starting a family, or a different use of your time. Now that you’ve got that situation in mind or that decision, or new vision, the first step is to identify the identity that is the old identity that is preventing you or blocking you from this new growth or new evolution. [30:03.7]

How to do this? Identify what you feel compelled to prove, or maybe a different way of putting it is, what are you afraid might happen if you were to fully step into the new you that would naturally have that goal or that vision? Yeah, identify the old identity.

Okay, second, consider the new identity that would lead naturally to this new vision or new goal.

Third, and do this right after the second—allow the emotional response that comes from considering fully adopting or stepping into or having that new identity. Notice the emotional response, the thoughts and feelings that come up. Notice those. Allow them to take place without immediately defending yourself or fleeing back into the old identity. [30:54.1]

Now that you notice those thoughts and feelings that naturally come up when you imagine that second step of taking on that new identity—okay, so now we’re in the fourth step—examine what you’ve learned that forces you to revise something that you’ve held to. Maybe it’s a fact that you had wrong, or an interpretation of yourself or the world or someone else that you defended too quickly and fleeing back to the old identity, or maybe it’s a priority that now deserves reconsideration, or maybe it’s a habit that obstructs the life that you now want in order to realize that new vision. What is this new way of being asking you to revise?

Then, fifth, practice. Practice acting as if you’ve got this new identity. Practice the conduct and the way of being, the behavior and thoughts that your new vision would require of you. So, in considering whether to adopt a new identity to respond to or adapt to new circumstances or changing contexts, give yourself room to become—to become something new or different. [32:07.1]

In the examples that I started with, the post-exit founder maybe will choose to begin another company. Ideally, he can choose it because he has deemed that undertaking to deserve his years, his next five or 10 years or whatever, or maybe he will discover ambitions that his previous definition of success excluded, ambitions such as starting a loving family, and maybe decide that that undertaking deserves his time.

The family principal might retain and not sell the family enterprise, and ideally, he will do so after objectively examining its value and its obligations, and if he has learned to hold his identity as an heir more lightly, he can also have the freedom to revise what he believes and how he understands stewardship to require as he learns more about the family and its future, and he thinks more about the future. [33:07.6]

So, a familiar identity can make change feel threatening. It can also restrict what you learn and what information you take in, and what you allow yourself to want. Greater flexibility with your identity allows your values, your understanding, your knowledge, your wisdom to properly develop and grow and evolve.

A new vision will ask you to become a new person whose behavior and thoughts naturally make that life possible, naturally create the conditions for that life and makes that something that will happen over time because you have become the person for whom that vision ensues. [33:49.0]

If you don’t do this, if you stay stuck in the old box of thinking and being and feeling, there’s a massive cost to this obviously. In the example of the post-exit founder, he spends and wastes another decade of his life proving to himself that he can build and stays fearful of the discomfort in stepping outside his comfort zone to create that family, and so he postpones the family life that he says he wants for yet another decade.

He can achieve impressive results while repeatedly frustrating his actual deeper ambitions—or if you’ve learned to hold your identity lightly, you can learn something that changes your view, improves your view of your parents, for example, without losing your love for them. Or you can acknowledge needing help without diminishing what you have accomplished in the past. Or you can become a total beginner, a complete white belt, without treating that experience as some kind of humiliation. Or you can develop ambitions that require patience or cooperation or courage that you haven’t yet practiced in those new contexts. As a result, your life can become far richer than the old view or account of yourself that you had before. [35:02.3]

Who you have been matters a lot. Okay, so, yes, you have learned important things. You’ve built things. You’ve created things and you’ve carried important responsibilities that, in the past, have changed you, but you still have new things to discover about yourself, about other people, about the world, and about what you want your life to become. Let those discoveries change you. Allow yourself to want something that you couldn’t have imagined wanting before.

Then what you need to do is to begin to become the person whose choices and habits, and ways of behaving and thinking make that new life increasingly natural. Okay, so hold your identity lightly enough that it can grow with you, with what you learn and what you come to love in the future. Who you have been in the past doesn’t have to determine who you can become now and in the future. [36:03.7]