The Exchanges

Q Well, on that topic, I'd love for you to just walk us through the path that you've taken. Basically, you were kind of like me, in a sense, you were helping companies build product, drive growth, worked with some of the best companies in the world, and then things kind of took a turn. And so could you just start with kind of a brief overview of what happened?

A Sure. So, you know, the, the short background is I spent, uh, about 17 years working in the world of startups. And I think on the whole, it was a successful experience. I managed to land at a handful of, of, uh, really good companies and had a great experience. But along the way, despite having built somewhat of an impressive resume, I guess you could say, I was also struggling quite a bit in terms of my emotional, psychological, and spiritual health. And so in some ways it feels like the cliche that as my career sort of reached its pinnacle, that from a professional, from a financial perspective, I was at my highest, but when it came to other aspects of my life, I was arguably at my lowest or close to my lowest. So, you know, even though I had those successes, there was a lot that I needed to work through that was under the hood, which I eventually came to understand very, very deeply. As a result of turning inward and doing a lot of work on my own, uh, my own path towards self understanding and healing some deep emotional wounds.

AI assessment note: “I spent, uh, about 17 years working in the world of startups.”

Q Awesome. I'm willing to that in the show notes, but it's an easy URL to remember. Something you spend a lot of your time on as you've talked about is helping people through deep personal transformation. That's kind of the, the way you describe it. What is involved in that process of someone going through a deep personal transformation?

A I love this question. Um, so yeah, most of the conversations I have are with folks who are going through significant change. Now what's involved in that? It can happen on a spectrum where everyone's process is unique. We don't know all sort of change and unfold in identical ways. Some can go through subtle shifts. Um, I've heard this referred to as a micro transition where, for example, they may be working at a tech industry or at a tech company, but the specific company they're working at, they have no, no real sort of values connection to it. And, and so part of their suffering is the fact that they, they feel that the work that they're doing doesn't really matter or they don't feel a connection to it. And so switching Uh, to work at a different company that's aligned with something that's consistent with their values, that may be enough for somebody to sort of go through a small transition and then find themselves in a happier place. But the transitions that I talk about are the, the big fundamental ones, uh, like the transition that I've been going through myself. Now what's involved in that? I think that there are four parts just to give it a simple general framework. Step one is it begins with suffering. These large transitions in life rarely take place in the absence of suffering. So step number one is suffer. And usually the deeper somebody suffers, the more significant…

AI assessment note: “I think that there are four parts just to give it a simple general framework.”

Q epiphany of like, oh, wow, it's really this moment in my childhood that really led me to need to achieve and do all these things. The next step is self-compassion and recognizing that it's not your fault. That sounds very easy on the surface. Like, okay. I understand this is not my fault. I know it's not that easy. Well, how do you go about actually deeply doing that steps?

A It's likely this deeply internalized self-belief, right? And you can think of that as one of the deepest grooves in the neural pathways in your mind. Now that was the case for me, uh, so deep that you don't even realize that it's, it's there, right? It's omnipresent. And it's going to take time to rewire that because what you're effectively trying to do is take an internal narrative and edit and rewrite that thing. And this internal narrative is probably at a foothold in you for years or decades. And so it's reasonable to believe or to understand that, okay, if I have not Had a high opinion of myself for 30 years. That's not going to change overnight. For some people, it kind of miraculously does. That's not the norm. Uh, for most others, including myself, it starts with that truth stage because with truth is the awareness. Okay, I understand that I have a low sense of self-worth, and I understand that it plays out in all these ways, and I have the awareness of it that now when I'm doing something that is a conditioned behavior or a conditioned response born out of that deep self-belief or that negative core belief, Then when I spot it, there's an opportunity for me to intervene. And it starts in the simple ways. For example, uh, I had a boss once where he, he would come over and he would give me praise all the time. He was wonderful human being. And I think I was doing a good …

AI assessment note: “starts with that truth stage... when I spot it, there's an opportunity for me to intervene”

Q teacher. I like, I want to stay on this path. I want to have a successful career. I want to continue to, you know, make a bunch of money. How often do you find there's a path to stay on that path with a rejiggering of how you see the world? Or does it, if you're suffering enough, does it almost always lead to something completely different in your experience?

A Again, it's a spectrum. I, I, what I've experienced is that the vast majority of people who feel, uh, some tug to undergo a process of change, I'd say. 90, 95% of the time, pretty confidently I can say that those changes are more of the micro transitions. It's okay. Let me change my job. Uh, let me downsize my house. Let me break up with my partner. Still hard things. And for them, that may be all that is needed and necessary. Uh, there's no moral judgment on my side about, you know, everyone's gotta dive into the deep end. That's certainly not the case, and I'm not advocating for it. I honestly don't even know if it's a choice. There's a part of me that Based on some of the experiences I've had sort of believes that it was somewhat preordained and that this, this was going to happen for me. But it's in the minority of cases where the radical transformation of one's sense of identity takes place. It's not common. Um, my general sense is it's definitely less than one percent of the population. Um, and I suspect that's just kind of the way things are.

AI assessment note: “90, 95% of the time, pretty confidently I can say that those changes are more of the micro transitions”

Q Any advice on how to figure out who the right therapist or wrong therapist is for you? I know you've, you've actually shared somewhere on LinkedIn once that there's also a lot of disagreement within the mental health community of what is the right approach and what's the right solution.

A Yeah, it's, I mean, it's kind of like speed dating at first, because I would argue that the most important factor is that you feel safe. You know, think of, uh, animals can teach us so much about what it means to heal ourselves. You know, think about magic going to, uh, to the pound and you go in there and there's a bunch of dogs that have been picked up off the street or that have been abandoned. And the vast majority of them, they're a nervous wreck. Right? Their tail is, is down in between their legs. They're hunched over and they might be shaking. Right? They, they, their nervous system is completely overwhelmed. That is not the time to teach a dog tricks. When the dog still can't come out of the corner of the kennel is not the time to teach it how to sit. And once that dog can make it into the arms of an owner that it feels safe with and loved by, that's when you see the dog transform and change. And that's when you can teach it a lot because it's open and receptive to it. So that's, that's number one. And my advice is, you know, speed date. If you've got the opportunity to, and try out a few therapists and just go based on intuition. What just feels right to you, right? And you're going to want to fall into that feeling of comfort. Now, a quick asterisk on that, of course, if you're in real distress, if you're in a bad place, just see whatever professional you can as soon…

AI assessment note: “try out a few therapists and just go based on intuition.”

Q Andy, what a beautiful way to wrap up our conversation. Before we do, is there anything else you want to share that you want to leave listeners with? And then also I'm just curious how you're doing these days.

A Sure, sure. Well, let me answer the first one, you know, a message to leave to folks. You know, I would imagine that there's a lot of high performers, successful folks out there. Some of you, you may feel like you're on the verge of answering a call towards a new chapter in life or towards finding a way out of whatever situation you're in that you don't want to be in anymore. The thing I guess I would say to you is that having undergone some change myself, all I can promise you is that it's going to be in some ways the best thing that's ever happened to you, but also the worst thing that's ever happened to you. But those are the experiences that define a life. And if you feel that call inside of you To seek a new way of living, just know that you're not the only one out there doing it, and that there are others out there, such as myself, and that I can always be reached. So, I wish you a happy journey, and just know that things are gonna be ok. Now the s, uh, second question. What am I up to nowadays? How are you doing?

AI assessment note: “Well, let me answer the first one, you know, a message to leave to folks.”