thinking on thinking · S3E3

After Success, with Pradeep Singh — Success: Part 3

December 18, 202449 min businessbehaviorcreativegrowth

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What happens after you build a successful company, make a fortune, and achieve the goals you set out to achieve? What is success in the afterwards?

In a conversation spanning success, purpose, motivation and satisfaction, Divya interviews Pradeep Singh, the founder and former CEO of Aditi Technologies, Talisma & Vidyanext / Pengala. Pradeep also was the first product manager of Microsoft Excel, and part of the team that grew Microsoft in its decade-long (~1986-1995) domination and explosive growth post-IPO.

Pradeep is also co-host Kahran Singh's father.

notable moments

When people are at an early stage in their life, they have a very borrowed definition of success — what their parents think, what their teachers think, what their peers think.

The notion of big, hairy, audacious goals really gets amplified when the lottery ticket actually turns up and you have to decide what to do with it.

Read full transcript

Hi, I'm Divya. Hi, I'm Kahran. And this is... Thinking. I'm thinking.

Welcome to this episode of Thinking on Thinking. Today we talk to Pradeep, who is current dad and a very successful person who has lived a long life with varied life experiences. And we talk about everything from life to getting older, to success, purpose and more. We hope you enjoy. The reason why Kahran and I thought you would be a good person to talk about success with is because I think when people are at an early stage in their life where I can say like act the one of life,

I think you have a very sort of borrowed definition of success. Like what your parents think is success or what your teachers think is success or maybe even what your peers think is success. You try to sort of adopt that definition. As you grow a little bit older, and that's what Kahran and I were discussing that we have like evolved definitions of success. Kahran was better at articulating it that like his definition has recently grown a lot.

And we felt like it would be interesting to talk to somebody who has lived a lot of life and has seen like, you know, multiple phases and multiple stages. And what does that look like? And what does that mean? I mean, I'm assessing, I'm looking at myself, 67, what are we going to talk about? And it was, how does one think about life's goals and ambitions and so on and so forth. So in a sense, I was thinking on the same lines without actually really knowing that that's what we were talking about.

And it struck me that both apps, I think it happened at Harvard and it really got amplified at Microsoft. This notion, I think it's borrowed from a book whose name will come back to me. But the notion of big, hairy or decious goals, you know, given that from a little perspective, the lottery ticket had really turned up. I had applied to admission into business schools, not expecting to get into anything fancy and I get into Harvard Business School. Whoa. And then I have like a 10 year rocket ship at Microsoft.

I mean, it's really a rocket ship. It's hard to visualize, you know, in the modern context, because it's an unknown company the day I joined. And nine years later, we're king of the heap. And there is nobody else who displaced IBM and, you know, Amazon and Google and Facebook and all these guys don't exist and Apple's about to die. You can't imagine a 10 year period where a company has dominant control and emerging industry. So that's a rocket ship. So you come away from that thinking that's what the meaning of success really is. You know, you've got to build organizations and companies that have enormous global impact and it really fits with this whole notion of big, hairy or decious goals.

You know, yeah, all right, I'll start a company and, you know, my rallying cry was, we will do what Sony did for this expression made in Japan. Wow. We will change the meaning of the expression. And talk about big, hairy or decious goals. We're not going to build a successful company. We're going to change the meaning of a phrase. And especially, I think, like for a country with like over a billion people, that means even something bigger.

In hindsight, as I look back, it's the audacity of youth. Now amplified by this, you know, rather peculiar 12 years that I've just had prior to that. Now, for one, we didn't get to the goal. We built a reasonably successful company. It still survives. And, you know, had a couple of liquidity events of the way. So that is an interesting thing, right? Like you had a goal in the beginning that you thought would mark success.

But then like right now your phrasing was and we built a reasonably successful company. What does that mean? I mean, depending on your perspective, you would say, hey, 30 years later, this company still exists. It has, you know, 1,000, 1,500 employees, it does 200 million in revenue by any normal metric. Hey, that's a success. And by the way, that's true. It is a success. It contributes a very large amount of the quality of my life, both intellectually and financially and everything else. But in the large scheme of things, I could be a disappointed man that I set out to change the world and, you know, oh, didn't.

Interesting. Did you feel like at Microsoft, you guys were changing the world? Oh, yeah, we totally believed that. You can imagine, we were all, Gates was a year older than me. I'm 28 when I joined the company. This is a really, really young company. The oldest guy is the president, John Shirley, any of those early 40s and everybody else under 30. And along with success comes ego. And of course, we can, you know, you don't essentially give credit to fortune and good luck.

You give credit to yourselves. So we're all quite full of ourselves. And now that I reflect back and I look at it, it's not clear to me, especially because I look at really grand successes that I've now seen happen these past 30, 40 years. You know, yes, the history books will take the names of the most successful of our, of my generation. But history books are eventually short, you know, I mean, they go away. Nobody remembers who your name was, you know, vaguely, you might remember that there was Mr. Jobs and Mr. Gates, you know, 50 years from now.

But beyond that, you know, that's about it. Musk might survive for longer than that because he is moving the needle. Even that's relatively not that's even that's not a telepathy relevant because the day you keel over, you keel over, it doesn't really matter that somebody remembers you a decade from now or 200 years from now because you're long gone. That is so interesting because like the age group that you mentioned that you were at Microsoft, right? Like that is where my friends are at. They are doing their startups, right? Like most of my friends are between the ages of 28 to 40, and they are trying to like, you know, do these big things and legacy is like a word that is thrown around quite often and people like really, really care about it.

And surprisingly, maybe because I'm in a cohort where not a lot of people want to have children, then like, you know, legacy suddenly becomes even a more societal level thing. Like you need to change the world if you want to leave a mark. So it's interesting to hear you say like as a more mature person, they're like, if you die, then like, you know, if you die, then who cares if somebody remembers you for 20 years or 2000 years? It's really a fact because really the only person who really cares, the person who's wanting to make mark is you and me, right? And therefore the people who really care don't really matter anymore because they're not, you know, conscious humans anymore. So there's kind of fundamental flaw in that, particularly if you go back and you think for a few minutes about what should be the humility of our species, but it isn't there.

You know, we are so tiny and so minute and we last for so short, such a short amount of time that any grandiosity fails. It doesn't matter what scale you think of. It doesn't matter. The scale is still too small. You know, you could be Jesus Christ and it doesn't matter. Who the hell cares about a couple of thousand years? A couple of thousand years is rounding error. True. Carl Sagan's pale blue dot is like one of my favorite speeches because like it just tells you how insignificant humanity all of it is. I mean, sometimes. So anyway, so that that by the way, that's a dominant part that sits in my head these days.

So it does color the way I think about things. It's kind of the reason why I have a very, very indifferent attitude towards the way we fight our stupid local battles about religion and stuff like that. Come on, man, wake up, wake up, wake up. You know, you think you're so important in the species. If you compress the sun to the size of a grain of sand, the milky way alone, we're not even done with the other galaxies is 300,000 kilometers long. I mean, if the sun is a grain of sand, let's not even talk about how small I am. I don't even make subatomic level. With that, the fact that the species has been here for 200,000 years, the universe has been here 15 and a half.

Once you keep those two numbers in mind, a lot of stuff starts to take a different context. Okay, that's one. And the more important thing actually, as you get to beat 67 is and I don't know how often gets talked about, you know, as a kid, you're immortal. You're willing to go die because you don't think you'll die. It's exactly for that reason. When you're in your late sixties, you can see the clock. It's not far.

A decade from now, I'm 77. When I'm 77, am I climbing a mountain or it's not high? Am I navigating that boat through the waters of the North Pacific? No, probably not. The least thing that I could do that I can do anymore is growing. I don't want to ski anymore. I still down ski, downhill ski, but maybe not.

All right, so once you get the five-nightness of time, it's funny how success becomes really small. Interesting. So then what makes you go? I got my shoes on and I went for a really nice three-hour hike. It was tough and the sun was out and the skies were blue and wow, what a nice day and that success. And, you know, hey, I got back and, you know, well, I spent 26 days in Japan and it was fabulous.

But, you know, it was, hey, got back in the two grandkids have grown a bit and they're really funny and fantastic. I really didn't want to talk to you yesterday. It's narrow. Does it narrow or does it expand? Because like I just feel like your definition of success became like, you know, earlier, maybe while it was about the world, it was not about yourself. And now this sounds more about yourself like I had a nice day. I took a nice walk.

These are my people that I spent time with. You could need more of the money. That's the other aspect of having grown. It's having got older. And I think partly also the increasing conviction of your own finiteness. If it's not too heavy, would you like talk a little bit more about like what you just said, conviction of your own finiteness? Finiteness, as it just described, you're small. You are in fact is limited.

The number of days you've got to make that impact are shrinking and your physical mental intellectual abilities are fading. It's just a conscious awareness. That's finite. That's the finiteness as distant from you met me 31. Hello, what's the problem? We'll change the meaning of Indian. Hello. That's not finite. That's like, whoa, you're going to take a developing nation and you're going to change the meaning of its expression. When I say finiteness, I mean finiteness personally, and I have been examining it.

And not everywhere. I don't think it's true of every 67 year old because I know others who are not doing it. The conviction that one can be a change agent beyond oneself, or should we say the desire more than the conviction? The desire has faded. Do you see people having that? Like because there are people in my age group or younger who also don't have that. Or it may well be a defeat thing.

Do you feel like it's a maturity or an age thing? Or do you feel like it's almost like a shifting of attention? Like where are you looking now? Yeah, I had for me to self-analyze this and I think they're all playing a part in it. There's the finiteness as distant from you know, hey, I got like five decades ahead of me. So what if it takes another two decades? I'll get it done.

That certainly is the finiteness side of it. There's also, I set up with a very, very large audacious goal. You know, I did get hammered. There was a period. Yeah, obvious. The three years were tough as hell. I mean four layoffs and you know, net worth going to zero and all kinds of rather, you know, very hard, some of the emotional things.

I mean again, not hard the way things can be hard. Every time I tell myself something was hard, things can be hard. No, no. Things can be harder. Things can be much worse than they were. I mean, things can always be harder, but I also think that like all the challenges that we ourselves go through are still challenging.

Like, like my father, I don't know if you're aware of this. My father passed away right as I graduated from college, like literally the day after I got my degree, my dad died. And I'm the eldest of three and like my mom was a homemaker and all of a sudden it was like, I also like generally people when they go to work, they sit for placements. I had no placements because I was like, I'm going to design and it was a very interesting, unexpected, like hard ship, one can say. Of course, like the temptation in that moment is to find the worst examples because there are definitely people who have worse.

Like there was a batchmate of mine whose mom passed away because her in laws wouldn't give her treatment while he was in college, like in final year. And it's like definitely worse than whatever happened to me. But it's like there is no point in that comparison because like his pain was his pain and my pain is still my pain. Right. I know, but the variation of that is the following.

One recognizes that one's perception of pain, one's perception of anything is a function of expectations. Okay. That's in if life has been rough from the day you were born, then hey, it continues to be rough and you know, you're all with it. Your expectations aren't that, you know, life will be great or everything will work out just fine. What I'm getting at is that I think attitude matters in how you perceive pain, how you perceive disappointment, how you perceive almost anything that you know, downside that happens to you.

For that matter, even the upside, the attitude matters. You're willing to celebrate it is a function of, as I said, I have a successful business and yet I said, you know, oh shit, I lost. Right. So I'm realizing that. So therefore, when I think about myself and like, you know, every now and then you turn to yourself with some mode of self pretty.

At that moment, you remind yourself you idiot. You're in no position to do that. If you had been born to a mom in Sudan in the desert, then you can have an argument of until then, you know, you've been privileged on the day you were born, but you've been privileged and get on with it. You know, there's no excuses to yourself and no feeling bad for yourself. Shit happens.

The dice rolls. Folks died. Parents died. Got along with it. But one also has to make you don't think that like some of these things are like the only way out is through.

You can't skirt your way around it. Like, you know, I think I did fairly well for myself. I think I like, you know, took care of my family reasonably well. They like, you know, did good things for themselves and I did it without resentment, which is generally a thing that often happens to eldest kids when they lose parents early. They feel resentment and I'm like, I didn't give up on things that mattered to me.

But I don't know if I could do it. How should I say like assessment of difficulty at the accurate level of difficulty and challenge helps you navigate it is what I'm trying to say. Like if I just told myself it's not hard, then like I don't know if I would be able to do it well. I totally. Okay.

No, I didn't. I didn't mean it that way. I am from the perspective of absence of self pity and just getting on with it. Recognizing the world you live in and saying, Hey, stuff happens. Now I got to do something with it and I'm going to do something with it.

Now it's like many years since you realized, okay, it would be hard to change, make in India. Right. Like what happened in that gap? Like from that realization till today, like how did your sort of, I would say like trajectory evolve? You know, a forcing function in a lot of what we do is financial circumstances.

So three layoffs later and getting fired. I'm now the chairman of the company. I found it, but not the CEO and I have less than a 1.5% stake. I'm also broke and I have a company. I have actually spent the kids college education and I have another company which I don't want to run.

It's a services company. It's not, doesn't fit my definition of changing what I wanted to do and so on. But I have no choice for the circumstances that I would have risen before that. Oh, you know, you put your shirt on, you buckle up your belt and off you go. And that's basically what I did for the next decade.

I ran that services shop even though I didn't bring anywhere near the same level of enthusiasm that I had the prior decade. The prior decade I'm obsessed driven, 70-hour weeks. I'll be on a plane anytime you want. The next decade is, oh, Christ, man, gotta do this. Get up in the morning and go do it.

And then I fundamentally stepped out. I found a, I did, you know, I had got Patty on as my president of North America. I handed him the keys and said, hey, you're the CEO. And about six months later, with about six months, I mean, or certainly within a year, my engagement was at a quarterly, you know, I'd come for a board meeting once a quarter.

So now this is coming on 15 years of have gone by. I'm 67, I was 52. It's kind of early to hang up your spurs. So you're a fairly passionate person, a fairly like energetic person. Where did you put all that energy?

52 is not that old, right? I'm for that matter, even 67 is not, you know. Correct. I feel it right now. I'm like, yeah, man, I've just come back from 26 days in Japan,

which I high-carve of them. Yeah, it was crazy. Like just hearing current talk about it, I was like, you are with four people who are really old. Dear God, if I had that energy when I'm in my sixties, I would be like, this is a good life. No, it wasn't bad.

And you know, it wasn't like we were staying in, we stayed, spent three nights in a hostel. So this is not even, you know, old folks living in, you know, fancy hotels in the city. So in a sense, yes, it's a complicated question and I don't have a good answer really. I mean, in hindsight, I still, I'm still plagued by it, whether I should have stayed the course and stayed ambitious and kept myself on, you know, so to speak, kept the drum beat alive or do what I did, which is really, I've lived this last decade, particularly the last first four, five years might have been a little more confusing. But I've lived this last decade with a increasing self focus, the narrow circle that we were talking about, you know, family, friends, myself, you know, what things do I want to do, what skills do I not have.

And I'm still drumming, they're going down that path. The terrible language I've eaten. I know why. I just awful memory. I've had it ever since I was a kid.

Really, really, really bad. It's, I'd have to be in the bottom of 5% of humanity, I think. That bad. I can't remember people's names. I can't remember people's dates.

I can't remember, oh, Rukmini Banerjee, whom I really can't about the CEO of Pratham. And I've spent a bunch of time with her. She was here. Ruby was gone after India. This is back in September.

And Ruby asked me the other day that he was sitting over there on the dock with her and what did you guys do for dinner after that? I have not the faintest recall. I think what she said for like a week turned out to be a memory. People's names, all kinds of stuff. So language has come hard because you just can't, you know, I mean, surprisingly, I can speak the English language, but you know, it's quite hard.

But I'm doing the Spanish anyway, very deliberately. I have a 347 day unbroken streak or something. And the only reason is... Oh my God. That is definitely celebration.

So I have some long number. It's the only reason it's broken is because I had to spend a week in the Himalayas with no reception. Got that one. That is awesome. No, it's again a brief personal focus.

It's not like, you know, I'm going to do anything with slang, which I'm not, you know, going to become a... When my friends would ask me, especially in my twenties, what would you want to do when you retire, etc. I was like, not only do I not want to think about retirement right now. I don't think I want to think about retirement ever because I don't think most artists retire and that's the group that I most identify with. Like people keep painting or drawing until the day they die.

And then they're like, okay, I died. And I'm like, okay, that's the life I want to live. But like, isn't most people's idea of retirement the fact that like they get to travel the way they want and spend time with family the way they want? Isn't that like the definition of successful retirement that you can focus on all of the things that you want to do? Yeah, at the same time, not be careful that you don't become a couch potato.

I mean, what happens is that once you take the forcing functions of your profession out, most of us are professionals that have forcing functions. You know, hey, you got a full calendar, you got up in the morning and Monday morning, you got like, you know, stuff to do. They hate no choice. Get on with it. So when you take that forcing function out, the risk you run is you have no purpose left. And without purpose, the day can go on.

Get up in the morning and it's evening and the day's gone by and you haven't really got anything done. So by the way, as I think about it, so we've gone from the definition of success to actually what it means to be getting older. This is okay too. Yeah, oh well, maybe. All right, we can come back to success in a few minutes.

But I do have a professional regret, which is that my professional competence is structurally around organizations, as in building organizations, you know, hiding a bunch of people who have congruent values and then building on that. It's a set of ideas and themes and it's many ways what I think is mankind's most remarkable capability, which is the ability to work for more than two people to work together. It's really what differentiates the species from every other species. And that is a good skill to have. And it's been a skill I've had for a very long time, but it's not terribly useful anymore.

As soon as you step, as soon as you hang your spurs up, the organizational capability of being a driver of getting people excited about things, about keeping people somewhat, you know, within a constraint of guardrails about the values that you operate under and so on and so forth. You think so? Those are the functions of having an organization. You have, don't have one and you're limited to a spouse who doesn't think she's part of any organization. I mean, she, I think she's like, I've been a part of this organization for 30 plus years.

I don't need to be a part of any organization now. I know how to run it. More importantly, I know how to run it. So, no, that's what I look at. Both artists, people who can, you know, you can, you can pay until the day you die or what matters doctors, medicals can become competent for a very, very long time.

I mean, not too long, especially with the surgeon, try not to be competent after a certain amount of time. But you can. Now, you know, it's one of the things I would actually, if I were to give counsel to somebody who's young today, I would say, keep that very much in mind. With retirement comes that price. On one hand, you get the latitude to say, I don't have forcing functions anymore.

I don't have to march to somebody else's beat. I don't have to get up and do this just because I have to do it. I do it by latitude, by choice. But within that, right, two structural problems. A, do you have enough of a personal inborn desire and drive to keep yourself, you know, capitalizing on this gift you have?

By the way, I have summarized my life into one simple thing, which is life's a gift and it's short. That's it. Beyond that, it has no other obligations. You have a gift. Do something with it because it's short and it's going to go away.

It's the sinning idol and doing nothing is the sin. That is so interesting. It also makes me think of like somewhere a little while back, you mentioned this idea that like sometimes if you are just sitting and like, you know, not focusing on something, you can lose purpose. And that made me think about how like the way Kahran and I have like, they've had two conversations about this topic and like the way we have thought about it. It's a bit, I think somewhere purpose and success are intertwined in our head as concepts.

Like it's that drive to wake up every day and to do something or like, you know, to maybe help people or whatever, like, however one defines it. It feels like I hadn't thought about it until you mentioned the word purpose. Like there is almost this intertwining of purpose with success, with growth, forward momentum, like whichever. And almost this conversation is making me think about like, you have at some level almost emotionally realized that time moves forward. Like the forward momentum is going to keep on whether you do the success, you do the like purpose, you do anything like time is going on.

And I think between this is an important distinction between purpose and success. There is an important distinction. Success is a weird thing because success is inherently disappointing. Success is a milestone usually you define a milestone one faster or another and you hit the milestone. It's actually very anticlimactic. Okay. What do you mean?

It's kind of done. You spent like two years, five years, a decade saying, I'm going to take this company public. I'm going to take it to the public markets and I'm, you know, we're going to be driven for it and you know, take the wires that one example. And then it happens and it's like, hello. Okay. Now what? And I actually think it's dangerous is you redefine the definition of success at that point.

And you actually, you've already been redefining it. Did you get to the point because you are anticipating the anticlimactic moment and the kind of you are because you know, it's as it gets closer, it doesn't look that distant anymore. And when it's close enough, it's close enough, you know, it's six months away. So right, I'm going to be thinking about month seven. The scary thing about that is that you change your competitive bar. You've already seen this happen.

And the seven year old you're competing with other seven year olds in audio. Then at the IIT you're not competing with the seven year olds that you met with. You're competing with the IIT grads who are, you know, then you get successful and now you're the CEO of a publicly-debted company. And now you're trading at competing with the other CEOs of other publicly-debted companies. And then you get to be Elon Musk and you're still going nuts.

Yeah, I think a lot of that fun is in the Delta, right? Like it's not in the... The funds in the journey, the destination journey, it's the obsession, it's the wins, it's the losses, it's the dealing with the, you know, the emotional up and down, the social with that. It's all that. But like, would you say that when you climb a lot, like you climb a lot, right?

Like for the listeners, Pradeep climbs a lot. For any sane human, even in their 20s, whatever he can do right now, it would be impossible. So he can do a lot. That's not true. But like, would you say that when you have reached the peak, is it called the summit, whatever you say, right?

Like, do you feel like that's also a feeling of whatever? No, that is, oh, shit, I'm exhausted. I better get myself off this mountain before I die. Oh, no. I have never made it to a peak where that has not been the dominant thought.

That doesn't mean, oh, there has been one time at Kala Pathar where we did pull out a bottle of scotch and took a sip, but outside that, it's really okay, done. Like, I gotta get off this hill before. So then why would you go the next time? It's the journey. And it's the fact that it was hard, and you know, hey, come on, I can do that again.

But I'm going to go somewhere else with this success idea, especially success in a very public sense. I think it comes at the big price. I don't think we all, we don't assess the price. At least the complicated lives. And you look at it, look at the outcomes around you.

I mean, I certainly don't want to be alone musk. Just being that person would be, ah. But you reach that point because you can imagine the 18 year old who lands up in Toronto or wherever he landed up with 20 bucks in his pocket is aspirationally, he's a smart kid. He doesn't know where his life's going to go. And he's really quite unusually exceptional and, you know, does amazing things.

And then along with that comes this enormous ego feed. You've got 200 million followers who tell you on Twitter every day that you're like, you know, your God's gift to mankind. Unless you're Moundas Garmson Gandhi at the same time, it's, I think it's really hard to deal with it. I mean, actually, there is an exception. I watched Satya Nadella and Satya is unusual.

He's a very, very, very successful person in a relatively short period of time because 10 years ago, 15 years ago, certainly, nobody would predicted he'd be the CEO of Fortune 100 company. Fortune 1 company. And I mean, like Satya has really brought Microsoft to the front game with like a lot of his plays recently. I was actually going to ask you about that. Like, do you feel like it must always come with a price that one is not happy to pay?

Satya is an unusual exception. So I don't know how to generalize from there because, you know, 90% of Microsoft's market cap has been built after the guy came as CEO. Can you imagine? Only 10%. He had to be credited to the founder and the guy who followed him.

Yeah. I mean, especially in the last few years with the AI play, it's been crazy how Microsoft has grown. No, so clearly the guy's been very successful, but you don't see, when I meet him and I meet him that frequently, you see a lovely humility in the man. You know, you don't see any of the beat my chest after you see it. But I, you know, on the other hand, I saw another man I admire a lot.

Also get caught up in all of this. I watched Bill's journey these last 20, 30 years. What it felt like to go out of the company or it felt as you watch him and see his reaction, the fading years of Microsoft, then the recent divorce. So I don't know. I mean, in some sense is I wonder about it.

Let's face it this way. Personally, from where I come from, as I look at this, I'm quite happy. For one, I'm really quite happy not to have had fame. On one time, fame was very important. I was making magazine covers in India and I'm making the New York Times and Front Page sometime back in the early 90s, late 90s.

Somebody writes a story about India and you know, you're part of a news bunch of people. Again, you have to be very careful about how you take credit for things. Today, anonymity really matters. I want to be walking down the street without having people like recognize who I am. Just do my own thing.

I don't want all my behavior to be under somebody else's microscope. Did you also find that like one of the things that from childhood I have felt or thought that one of the dangers of success, not even the fame kind, right? Just that you sort of have a jump in maybe your financial success or maybe like certain other metrics of impact or change or growth in a short duration and how that affects those around you. Both the people who you care a lot about and people who are maybe slightly further away, but whose perceptions of you you are aware of. I'm always worried that like success can cast a shadow on all of these things quite badly, even if you're not famous, even if like, you know, none of that really affects you.

Have you observed that in your life and people around? The shadows you create are a function of yourself, the person you become. Yes, people do. Distant people do get colored by the resume, so to speak. But folks who are close, folks who know for any length of time, just like, you know, anybody you hire, you don't remember what undergrad school they went to after the first three days.

Right, it's really important that you have no memory anymore, you know, like what do they actually do? They become the person they are and you know them as the person they are. And I think that as you think about the shadow, the shadow is the shadow because you change. You're not the same set of molecules anymore. Success has a reaction on all that.

So if you change, fundamentally, if you are, if you, like most humans, get arrogance and pride, that casts a shadow by itself. So it's not the success. It's what the success is to you. Interesting. This conversation, by the way, is not going in the direction that I thought it would be going in, but it is an interesting direction.

I was wondering, when did you think I was going to say that? No, the thing that you'll be surprised by is today, or at least I am kind of surprised, my sense of self doubt, of doubt, so to speak, is much deeper than it was. Was there a point of time in your life that like clarity increased? I mean, I don't really about structural stuff about humans. I mean, you know, be compassionate, be considerate, you live in a society, be functioned because we can make this a society function, you know, leave any place a little bit better than when you found it when you got there.

I mean, in the smallest detail, whether it is you pick up a piece of trash or, you know, you'd be nice to somebody who's on the street corner whose life's not good. Beyond that, I don't know if there are any valid truths. You know, everybody constructs their own and you construct it in the circumstances that you find yourself in. This would be a very, very good conversation. Like, you know, once it's edited and current and I listen to it because it's definitely going to change how we are going to talk about things further because like, I think even for us as like, you know, people in our mid 30s going towards 40s.

Like certain things, maybe for you, it's like these children. What are they even talking about? But like, He is part of the same humility. He is part of the same humility. No, quite frankly, I admire my son.

He is very admirable. I watch his competence in a million different ways and I say, whoa, that would be pretty good. Pretty. You might want to learn something here. So just to be clear. No, literally, I have one thing I have got rid of.

I think I have got rid of most of my arrogance and there was plenty of it. There was plenty of it. I can visualize myself as 40. I was 40. I also think that like it is one of those traits of like, you know, being in a rising domain, like, you know, being a guy, I see that in like a lot of my guy friends who are techies, whether they have worked at like, you know, big companies or even if they are like, you know, doing things of their own straight out of college.

There is that thing that like when you know that your floor is super, super, super solid, that breeds a certain kind of what I would say like, what's up. I don't know if I would call it arrogance, but like there is a certain kind of what's up, which is just like, oh, yeah, sure, I can enter any room and I belong in every room because well, life has never told me otherwise. You see, but that's very interesting because I that's kind of where I am. I'm very comfortable walking into any room, but it doesn't intimidate me. Partly because yes, I've had the good fortune.

You know, you can give me a brand name list of brand names and I'll say, you know, I know a few of these guys. Say, hey, you know, if I can talk to Mr Gates, I can talk to Mr. Musk or what the hell, what's the problem? And I talked to them, you know, in years that I was still young and hard. No problem. So the comfort of walking into a room that got established fairly early and that was fortunate. I don't think I had a kid.

It was partly partly the Harvard years, partly the Microsoft years that you come out with mothered sadigans or chutzpah. But the conviction of being right, that changes. How do you understand that? Like, what does it change? So actually, in some instances, I've been other than reflecting on it and kind of going a little backwards because most people when they get older,

get firmer in their views. I know this to be true. And I've actually gone in many ways the other way. I mean, to the extent that I, I'm not even sure if democracy and capitalism are the right marvel. Talk about religion.

I mean, that's religion to me. I have no other religion. The only reason you're left with is the belief system about the way society should function. And even then, I'm not so sure about it anymore. I mean, that's partly because my spectrum has widened.

That might also be because like you have achieved more maturity in terms of like just postmodernist thinking levels. So like most people have like, you know, some version of like enlightenment era philosophies, like most of society gets stuck there. But like, you know, then you get to modernist where you're questioning form. And then when you get to postmodernist where you're questioning the definitions or the reason for form. And maybe you're there.

Anyway, I am not sure how that is on topic. I think we should get back to topic. So anyway, so how does one think about success now? So let me think about success now. I don't think there's any doubt that life's a set of chapters.

And you should actually ideally think of those chapters rather than a single chapter. Rather than a single flow, you know, you're born, you die in the middle, you spend 20 years growing up and you spend 40 years working for one company. And then you're tired and, you know, put the grandkids to bed and go to bed and done partly because I think we are a set of our nature of consciousness changes. Then our nature of physical changes are emotional capabilities and flexible capabilities change. So as everything changes, I think we become different humans.

I think just this explicit recognition that you're not the same person you were, you know, we label ourselves with the eye that I did this and I did that and I am this and I am that. In reality, you are not that, you know, at what you are, you know, one second later, you're not the person you were a minute ago. Okay, so recognizing that you live your life in chapters, there is certainly different portion of your life where the meaning of success is different. So the thing I will throw into this whole mix is without big judgmental kids do are a monkey wrench in this whole thing because they've got the same problem that you have, which is that they've got a ticking clock as well. The one year old is different from the two year old.

The six month old is different from the eight month old. Visibly so. So as I think about chapters, the one chapter which I could and I couldn't have done differently is my own kids from the age of zero to five, because that's a radically changing period. In fact, if I had really my life, I'd say, okay, I'm reliving it today. I didn't have it then because I was working in Microsoft and totally obsessed and working 70, 80 hours a week. And I can barely remember what time or what I did with them. Ruby can remember it vividly because she did 90% of it. Now on hindsight, I'm living it now with my grandkids and I'm trying to do with the grandchildren.

But as I think about that's a chapter. I'm thinking of them that way. Then there is the whole you come out of college and you're going to find yourself, you know, your feet. And that in some ways is a decade of, I think, kind of what you've done, which is throw caution to the winds. We have to lose. It's such a good time to just go out and discover and discover not just the world, but discover yourself. That's really what that decade's about. Where does competence decide? What do you like to do?

How do you really figure it out? You've do it out by putting yourself into difficult, awkward circumstances into things which are not comfortable context. And there is no better time to do that. So the 20s have really meant for that. You know, you want to go to grad school, go to grad school, but it's all part of that same journey. By the time you're in your late 20s or early 30s, I think obsession is a good word. You find something that you really dig your teeth into.

Because what you're trying to do is you spend, try to give yourself a few years, five years, a decade to become really competent. You've established yourself, what you can do, and here's something you can get really good at. And by the way, under the slight tangent on that, success is becoming really good at something. Eventually success is not about how much you change the world. Success is about how much you change yourself. That's deep.

No, it is true. Because everything else goes by. The only thing that doesn't go by is you. Which is part of the artist's attraction. For that matter, you know, this is one of the things I went to Japan. It's surprising how deeply competent everybody is. It's astounding. I mean, both the competence and the respect. The person wiping the dust, dusting the street at seven in the morning, he's got a hat on, he's got white gloves on, he's got a nice little broom, and he's doing a really good job.

There isn't stuff flying anywhere. It's like really tucked in. There's 75-year-old, 70-year-old. I don't know how old these drivers are, but the bus drivers are old. And the guys have to be in their 70s, and he's got his gloves on, he's got his hat on, and he's very, very competent. You're coming down a really, really nasty, steep hill that I would think of myself as a competent driver. I'm good. I'm like, whoa, whoa.

There's 70-year-old guys, just driving it really competent. So competence, it's, I think, a big deal. It's in the little stuff. It's in the language, it's in the ability to be able to do just the little day-to-day stuff. I watch, I look at Ruby, incredibly competent in the spaces that she's interested in. She knows more about this garden and the yard, and plants that grow, that most people she runs into.

And, you know, she can open a fridge which is stock full of all kinds of random stuff, and say, what should I make today? Those are not trivial skills. These are complicated skills. They are hard to do. Somebody's got three things going on the pot on a stove. Hey, don't tell me running a company is more complicated. And that moment, that is really complicated. It takes you just a little bit to screw up. And you don't have dinner available.

So that's what I, okay, so going back to the success notion. So I think the thirties is when I built, when you build competence. You find a space and you get ready to go to it. Now be careful that you don't build competence in a space that's, you're going to then discard 20 years later. Which is kind of what I did. And if you are, then find yourself another interest that you can build in parallel at the same time. It would be wise. And I think the forties is when you're, if you're going to be a change agent, that's the time.

You're forties in your fifties. Those 20 years is change agent time. At least they were okay. When I was at my walk into a room and I'll hold an audience. Put me in a podium and I'll change people's minds. That's when everything's firing, including your own absence of humility. I only need all of that. You can be a change agent if you stand in the podium and doubt the meaning of life. You've got to have a lot of community. This is the answer. I know it to be true.

And I can tell you it'll be true. Yeah, you need a little bit of over self conviction to be able to say, I'm going to push things in this direction. All the things that actually don't add up to being really happy people at the end of your life. Those are all qualities that are really important at that moment. And then I think two journeys happen.

You can get either obsessed with the success and then when it wanes, because it will wane, all successful will eventually go away. Because you will go away. It's the nature of the beast. Then you've got to deal with the journey of what it means to not be there anymore. And that's kind of what we spent some time, that's been 15 years since I hung up my experts. And the first three, four years it was kind of, what am I doing?

And then I just kind of relaxed into the latitude. The latitude is, I lived very stressful 30 years and now I don't. Not having any responsibilities is kind of, it is freeing. As long as I said you don't bring the couch potato, the risk is the couch potato. It's the reason why there's a very high number of career minded people who die very soon after they quit.

It's just a common phenomenon. That's a little scary. I don't know if it still is, but it was a common phenomenon. There's a spike in male deaths 12 to 24 months after they quit work. Yeah. Losing purpose is quite a thing. Losing purpose is all kinds of concepts.

So you've got to get through that journey. The definition of success changes, especially now, there's not going to think about it. The only way to think about it is the coordinates on which you measure yourself. All of us measure ourselves. So as a kid, you're measuring your coordinates on how did I do in school and how did I do on the playing field and how did I,

when you get a college, when you get to be my age, certainly the next decade, it's very clear what the coordinates are. How much time do you spend talking about your health? If you walk back on an axis, a frequency in time, they'll tell you where you lie on that axis. Because at the end of the day, the human desire to live is quite a starting note.

You don't know it yet. You don't know it yet. You do it only intellectually. You don't know it emotionally. At least I don't think so. I didn't. Thank you for thinking with us. Visit Thinking on Thinking on the Web at joyus.studio to get show notes, past episodes and transcripts. Before you go, can you do me one small favor? Go online right now and share the episode with one person who you think would love it. Until next time, bye.

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