This interview was done by The Early Birds Club as part of the series Personal Effectiveness. EBC was founded by Mohanji with the objective of creating a powerful and stable society. The objective was to encourage people to wake up early, adopt an early morning routine, and give people the time to reconnect with themselves and reflect that inner stability to the outside world, and thereby making the world much cleaner and purer. As part of the Early Birds Club, we welcome guests from different walks of life, to share their insights and their experiences and add value to all the members of the club.

In this interview we talk with Deepak Jayaraman, the executive coach, the CEO of a firm called Transition Insight where he works with leaders at various stages of their careers and their lives, helping them navigate transitions, find answers to the questions in life, and simply talk and also share various insights on leadership. He also runs an award-winning podcast called Play to Potential.


The topic that we decided we would spend some time on is something that’s close to your area of expertise, which is really playing to potential.

Your choices, especially once you moved away from consulting into something that you feel you will enjoy more, are off of regular track. You said it is because you realize you enjoy that more. How does somebody figure that out? For an average person who’s navigating life, how does one figure out what their potential is?

Deepak: It’s a good question and the notion of potential is quite nebulous. I don’t have a textbook answer to the question: ‘What is potential?’ One of the questions I ask all my guests as a concluding question is, ‘what does the term ‘play a potential’ mean to you?’ All of us have a set of skills, values, beliefs, habits, mindsets, attitudes, and so on, which define who we are, which define not just who we are today, but define who we could be. If I had to codify it a little bit is us reflecting more and more on what feels like play all the various things we do. What would we do if nobody paid us any money? Of the various things we do, there are a few things that are energizing, there are a few things which are less energizing, we sometimes spend too much time thinking about our skills and what we are good at and much less time thinking about what we are enjoying and what comes naturally and what’s energizing and fulfilling. Of course, this plays out contextually in a different way in different people’s journeys, but that’s the crux of the distinction I’d like to bring to people’s attention.


What you do if what you enjoy doing and what the skills that you’re trained in are not in sync? Should you follow your passion or you need to focus in your career or maybe there is a bridge and maybe there isn’t a dichotomy between the two. How does one figure out whether to make your vocation fun or whether to compromise and do both?

Deepak: It is a complex question. I agree with you that it’s possibly not a dichotomy, not an either. One of the things I learned from one of my conversations at the podcast, with a Professor Stuart Friedman: He talks about four different domains of life, self, work, home and community. And he says all of us need to think about this four piece jigsaw. When we think about work-life balance, work-home balance, we’re often talking about a two piece jigsaw, but he says we need to think about ourselves, how we replenish ourselves, we need to think about how we come to fulfill our commitments at home, how we think about work and the broader community we live in. You need to ensure that the choices you make are in harmony with what matters to you. All of us know what our realities are in terms of our commitments across those four domains and we need to have meaningful checks and balances. It’s a bit like, as a venture capitalist, how would you fund a company? You have your metrics, you have your stop loss point, at some point you’d say, ‘Maybe this is not worth funding anymore.’ Having that experimental approach is what I would advocate. I feel it’s a journey. Tasha Urich uses the terms, ‘internal self-awareness’ and ‘external self-awareness’ and she goes on to say that often these two could be orthogonal, the insights you get from reflection, could be quite different from the insights you get when you talk to the people around you. For example, I might see myself in a certain way: I’m a consultant, I’m a problem solver, I’ve done healthcare work…One of the partners looked at me and said, ‘You seem to have a people orientation, you’d be good for search.’ That’s like an orthogonal input, that he looked at me on a dimension that I hadn’t even thought of. What I’m saying is, when you ask people for feedback, they sometimes see aspects of you that you take for granted. That can sometimes open up new possibilities that you wouldn’t have considered. That’s the last piece I leave you with in terms of figuring out where potential is.

People often are very afraid to make choices that may be closer to what they want to do, because there are stakes at various stages in life. I’m sure you’ve seen a lot of people struggle with these dilemmas of even being afraid to think of what they would really want to do, forget about knowing what they want to do. How have you typically help people navigate that?

Deepak: Harvard psychologist called Bob Keegan talks about the 4 or 5 stages of adult transition and he calls the time from teenage to mid-40s, the socialized mind, which is basically conforming to what the society wants. Some of us transition to what he calls the self-authoring mind, which is more of an inside out life, saying, ‘This is what I care about, this is what matters.’ That’s not to say that you don’t take into account your responsibilities and your commitments, but the point is, inside out, ‘I make these choices on my terms based on what is resonant with who I am and what I care about, while fulfilling whatever obligations I have.’ Statistically, if you look at the numbers, his research suggests that only a small portion, I think 20% to 30%, transition to stage four and 1% become enlightened like Buddha and so on, but if you really look at the meaty part of the bell curve, a big chunk 50% or 60% are in that socialized mind where we are busy trying to live to someone else’s standards.

If somebody were to come to you and say they’re not really happy and they’re confused and they want to figure out what they should be doing next, is there a process somebody can go through to help identify? Very often the problem is not necessarily how to go about it, the problem is often even figuring out what. Without even knowing what you would like to perhaps be spending more time on, how do you even figure out the transition? Very often people are just, literally on the treadmill, right there is some want to take the time to pause because maybe sometimes, it’s scary. Is there a process?

Deepak: What I try to do and this is not to say this is the preferred way, but just the approach that I find helpful, is to really over invest in building self-awareness in the individual. If I’m working with somebody, there are typically 3 or 4 legs to self-awareness, the way I see it. One is a series of conversations that I have with a person to understand his or her context, number 2, I try and work with the person and get them to reflect on a few questions over a period of time, just like we talk about guided meditation, call it guided reflection. I give them a question to marinate on for a week and when they send the responses I give the next question. It’s a combination of things about the past, what gives them energy, and so on, and so forth, as a set of questions. Thirdly, in the context of external self-awareness, I like to talk to a few people around that individual. Typically, when we think about a 360, we only talk to the current colleagues at work and I ask people, ‘How 360 is your 360?’ Very often, it’s a 180, or a 270, because it doesn’t really capture who you are. So I like to talk to people over a period of time, not just the people around you right now and I like to talk to people outside the work context. Typically a spouse, a couple of close friends, because they see us for who we are. A half an hour chat with my wife Kamini, or with you, would be much more valuable than talking to 10 people, if somebody wants to get to know me, because there are facets of me that you know. I also find that our operating system is often wired, by the time we are 18 or 20, a lot of the hardwiring and going a little back in the past is helpful to understand that default, hardwiring. The last leg, I would say is a psychometrics. I use a couple of psychometric tools, which often provide a little bit of language to some of these things. I would over invest in these 4 things, over the first 2, 3, 4 months to really build the awareness of the leader. From then on it moves into a sounding board kind of conversation. Each person takes a different trajectory. It’s a bit like decision making. When you have a decision to make and there are 5 options to choose from, what is the criterion you use to make a decision? The metaphor, which I find powerful here is, now I’m trying to force fit four years of mechanical engineering learning into a metaphor, but we grew up in a paradigm where the emphasis was on building the engine, but I feel that for us to navigate through life, we need to have a good steering wheel and to me, a big portion of that steering wheel is self awareness. It’s all the more important because I think we are moving into a world where careers are going to get more and more bespoke given the multiplicity of pathways that are exploding in front of us. So I just feel focusing more and more on the steering wheel. Of course, the engine matters because you need to have momentum whatever pathway you choose, right, but those are the pillars of the approach I use.

When what you want to do is really disconnected with a larger purpose, I think somewhere people begin to run out of steam, because then they are on the treadmill. How do you weave in the sense of purpose or the sense of wanting to be part of something bigger, so that you think beyond yourself and your immediate unit? The reason I’m asking is one of the mottos of what we’re trying to do through the Early Bird Club is, if people have enough time for themselves by starting early, the hope is that they will have some time to actually give to the world, to others around and within the community, or at a larger level. Have you found the purpose to be something significant in terms of driving people towards a greater sense of fulfillment?


Deepak: Back to Stewart Friedman’s metaphor: Home, work and self basically take care of our immediate circle. If we just treat it as a three piece jigsaw, then I think it will lead to happiness, but for us to feel good about ourselves, I do think we belong to a bigger planet, where we want to be seen as not just having lived our life in one corner, but having made some difference of sorts. Personally speaking, it’s made a difference to me in terms of how I think about myself and my self-worth as I go through my journey. The only thing is some people are lucky to find that in their profession, other people have to carve time for it outside of the profession. That piece has to be solved contextually and if you can’t find a way of commercially finding something that’s purposeful, that will take care of all your needs, then you need to make choices which ensure that you fulfill your financial commitments while ensuring you’re leading a purposeful life.


Is there anything called too late to make a transition?

Deepak: Last week we saw David Attenborough’s recent Netflix special. He’s 94, he was born in 1926 and I was just marveling at the man thinking, ‘You’re 94 and you make a documentary, which is world class as a witness statement. I’m sure it comes from a deep purpose of wanting to save the planet and it was super inspiring. If a man at 94 could have the drive, the passion and the desire to make a difference, I’m sure some of us in our mid 40s can find a desire. I don’t think it’s too late. We lead incredibly long lives. Better late than never and better late than sorry.


There are these buckets: What I feel I’m very good at and then there is another bucket of what can earn a living? Then there is another bucket of what the world needs? How can somebody actually navigate through these different circles to actually find out where they should really play?

Deepak: It goes back to the notion of ikigai guy that the Japanese talk about.


Have you met the one who found that ikigai spot?

Deepak: People may not say it in as many words, but you can tell when somebody is leading a full life, they’re having fun, they’re in flow and you can see them playing the long game. You can see a lot of people well set off for the beginnings in a certain direction. To your question, one of the books that I found interesting, was a book by a professor in the US called Cal Newport. He’s written a book called ‘So Good they cannot Ignore You’ and the crux of what he says is, follow your passion is incomplete advice and it’s borderline bad advice. The reason he says, which I find quite clarifying is that, in a world with an abundance of talent, let’s say we work with the assumption that the world is flat and there are different kinds of people competing for similar opportunities, then skills are going to matter more and more. People do want to know how good you are in something, because finally people care about what value you can add.

I suggest to people it’s helpful to understand what are the distinctive skills we bring, because that is a ticket to play, or ticket to a casino. Then around that, say, ‘Given this, what is the universe of opportunities where I can be a value and what of that can be energizing, and purposeful. Rather than a multivariate equation, where there are too many variables to solve it in you, I suggested, why don’t we start with what makes us distinctive, what’s our driving force. Now, this comes with the assumption that only if you have skills, you’ll be able to monetize your time in doing something and be distinctive with something. It comes from an implicit assumption of money being a key variable to solve, but for a minute, if you told me, ‘I’ve taken care of my material needs, all that is done. I’ve solved for money I have the time’, then that’s not a constraint anymore. Then you start with what really gives you energy and then you start crafting experiments around it. A lot of people treat this as a step jump, but I find that people who are a little more experimentative and try 3 or 4 things, see what appeals to them and slowly, organically grow into being more fulfilled. The only reason I say this is that sometimes what you think and the way it plays out are very different. You might say that the social work is interesting, and you might go in, but six months in, you might say, this is not what I had in mind. Having a little bit of that feedback loop of whether it is what it you thought it would be; is helpful in these situations.


The world’s obviously, especially this year, gone all topsy-turvy. A lot of existing models have been severely compromised, many businesses have been upended. So in all of this, does playing to potential become all the more important? Does it stay the same? Has it gone down? Is it time for everybody to actually reflect on this whole game of what is your potential?

Deepak: I would say the need for playing to potential is possibly even more pronounced today. We are living through a time where a lot of people are on the edge in terms of whether it’s jobs, whether it’s mental health, whether it’s relationships, there’s a lot of stress in the system, residual stress in the system. What I’ve frequently observed is, when you’re playing to potential at some level, you’re in harmony. There is an implicit assumption that you’re resonant with who you are, when you’re doing what you can, given what you have, but in essence, you’re in harmony. For me, the second benefit of playing to potential is; who you are being and how you come across, and how you show up in other people’s lives. I feel in the times we are in, the cost of not playing to potential is much higher, because the residual stress is going to tip a lot of people over the edge,

I feel playing to potential will not only help you get the most out of what you can offer, but also will profoundly change the way you show up in other people’s lives around you, whether it’s your family, whether it’s your friends, or whether it’s your wider community.

I think if you are more at peace with yourself, it’s much easier to deal with what comes your way, because challenges are never gone.

I have one last question and this comes from knowing you for a long time. This is the Early Birds Club and it’s always been a subject of much mirth, you retiring early and waking up early. Can you share how you have found it actually helpful to you in your life?

Deepak: Maybe my default setting is that I get more energy in the mornings than in the evenings. For me personally, it’s a bit like people saying, ‘I go to office half an hour before everybody else comes, because it gives me clear time to be with myself before the chaos of life hits me.’ For me, morning time is a bit like that. I wake up, it’s my time, sometimes I go for a run, I learned an instrument; I learned the guitar over the weekend, so I try and spend half an hour practicing it. Sometimes, it’s about writing a piece of work or editing a podcast where I need to apply my mind. If I compartmentalize the different things I do, there is a small portion of what I do, which requires a little bit of deep work and a little bit of focused attention without interruptions. Back to that four piece jigsaw, self, work, home and community, I think that morning time gives me the opportunity to take care of the self, whether it’s in terms of health, or whether in terms of hobbies, or in terms of work. It’s helped me over the last few years.


Interview by Madhusudan Rajagopalan, EBC board member

For more information visit

For more information about Deepak and his podcast visit

Leave a Reply

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.