WOW 174 | CEO Exit


In the previous episode, we discussed the process of transitioning to become a first-time CEO. Now, Executive Coach John Maxwell returns on the podcast to talk about the other end of that journey. We reflect on what it’s like to transition away from being a chief executive, and what comes next after this key inflection point in a leader’s career. And what an inflection point it is! Transitioning out of the CEO role is not as easy as it sounds. A lot of people struggle with the uncertainty of what to do next and with the unavoidable consequence of diminishing status and importance. How do we navigate that when the time comes for us to make that journey? Join the conversation and open yourself to the possibilities.

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Moving On From Being A CEO With John Maxwell

This is the second in a two-part miniseries with John Maxwell, a good friend. We are in the room again, having another episode. How exciting. In our first episode, we talked about the journey, process, and development of becoming a chief executive, what’s involved in that process, and how to navigate that. In this episode, we’re going to look at the other end of that journey and reflect on what it’s like to transition away from being a chief executive or a particularly senior individual in an organization and navigating that transition into what comes next.


WOW 174 | CEO Exit


Before we get into that, though, John, can you say hi and introduce yourself to the audience again?

Will do. It’s nice to be back with James in the room. I’m John Maxwell. I spent many years running global businesses in different places around the world, including China, Germany, and US. I like your euphemism for moving on. As CEOs will know, most CEOs exit because they get fired. I would fall into that bucket. I’ve been plowing my own furrow and doing my own thing since 2018.

It’s coming up to five years. It’s 2023. I’ve had a few conversations with people who are quite senior who are saying, “I’m in this role. I’m successful in this role but ready for something else. I’m looking and I feel it’s time. I want to go before it’s too late. I don’t want to overstay. I want to do what feels right for me,” but it feels like there’s some difficulty in exploring and figuring out where to go. Hopefully, we’ll cover a little bit more of that. You said you’ve been plowing your furrow. Before we look at the transition piece a little bit more, what is it specifically that you’re focused on?

When I left in 2018, I had a couple of things that I wanted to do. I’d always been attracted by tech. I thought an area there that I felt was underrepresented was the travel tech space. With a partner, we founded a small business called Hidden Trax. It was focused on audio walking tours in big cities with the aspiration of connecting local creators to tourists. People are piling into these cities. There are all these people that already live in these cities and have great stories and great access to what the cities are about. We wanted to create a platform to connect those two.

I had been passionate about the people side of leadership as a CEO. I’ve had some great coaches in the last couple of years in my roles. I thought, “I’ll go get qualified as a coach. Maybe I can stay connected with the business world in that way.” I like working with people, especially people that are coming up in their careers. That was the second string.

That’s a nice combination and desire to stay involved in creating something in the business space. If you’ve been in business, it’s pretty common. In your instance, you said you were somewhat pushed. I’ll use the word pushed a little bit. You said fired.

I agreed to move on.

You decided to spend more time with your family.

Everyone has a boss. Sometimes, it’s time to go.

Sometimes it’s just time to go.

I get that. The sense I’ve got from speaking to you a little bit is that perhaps, there were signs or signals at that point or even before that point that maybe it was time to think about moving on with a new chapter of life, to use another euphemism that’s out there. What signs, feelings, or signals did you notice that were occurring in your day-to-day, your work, or after you left that maybe you think maybe it was right to explore something?

For me, it was repetition. I started to find that I was doing the same thing. It’s to agree to the budget. It’s to figure out what the strategic plan is. It’s to hire, fire, and develop key roles on the team. It’s to go visit all the sites and do town halls at different locations around the world. That felt like it was becoming a bit repetitive. The travel and the time away was a factor that had been part of my life all the way through. I felt like maybe it was time to change that a little bit.

The main driver was, “This is becoming repetitive. Am I learning anything? There are other things that I want to do, but I don’t have any time to do any of them. Can I make time to do some of these things? What could I do that would be different than what I’m doing today that would allow me to do some of these other things?” My kids were heading off to university. A lot of things came together at once that made me think it was time to try something different.

I liked your phrase about learning. Learning, for me at least and for many people, is a powerful motivator and contributor to our overall subjective well-being. The ability to learn is great. When it goes, it’s hard. People talk that we have difficulty with a steep learning curve and all the strain with that, but when the learning curve isn’t steep, we diminish a little bit in ourselves and in the way that we experience things.

Learning is a really powerful motivator and contributor to our overall subjective wellbeing.

When I speak to people who are in some of these more senior roles, when we’re being candid, we sometimes talk about the two sides of things like this. We talk about the going from, and we talk about the going to. That’s change-y speak, if you will. How much of that balance do you think was there for you between leaving something that was maybe feeling less fulfilling and being drawn to something that was attractive to you? Is there something that matters in that?

For me, I was being drawn. Getting a little extra push pushed me out into that world where it was like, “I have to make a decision to stay in the industry, stay in the corporate world, find myself another role, and double down on where I am,” which is easy as option one.

It’s a bit defaulting, isn’t it?

It’s a bit defaulting. You keep doing what you’ve been doing and do it somewhere else or do it for someone else or go towards some of these other ideas, which is to coach, be a tech entrepreneur, be a solopreneur if you like, or at least think of yourself as a solopreneur. In that, feel like you control your own time. You control your own, “What am I going to do this week?” That’s because you don’t in the corporate world. You might think that you do, but you don’t.

You’re such a stakeholder manager. You’ve got so many other people. That speaks to autonomy and the power of autonomy as a tool for job satisfaction and managing our demands.

I had a lot of autonomy in my roles. Most of the time, my boss was on a different continent. I found I always performed better when my boss, whoever they were, was generally at least a six-hour time difference away. I seemed to work really well. In that corporate role, you make your own autonomy. In these roles, you have the space to decide what you want to do and where you want to go, but you do have to go somewhere. You don’t get to sit in the office. That’s probably what was most different around it.

You were helped into this situation. As a sad conversation, in one of my old roles, I used to fundamentally be part of a team that would go around and close down countries. I did that for a little bit to the extent that when I turned up in a country to speak to people, they were like, “That’s what’s happening.” What I found is that, and maybe this is a biased memory, a huge number of the people that I spoke to that ended up leading through a redundancy process in those both years, in a year or two, expressed satisfaction and pleasure at having had that opportunity to make a change.

I’ve got a mixed relationship with that, but certainly, there are stories that I remember. We’ve had people who retrained as private investigators, opened a kitchen shop, or moved to a different country. There are all these lovely stories that I remember something in that. That space and that opportunity to do that come with a bit of a push.

You’d been pushed. You’d been thinking a little bit about changing and going from and going to. In those moments, what were you thinking about? What were some of the concerns and things that you were balancing when deciding to pursue Hidden Trax and pursue your role as a coach?

You start off very positively. You’re drawn towards it. It’s a different world. You start to discover quite quickly how challenging it’s going to be and how difficult these things are. It’s going to require a bunch of hard work. You don’t know much about the marketplace, so you’re trying to figure out how it operates every day. You find out more stuff and it fills the picture in. Usually, for me, your optimism starts to wane a little bit as you start to see what’s going on. The pandemic happened right around that time, and that was probably the biggest challenge. With that big shock and instability, the first reaction was flight to safety. It was like, “Let’s go back to the corporate world. I can make a living there. I can make that work.” I had a few of those conversations.

How did you feel when you went into one of those conversations about going back to that world?

I was super conflicted.

What was drawing you back?

The security was what was drawing me, which, in some ways, is a little ridiculous. You know you’re going to be fine. It’s that security. Also, maybe a little bit about value. When you’re a solo entrepreneur, you’re doing it for you. You‘re leading the business. In my last business, I led 4,000 people around the world. You feel like, “I can make a difference to a bunch of people.”

It’s significant. You can have an impact and have all those lovely ego-ish massages, but also make a difference and all that stuff. Status is a beautiful thing.

When you’re on your own, that changes a little bit. I doubled down and stuck it out in the coaching world. The pandemic had pretty much a terminal effect on our Hidden Trax project.

WOW 174 | CEO Exit

CEO Exit: Status is a beautiful thing. When you’re on your own, that changes a little bit.


That makes sense.

In a way, it allowed me to focus my time on coaching and leadership development and a little bit of strategy consulting space.

When you were talking there about the direction that you wanted to go at this moment of transition, you seemed fairly clear on those two paths. You talked a little bit about them. What was it that drew you to them? How did you get a sense that maybe these were things that would give you satisfaction in a future role or meet your needs? How do you understand what you felt your needs were and try and find something that would map up with that for you?

With the coaching one, I experienced some great coaching. I felt like it makes such a difference. I felt like that’s something I want to do. I was drawn by the feeling of, “I can continue to make a difference.” I have a perspective because I understand the business side. I’m coming at this from a business perspective, not as a psychologist. I’m not going to pretend to be a psychologist in the room. I’m a business guy that understands a bit about leadership, how businesses work, and what some of those challenges are that come up again and again. I felt like that’s something that can be of value to people as they’re progressing through their careers. I like spending that time. It makes me feel good supporting people and seeing them be successful. That was the main driver.

It feels good to support people and see them become successful and progressing in their careers.

It’s interesting. I was chatting to somebody who is still in a role. They were talking similarly to you about some of these things. They were thinking about making this leap out themselves. The words they used were performance and purpose. They’ve been in senior roles for decades and are good at performing or achieving performance and achieving these things, similar to what you said. You talked about that annual cycle of strategy, your financial forecasting, managing people in and out, and all that stuff. They can do that.

They said they were less interested in performance and more interested in purpose. I’m trying to find that space. When you were speaking, it seemed that you were using what you’ve learned. You were using that knowledge and those skills and giving them to support others through that. There’s a little bit of motivation in there for you in that helping motive or in that giving back motive.

The other piece is there was this realization. What made me a successful leader and creator of teams and was able to deploy, motivate, and make things happen was this inclusive lens to leadership I’d had. Without recognizing that or without putting that name on it, we didn’t call it that. We called it collaboration. We called it team. We called it bringing all the voices into the room. We called it all those things. We didn’t, at that time, specifically label it as inclusive leadership.

Some of the coaching and development work I did was with a company. I had done it in London. They’re called Meyler Campbell. They did a great job. I enjoyed that development and network I became part of and accessed, leveraged, and learned from. That time allowed me to think this was about inclusive leadership.

In 2018, I started thinking, “What is inclusive leadership? What does that mean? What do we think about it? What’s leadership for the future versus leadership for the past?” People that are coming up into senior roles look ahead of them. They see what’s gone before them. The tendency is to emulate what was there. They’re like, “Let’s emulate what worked.” I felt like that was not going to work when I looked at the next fifteen years. I was like, “How do I take this inclusive leadership idea and take that into the business world and make it something that people are thinking about and talking about?”

That speaks to a clear driver or a clear change that you want to effect on the world, to some extent, or something that you are drawn towards doing to change the world around you. For everybody in these situations that are in a senior role thinking and leaving or outside thinking about what to do, they won’t necessarily all be drawn to that cause. How can people explore, think about, or maybe try and identify what that calling is or something that’s drawing them in? How can people find space to work out what they are drawn to and motivated to?

It is about creating some of that space. It is giving yourself a little time and trying different stuff. With the expectation that I’m trying this out to see what it feels like, how does that work out? You have to try. Don’t think about it too much. Don’t try and plot out all the steps because by plotting out all the steps, you don’t know what’s past step 1 or 2. It’s about jumping in and trying things.

WOW 174 | CEO Exit

CEO Exit: Give yourself a little time. Try different stuff. Don’t try to plot out all the steps.


Minimize the risk as much. Don’t invest tons of money. If there’s a bit of the world that you’re interested in or an industry that you’re interested in, how do you get exposure to that? How do you find out what it’s like? How do you try before you buy or try before you commit? That can be through training, meeting people, and getting access to the industry. That could be taking a part-time job or a volunteer job or getting involved in whatever it might be that could be moving somewhere else in the world.

If you are like, “I always wanted to be somewhere else in the world.” Before you go buy a business in that world or that part of the world, why not go live there for three months and figure out, “Is this where I want to be?” Try before you buy or try before you commit. Be willing to try 3 or 4 things and then say, “What did that tell me? What did I like? Could I see doing that in ten years? Would I be happy if this is what it looks like in ten years?” Ask yourself that stuff.

There are some interesting things in there, in my view. I’ve scribbled down a few things. One of the things that stands out to me is this sense of emergence versus planning and structuring. That’s sometimes a hard thing for people to navigate. I know it’s something I’ve found difficult to do. I’m quite analytical and I’m quite a planner. I will map out a plan and do all that. There are benefits to that at times. Being able to be in that emergent space, seeing what happens, and trusting yourself to respond as the world changes and things that emerge is an interesting place to get to in a developmental place that helps people navigate this.

It is also being supported to do that. In your family situation, are you able to do that? I was fortunate. Martha has always been there and happy to go along. She is happy to explore beside me. She is happy not to come along for the ride. She is not coming along for the ride, but she is happy to be there and to see where it goes.

I’m lucky to have similar support that does de-burden and de-risk and makes these things more of an enjoyable process. There was something else that you mentioned. It came up in our last conversation as well. It’s interesting. You talked about trying, trialing, experimenting, being open to newness, and finding things within there. The way I think about things myself a little bit is I’m trying to navigate, find something, or be creative. I need a variety of inputs to help me do that. I need to be fed by variety before I can navigate through a variety and create something that feels good in there.

For me, a lot of that stuff can be intersectional. It doesn’t need to be deeply focused on one area to give me inspiration about a different area. Sometimes, it is going to the museum and looking at some paintings, which I don’t do all that often. Doing something like that can help me process a problem related to my business. Going for a run and speaking to somebody about their childcare challenges could help me navigate some other part of my life. That ability to draw from different sections is helpful for me in navigating. I love that intersectional space as a way to learn and figure out what’s right for me. What are your reflections on finding stimulus in different sources as we navigate what’s right for us?

For me, connecting with people is probably the biggest one. It is having an interesting conversation, being curious, and not feeling like you’re doing it for any specific reason other than to learn and understand a little bit more about what’s going on in that part of the world. It is not having an agenda around, “Is this going to be a great contact? Am I going to be able to sell something here? What am I going to learn?”

My tendency is the learn and explore side. That could come at the cost of the commercial side sometimes because you could make the argument that you should be closing more often. I’m taken by the bid around, “I want to learn. I want to explore. What do I take from that? I want to meet some interesting people and make some interesting connections, some that continue for years.” You and I met a few years ago. I remember I came to an event that you were hosting. I also met a number of people through that.

It is those types of things. It is getting out there, having conversations, seeing who you connect with, being interested, and finding the people that are willing to share. Maybe that’s the other piece that’s there. It is finding your people. It is finding people that you know are your people. In other words, it is finding people that are open. They’re willing to share and you share some values, principles, and ideas about something. In my case, that tends to be about this inclusive leadership piece.

Find your people. Find the people who share your values, principles, and ideas.

It is finding those and then having a conversation, like, “What can we do about that? Where are the opportunities to work together?” without getting into where the opportunities to make a bunch of money together are. The commercial piece will happen. It’s necessary. It needs to be there, but I find that if you make that the starting point, it tends to shut down a lot of the creativity. I find you make that the second or third point and then it becomes a much more interesting discussion around, “How do we collaborate?” That’s the other point. It is collaboration. In this world, this development world, and this coaching world, as a solopreneur, you’ve got to collaborate. This is a critical skill, so how do you do that? How do you create that network? Those are some of the pieces that are important.

It feels to me like one needs to step into those spaces with the right mindset to do that. It is that space where you are open to learning and creating that generative space where you have a conversation and see what comes up. There’s something of interest in there. Its values align with yours. There’s something there.

You talked about spending time with people who are willing to share. There’s also something about being willing to give into those spaces. To collaborate, it’s about giving ourselves to those spaces and those relationships and navigating towards that purpose. I’m quite a believer in the build-it-and-they-will-come type of things for this.

I don’t know if you’ve ever had this. I’ve had some stuff sometimes where I’ve got locked into a piece of work we’re doing here and I feel like, “This is going to happen. I can’t not do this. This is an inevitability. Even if I’m not doing it, somebody’s going to have to do this, so it might as well be me doing this because it’s going to happen.” Finding that little space of purpose feels wonderful when I’m there, but trying to find that for ourselves isn’t always easy. What are your thoughts on giving back?

You have to give. That maybe links to how everything doesn’t need to be commercial. There are some things that you want to do because you want to do it. People ask me all the time, “What are your raises? How much do you charge?” It’s a fair enough question, but I’m like, “I charge anywhere between £0 and £1,000.”

The answer is, “It depends. Who are you? Where are you? What is it? What do I want to do? Why do I care?”

I’m like, “What’s the need?” I remember when I first started, I had a little box on my website that said, “If you want some coaching and you’re not in a position where you feel like you can pay for it, you send me an email and we’ll have a discussion.” I’ve only had 2 or 3 people tick that box, thankfully. Maybe. I don’t know. This is not a, “I get flooded by that.” The people that did connect with me, we did six sessions together. It felt great. They got something out of it, and I got something out of it. They’ve gone on, but we continue to connect and do a little bit of work together. You’ve got to be willing to do some of those things for a cause that aligns with you.

More broadly, if you are speaking to somebody. Sometimes, I get a sense of it. Sometimes, people aren’t ready or haven’t made that journey to step back from the immersion of being in that doing, always involved in a role, getting stuff done, and that active being in a senior role thing. People sometimes haven’t found that space to find what’s right for them.

We talked about the intersectional space, the thinking, or the stimulus. Are there books people can read? Are there specific activities that people might do that would help them work on this? Would you say journaling is a helpful thing? We talked about exploring and trialing things. To find that cause of motivation, should they reflect back on moments they’ve been happy? Should they ask other people what motivates them? Should they think through their values? Should they keep a journal of the moments that they were deeply in flow in their work? Should they read newspapers and circle, “This is something I care about. This is something I don’t care about.”

The short answer is yes, but it’s got to be what works for them. Do whatever works for you. What worked for me or what works for me is listening to stuff. Podcasts and audiobooks, that’s what works for me. Writing and reading have never been my strong point as an engineer. That’s what works for me. Find out what works for you. Is it a conversation? Is it journaling? Is it that little bit of time?

If you see and hear a number of people that have been successful in various different worlds, whether it is media or business, a common theme that I see anyway is that people make time for themselves. That can be ten minutes a day. They make time for themselves to think about what that is. That’s a journal that’s, “I’m going to take a run.” That’s whatever it might be. That is a common theme. If you’re in deliver mode and too busy to do anything, you’re the proverbial hamster in the wheel.

When you look at people that have been successful in different worlds where it’s a common theme is that they make time for themselves.

When senior people step away from a role and go into something new, there is the removal of all those embedded statuses. Important calls on our times, salary, and all those social, societal cues that make us feel successful can be pulled away when we step out and we’re suddenly on our own. We make that journey. Many of our peers or the people we know around us are probably still from those old-world situations and still in those powers of social importance and stuff. Suddenly, we’re in a vulnerable place of being something different. That can feel a little bit strange. How do you hold onto that value of self in that space? How do you navigate healthily through that without feeling like you’re overwhelmed by that change?

It’s an uncomfortable place. It’s a question of how long you stay in that zone and then which way you go. Do you go forward or do you go backward? For 6 to 12 months, I had feelings of doubt. I had feelings of, “This is uncomfortable.” I had feelings of not so much loss of status but loss of importance to some, which may be the same thing. Everyone goes through that to some degree or another. It is recognizing that there is going to be some discomfort.

What do you do to get to the other side? In other words, what do you do to get to wherever it is you want to go, whether that’s a new role, a new career change, or to prevent falling back to, “I like all that stuff. I’m going to go back there because that felt great,” because then, you’re stuck in the wheel? I don’t know what you do. Have good support. Talk to people. If you sit on your own and think about it, that’s not a great position.

WOW 174 | CEO Exit

CEO Exit: Talk to people. If you just sit on your own and think about it, it’s not a great position.


It’s dreadful. One of my favorite podcasters talks about stewing in your own soup. You can stew in that soup of uncertainty.

That’s not a place to be.

One of the things I’ve found is that as I’ve engaged in a community of people who are interested in similar purposes that I do, I get some of that social validation in that space. I enjoy that, which makes me feel good.

I would agree with that. In the coaching community that I’ve become part of, with some of my clients, that is where it comes from, for sure. Let people know what it is that you care about because then, they understand a little bit more about where you’re coming from. If you’re willing to share some of that stuff, that helps a lot.

It is that openness and that vulnerability. I’m going to start to wrap this up. If there was somebody at this early stage or maybe somebody’s got some of those niggles that are like, “This isn’t quite right. It’s time for something different. I’m going to think about it,” what advice would you have for them? How would you help them at a point to start this journey?

I would encourage them to look forward a little bit and maybe write down, “Where am I today?” Think about, “What do I want life to look like in five years’ time? What are the five most important things that I want to have? Is that about time? Is that about the experience? Is that about money?” What is it that you want? I would start from that perspective. I would write those five things down. I would encourage them to start thinking about what their options are and how their options match up with where they want to be. Five years is a good time because it’s far enough away but still a little bit aspirational.

We can aim big or aim bigger in that space.

That’s the first step, and then once you get it down to 2 or 3 things, go experiment. Go play around. Even before you’ve left, go find a way to get involved in something so that you can understand a little bit more and color in the picture. Don’t put all your bets on one thing. Try some different stuff.

Thank you. We’re going to wrap up here. To close out, how can people learn a little bit more about you and what you do? 

You can find me at or John Maxwell on LinkedIn. I’m happy to have a chat with anyone that would like to have a chat.

It’s wonderful to chat again. Thank you very much.



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