Navigating the Modern Chaos: Reconnecting with Yourself and Leading Through Change with Thom Dennis

In this episode of The Unnoticed Entrepreneur, host Jim James interviews leadership coach and former Royal Marine Thom Dennis about his 5‑day retreat “Leading Through the Void.” The conversation explores why senior leaders often lose touch with their inner purpose—what Thom calls “the void”—especially during mid‑life transitions, and how that disconnection can erode personal authenticity and organizational health. Thom explains the retreat’s setting on Lake Atitlán, Guatemala, and its aim to give leaders space for silence, self‑reflection, and deeper self‑awareness. He discusses the psychological barriers that keep leaders from confronting the void, drawing parallels to institutionalized prison mindsets and the fear of stepping outside long‑held expectations. The interview examines the ripple effects of unaddressed purpose on culture, citing examples of high‑performing yet fear‑driven managers, the Great Resignation, and the need for inclusive, flexible cultures. Thom highlights the importance of purpose congruency, using Patagonia as a case study of external‑internal alignment, and stresses that authentic leadership requires inner serenity to hear the “quiet voice” in the gut. He shares his own branding journey—from “Captain Tom” to “Phoenix Obsidian” to “Serenity in Leadership”—and uses a rafting metaphor to illustrate agile, gut‑driven decision‑making. The episode concludes with practical information on how listeners can learn more about the retreat and Thom’s work via his website, LinkedIn, and YouTube channel.
Chapters
Hello and welcome to this episode of The Unnoticed Entrepreneur with me here, Jim James. I have Tom Dennis who's in a place called Colchester in Essex in, uh, the UK. Tom, welcome to the show.
Thank you, Jim. It's great to be with you. Thank you for inviting me.
Well, it's my pleasure because you're going to address an issue that faces really all leaders at some stage. I know it's affected me Leading Through the Void, that moment when you kind of lose touch with why you're doing things and it gets harder and harder to lead and to communicate the vision for the business. So, Tom, you've got over 30 years of organizational change. You've got 17 years in the Royal Marines as well. So, you're a man of great wisdom and experience. Tell us about Leading Through the Void. What is it and why would people want to attend?
Well, Jim, thank you for asking. It's a retreat. It's a 5-day retreat that we're going to run in a place which is of mutual excitement, I think, because you've actually been there unusually. It's on the shores of Lake Atitlán, surrounded by, I think, 6 volcanoes in a beautiful retreat center.
Yeah.
And the idea is that there's lots of very successful people out there, but there's really a question about what is success. And when people have really driven and been entrepreneurial and created an organization, There's often a moment that arrives where they need to take a step back and say, well, am I the best leader for this organization now? And what is it that's driving me? It's fascinating how often as a coach I've had this conversation with leaders and it's almost always, not always, but it's very often coincided with the children leaving home. And there's this kind of slight crisis that takes place internally in people and saying, what is this about? I've been a parent and I've been the leader of the organization, but where do I go from here? And so leading through the void is an opportunity for people to come and just explore themselves and begin to ask themselves, what is this? And the void is that place from within where these drivers come from, but we don't really address them. We don't understand them. And I think very often, you go into, for a lot of people, they work all day, they go home, and the first thing they do is switch on the television. or they switch on the music. And it's like we can't— we've got to a stage where it's very difficult to be in silence. And I think that one of the things that we really sort of try and help leaders do is to hear that inner voice, because the inner voice speaks very quietly. And unless you give it the space, you don't hear it. So It's like we're being driven and we don't really understand how or why. And we're going to give people the space to really explore and understand themselves. And for organizations that send people on a program like that, they're going to get back a better leader, somebody who's much more self-aware. And in my estimation, that is the most important skill for leaders for the future is that a deeper level of self-awareness.
I love that, Tom. And yet Lake Atitlán, for those people that aren't aware, is in Guatemala in Central America. And yeah, thanks for referencing that. I went there in 1989, a little while ago, on my own personal sort of journey through Central America. Tom, let's just back up just a little bit. Why would someone not want to address this issue? Because as you say, most of us, especially as we get to our 50s, start to really question maybe what we've done so far, but also what we're going to do in the future. Why do you think people don't want to tackle that issue? Let's just talk about that for a moment if we can.
It's a very interesting question. I, I, I think honestly It's kind of scary. For a lot of us, our characters have been formed from a very early age to conform to other people's expectations. It could have been your parents, it could have been your grandparents, it could have been a very influential teacher at school, or a role model that you found outside. Somebody or some few people have created this sort of frame within which some people live their entire lives. And actually, I think for a lot of people, that's what a midlife crisis is, is actually saying, I have been in this frame, which actually is a kind of prison.
Actually.
And I remember working with prisoners years ago at a couple of Category A prisons when I was taking, I was part of a team taking sort of healing modalities into prisons. And one of the things that so struck me was how terrified a lot of prisoners were about going outside into the outside world because they had been so institutionalized. And there is a parallel there. We drive and we use all our energy to create whatever it is. And a lot of entrepreneurs, I mean, you need to be really driven. My goodness, it's hard work. But all of a sudden it's, what is this about? And I talk about purpose, personal purpose, organizational purpose. And I think Sometimes people get stuck in a particular view of a purpose, which is theirs. But I actually witness people whose purpose morphs, it changes as you develop, as you come to different phases in your life, you have different challenges in your life. And so getting a sense of actually, what is driving me? What is my purpose? What do I want to achieve now? I've been successful, so where, where, what does that mean? Where do I go from here?
Um, yeah. And those are all the topics that you're going to be covering on this retreat. And you've got a background for over 30 years, Tom, of organizational change. And with your experience in the armed forces, in the Royal Marines, you've gone into you say, to prisons, which is, uh, amazing work as well to be doing. How does it impact an organization if the entrepreneur doesn't address this sort of fundamental driver that will motivate them and, and keep them, if you like, sincere and authentic over time throughout the organization? How does it impact organizations and, and how can we, if you like, trying to avoid making those mistakes?
Well, I can take that at several levels. I mean, particularly in the banks, I've been called in a number of times. We've got this guy, it is normally a guy, a man, sometimes it's a woman, but mostly it's a man. He's really driven and he's getting great results. But his people live in fear. And what was acceptable as a management style is not anymore because as they say, it creates too much noise. There's always noise around this person. And the organizations get into this sort of paradoxical bind of, we don't want to stop him because he's making loads of money for us, but actually he's damaging the people and they're beginning to leave. So how do we do that? So you call in the coach who tries to help that individual. So that's at one level. I think that cultures, organizational culture is something that is changing all the time. And I think what's interesting is that In the old days, big organizations, institutions used to dictate what social culture was like. But I think things have changed now, and now it's the social world that is putting lots of pressure on the organizations to change their cultures. To acknowledge what in the past they've kind of avoided, which is things like wellbeing, mental health, the incorporation or the inclusion of all sorts of different people. All these are really important aspects today and organizations that don't acknowledge that and don't work with those changes are suffering because people are leaving, you know, the great resignation. And, you know, that's one of the byproducts of COVID is that an awful lot of people have said, I've lived my life like this up until now. And actually on reflection, I don't really like it. I want to change. I want to work in a different environment. And so there's this tension now developing between organizations that say, nope, come back to work and this is how things are done. And other organizations are saying, well, okay, let's see how flexible we can be and so on. But that calls for flexibility of thinking and a willingness to accept that as a leader, the way I have led up until now is not necessarily appropriate for how I need to lead in the future. I need to learn new skills. And there aren't actually that many programs out there that are offering that. So that's what the retreat will do. But also we're designing our own leadership program, which isn't quite ready yet, but it's going to be soon, where we're really going to help people know themselves in a much deeper way so that they can then lead Other people. People talk about the golden rule, treat other people as you would wish to be treated yourself. And that is such a myth. It's becoming clearer and clearer now that you need to treat people the way that they want to be treated, not how you think they need to be treated, which is the way that you are comfortable. So that requires a sophistication of thinking and approach And a recognition that we're all different. And there's such a beauty in including everybody. But in order to do that, you've got to create a space that is safe and welcoming for difference. And difference is difficult to manage.
Well, and that leads to a very interesting question, Tom, as well about how do you create an organizational culture that is consistent to the outside world, that represents for potential customers, partners, and employees a consistent and coherent framework, and yet is so inclusive and so flexible and so able to change. How do you reconcile the need for structure with the need for lack of structure?
I think it's, this is where purpose comes in. And I think that, I remember working with one multinational, well, it was pretty much a global company a while back. And I said, well, what's your purpose? What does the world see of you? How are you represented? And it was an organization that didn't sell to the public in any way. It sold to other organizations that made things that, you know, and so the comment was, well, we don't have one and we don't need one. And then all of a sudden something happened and they were all on the front pages of all the newspapers. And so they got a representation, but it was completely out of control. And this takes you into the whole conversations about risk management and how the world sees you and how— That affects the way that they want to buy your products. I did a podcast interview with a guy who'd been very senior in Patagonia for 6 years, and it was the most amazing conversation about how because they have such a very public persona, everybody loves them and they love the product. But one of the things that enables them to do that is they are completely congruent throughout. So in other words, the way they present themselves to the outside world is exactly how they present themselves internally and how they live. And when you get that authenticity and that congruency, then actually people want to buy your product. It's kind of funny, but it stretches out. And I remember working with one organization some years ago where it was clear that their PR arm was presenting them as one thing, which was amazing, but the internal culture was quite different. And you get that dissonance. And when you have that, the people working in the organization, they recognize it. And the people who have to deal with the, on the phones, you know, when phone people are phoning in and complaining, it's really hard because they can see that what the company, how the company is behaving is just not the same as how they say they are. And people don't want to buy from places like that. You know, you can't carry on. living a lie. It doesn't work. It doesn't work in any relationship and it doesn't work in a corporate relationship with the outside world.
Very interesting. There needs to be this congruency between the ethos and the behavior, Tom. I think that's absolutely brilliant. And Patagonia is a great example because they have the whole company owned now, don't they? There's a shareholding structure by the employees. Yeah.
It's they have they've given it to the earth, so nobody owns it, and that and it costs them a fortune in tax in order to do that. But you know, even Sri Nal and his family said no, that we want we don't want anyone to control it. We don't want any shareholders telling us what to do. We don't want to be beholden because what we're doing. we truly absolutely believe in. They are role models for so many organizations to follow, but it's a challenge. My goodness.
Yeah. But as you say, that alignment between purpose and action is felt by the people within the organization, isn't it, as well? So, Tom, you'd been an entrepreneur for 30 years. You were in coaching back in the early '90s before we even had terms for it. coaching, really. How have you as an entrepreneur and as a coach managed to build your own personal brand? Because plainly there's a huge amount of wisdom and authenticity in what you're doing. But how have you shared that to get noticed?
It's very interesting. I mean, because the first company I set up was called Captain Tom. And that was in homage to the Bowie song.
Right.
And it was my printers actually who called me Captain Tom. And we had a tomcat image. And then I went through one of my huge personal transitions in '94. And I set up an organization that I called Phoenix Obsidian. And that was about having the phoenix, which is a mythological bird, but it's very beautiful and it flies high. It was a sort of thought of, how do you— come work with me, climb on my back, and we can then look from a high level at what you're doing and where you're going. It was that sense of— getting a real view of the future and how you're going about things. And the obsidian was healing. Well, obsidian is volcanic glass, and a lot of people use it for healing, but also it's a very grounding glass. So there was that feeling. Now, in 2016, I'd That was a year when I did many retreats all over the world going inside because I can't tell leaders to go inside if I haven't done a bit of that myself. So I did a whole load of that. And out of that came this sense of serenity in leadership. And so Phoenix Obsidian was put to bed in a sense and serenity in leadership arose. And the idea there is that I often give the image that was very strong for me. I was privileged enough to go down the Grand Canyon rafting and we had canoeists there as well as the rafts. And before each of the rapids, which are— photographs don't do it, it's when you're on them, you think, oh.
Yeah.
And people die. It's not It's not something to be taken lightly. So before each of the rapids, we used to get out and then recce it and see because the flow would always be different. So even for very experienced people, you'd have to plot your route through the rocks. But when watching the canoeists go down, and actually it was the same for the people guiding the rafts in a sense more so because you've got so little control. But when you, you, you have to plot your entry route, right? And then once you're in the rapid, there's no going back. You can't start turning back. You, you, you're in it and the flow takes you. So all you can do is to make small adjustments as you go through to, to, to, to just steer through all the rocks. And that is the metaphor for leadership for me, because they do that not from the brain, but from the gut, from the heart. You listen to the brain cells that we all have in our guts and our heart, which people are beginning to, scientists are beginning to realize, which the ancient civilizations knew thousands of years ago. We have this wisdom in our gut. So you listen to that. And in order to be able to hear it, it's a very small, still voice, as someone amazing once said. And in order to listen to that, you have to have that inner peace, that serenity. So that's what this is about now, is how do we create leaders who have the inner serenity to hear their inner guidance? Because things are going so fast now that you don't have the time to use your old structured thinking, the old rules about leadership. They don't apply anymore. So we have to be very— I mean, people love the word agile. I mean, this is real agility, but it's agility that comes from within.
Tom Dennis, thank you so much. And I guess the metaphor is that you do need to still get out of the raft, take a view at the rapids before getting back in. And that's really what your Leading the Void program is going to help people to do, isn't it?
Absolutely.
I'm with you on the Colorado River. It's an amazing rafting experience, isn't it? If we want to find out more about you, Tom Dennis, you're a long way away from Colorado. You're just in Essex, but you are going to Guatemala. How could people find out about you?
Well, the retreat is leadingthroughthevoid.com. I'm on LinkedIn. I spell my name Tom with an H, T-H-O-M, Dennis, D-E-N-N-I-S. So find me on LinkedIn. I'd love to hear people's comments and thoughts and responses or reactions to what we've been discussing. And the main website is serenityinleadership.com. And I write a lot of articles for various publications. So look me up and comment, engage. And of course, we have a YouTube channel and I'd love people to subscribe there because it's jolly difficult getting subscribers, but we have some wonderful material and I love to share it. So thank you, Jim.
Tom, well, thank you. Thank you for sharing. It's come across really, the passion and the sincerity as well. Tom Dennis, thanks for joining me today on the Unnoticed Entrepreneur Show.
It's been a great pleasure, Jim. Thank you.
So I'm sure that you've been as inspired as I have been today by Tom's sharing. And I'll put, of course, the links to all those places he's mentioned in the show notes. And if you've enjoyed this or know an entrepreneur that you think might also enjoy learning from Tom and his wisdom, please do share this show. And just like Tom, I also would love you to review my show, and it's also available on YouTube too. So until we meet again, just encourage you to keep on communicating, and thank you once again for listening.
Thank you.
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