Episode #993
Ever feel like you’ve checked all the boxes—career, family, success—but something still doesn’t feel right?
You’re not alone. And more importantly, you’re not broken.
In this episode, Tim Matthews is joined by Gregory “Dynamite” and Derek “The Redwood” for a down-to-earth conversation about what it really means to feel lost as a man. They get honest about the times in their lives when they realized they were completely off track—and what it took to admit it, face it, and find their way forward.
This isn’t about having a breakdown. It’s about having a breakthrough.
They share what it feels like to build a life that looks great on the outside, but doesn’t feel right on the inside. The pressure to have the answers. The temptation to sedate with work, alcohol, or just staying busy. The fear of admitting you’re not sure who you are anymore.
But they also dive into the shift that happens when you stop fighting that feeling—and start listening to it.
In this episode, you’ll hear how spending time in nature, reconnecting with purpose, and leaning on brotherhood helped each of them move from feeling trapped to truly alive again.
If you’ve ever wondered, “How did I get here?”—this conversation is for you.
Sometimes being lost isn’t a problem. It’s a wake-up call. And it might be exactly what you need to finally find yourself.
Feeling lost in your marriage too?
Just like in life, the first step to fixing a relationship is admitting you’re not where you want to be. This free training shows you exactly how to get clarity, connection, and that spark back.
It’s time to stop drifting and start leading—at home and in life.
Hungry for more?
Head over to our BONUS page for special access to some of the deeper tactics and techniques we’ve developed at The Powerful Man.
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Transcription
Derek 0:00
By being able to be out in nature and to truly and intentionally observe beauty, to acknowledge and recognize beauty, to see it in a natural form—because my belief, I’ll share that—is that the divinity of the universe is within all living beings, agreed.
And if you can, when you find and when I find and see beauty in nature, that is a reflection of the beauty and the light within me and what that is. And in that moment of surrender, I can be found. You.
Tim Matthews 0:45
Hey guys, welcome to another episode of The Powerful Man Show. I’m your host, Tim Matthews, with two incredible guests today, Mr. Gregory Chard Jackson,
Gregory 0:57
AKA Dynamite,
Tim Matthews 1:01
There we go, and Mr. Derek Drake,
Derek 1:05
AKA The Redwood,
Tim Matthews 1:06
There we go. I love the energy of you guys, so let’s talk about feeling lost. Not that you guys can relate. I can relate to that.
Gregory 1:27
We can relate to that.
Tim Matthews 1:29
Tell me more.
Derek 1:29
I think that’s something that—it’s a good topic, Tim.
Tim Matthews 1:34
Tell me more. In what way can you relate?
Derek 1:41
I didn’t know I was lost until it was very clearly pointed out to me by the other brothers in The Rising. I was sad at that realization, but in the way, it was also comforting to know that I’m not perfect.
And would you like to know how I’m lost?
Tim Matthews 2:05
Well, I mean, if you want to share, that’s always great, and then we’ll dive in a little more about what it feels like to be lost.
Because I’ve certainly felt lost at times—at times, longer than other times—and it’s tough, right? Especially if you have a business to run, or a family, or whatever. It can be very easy to want to keep up appearances and pretend like everything’s okay, right?
Because it’s a really scary admission. I think at least it was for me—to admit that you’re lost. Because in doing so, you also need to accept that you don’t know the answer in that moment, right?
Not that you’ll never know, but in that moment, you don’t know the answer. Which, for a lot of guys who pride themselves on knowing what to do, and pride themselves on being able to solve problems—be it them, their own, or other people’s—and also for guys who everybody else looks to for the answer, to then not be able to answer the question of either “What do I want?” or “Where am I going?” or “Who am I?” whatever it may be, right?
It can be tough. A lot of guys will push it down, right? I think there’s some pride that comes into it as well, right? They don’t want to admit that, like, it’s a weakness or a failure or whatever it may be.
But it doesn’t go away. No, no. You can’t outwork it. You can’t out-earn it. You can’t outsmart it.
It requires you to face it and to be with it, and to be, I guess, and with it. There’s nothing you can do, really, in the moment of inquiry to—like I said—outwork it.
Derek 4:05
Yeah, I think that’s a really good point, Tim. I think, you know, for me, I will say that I spent a good portion of my life being lost and then thought, especially after The Alpha Reset a few years ago, that I wasn’t lost anymore, and made a lot of progress in finding myself. But it was progress, and this last week here at the Alpha Rising, I realized that, in fact, I’m still not found yet—how to be really me and where that is—with more of that inquiry and more of that.
And I think one of the insights for me in the topic of being lost and what that is—for me, it was about really living for others and losing sight of what it meant to really want to live for me, and what it is being who I really am, and what that looks like.
And it’s easy—it was easy for me, just my story—it was easy for me to let go of and walk away from, you know, who I am, because the rewards for doing things for others, not necessarily out of just genuine service, but because that fulfilled a need for me…
You know, it was like being in the forest, and, oh, well, there’s a berry, there’s a berry, there’s a berry, there’s a berry, there’s a berry, there’s a berry… and just, you know, gathering, gathering, foraging, foraging, all of that stuff. And then all of a sudden, you stand up, and you look up, you’re like—maybe you’ve had all these rewards and all this stuff—but you’re in a place that you don’t recognize or you didn’t want to be. And that was my experience.
Tim Matthews 6:11
Yeah, it’s tough, isn’t it? Because a lot of guys have told me instead of building a life, they feel like they’ve built a prison. And they can often feel kind of trapped by it—whether their burn rate is so high because over the years, they’ve gone and have built a home or acquired things, or that their cost of living has grown so much as they’ve tried to avoid the feeling of being lost by filling that space or that void, if you will, with something outside of them.
Obviously, it never works, right? The way to overcome feeling lost is to get unstuck and get clear, right? And I think what you said is so true, because you know where you were at after The Alpha Reset. It was so much better than where you were before, right?
But equally, where you were going is so much better than where you were after The Alpha Reset. Yes, right? There are levels and layers to the game, right? So it makes complete sense. What about you?
Gregory 7:17
As I said, I didn’t know I was lost, because I do know that I’m not eternally lost. Thanks to my faith, I know—I know exactly who I am and why I am. And I think—no, I know—I needed to be here, this very moment in time, to find out that I was lost at this very moment in time.
So for me, it’s a temporary state of being. It enabled me to both accept that fact—that I am lost—because it was told to me by others in a way that I was very open to receive. And in the very moment that I was able to accept that, I also found the solution.
Tim Matthews 8:09
Nice. I love that. I think you’re spot on, right? Because I think there’s so much stigma around men admitting that they feel lost at times—that it is a temporary thing. You’re completely right. Or it can be a temporary thing, if you’re willing to accept it without ego, and thus then gain the clarity, right?
And once you get the clarity, it’s easy to then move forwards. But I think so many people wrestle with the idea of being lost, because as men, we should always know the answer, we should always know what to do, we should always know where we’re going—we should always—all the things that society says that we should be, right?
But underneath all that, we’re also human, right? So inevitably, there are going to be times when we get lost.
Derek 8:57
And that’s—that’s the first step to being able to be found: is to acknowledge you don’t know where you are, you don’t have that answer, you don’t know what that is.
And there was a moment in the Rising this last week where, you know, I was asked a question, and my answer to that was, “I have no idea.” And your observation of that to me was, “Hey, that’s the most honest I’ve seen you all week.”
And I felt that as well—like that’s actually the most honest I’ve been. And the process of this week in particular, for me, was building to that acknowledgement in a different way than you got it, but it was the same—the same kind of place that we got to, which was a place that neither of us knew we were.
Tim Matthews 9:41
Reminds me of mountaineering, right? I’ve gotten lost a few times in mountaineering. It’s always been because I’ve had a little bit of bravado, right? I don’t need a map. I know where I’m going. I don’t need to check the forecast. The weather will be okay.
But luckily, in those moments of being lost, I’ve had connection. It was internet connection—well, there’s so many metaphors, right? The need for the right map, the need for the right guide so you can understand the forecast and what might be coming, right?
And then the need for connection too. Because oftentimes, when we’re lost, we’re also disconnected from ourselves and what we want, from something bigger—in my opinion, whether you call it God, the universe, whatever it may be.
Being lost and being disconnected often go hand in hand.
Being lost and not having the right map often go hand in hand.
Being lost and not being able to see what’s coming often go hand in hand.
Luckily, I was able to get out of it.
Derek 10:58
Luckily for all, absolutely, absolutely. But I think there’s a part of that that’s—at least for me, and I think a number of guys that I’ve witnessed and been through some of this stuff with—there’s a tendency for us to look to ourselves: “Okay, what is my compass? What is my map? What is my guide? What is my connection? What is it in me?”
Instead of really being able to surrender a bit and go, “What is beyond me that is available, that’s coming to me, that can be my map?” Maybe I need a new one—mine’s outdated. Exactly. “That can be my guide.” Maybe I need a different guide, or more guide, or a change. And maybe I need a different connection than what has brought me to this point, to get me found again and unify myself.
And I will say I experienced probably all three of those this week—nice—and really looking at, okay, I’ve made progress, but I’m off track. And I think that’s just something that if you find yourself in that space of trapped, in that space of disconnection, and you feel like you’ve built a nice prison for yourself—having money, I’ve built some nice prisons for myself over time—I can appreciate that.
Doug Holt 12:20
Hey guys, I just want to share something with you. I’m sure we can both agree that in order to fix something, you need to know what’s broken. And not only need to know what’s broken, but a step-by-step methodology on how you can fix it. That’s the easiest way to do it, right? Otherwise, you’re going to be toiling with things.
That’s why I created a free training—a training that not only shows you how you got to where you are, where your relationship is missing that love, respect, admiration, and even intimacy that it used to have—but how you get it back.
How do you retain that? Where your wife’s looking at you the same way she used to look at you when she said, “I do.” You know, I don’t know about you, but for me, when my wife looks at me like I’m her man, I feel like I can conquer the world. And I want that for you.
Simply go over to thepowerfulman.com/scales. That’s thepowerfulman.com/scales. And I have a free video training for you. You can just click play and see if this resonates for you.
Now, back to the podcast.
Derek 13:22
Then you maybe take a look at those elements—it’s a good analogy. You know, what’s guiding you? What’s your map, right? Who you have on this with you that’s helping chart that territory? And does that really connect in your heart, and what that looks like—and the connection that could get you there?
Open yourselves up to it. Because my guess is—if you’re not—my guess, I know that if you’re in that space, the energy of the universe, your faith, God, your movement, the men here—they’re there for you to help that happen. You just need to open yourself up and receive that. I needed to do that—open myself up and receive that.
Gregory 14:11
And there’s a very reason for why you are in that state of loss in that very moment—because it’s a time to shift and look inwards. And for me, it was highlighting the very reason why I was lost—my strength, my resilience, that I can do this on my own—and equally highlighting my strength that, as I’m strong, I can also lead, lead others and attract others. And that was my solution.
Derek 14:51
And we all got to see that this week, which was a beautiful inspiration for all of us, and a beautiful digestion for all of us. Because you took lead in the kitchen and worked with the team and orchestrated some gift—amazing gifts—for all of us.
Tim Matthews 15:10
I think faith is a really important piece in not being lost. Like, I remember before I started TPM—so back then, as you guys know, I built one of the UK’s fastest-growing fitness franchises within its niche—but I just felt this pull. I mean, you guys will resonate.
Gregory, I felt this pull for something more. I wanted to impact people in a bigger way. I just had this itch that I was trying to scratch. So I’d set up the business, they didn’t need me, and I just sat in this space of surrender—really spent a lot of time in nature—and just asked myself, just asked the questions.
And I never felt lost. Because although I didn’t know what was coming, I didn’t know how, what it looked like—I also kind of knew that something was coming. And I felt deeply connected, actually—both to myself and to the universe, or whatever you want to call it.
I was super inspired. I was just living with so much flow and ease, right? It was a really magical time. I just think it’s key—it’s key to have that faith, whether it’s religious, spiritual, whether it’s from other men, whether you borrow belief, right? And you can borrow the belief from religion, from the universe, from people. That’s a key component in not feeling lost.
Derek 16:46
And I think, I think you made a really important point there that I know I would like to go back to. And I know it’s been key for me—but time in nature. And what I mean by that is by being able to be out in nature and to truly and intentionally observe beauty—to acknowledge and recognize beauty—to see it in a natural form.
Because my belief, I’ll share that, is that the divinity of the universe is within all living beings—agreed. And if you can—when you find, and when I find and see beauty in nature—that is a reflection of the beauty and the light within me and what that is. And in that moment of surrender, I can be found.
And much like we were talking about even in our last topic in podcasts, it’s about, you know, permission—giving permission. Sometimes in that state of being lost, it’s just allowing yourself to be found and surrendering to that.
And I’ll say my experience here this week—and acknowledging that I’m not as found as I thought I was—what came out in my King’s Court last night was like, wow, the next step for me is actually what I’ve been dreaming about but wasn’t giving myself permission to really open up and explore.
And so I think a big part of that this week was a bunch of the time in nature and the observation and acknowledgement of that. But I think that’s—if you get, if you’re feeling that, if you’re a guy who’s like this—the sense of being lost, being detached, not in a good place, not knowing what to do—spend some time intentionally in a forest, in the mountains, with yourself.
Observe beauty. Feel the beauty within your heart, within your body. Man, I’m a bit of a hippie, but I would invite you into that in a big way. And if you need a forest, or you need a place, give me a buzz. We’ll work something out.
But I think that’s something I would encourage guys to do, for sure.
Gregory 18:59
That resonates so much with me, because the way you’ve just described that, I see it in exactly the same way, but using completely different words. What are those words? That the beauty in us is the imperfection, but the truth is that it is perfect. So we are perfect in our imperfections. When we accept our weaknesses, we can love them, we can love ourselves, and we see that in nature all the time. You know, broken twigs—they’re imperfect, but they work. They then have a use for us. The time in nature is seeing creation in all its perfection and imperfection at the same time, and that’s how we are as well.
Derek 19:56
And I think that’s a really good point—being able to accept those emotions that you’re feeling right now that give you that sense of being trapped and engaged. Maybe that’s anger, maybe it’s shame, maybe some guilt, maybe it’s some rage, and being able to look at those and give compassion to yourself for what you’re feeling in those moments and lean into compassion. It’s all valid. Accept what that is. And then once you can give them compassion and what that looks like, then you can take responsibility for where you’re at. And that responsibility, I think, can give you the permission to say, “Okay, I want to be found now.” But I think instead of being hard on yourself or being—you know, at least I have been when I’m feeling those things…
Tim Matthews 20:48
“Why am I feeling this way? What’s wrong with me? I’m stupid. I should know the answer.”
Derek 20:55
Yeah, you know, give compassion to yourself for those feelings.
Tim Matthews 20:59
So easy in those moments as well for people to then want to drink more alcohol, or just lots of forms of sedation, because they—and it could be work, could be food, could be alcohol, could be porn, could be social media, could be whatever. There’s lots of different ways people sedate. But if you resist the urge to do that—I mean, going back to your point with nature—there’s a lot of science now proving the beneficial nature of nature.
Yep. Whether it’s through grounding, whether it’s through the… there’s—I won’t go into all—but there’s a lot of science. New podcast on that one. There’s a lot of science, right? And there’s a reason why, in movies or documentaries—it’s commonplace in certain ones—you’ll see people stressed out in the city. They’ll leave the city to go on vacation, to maybe a retreat that’s in nature, that’s steeped in nature, right?
And I love it—when you and I were living remotely, we went to this beach on one of the Greek islands, and there was no Wi-Fi, which was perfect. But the sign said, “There’s no Wi-Fi here, but you’ll find a better connection than anywhere else.”
Nice. I just loved it, all right, because you’re forced to just be with each other. And point being is, when you’re able to feel connected—both to something bigger, to yourself, to each other—in my experience, that often accompanies a great deal of gratitude. And when I feel good, and I feel grateful, and I feel connected, and I feel present—ultimately, as well—it’s very difficult to also feel lost at the same time.
You know? Because feelings of being lost will typically come with being disconnected and feeling alone. So I think we can overcomplicate the idea of feeling and being lost, right? And thinking there needs to be some huge shift that has to happen in life.
In actual fact, it could be a temporary thing where, if you just accept that you’re lost and you surrender to being found, and you choose to go and find some connection, that moment of being lost can actually result in you being found. And you’re going to go through phases in life.
We are going to go through phases in life of being lost and found. I want to go through phases in my life where I am lost and found—because it means I’m growing. It means I’m changing. It means I’m moving. Right?
Derek 24:04
I think that’s a beautiful point, because especially as—oftentimes—the men we are, in those moments, achieving, driving: “We’re going to make this happen, going to do this, take the bull by the horns,” whatever analogies you want to put to it—that sense of “I will grow myself,” instead of allowing myself to be nurtured and grow and receiving that, and that sense of being found.
You… Where are you? You know where you are. You are where you are. Another force needs—I feel—another force needs to find you. And surrendering to that and being open to that, I think, is key.
Gregory 24:50
We have another term for it in TPM, don’t we? It’s lone wolfing it sometimes. And yeah.
And as I was journaling this week, I realized that that’s the antidote to one of my triggers—is actually just calling, calling a friend, calling a friend in the movement, and just reconnecting with him on his life, on my life, and filling each other’s cups—just through that little connection. And it’s so simple and so easy to do, because we have this community.
Derek 25:21
Yeah, that’s true. Very true.
Tim Matthews 25:25
Beautiful. So guys, as we always say, at the moment of insight, take massive action. We’ll see you next time on The Powerful Man Show.
