MGU 470 | Embracing Uncertainty


In a universe dominated by chaos, our purpose emerges through the ripples of our actions, as we create meaning in the midst of uncertainty. Join us as we explore the depths of life’s challenges, the thrill of adventure, and the art of embracing uncertainty with our extraordinary guest, Scott Davis. Scott uncovers the essence of balance as an active verb, going beyond mere equilibrium. As an adventurous soul, Scott transitioned from a traditional life to one on the open waters. Life on a boat taught him the art of self-reliance, where leaving everything behind became a daring call to authenticity. Scott shares how he escaped the orbit of routine and comfort, walking the emotional plank toward significant change. He talks about the importance of doing things for your soul, even if it’s “selfish”. Scott enlightens us on how strategic planning isn’t about rigid plans, but about identifying the core elements that truly matter in our lives. He also emphasizes how balance isn’t static but an active verb, and how getting comfortable with tension can lead to personal growth. As he reflects on life’s purpose, Scott reminds us that in a universe dominated by chaos, we have the power to create meaning by influencing others and leaving a legacy of change. Embark on a journey of island hopping, not just through exotic landscapes, but across the vast ocean of human experiences. Break free from echo chambers and tribal mindsets, and learn from those different than us. Tune in now! 


Listen to the podcast here


Surfing The Balance: Embracing Uncertainty In Life’s Changes With Scott Davis 

I’ve been having a wonderful chat with our guest, Scott. He mentioned one thing that I really wanted to ask him at the moment and thought, “No. I’m going to wait until we start.” We were connecting over various loves and experiences of nature. Scott, you mentioned that you’ve done a lot of island hopping, and I would love to know which islands and why were you doing the island hopping.

Every island in the Southeastern Caribbean and many of them in The Bahamas, so think about if you draw a line from Florida to Venezuela. I’ve been to every island there, many of them multiple times. I lived there for six years, most of it on a sailboat, just sailing around, embedding myself in those communities and spending a lot of time in nature, alone and with my wife. Why was I there? It’s because at about age 40, I had a successful career. I’d been really lucky that I was plucked from the masses by some powerful people early in my twenties.

By the time I was even 30, I had worked with some incredible legendary figures like Robert Crandall, Gordon Bethune, and David Bonderman. I could see where that was going. It was just going for more. It was never going to be enough and something different. I did a crazy thing. I sold everything I owned and gave away everything that I couldn’t sell, turned in the keys to my companies, bought a ratty old sailboat, and took off to live on the islands.

What did that feel like to go from more to less?

That was the first few weeks or months of that were difficult because what you want to do is you want to set aside some things from your old life and you want to bring them with you. It’s just natural. I want to have this new experience, but I also want to smuggle all the old stuff in with me. The problem is that you can’t really bring a convenient life in the retail republic of the United States with you to Barbuda. That’s not going to work. There are almost no stores there for starters. If you go in to go grocery shopping, you don’t even need a grocery list because they might not have any milk or the milk you want, period. There was just a lot of unlearning, a lot of stripping away of all of these false ideas that accumulate over time when you live in this artificial reality of Western civ.

That is so fascinating to me. I’m very drawn to it. I still feel like there’s such a long way to go because perhaps I haven’t chosen to strip away those false ideas yet. It’s appealing, but it feels a little bit scary to me. I mentioned to you, Scott, that I became interested in mountaineering. One of the things that’s always involved, and I’m still a beginner, is backpacking because it takes multiple days to climb some of the top mountains in the world. I’ve been slowly learning about lightweight. It’s the concept that when you go backpacking, you don’t want to have a lot of things with you. You really want to have the essentials. Even that concept feels a little bit uncomfortable and scary, and yet, as scary as that is, it’s also intriguing. Is that how you were feeling?

Yes. I tell people that life on a boat, on the ocean, in third-world countries is self-reliant, it’s adventurous, it’s exciting, and it is a little bit scary sometimes because Mother Nature is incredibly fierce. Until you’re very far away from the safety and security of life as you know it, you don’t appreciate just how fierce Mother Nature can be. That being said, the remarkable thing for me was that when I came back after those six years, I saw fear everywhere in the United States. Everyone is absolutely soaking in fear, like fear of not having the right clothes, not being on the right team, having read the right book, not having a vacation in the right spot, not being beautiful enough, or being alone.

When I came back, I saw fear everywhere in the United States. Share on X

It is a million other things that Madison Avenue tries to convince us that we should be afraid of so that we will buy the product from them to cure the fear that they gave us in the first place. It’s such a racket. You don’t even see it because we’re like fish immersed in the water in it. When you go away and you’re outside of that for six years and come back, you’re like, “Everybody here is so afraid all the time.”

That’s resonating with me. I’ve been thinking about it, but as you’re speaking on it, I realize I’m still very much immersed in that. It’s a sense that I have but maybe not the knowing yet because I haven’t stepped out. I’ve never stepped out of this world or the society that I’ve been living in for an extended period of time. I’ve traveled internationally, but it’s brief, maybe a few months when I was in college studying abroad, but the country and feeling so ignorant about what’s going on elsewhere, what the experiences are, and even the privileges. Did privilege come up for you in addition to fear? Especially given what you were describing, you had the luck or privilege of a lot of great opportunities when you were in your 20s and 30s and then made a decision to do things differently. What was that revealing to you?

It is true that I had a very privileged life, no question. It is the opportunities that I was afforded in these crazy special moments of meeting these incredibly powerful people when they were in a good mood and they decided they liked me. It’s just that. At the same time, I’ll tell you that there are thousands of people that we met in the Caribbean who were down there living on $1,500 a year on a boat. They had a small boat, not a big boat. They had a simple boat, not a complicated boat. They weren’t going out to five-star resort dinners all the time, but they were living on the islands. They were doing the thing they wanted to do. These people could be truck drivers. It could be anybody. It’s not just silverspoon people who are down there doing that, although the ultra-rich are also down there doing it.

There’s this sense of privilege that we talk about socially now, and that was certainly there, but it’s not necessary. People can do this, and you’d just be surprised. The problem is not a lack of privilege. The problem is that another falsehood that we’ve adopted is that good intentions matter. It’s the thought that counts. People will say, “You are in the Caribbean living on a sailboat? I’ve always wanted to do that, and maybe someday I will.” Our response to them was always, “That’s great. You can certainly do it. All you have to be willing to do is literally leave everything behind. If you’re not willing to do that, no amount of planning is ever going to get you there.”

Another falsehood we have adopted is that good intentions matter. Share on X

We used to talk about escape velocity. Imagine this rocket and it’s got to get out of Earth’s orbit. The amount of energy that’s required is unbelievable just to get it out of that orbit so it doesn’t fall back to Earth again. Socially, it’s the same thing. If you want to move very far from whatever this sphere is in which you’re in a rut, it’s going to take an unbelievable amount of energy for you to escape that. The intentions are not going to be enough but very big actions like seemingly risky actions.

At one point, I sold everything that I owned in the world to fit into nine of those Home Depot crates, the black ones with the yellow lids. My whole life, nine crates. If you can’t get to that point, then you probably can’t have the experience that I had. That has nothing to do with having a bunch of money. That has to do with just saying, “I really want to move from the place where I’m trying to launch my rocket to whatever this planet is that I want to get to.”

What is the gap between wanting and dreaming of something and actually doing it? That makes a lot of sense in theory, but the way you describe the rocket, there are still a lot of forces that people are up against. That could be their upbringing or their circumstances. There are so many factors there. How did you get from a thought to the action?

One of the sticky tentacles of my life before was that I had a very strong nuclear family and strong friendships. All of those relationships felt that I was turning my back on them. It’s natural. It’s an extension of love. They were so accustomed to me being there. They wanted me to be there. They wanted me to be safe, particularly my mom, “You’re going to go where pirates are, are you kidding me?” It was them saying, “I like you and I want you to be around.” The practical difficulty is to be able to say, “Guys, I love you too, but my soul needs this thing. I’m going to have to step away from you for a time because I need this.”

My soul needs this thing, but I'm going to have to step away. Share on X

I had my lifelong mentor at one point accused me of being selfish when I was talking about this. He said, “You sound like you’re really being selfish here.” I said, “If I don’t do this to take care of this part of my soul, there’s not going to be anything left for me to provide to anybody else.” On some level, even selfishness, there’s got to be a little bit of it. If all we are is making ourselves a draft horse for everyone around us, we will cease to be who we are. It’s a lot of stuff like that. When I talk about escape velocity, it’s not about how you shut down all your bank accounts. Honestly, that’s dribble. What’s hard is being able to walk away from your mom and from your friends.

How did your relationship with your mother and friends change during that time and afterward?

At first, they don’t understand why and what you’re going to do because nobody’s ever experienced this. One of my dearest friends asked me, “How many sunsets can you see?” You can imagine there’s disdain embedded in that question. This judgment, “You’re being stupid, Scott.” My only response to that was, “You remember the Tootsie Pop commercial? How many licks does it take to get to the bottom? The world may never know how many sunsets because I have seen thousands of them. I’ll still be happy to see a thousand more of them.”

I know that’s a strong word, but I had a lot of friends and family who sensed that I was abandoning them. A natural response to that is to pre-abandon someone so that they can make me walk the emotional plank if I’m going to abandon them. There’s a little bit of that going on, I’m sure too. Overall, it was not knowing, like, “What are you going to do? How are you going to live? Are you going to be okay? Are you ever going to come back?” Those are questions to which I didn’t have any answers at the time.

How did you know when the journey was over? Six years I imagine you went into it with a bit of openness and lack of clarity, but that’s an assumption. Did you know it would take six years? How did you navigate that?

It started off with, “I’m going to go take a month’s sabbatical.” My partner of twenty-something years, my work partner, said, “You should take a sabbatical.” I did. When I was coming back, he said, “I don’t think you should come back yet. You should keep going.” That one month became a year and became 5 and 6 years. How did I know it was time? There was a longing. What I was longing for was change, for quiet, for stripping away things that I realized weren’t right. I was longing for time to read, write, and draw. I was longing to use my hands because I’d worked in the abstract world of logic for a long time. I needed to rebuild my sailboat, I needed to do things with my hands and become a different person than I was before.

What I was longing for changed. Share on X

Eventually, what I was longing for was conversations like this. I was longing to talk to somebody who had a bit of the same shared cultural background that I had and wanted to think about society and the health of other people. I missed my friends and family very deeply. My kids were now out of college, and it was time to be around for them to have their adult lives. It was natural. It didn’t feel like a big come-to-Jesus moment. It just felt like I noticed that these are the things I’m thinking about. All of those things happened to be people who lived back in the States. It’s probably time for me to sell the boat and move back.

As you were sharing that, I was thinking about the movie Interstellar. Have you seen that?

Yes, that’s a great show.

I watched it for the second time. It came out in 2014 or something. I just re-watched it for only the second time. Part of the story is this father who is very called to do something different than his life. I don’t want to have any spoilers, so I’ll tell the story lightly for anyone who doesn’t know it. It takes place sometime in the future when the climate is not in great shape. He’s working on this farm. I think he had worked for NASA or something. He might have flown planes. He was doing something in his daily life to survive with his family, but he was called to do something else.

He gets this opportunity and is also very tied to humanity and saving the Earth. He has to make this decision to leave behind his loved ones. That’s a huge part of the story how much he wants to do something bigger than himself and something big for himself, but it requires leaving people behind and not knowing who they will be when he returns if he returns too. That’s a big question.

It’s a very difficult situation that we can get into. All change in our lives doesn’t necessarily involve leaving people behind. There are habits, routines, and priorities that we can have that we need to set aside and we need to get away from. That can be hard to do. Many of those don’t, in fact, require literally selling everything you own and moving to a third-world country. I don’t mean to make this hyperbole for everyone.

All change in our lives doesn't necessarily involve leaving people behind. Share on X

There are any number of eating issues, exercise issues, and social issues that we need to either embrace or unembraced from time to time throughout our lives. The point of that is simply to say that every time you want to make a significant change in your life, there are going to be a lot of otherwise well-meaning people who are going to say, “No. I’m so comfortable with who you are.” It requires a lot of wisdom at that moment to separate, “Should I be listening to these people as voices of reason in my life? Should I appreciate the love and the gesture and then walk away anyway?” Change is very uncomfortable for other people, but sometimes change is necessary for us.

In your experience, observing yourself and other people, why do you think change is so hard?

First of all, change is the universe. It is this cosmic soup within which we exist. From time to time, we’re able to carve off a little microcosm. My wife is French and took her around to lots of different places in the US to show her things about the US. We went to Niagara Falls. The thing that I remember most about Niagara Falls is it’s enormously powerful. It’s unbelievable chaos. As we were walking on the river above the falls before the water got to the falls, I noticed these little spiral back eddies where the water near the shore would bend backward very slowly, and it was collecting little leaves and making little pinwheels of the leaves. They’re just suspended. They’re not going over the falls right now.

At any moment, a duck could step in the water, the change in the water level and the wind, and those calm little leaves would be sucked over the falls and blown into a million pieces. At that moment, there’s this peace and this order. It’s important for us to look at it and say, “Your life right now, that sense of order, harmony, and peace that you have, it’s that little spiral back eddy above Niagara Falls.” The falls are around the corner.

If you can get to grips with that, it will make you a lot less sticky with the way things are. It will just let you appreciate, “This is a moment. This is not forever.” Whatever that thing you can’t imagine yourself setting aside, it’s not forever. It’s going to fall apart. Entropy is the way the universe works. You need to suck all the marrow out of it right now. When it’s time for that to go away, you find another thing.

It sounds so obvious, but I notice myself even with the fear. I’m aware of fear, but it feels so embedded in me. My whole life I’ve been very drawn to spirituality and wellness. I wondered if that was my own version of control, gripping, and trying to prevent things. Always trying to anticipate is a tendency for me. I’m a planner. I like to know things in advance. If I’m going to go over the edge of a waterfall, I would like to be prepared and I want to have the best outfit on to have less harm on my body or be in the best boat. It’s this desire that I can always be okay on the other side, but we don’t fully have control over whether or not we’re okay, yet the more we release ourselves into those situations, that’s how we end up being okay.

That’s true. Unless you embrace the idea of chaos and entropy being the norm, you aren’t really appreciating the specialness of what it is that you have in this particular moment. One of the great life lessons about sailing is that you can’t simply drive the boat wherever you want to go. The wind and the waves dictate where you can take the boat. You may not like that, but your liking it is irrelevant. You can be a bad sailor and it’s not going to work out very well. You can be a good sailor and it’s going to work out pretty well, but under no circumstances are you going to be a sailor that can control Mother Nature. That is not on the table.

Your liking something is irrelevant. Share on X

There are these two things that we have to be able to grasp and understand. It’s one of my favorite quotes from F. Scott Fitzgerald. “The mark of first-rate intelligence is the ability to grasp two contradictory ideas at the same time and retain the ability to function.” On the one hand, Mother Nature, you cannot beat her. On the other hand, you still shouldn’t be a schmuck.

You still need to develop some skills and make good choices, and you do the best you can and then realize that she may just backhand you, or she may give you this amazing rainbow on this unbelievable champagne sailing day. It’s both and. It’s not either/or. You cannot tame nature, but you’re definitely responsible for making good choices. You’re right that there is a bit of planning, but I don’t think that any amount of planning is ever going to fully insulate you from the reality of the universe, which is entropy.

I wonder if that concept is what draws me to things like mountains. I’m not very drawn to the ocean. That’s part of my curiosity about you. I’m drawn to the ocean in the sense of milder experiences, but boats, for some reason, I feel a lot of discomfort around, yet mountains I don’t feel a lot of resistance to it. As I’ve been studying mountaineering, preparing my body and my mind, and learning all the elements of it, one thing that comes up a lot is you can be incredibly prepared and go to a place like Mount Everest.

Even with all the preparation and all the money that you might put into something, if the mountain is going to do something, that’s just the way it is. Your preparation’s not going to prevent you from being injured or maybe not surviving it. You hear these stories of incredibly skilled people losing their lives because that’s nature as you’re describing. I don’t feel turned off by that. I do feel turned off by the ocean. There’s something more unsettling. How do you feel?

I live in the mountains. I live at 8,000 feet. What I tell people is that when I’m here, I feel like nature is giving me a hug. There are trees around me, which from an evolutionary biology perspective, are all kinds of signals of security, home, and safety. The mountains, I can see them. I can see very far. I’m not going to drown walking on land. When I go to the edge of the ocean, even though I’m a very skilled sailor, I would tell you that I feel something very different. What I feel is respect. That place right there is not my native element. Things can go very south very fast. I need to be very careful, prepared, and respectful, and I need to accept the fact that even if I am all of those things, I may still die. It’s a very different experience, even for me on the ocean than it is in the mountain.

One of those things that you talk about that’s difficult for us to embrace is uncertainty. We are, especially in the West, just programmed that we’re supposed to be lead pipe certain about everything. We’re supposed to be certain about what we think about politics and religion. We’re supposed to be certain that this is the love of my life, my soulmate and this is forever. There are 100 different ways that we’re supposed to be certain about things.

In my experience being in the islands, one of the things that got stripped away was this notion of certainty and to begin to accept the fact that uncertainty is actually life. We have to find a way to exist in that uncertainty and in that ambiguity in a way that is mentally healthy. We think about how predictable things are, and people talk about the ability to forecast the future and build a plan.

MGU 470 | Embracing Uncertainty

Embracing Uncertainty: Begin to accept the fact that uncertainty is actually life. We have to find a way to exist in that uncertainty and ambiguity in a way that is mentally healthy.


Let’s think back to the last couple of years and think about the things that did not exist years ago. Let’s start with Google. The whole thing did not exist years ago, an iPhone, Arab Spring, Bitcoin, Twitter, not Elon’s Twitter, the original Twitter. None of these things existed even. If you keep going at that, you can realize that something huge and totally surprising is happening every single year, probably every month. You can’t forecast which one of those is going to happen, but you can say with some certainty that it’s unforecastable. Some crazy surprise is going to happen in the next couple of months or the next couple of weeks. You’re going to say, “That was so rare.” It’s not really that rare. It happens all the time.

Uncertainty is actually life. Share on X

I agree. I have felt that very profoundly, more and more. The pandemic showed us that in a lot of ways, but I have been particularly noticing it during this trend of artificial intelligence. In my industry, from the social media standpoint, content creation, and this digital realm of entrepreneurship that I’ve been in for years, 2023 feels very different in the sense that there’s a shift in how we’re doing things. There’s some fear. There’s almost like this tension I’m noticing from other people to get their footing. I don’t know if they’re trying to hold on or they’re trying to anticipate, and I’m in this place of thinking, “I don’t think we can really anticipate a lot.”

MGU 470 | Embracing Uncertainty

Surf the Seesaw: Unconventional Essays on Balance, Beauty, and Meaning in Life

I saw that the AI trends start at the beginning of 2023, and then as months go by, it’s just boom. A lot of people are trying to figure out what that means for them. Is it sustainable? Is this just a trend that’s going to go away? There are all these questions, and I’m sitting here thinking, “Is it even worth trying to figure out the answers?” If it’s constantly changing, the answer you might have now about something might not work weeks from now.

How do you operate in that world? It’s a metaphor a lot for what you’re describing and also ties into the theme of your book, which is about being on the seesaw and finding balance. When something is so volatile, how do we move from that place of wanting certainty and security so badly to a place of embracing, “I have no idea what’s around the corner, so I want to find balance.” It’s like that F. Scott Fitzgerald quote that you mentioned. Can you look for certainty while also acknowledging that there’s no such thing?

My mentor, who was a great guy, changed my view about what strategic planning could be. One of the ways that he did that was that he said, “Strategic planning is not about the plan. Strategic planning is about identifying the things that matter, the things that could make you wrong, the things that could hurt you, and the things that could help you. Strategic planning is about understanding what forces are at play or might be at play between now and when you get to whatever you’ve defined as the finish line so that you can be monitoring those things.” Instead of saying, “I can identify all the forces,” which is relatively easy for us to do, to identify the relative forces, what’s hard for us to do then is to say, “I know exactly how each of those forces is going to play out.”

MGU 470 | Embracing Uncertainty

Embracing Uncertainty: Strategic planning is about identifying the things that matter, the things that could make you wrong, the things that could hurt you, and the things that could help you.


That ability to foretell is very limited for human beings. A lot of times, we get caught in a planning process where we say, “I’m going to make this amount of money for this many years, and then I’m going to get this promotion, get married, and save this amount of money. I’m going to have these kids and send them to this school.” In my experience, maybe 2% of that plan is going to happen that way. What will happen is there will be a need to save money. There will be a point at which you change jobs. If you’re fortunate, there will be some kids. It’s not going to happen exactly the way that you think.

If you develop a plan that’s all about these exact things happening in this exact sequence at this exact time, you’re going to be disappointed. If in the planning process, you identify that there are some things that are important and we need to keep an eye on those things. As the conditions evolve, then you can say, “I’m accepting uncertainty with respect to some things, but I know that some other things are going to be important, so I’m going to spend my attention on those things as well.”

I had a lot of success as an entrepreneur, but what I try to tell people when they ask about how we built our plan for our business is I’d say, “You’re really asking the wrong question because the plan that we put together was 90% wrong.” I still have the PowerPoint deck and it’s a great exercise to go back every once in a while when I’m feeling a little bit too much pride. You go back and read that PowerPoint deck and you’re like, “See, you are really stupid.”

As you’re speaking on this, it so much makes sense to me and resonates with me. I find that my personal seesaw balance is being in this mentality that you’re describing in this conversation of just balance, embracing, and not planning, but also knowing that it’s not all going to be right and all of this. That’s one side of the seesaw. The other side is what I feel like I encounter with at least what I perceive to be the majority of people, I could be wrong. It’s a common experience for me to experience people who want certainty so badly. They’re almost rejecting the other side of my seesaw. It’s my work to say, “Maybe I think a bit unconventionally, at least in the United States now.”

I want to stay in that because it resonates with me, yet, based on where I live and on the work that I do, I still need to participate in a space that wants me to operate in their realm of, “No, let’s make a plan. Ten percent success rates are not acceptable. We need to go for a 90% success rate.” It’s a little hard to even describe, but I know you understand what I’m trying to say, Scott. It’s like balancing between two ways of thinking while embracing what feels authentic and true to me, yet operating in a bubble of a different way of thinking. I could choose to leave the bubble like you did, but I don’t even know if that would be permanent. I’d be entering another bubble and another way of thinking.

There’s this great book by Jonathan Haidt, and it’s called The Righteous Mind.

MGU 470 | Embracing Uncertainty

The Righteous Mind: Why Good People Are Divided by Politics and Religion

I’ve read that. It’s so funny you brought that up. I was reading a quote from that book.

It’s a wonderful book, and it’s right on topic for what you’re talking about. The reality is that when we try to explain why we want to do something, we are often just making stuff up. We don’t know why it is that we want to do things a lot of the time. It’s our intuitive self that instinctively wants this thing. If I ask you, “Why mountain climbing?” you’ll give me a very well-reasoned answer for why mountain climbing. Here’s the thing, It probably doesn’t bear any truth to why mountain climbing because there was something inexplicable and something intuitive and non-rational that drew you to mountain climbing. The explanation is your sacrifice to the social gods who expect you to be able to explain yourself. I honestly am less concerned about the explain yourself side of things.

On the other side of things, I don’t want to be in the position of giving someone an excuse for not balancing their checkbook and for not watching what they’re spending on their credit cards. There are practical considerations and those things you can’t look away from. I made sure that my kids finished college and took care of their expenses. I attended to all of my commitments, but there’s also more to life than just those things. It is this balancing, this mini forces. In the book, surfing the seesaw is standing on top of the seesaw with one leg on each side of the fulcrum and keeping both seats off of the ground. It’s using a seesaw in a way that wasn’t intended, but I find it a lot more fun than the way that it was intended.

We're often just making things up. Share on X

It’s one of those examples that we have from our childhood about balance as an active verb. For instance, we would say, “Balance this broomstick in your hand.” You just hold it and you’re moving it around and it’s active, or walk the balance beam or balance a bicycle without training wheels. All of these ideas are dynamic. They’re pulsing. They’re not static, but as adults, we’ve smuggled in this notion of balance as a static equilibrium. We need to find a position on some spectrum, and we need to defend that position forever in all circumstances. For all points in time and all people, there’s a position. That static equilibrium a kid knows right away. That’s just depth. A biologist also would tell you that stasis is death. Life is evolving, its flow, it’s pulsing, it’s changes in the environment to which we adapt.

MGU 470 | Embracing Uncertainty

Embracing Uncertainty: Stasis is death. Life is evolving, it’s flow, it’s pulsing.


What I would say is balance, like I’m talking about, is like a dynamo. It’s oscillating between my intuitive and my rational. It’s oscillating between my artistic and my analytical. It’s oscillating between my selfish and my selfless. It’s pulsing and ebbing and flowing. As it’s doing so it’s just like a dynamo. The positive and negative on that dynamo are generating energy and generating life for me. It’s healthy that you feel this tension. It is because I feel that tension and I’ve gotten comfortable with it that my life in the next few months or next few years is going to be different than my life now. There’s something wonderful and exciting about that.

There really is. That example of explaining yourself resonates with me because I am a very deep-thinking, intuitive person, and often felt misunderstood. That’s because it’s very hard to express some of these things. I might try as a podcaster speaking about these big topics, trying to figure out how to say them, and knowing that each person I’m sharing that with, is interpreting it in different ways. It is a great reference to The Righteous Mind. It makes me want to reread it. I was blown away by that book and how challenging communication is, yet we live in a world where it’s expected for communication to be a skillset that’s easy. It’s like, “Are you a good communicator?”

I started looking for some different freelance work and went through it for the first time in many years, like a job search. I was curious like, “What is it like to apply for jobs?” I felt so disheartened by it, yet it was very revealing that I don’t fit into these worlds that want to put me in a container. Whether it was through an application or an interview, I noticed people wanted me to have this perfect response that was easy to explain and that fit into the way they were thinking. It was this fit in.

That leads me to the question, “What if you don’t fit in? How do you still survive in a world that’s very capitalistic?” In the United States, at least in many similar countries, it’s about making money because you need the money to pay for your rent and to pay for your food. We live in a society where we have to generate money, but how do you do that if the way of making money is completely at odds with your soul?

I don’t know how to square that circle. There are infinite shades of gray between those two poles that you described. There are ways to feed yourself that do not require bastardizing your principles. They may require an adjustment to your standard of living. The question becomes, “Are you a prostitute or are you willing to make changes to your standard of living to accommodate the level of income that you can generate from doing something that doesn’t destroy your soul?”

When I was living in the Caribbean, I lived on $2,000 a month because that’s what was necessary because I had walked away from all of my commercial interests. You don’t get to complain about that. That’s just the nature of the choice. When I came back, it was really important to me to do some things that had more of a social bent. That’s what I’ve been doing with writing the book and with pure sailboats, a company that I started to manufacture boat kits for people that want to build their own boat at home so that they don’t have to buy their own boat, they can build your own boat. I’m also working on a housing venture that’s got social overtones to it too.

These things do not, they will never pay the way that the strategy work and the technology work paid but I’m comfortable with that. There is enough now there is this concept of enough in my life because I went away and stripped away all of the more. You can just simply say, “This life is really good. There’s a lot to be grateful about this life.”

I went to make a withdrawal, to get a cashier’s check for my taxes because I have to make quarterly tax payments. The teller in a sorority semi-prepared way said, “I’m so sorry. It sucks to have to pay taxes.” I was like, “No. You don’t understand.” It’s such a huge honor to be in this place. The roads are great. I don’t worry about fire suppression, about somebody breaking into my house. I can shop anywhere I want to shop. My phone simply works.

There are a hundred reasons for me to be so grateful to live in this country at this moment. This is a trivial price for me to pay but that person had completely lost perspective because they haven’t seen anything else. They haven’t had to live in a place where the citizens don’t trust the courts. You can’t even wrap your head around that idea. Somebody breaks into your house, steals everything that you own, kills somebody that you love and nothing’s going to get done about it. Wrap your head around that for a minute before you complain about anything about living in this country.

When I’m here, I feel an incredible honor and privilege. Not because I make millions of dollars a year, I don’t. I have a modest life and I’m so grateful for that and I get to choose to do the things that I want to do. It would be totally inappropriate for me to complain that “I can’t make a million dollars a year by doing these social entrepreneurship things.”

Does that tie into the theme of the echo chamber? That’s what it sounds like to me. I’d mentioned to you before that the term echo chamber resonated because maybe what that bank teller was expecting was for you to echo back her sentiment. She wasn’t expecting you to say, “I have a different perspective on this.” I often wonder, when somebody makes a statement like that, are they just echoing it back without really giving thought or is it just a matter of ignorance or a different perspective?

A lot of the stuff that we repeat is more of a tribal mantra. It’s more of a secret handshake. I’m just doing this thing so that I show you that I’m a part of this tribe and not really thinking very hard about it. Everything in the states in particular has become symbolic. We don’t respond to things for what they are. We respond to things for what they represent. Somehow everything takes on this just huge mythic proportions.

I promise you we will hear no less than 10,000 times over the course of the next years how this is the most important election in the history of the country. No, it’s not. It’s exactly as important as every single other election that has ever happened or will ever happen. It’s an election. You process the candidates and the issues. You try to think about yourself and your family and other people, and you try to make the best choice. It is in no way different. Anybody who tries to tell you otherwise is trying to get you to turn off some part of your brain that can process things for what they are.

This idea of echo chambers, to me, it’s incredibly toxic because when I was writing the book, what I wanted to do was to try to get people to see that in cultures that are very different from ours, with people who live very different lives than ours, we can still see incredible truth. We can still learn incredible things. If that’s true, then we ought to be able to learn from the next-door neighbor whose politics is different than mine. We ought to be able to learn from the person sitting next to us in the movie theater who has a different lifestyle choice than we have.

I quoted Stalin, “One death is a tragedy, but a million deaths is a statistic.” I didn’t say it was Joseph Stalin and the person I was talking to was an Evangelical Christian. They’re like, “That’s a great quote.” I said, “Yeah, Joseph Stalin.” The face just fell. It’s like, “That can’t be true.” Evil people can say true things. They can see the truth. What makes them evil is not that they don’t see the truth, it’s how they respond to the truth. This idea that I can’t learn from somebody else who sees things differently than me or that I somehow have switched teams, if I say, “There is some truth to that other statement.” I just think we’ve lost it.

Evil people can say true things. What makes them evil is how they respond to the truth. Share on X

In the book, there are two chapters on diversity in the book and I honestly put them in there out of just sheer rebellion because those are hot-button topics right now and there’s a segment of people that don’t want to read about anything about diversity. To me, diversity is the human species’ superpower. No other animal on earth has a diversity of preferences, interests, tastes, styles, behaviors, hobbies, and everything else that the human animal has. Think about dolphins. There’s just not that much difference between the dolphins, or all the humpback quails, or tortoises. Human beings, good luck finding two of them that are alike.

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This is what makes us so special, and it is the source of our adaptability. It is the source of our genius in the face of unforeseen circumstances. To get people to realize that diversity is not a penalty that we pay, it’s not some social tax. Diversity, it’s an incredible mind full of treasure. In order to be able to take advantage of that, we have to approach it as such and we have to approach it not as, “That’s different. Don’t want any of that different stuff. That stuff is really scary. If I embrace something different, I might lose control or I might be judged by my tribe.”

If we can set all that stuff aside and just process this and realize that diversity is our species’ superpower. It is the source of so many different ways to fish, farm, raise a kid, take care of your neighbor, make a road, whatever the problem is that you are looking at. There are 100 good ways to solve that problem that you cannot imagine. You need some people in your life who’ve been through different things, who’ve read different things, who’ve experienced different things so that you can just get a hint of some of these other ways of skin in that cat.

I’m so glad that you touched upon that because diversity is a big focus of mine personally and professionally, and looking at my own biases, experiences, and fears. One thing I’m curious about for you is when it comes to diverse people and experience is if you found yourself being fearful or noticed other people reflecting fear, that comes up a lot for me as I travel. I don’t know if it’s because I am female, maybe you don’t have the same experience as a man, but there’s all this fear about other people.

Where are you going to be? What part of the country? What are those people going to be like? Are you in danger because you are a woman traveling by herself and entering into these places with “different types of people,” and there’s an assumption that you are unsafe around people who are different than you? That’s not just the case in my travels, that’s the case in so much of our mentality. Yet it doesn’t make any sense to me because I don’t usually feel unsafe, but I notice other people projecting their fears onto me.

I’ll just give you two examples from my experience. In all of my travels, I’ve only ever been attacked one time. I was attacked by a man with a machete on a beach. The beach was in Hawaii and the man was white. When I was telling you that story, you did not go to Hawaii and you did not go to white guys because they’re just the way our brain works. Our brain works as other is where the danger comes from. I would just tell you, I lived amongst a lot of people that were very different than us, and none of them ever raised a hand against me. That’s certainly my unique experience.

I have a dear friend whose husband was killed by pirates in St. Lucia and they were anchored 200 meters behind me. Why did those guys ride their boat past my boat to get to my friend’s boat? I’ll never know. That’s one of those uncertainties, the unpredictability of life things. I do know that from her perspective, sailing to some of these places is very dangerous because it costs her husband. I don’t mean to say there’s no danger out there. What I do mean to say is that the danger out there is not from people who are other, it’s actually from people who are exactly like us. They are motivated by hunger, greed, envy, by all of the same bad things that motivate us to become the worst versions of ourselves. There’s nothing about that that makes them other, it makes them us.

Danger is not from others, it's from people who are exactly like us. Share on X

I would say that a lot of the danger that happens with people who travel abroad is that they’re not situationally aware and that they’re tone-deaf. That $1,000 watch that you wear, that’s just your beater watch because you wouldn’t be so pretentious as to wear your Rolex when you travel abroad. That $1,000 watch is worth a six-month salary in most of those countries. You’re not situationally aware, you’re just putting something in front of somebody that is going to speak to not their angels, but their devils. We all have them. It doesn’t mean that they’re other. In my experience, if what you’re doing is you’re being aware of the people that are around you and you’re trying to live in harmony with them, there aren’t these differences that elicit these bad behaviors that everybody wants to make you fear.

That’s such a beneficial perspective, whether you’re traveling or just walking down the street and seeing people who are different. That’s a privilege to be around different people. More and more I seek out spaces in which people around me are unique. Yet to your point, there’s so much commonality around us and it’s that surfing the seesaw moment where one end of the spectrum where we might be different based on our circumstances or backgrounds, and what we look like. On the other end, we’re all human and we have very similar brains, experiences, needs, and desires.

It’s acknowledging the differences and similarities at the same time. That requires a lot of awareness. To your point, situational awareness is not just being mindful about who you are and what you’re bringing into these situations that might be different, but acknowledging each other, and I feel a lot of yearning for that acknowledgment. Not just within myself, towards others, but hoping that they embrace that about me too because then we have that synergy. I’ve been in places where I felt rejected for one reason or another, or maybe people assume something about me because of how I look or present or whatever. Maybe they felt unsafe because of what I represented to them.

It’s not just you. That doesn’t have anything to do with you. Human beings all have the same core aching needs. We want to be seen, we want to be known, and we want to be valued as what we are. I don’t think that that differs whether you are in Dubai, Trinidad, or San Antonio. Those are the core of our experience is so shared. The core of our experience is a little bit frustrating, realizing that we are not God, that we do not just get to do whatever we want, and that Mother Nature will from time to time, flick us on the ear. All of our experiences fit into this thing.

One thing I would tell you is, I didn’t actually cover this in the book, but maybe I’ll cover it in the sequel, in my experience, there’s an internal clock that everybody has that they’ll see you, they’ll pass you on the street, or they’ll see you at the office and they’re going to make some very surface assumptions about you while that clock is still running. They’re going to see you again the next day and a few days later or in a different meeting or the line. Eventually, a little bell’s going to go off. “I’ve seen that person enough times and I’ve watched them enough times.” Suddenly, there’s this radical shift in how they relate to you.

Generally speaking, in most of the islands where we were, that clock would go off at about a month. If they see you for about a month, then you’re not a tourist anymore. You’ve been here a long time. What’s your story? That’s the next, is it’s very natural to ask “What’s your story?” What a wonderful way to start. Not what do you do? Not where are you from? What’s your story? I’m seeing you. At that moment when I ask that question, what’s implied is, “You’re interesting.” It happens in all these different cultures whether they’re speaking French, English, Creole, or whatever it is that they’re speaking. That question translates. It’s just a question of interest. “I’m curious, tell me your story.” What a great way to approach someone like that.

I’m grateful for that because I yearn to know someone’s story and I still find myself in the habit of asking something like, “What do you do?” Every time those words come out of my mouth, I go, “Darn.” What can I say instead? It’s so true. As you and I were talking, just like how uncomfortable it is to have to explain what you do because people often want that short answer. They want a quick explanation and then they want to move on. The story is inviting something so much bigger, and that’s one of the most beautiful things about how you speak, Scott, you lead with all these stories, not just of your own, but of other people, the people that you’ve encountered along the way and the lessons that you are gaining from all these different perspectives.

The visuals that I’ve had from this conversation, I have Niagara Falls, Hawaii. I won’t mention what state you live in unless you want to mention that, but the mountains can certainly be there. All the islands, which is interesting because that’s one place where my brain gets a little stuck because I haven’t spent a lot of time in those islands. I can guess what they’re like, but I don’t know. There’s so much in this world. We talked about that too. There’s just so much to see, and that’s exciting. Sometimes I have this moment of, “I’m not going to see everything.” Isn’t that incredible to know that the world is so big that we can’t see it all in our lifetimes? Unless we dedicate our whole lives to seeing things.

Even then you couldn’t do it. No. My dad used to say that boredom is a character flaw. That’s true. There’s so much to see, so many people to see. When we start thinking about all of these things to see and all these people and all these different perspectives, to me what draws it all together is that to be seen, to be known to be valued, that that’s core to every human being. Also core to every human being is to want an answer to the question of, “What is the meaning of life? Why am I here?” That’s going to be true.

That’s true for the people that I know in The Bahamas, Grenada, and Saint Lucia. It’s true of the people who are pirates, who killed my friend’s husband. It’s true of the dude wielding the machete. At some point in their lives, they’re all asking the question, “What is the meaning of life?” If you get the answer to that question profoundly wrong, your life is going to be quite a ghastly thing because a human being can be contorted into quite a monster. If you get the answer to that question right, it can be marvelous.

There’s this French philosopher, Jean-Paul Sartre, who famously wrote, “Hell is other people.” He’s dead wrong. Absolutely, positively dead wrong. The picture that I want to paint for you here to define the meaning of life is to imagine that you could boil all of the universe and everything that’s happening in the universe into a line. It’s a timeline. It comes up to the point at which you are born. The timeline forks and there’s a path that the universe would go on if you hadn’t been born. A path that the universe would go on if you had been born. You survive for some period of time and then you die. Chaos is injecting randomness and erasing things. These lines will be separate from each other as they move out into the future.

If those lines are the same, if there is no difference, you can’t see any difference between those lines, then there’s no evidence that you actually ever existed. You can’t prove that you existed because there is no difference. Everything is exactly the same as it was. If you begin to make a difference through the things that you do, the people that you influence, and the things that you build, then for a period of time, there can be a very big difference between the world as it would be without you and the world as it is with you.

MGU 470 | Embracing Uncertainty

Embracing Uncertainty: If you begin to make a difference through the things that you do, the people that you influence, and the things that you build, then for a period of time you can have there can be a very big difference between the world as it would be without you and the world as it is with you.


The question becomes then how do you make the greatest difference? How do you make that difference sustained for the greatest amount of time? The answer is pretty obvious, other people. If I can inspire you, if I can give you a little something that you didn’t have, if I can encourage you, if you can build on what I’ve done, you’re going to take a little bit of my DNA, a little bit of my change in the universe and you’re going to propagate it to somebody else. It’s going to be hard for entropy to come along with its eraser and a race all these different places that we’ve had little bits and pieces of my DNA going everywhere.

To me, the meaning of life is how we inspire, encourage, uplift, connect with, and equip other people so that some little part of us propagates change into their lives and that they then propagate change into somebody else’s life. The sum total of difference from me in this universe line that we’re on will be so different. It will continue long after I’m dead. My book will live long after I’m dead. The ten people who have read it will be affected in some particular way.

I don’t know if any guest on the history of the show has ever tried to tackle the meaning of life, Scott. What an amazing way to emphasize the importance of our differences. Also, you help me understand why I just don’t like transactional things because they don’t feel different. There are so many times I’ve felt like if I don’t fit in, I don’t belong. Maybe that lack of belonging is actually what’s so much more important, because that’s about being different, and fitting in doesn’t feel so important. We can think about that from different concepts, but there is just a lot of pressure to fit in the status quo, the echo chamber.

I’ve faced that so much in my life and it feels like such a big force but you’ve inspired me. You’ve made a difference in my life to really help me talk through these big things. You have such an eloquent ease with which you express it. Scott, all this complexity I’ve just really enjoyed exploring with you. I’m deeply grateful. I feel it in my body. I feel a shift in my state in this hour that we’ve spent together. It almost felt like this meditation with you. Thank you for that.

That is high praise. Thank you. I’m glad that it touched you. I have enjoyed so very much having this conversation with you, so I won’t forget it very soon either.

What else could you ask for to make that little difference in someone’s life and the ripple effect and then hopefully the audience has felt something as well? If they have, we’ve mentioned Scott’s book and we’ve mentioned a variety of things. There are two places that you can take the next step if you want to dig in more if you want to continue, if you don’t want this to be over. It doesn’t have to be just because the episode concludes. What’s your preference, Scott, what should we put there? Your book or your website?

The website,

It’s such a great domain name. For anyone who just wants to branch out and see where their journey goes with you, Scott. You had so many great quotes. I was taking notes and thinking, “This is going to be hard to narrow down.” Usually, there might be 4 or 5 quotes that we highlight per episode. It’s going to be some work for me to narrow it down. That’s great because you can get it all in one place, including the non-highlighted quotes. Thank you so much, Scott, for this wonderful time.

This was so fun, just wonderful and encouraging. Thank you for making this happen.


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About Scott Davis

MGU 470 | Embracing UncertaintyScott Davis’ adult life has followed an explorer’s wandering path: corporate leader, tech entrepreneur, adventurer, inventor and essayist.

Profiled by Forbes at 30 as a rising star in corporate leadership, he ignored industry expectations and walked away from the executive suite to pursue a life off the beaten path, ultimately selling everything and heading off to sea in an old sailboat. Returning to the states at 50, Davis patented innovations in boatbuilding and founded a company to help sailors fulfill their dreams of building their own sailboats.

Today, Davis spends much of his time writing and speaking on how to create a meaningful life, guiding friends and family on adventures, teaching boatbuilding, and occasionally making something interesting in his workshop.


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