Episode 40: The Real Reason You Procrastinate With Money

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In this powerful episode of Wealth Strategy Secrets of the Ultra-Wealthy, Dave Wolcott welcomes a guest who completely reframes how we think about procrastination, self-sabotage, imposter syndrome, and fear. Rather than treating these as flaws to “fix,” the episode reveals a deeper truth: we don’t have a motivation problem—we have an alignment problem. When our goals are misaligned with our core values, the brain resists through procrastination, hesitation, and self-doubt. But when values and goals align, discipline, follow-through, and confidence become effortless.

The conversation dives into the science behind this transformation, introducing concepts from axiology (values), teleology (purpose), and neuroscience. You’ll learn how meta-values determine how you invest your time, energy, and money—and ultimately shape your financial outcomes. The episode explains why most people hit income ceilings, how “self-sabotage” is really value conflict, and how to rewire your brain for wealth using a proven, science-backed process called remyelination. This episode is a masterclass in aligning purpose, psychology, and wealth so success no longer feels forced—but natural.

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How’s it going everyone and welcome to a special solo series of Wealth Strategy Secrets of the Ultra Wealthy. I’m your host, Dave Wolcott. We get a lot of the same questions from our investors about infinite banking, tax efficiency, asset protection, strategy stacking, and how to actually build wealth outside of Wall Street. And we get it, we know you’re busy. So in this series, I’m breaking down complex wealth strategy topics into short tactical episodes that you can actually use to build legacy wealth. Whether you’re just starting your journey or fine tuning your portfolio, these episodes are designed to give you high impact insights in just a few minutes. So let’s dive in.

What we’re going to talk about today—and the reason that Dave asked me to come speak—is you’re gonna hear some things today about things about procrastination, self-sabotage, imposter syndrome, fear of failure, you know, fear of success, self-doubt, and all these sorts of topics that are very common mindset topics, but you’re gonna hear about them in a way that you’ve likely never heard about them in the past.

So how many of you would say that procrastination, self-doubt, self-sabotage, imposter syndrome, fear of failure, fear of success, or something along those lines has kept you from achieving goals in some sort of a meaningful way? Okay, and I know I get that some of what I’m gonna say that I’m saying right now flies in the face of conventional wisdom. But hopefully you didn’t come here all the way to Dave’s mastermind or workshop to listen to a guest speaker that’s gonna tell you the same thing that you’ve already heard a thousand times that probably hasn’t worked.

So what’s my point? Well, no one fails because of fear of success or failure, fear of failure or procrastination, self-sabotage or anything else that we mentioned. The truth is that we experience these things in some areas of our life, but not other areas. And the real question that we want to ask is: what can I learn from the areas of my life where I’m fearless, confident, and relentless that I can apply to the areas of my life where I’m stuck? Because when we do that, then we’re free to create any goal we desire: money, success, fame, wealth, love, intimacy, health, vitality, all of it.

So really quickly, a little bit about me, right? This is the version of me that most people see today. The awards, accolades, podcasts, media publications, you know, news interviews, television interviews, speaking engagements, and these sorts of things. But the reality is I’m really nothing special. This is me just a few short years ago working in a coffee shop. This is about 12 years ago now. Working in a coffee shop for minimum wage, living in my mom’s spare bedroom, 500 credit score. And it wasn’t for a lack of trying, I should mention, right? I had done network marketing, car flipping, real estate, forex, stocks, started a clothing line, trying direct sales, nightclub promotions—and that barely scratches the surface of all the things that I tried despite failing for 12 years straight.

And eventually, of course, I thought I was the problem. I started reading books, going to seminars, getting coaching, therapy, hypnosis. Went to all the guru seminars, pretty much any one of them that you would name and more. And for a bit, it helped. You know, I would feel better about myself. I’d feel, you know, create better relationships with my family, better relationship with my spouse. But no matter how many transformations I made, my bank account didn’t seem to reflect those changes. Regardless of how many transformations I made, I was a bit insecure because, you know, I kept saying that I want to achieve these things in life, but I really wasn’t amounting to much.

And I was worried that my girlfriend would leave at some point. In a way, I also felt like a hypocrite because here I was telling my son, you know, “you can be anything that you want to be in life,” which we often do as parents, but I wasn’t living up to it myself. And so when I looked in the mirror, I felt like a hypocrite and you know, my friends and family were making fun of me behind my back after 12 years of starting and failing at businesses, because you know, I mean, they just seen me set lofty goals a thousand times and get nowhere near them. But more than any of that, I struggled with the fear, right? Laying in bed at night, staring at the ceiling, wondering: what if I work my entire life and never become who I know I’m capable of being?

And maybe you can relate to some of that. So in 2012, actually 2012, a buddy of mine hands me a book. Inside that book, I discover a field of science I’m gonna be sharing here with you and I went on to study as much as I could get my hands on about that. And within seven months, I was leaving that job. This is a picture of my girlfriend and I at on a wine tour in Napa Valley. A few months later, we were on vacation in San Francisco. This is us at Pikes Peak. This is me just a few months after that speaking at a conference teaching. So my little internet business started taking off. I was speaking at a conference in Seattle. That one had about 400 people. This is me in North Carolina with about 1,500 people at that conference. This is me winning the award for best affiliate marketer or affiliate marketer of the year.

A few years later, you know, being featured in the news and in the media, being able to hobnob with billionaires, speaking on some of the biggest stages in the world, traveling around the world in private jets. This is winning an award from a company called ClickFunnels for crossing 100 million in sales. And I scaled my business to 140 million in sales and sold it in 2024. 12 years of struggling with procrastination, self-sabotage, imposter syndrome, fear of success, fear of failure, and all these different things that all the mindset gurus are talking about, going on to build a nine-figure company. That’s the power of what I’m gonna be sharing with you.

And I think it’s important to note that I’m not a personal development guru. Not a single ounce of the wealth that I’ve created up until exiting that company in 2024 came from teaching what I’m about to share with you. It came from just applying it. And in fact, most of what I’m gonna share with you, I never even shared with anybody except for my business coaching clients that paid me $15,000 or more. And it’s science-backed and proven. It comes from three fields of study: axiology, which is the study of values; teleology, which is the study of purpose; and neuroscience, which is how our brain works.

So there’s really three things we’ll cover. Why procrastination is your friend, not your enemy. Actually trying to guide you back to your life’s purpose, so that achieving success, love, health, wealth, for many of you, feels effortless. Number two, the mental sinkhole that keeps us trapped, you know, at an income ceiling despite working harder or doing more. And secret number three: the research-based, science-backed way to rewire our mind for wealth so that it happens subconsciously without working harder or doing more. You know, chances are you’ve not heard of what I’ll share with you in that third secret either.

So when we wake up every day, there’s the things that we value most in life down to the things that we potentially don’t value at all. So our meta values govern how we experience the world around us. And they also determine our destiny. Like literally, if I know your meta values, I can tell you your future—no crystal ball or psychic abilities necessary. So meta values don’t just dictate how we experience and filter the world around us, though. They also dictate our success, quite literally everything. And here’s why.

So now that we looked at it from a high level perspective, we can look at it more closely. So our meta values will determine how we invest our resources—our primary resources: our time, energy, and money. Would you agree that however we invest our time, energy, and money will become our destiny? Like, we don’t spend our time, energy, and money going in one direction and then suddenly wake up 10 years later somewhere else. That’s why Peter Drucker, the famous business management guru, said, “tell me what you value and I might believe you, but show me your bank account and your calendar and I’ll tell you what you actually value.”

So it doesn’t matter what we say, right? If we look at where our resources actually go, it is revealing to us what’s true about ourselves. So when our goals—conscious—and our meta values—unconscious—align, we experience inspiration, discipline, fortitude, follow through. But when they’re misaligned, we experience symptoms: procrastination, hesitation, frustration, self-doubt—to lead us back to our authentic selves. So think about how beautiful that is for a moment. That means that we are physiologically designed, neurologically wired to wake ourselves up to our true calling. Because what good is accomplishing a goal if it comes at the price of your soul?

But here’s what most folks don’t know, right? Your brain is actually a purpose seeking organ. It is designed to pursue what it believes to be most purposeful and meaningful. Meta values are what it perceives to be most purposeful and meaningful. So we don’t have a procrastination problem. We have an alignment problem. And the Power Code, which is what our curriculum is around, is the way to align those things to solve that issue.

So the real question is then, what’s keeping us from our values, right? If we all have them, why—what keeps us from being able to tap into those meta values? And the short answer is programming. Because from the time that we’re born and can understand language, we’re told who we ought to be, supposed to be, need to be, have to be, in order to be enlightened, successful, worthy, lovable, what have you—from our mothers, fathers, brothers, sisters, preachers, teachers, schools, media, social media, government, friends, and more. And I’m not saying good or bad. There’s just a lot of external voices that tell us who we’re supposed to be. And over time, we lose sight of the inner voice. So most of us are going to end up spending most of our life living a lie, chasing who we think that we’re supposed to be at the price of who we’re born to be. And that’s the sad reality for most people. And I don’t know about you, but I can’t think of anything worse.

Second part of this is about building—how, why we run into this like financial plateaus. Any of this making sense, by the way, so far? Just have a one in the chat for you—just making sense or landing for you or you’re finding some value in it along the way. Thanks. Thanks for the participation. It helps. I can’t see any of you because I can only see my notes and my slides. So I appreciate the comments. Thanks Mark, 100 percent. Thank you Mark.

Okay, number two. Why do we plateau financially? I bought two million dollars worth of cars over the last ten years or so because I valued having those cars more than I value having the money that it takes to get it. But Warren Buffett valued the money more than he values having a nice car. That’s why he’s a billionaire. What’s my point? We get in life exactly what we value. See, so if we want to know what do we actually value in life, we can look around in our life and it will tell us exactly what we truly value.

So again, we’re going to invest our time, energy, and money—our resources—in direct proportion of things we value. If we don’t have a high value on money, wealth, cash, financial independence, then we are going to struggle to have money, cash, wealth, and financial independence because we’ll keep trading the money for whatever we value more. Right? So until you tie money to your meta values, using what I call the Power Code, you’ll continue to trade it for what you actually value. And then we call it self-sabotage. Does it make sense? This is why everybody knows what it takes to build wealth. Jesus, I mean there’s a hundred, there’s hundreds of books on this. But so few people will actually do it because they don’t have the values necessary to follow through on it.

All right, so secret number three: the real research-based, science-backed way to rewire our mind for wealth subconsciously so that we’re not necessarily working harder, we’re just changing our behavior over time. So once we know what our meta values are, we have really two options. First option is change our goals to match our values. What I mean by that is Wendy, as an example—she would give up on building the business. It’s clearly not what she values. So she’s going to change her goals to match her values rather than trying to forcefully get herself to spend 40 hours a week on her business. If she makes that same goal of spending 40 hours of quality time with her kids, she’ll crush it on the weekend, you know, but she’s going to struggle to do that with her business. So changing her goals to match her values would be her shifting her—literally giving up on her goals and setting goals that are more congruent with her values.

The other option is that we change our values to match our goals. So our values are not static. They’re dynamic, they change over time. And this is kind of important. But I’ll say next: our values are actually dictated by our perceived voids in life. So whatever we perceive to be most missing will be what we value. So this is why trust fund babies tend to blow all their money. They didn’t grow up with a void around money. So they don’t value having money. That’s not what was missing in their life.

So we have two options: change our goals to match our values, change our values to match our goals. We can rewire our values to match our goals by creating neural connections in the brain. So what this does is it, quote unquote, weaponizes our mind to hone in on any target that we set. So one way to do this is by asking a simple question. And this is what I did. This is when I first started learning this—remember I’d done a lot of personal development leading up to this, but this for me was like the thing that clicked and there’s like my life before learning this and my life after this and they look almost nothing alike.

One way to do this is to ask a simple question: How is [insert goal] a benefit and service to my highest values? So in other words, how is whatever I want to accomplish a benefit and service to the things that I value most in my life? I’m going to look for 200—200 connections, 200 answers. So my first time doing this, I asked the question: “How is building a business that serves ever greater numbers of people a benefit and service to the things I value most?” And I just started making a list, and I was completely broke at the time. And eventually that list ended up being over a thousand connections. Mentor of mine—somebody who’s much more studied at this, whose work I’ve studied for years now—he’ll say that 200 connections is the minimum. That’s where the neuroplasticity really begins to take shape.

Okay, now what’s happening here is what process we call remyelination. So when I was putting this presentation together a couple of years ago, I kind of thought that this was gonna be a place where I would lose people, right? Like medical journals and whatnot. But I uploaded that stuff to ChatGPT and I asked it to just spit back the answers to me. So here’s “What role does remyelination play in the brain?” And so it broke it down. So when it comes to personal growth and transformation, remyelination plays a pivotal role in rewiring the brain for new beliefs, habits, and behaviors. As these pathways strengthen, myelin coats them, making the transmission of thoughts, behaviors, emotions more automatic and effortless. Remyelination accelerates the shift from old disempowering patterns to new empowering ones—faster, more insulated connections between these areas reduce reactivity to stress and fear, making transformation less emotionally taxing and more sustainable. This is why high-performance individuals seem to operate effortlessly; their desired behaviors are heavily myelinated. Right? That football receiver that you see running down the field that half the time isn’t even looking at the quarterback and seems to almost like sense that the ball is coming, turn around, catch it with one hand, and take it into the end zone. The person who rides, you know, a 20-foot wave—like that would probably kill any of us, but makes it look like he’s dancing—heavily myelinated neural networks in the brain. It’s all it is.

So this right here is the science of rewiring and you can really make it work for anything. My fiance and I, we’ve been together for 20 years—21 years now. We had a couple months. So we’re like, “Oh, you guys never got married.” It’s never been important to either of us. Obviously not higher values, right? She actually just proposed to me three years ago. But she’s still my best friend. And I’m still her best friend. You know, like we genuinely enjoy spending time with each other, 21 years later. I would say that a big portion of that is we both understand what I’m sharing with you here and we both understand what each other’s values are. She has a complimentary opposite set of values to mine. And so one of the ways that we keep intimacy and communication in relationship—especially when we’re going through hard times, because I’m not going to pretend that it’s not without its hard times—one of the things that we’ll do is I’ll sit down, she’ll sit down. We know what each other’s values are. And one of the questions I ask myself is, “Well, how is her values a benefit and service to my values?” Because she’ll do the same: “How is his values a benefit and service to my values?” She has a much higher value—I would say her primary value is relationships. It’s very obvious that my primary value is my business, right? Where I spend all my time, energy, and money—business. But because I’m so focused on the business, she has the time to build the relationships. Because she has a high value on relationships, she turns our business relationships into real authentic relationships. So that complimentary set of values means that both of us gets to do what’s most inspiring for us in our life because the other person is handling the other half.

And this one’s always an embarrassing slide. But this is me during the pandemic. Got on the scale one day, pretty sure I must have ate a fourth grader. Locked up for 70 whatever days it was. Look down at that scale. And I know I must not have a very high value on health and fitness because the scale just told me so. It doesn’t matter what my lip service is. The numbers on the objective data say “you do not value health and fitness.” So knowing what I’m sharing with you here: two things. First, I hired an accountability partner because I know I don’t value it. So I’m gonna need external motivation and accountability temporarily. So I hire a trainer. We start working out Monday, Wednesdays, and Fridays at 6 a.m. I also know what I’m sharing with you here. So every day we get back from that training, I would ask myself, “Okay, so how is this a benefit and service to my business? How does this make me a better CEO? How does this help me accomplish the business’s goals?” Right now I notice things: better cognitive function, better energy throughout the day, better decision making, better focus, better brain-derived neural factor—obvious, right? Six months later, I fire the trainer. I’m working out—I go from working out three days a week to five days a week on my own. So I actually end up working out more. This photo’s from four years later. It took me eight months to lose the weight and hit my goal weight, but four years later—this is last year—still keeping it off. Yes, yeah, so five years later, still keeping it off. Right, just— I naturally now like, I think about what I’m eating, I eat more on target. One of my biggest issues used to be I travel a lot for work; it’s also hard to stay on track when you’re traveling. Blah blah blah. Now like, I literally pick hotels based on their gym.

Right, so here’s what we covered so far, just to reiterate: the real reason that we procrastinate is because our goals are out of alignment with our values; the truth about fear of success and fear of failure; shiny object syndrome that less than 0.001 percent of folks know, right? Like, it basically doesn’t exist; only a fool seeks temporary motivation and real power comes from inspiration instead; how to tap into discipline, certainty, purpose, courage, fulfillment, alignment and more so that work feels effortless; and then the Power Code as I shared with you is like the secret to living an authentic life, you know, so that we’re not injecting somebody else’s values on ourself trying to be somebody else, and also not projecting our values on others and trying to force them to be like us; and then the secret of breaking through the income ceiling is increasing our value on cash, money, and financial independence; and the secret to rewiring your values and automating our mind to relentlessly attack any goal we desire is remyelination.

Thanks for tuning in to our special solo series. If this episode sparked something for you and you’re ready to learn more, head over to holisticwealthstrategy.com and download a free copy of my book. You’ll also get access to our investor community where we share exclusive educational content, new opportunities, and resources designed to help you accelerate your path to freedom. And if you want to take it even further, book a call with our team to learn about our virtual family office services, or join our mastermind group where we go deep into building true generational wealth. I’ll see you on the next episode.