Don’t downgrade your dream, improve your skills

Have you ever had a moment where you are not as confident as you would like to be about something? Simple question, right? I think all of us have experienced that moment or moments in our life, particularly as we build businesses and certainly as we try to be purposeful and intentional about how we use the gift of life to balance our work life model. 

I think that at some level we all are challenged at the idea of what we do when it seems that a dream is slipping away. And I want to talk about this because I think that there’s a couple points that are worth making. 

Watch this video to see what to do if this happens, and how to avoid it. 


The first point I want to make is this idea that your dreams define your destiny. I find far too often that people are not dreaming big enough. They’re not dreaming about the kind of future and the better version of themselves that they would like to be.

I think a lot of people have unfounded fears, and so the dreams are scary. I think a lot of people have not learned how to manage failure in a really healthy way. So when it feels like there’s a setback as we approach a dream, it’s awfully easy to give up on the dream because that then releases us from the fear of failure. I think it’s interesting because, as I’ve said for decades, the idea of being your best is about when the going gets hard, you’ve got to get going. 

When the going gets tough, you’ve got to get tough. When you feel doubt, you’ve got to be courageous. And we’ve got to move from this idea of fear and maybe incompetence or not feeling that you have the skill to instead, keep the dream alive and grow how you execute the skill.


I don’t want you to downgrade the dream. I want you to upgrade your skill, and I’m going to talk to you about this in two very personal ways. One is I’ve had a dream since I was in high school to become a private pilot. And I remember when I started getting my training as a private pilot, there were moments that were getting rough. I’d had moments of doubt on whether or not maybe I would ever be a pilot. I had moments of doubt on whether or not I’d be able to master this craft, this hobby, if you will. A lot of moving parts, right? I’m a vision guy. I’m not an analytical guy. Charts and graphs and maps and things like that don’t resonate with my DNA.

But I had a choice to make. I had a choice, no matter how hard it gets, how hard it might be, I’m not going to give up on my dream. I don’t care how long it takes. So I started flying in 2017, and I remember three major setbacks that I had in three years. Two had to do with family-related deaths. One had to do with a business decision that needed to really take some of my focus, five or six months of my focus. And then COVID hit. And the flight schools were shut down, and I found myself on the brink of finally getting my certification and becoming a certified pilot. And I’m good. I’m a good pilot. I have over 120 hours of flight time and I’ve passed my exams. And I could have easily given up on the dream, but instead, what I said is, “How do I get better at flying?” And I learned a concept called chair flying, and chair flying, as a pilot, is when you go through your maneuvers in a chair, like I’m sitting in right now.

Have you ever seen an Olympic athlete visually go through their protocol before they actually engage? And the answer is, of course, yes. And that’s what chair flying is all about. And so I personally had to deal with the very question I’m asking you, and I had to do the same thing. I had to make a decision. Don’t give up on the dream. Persevere. 


I have this 95% rule. 95% of the people go 95% of the way and get 5% of what’s available. 5% of the people go 100% of the way and get 95% of what’s available. I did that with flying. I’m not going to give up. I’m too close to the finish line. I didn’t give up on a realtor that took 18 months before she said yes to doing business with her. I was too close to the finish line. I did not give up on losing weight and hitting my perfect weight goal. I was too close to the finish line.

I didn’t give up on being financially well off and being financially free, even though I found myself about 10 years ago in the midst of not having any financial freedom and almost losing it all. But I just faced everything. And I just said, “You know what? I’m not going to change my dream. I’m not going to change my dream. I’m going to get my team skilled up. I’m going to get my partner skilled up. We are going to get good, because the dream’s not changing. We’re going to get better.” 

My youngest son is 23 years old and he told me the other day, he said, “Dad, I can’t tell you how great it feels to be a business owner at the age of 23.” Now, the backstory, and I’m going to make it very short, the backstory is that my son, Matt, has always had doubt. He’s always had fear.

He’s always struggled with the work required and the attitude to have to become what your destiny is asking you to be. And for him, it was a work in progress. It’s taken probably the better part of the same five years I’ve been flying. It has taken him five years to go from disbelief and negativity and failure to hope and excitement and joy. And the other day when he said, “I’m 23, Dad, and I’m a business owner,” he was at our office and he was shipping out 70 pieces of art that he handcrafted, he made from scratch. Each one was unique, one of a kind. We call them non-fungible tokens today, right, in the art and crypto world. And he had so much pride on his face and he had so much joy in his heart. And I had asked him four years ago, I said, “Do you believe that you can be an artist? Do you believe that you can be a musician?”

And his exact words were, “It’s really hard to believe it when it hasn’t yet happened.” And what I said to Matt is I said, “The way it’s going to happen is to believe that it will.” And you can see the paradoxical kind of juxtaposition of that, right? As soon as you believe, then you will do. But if you are not doing and not believing, then you are robbing yourself of your best life and your best future. 

Out of Matt’s first art order, where he packaged all these up and we sent them out, he got a guy that called that had bought a home in Breckenridge, Colorado and had received one of these pieces of art that Matt had built, which was a beautiful feather. And Matt’s in metalwork, so it’s a beautiful metal feather, right, beautiful detail and so on and so forth. And he asked Matt, “Can you recreate this picture of Breckenridge, because this is what we stare at out of our home that we just bought? I would love to have a picture from you, metal art.”

And when that order came in and I looked at Matt and I said, “So now do you believe?” And he said, “I’m getting there.” And I said, “That’s all it is.” The more you succeed, the more belief you will have. 


But the key is if your dream is purposeful, if your dream is big, if your dream is something you want to be in, you feel it deep, deep, deep in your soul, don’t give up on the dream. Don’t let the door shut. That’s the path of least resistance. The people that make it are the people that face resistance and they keep going. They get better. They change their strategy. They practice, practice, practice, practice. And in the end, the vision comes true. And as soon as the vision comes true, everything changes. I know how to fly now without a doubt. 

Matt knows how to make art now without a doubt. We’re going to face our challenges, but we’re not changing our dreams. We’re just going to get better, all right?


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