INWE 72 | High Earners


Do you feel like you aren’t good enough, smart enough, or rich enough? I get it. High achievers, this episode is for you.

Follow me on IG: @indestructiblewealth and visit me at for more resources.

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Mind the Gap: A Reminder for High Earners

Think about this for a second, 14% of American adults say that they are happy. Why is that? It’s because happiness is tied to something in the future. When we put it off to something that’s going to happen for us in the future, we are going to get to a certain level. We are going to hit a certain level of finances that we believe that we are going to be happy then. When we arrived there, we realized it wasn’t all that we thought it would be. What we are doing when we think about life, happiness, and joy in this way is that we rob ourselves now.

Understanding The Gap

We are in what’s called the gap instead of in the gain. I’m going to talk to you about how this relates to you in all areas of life, particularly in your financial life. It’s this book called The Gap and The Gain. It’s probably been one of the most transformational books that I might’ve ever read. This is a must-read for any entrepreneur or high achiever type mindset. Here are some things that it says right here in the book about the gap and the gain.

“Your future growth and progress are now based on your understanding of the difference between the two ways in which you measure yourself against an ideal, which puts you in what I call the gap, and against your starting point, which puts you in the gain, appreciating all that you’ve accomplished.” The author is Dan Sullivan.

For fifty years, he has been teaching entrepreneurs and famous marketer as well. Think about this too, “High achievers are particularly prone to being in that gap where you are always striving for something more. You never take time to appreciate, enjoy, and recognize yourself for all that you’ve accomplished. For instance, research shows that CEOs are twice as likely to have depression than the general public. Entrepreneurs are prone to substance abuse, as well as depression, and even suicide. Even after some massive victory, their mind quickly goes to the next unreached achievement.” I am guilty of this.

This is describing me to a tee, except for the suicide part. “Although I have at certain points in my life, I have been down for sure. Although this can lead to a great deal of external success, the problem remains unresolved internally. Many, if not most, high-achievers remain unhappy. Their unhappiness grows deeper and deeper with each external accomplishment. That is if they stay in the gap.”

How It Ruins Your Day

Let’s dive into here under this concept. This is going to be enlightening for you. I took my family skiing, a three-day trip. We’ve done three ski trips so far. We took a gamble and did some spring skiing, which rained for 24 hours. Despite all of that, we still had a wonderful time. We got to ski in the mornings. We skied in some of the rain, and it was fine. We made the absolute best of it that we could. We tried to focus on being in the gain. We were on an awesome getaway. It wasn’t the ideal conditions. We knew that when we were going into it, there was a possibility that with the spring and the warmer weather, it wouldn’t be actual winter skiing.

There's probably no net worth that's ever going to be a place where you're going to say “I'm perfect here. I'm totally happy with where we're at. I don't need anything more”. Share on X

We found ourselves enjoying it because we made sure that we focused on being grateful for where we were and what we did have. Contrasting that, we went up North and took the fam three days. It’s an expensive trip. We had a wonderful time. The last day was a Friday morning when we were going to leave, but we always ski for about 2 or 3 hours on that final day before we pack up and leave. We love the morning skiing and the freshly groomed trails. It is the best skiing that you can get. We get all our ski equipment, the boots, the poles, the skis, and all four of us. We got up to the front of the line, where they scanned our passes and kept getting the red denied.

This ticket is no good. All four of us were stuck in front of this line of people all behind us. We were holding up. I was like, “What the fuck is going on? I paid for these passes. I paid good money.” It turned out that I had booked the wrong days. I have booked the three previous days that didn’t include that day. I went up to the ticket booth, and they said it was going to be $400 bucks. I’m not paying $400 to ski for maybe an hour or two. I lost my shit. I’m not going to lie. I slammed my board. I paced around. I was so upset. Why? I was focusing on the gap. I disappointed my family. We put all this effort into getting all our gear on and to the front of the line.

We were excited to ski in the morning, and now we weren’t going to be able to do it because of my mistake. My wife talked some sense into me, calmed me down, and said, “It was okay. You didn’t disappoint us. You took us on a great trip.” Instead of focusing on the previous two days of amazing times and the whole trip as a whole being a powerful game, nobody got hurt. Nobody had any wipeouts. We had laughs. We had great food.

At that moment, I was powerfully stuck in the gap. I can say this in all honesty, I have been in the gap. I’ve probably lived more in the gap over the last several years as an entrepreneur and an investor than I’ve ever lived in the gain. The gain is looking at from where you are now going backward. That’s looking at all that you have been able to achieve and all the progress that you have been able to make from where you started.

Instead, when you are in the gap, you are looking at what you haven’t achieved, what went wrong, what didn’t work out, and where I am falling short of the expectations that you had set for myself. As a high achiever, I know you are probably a high achiever in all likelihood. If you are reading this, you are not going to tune into me long, you are going to listen to an episode or probably check out if you are not a high achiever type mindset, so I’m talking to the right audience.

Acknowledge Your Accomplishments

We focus so much on this ideal of where we are going that this can cause an incredible amount of discontent and unhappiness. It causes problems. For example, in business, I’m in a direct sales company. We are in a culture where you constantly hear about others that are moving faster, moving bigger, doing bigger things, and achieving more.

INWE 72 | High Earners

High Earners: Take time to appreciate, enjoy and recognize yourself for all that you’ve accomplished.


It’s both inspiring but also causes myself and a lot of other people. I believe to be in the gap. Looking at what we have been able to do, we’ve had some incredible accomplishments. We’ve done over $3 million in lifetime achievement in sales. We’ve hit three diamonds, which means we’ve helped three people become the top 1% of the company. We’ve hit some incredible organizational goals.

We have over 10,000 people on our team, yet most of my time is spent, “I’m not five diamonds. I’m not at this level where this person is. This person did in what took me 25 years have accomplished in 7 or 8 years.” All of these thoughts are constantly going through my head. That’s being in the gap. When I’m thinking that way, I’m not looking at, “We are top 400 or even probably better, maybe even top 100, I don’t even know, in the entire world. We got all these incredible things that we have been able to do. Why don’t I focus on that?”

Knowing You’re Worth

As a high achiever, my mind gravitates toward the ideal of where I should be versus the reality of where I’m at. Where I’m at is I’m whole and complete right where I’m at. One of my avid followers, we will call him Gee, was doing a net worth and down about it where he was. This is one of the exercises that I have people do when they go through my course, which is about to launch, which is exciting. Both courses and my book are coming out. I put in a ton of time, effort, and energy.

I’m excited to get these released. The beta testers go through and talk about on the intake form that they fill out when they join. They go through their net worth. Usually, they are disappointed. You can tell them the way they are framing it. One thing I had to point out to this gentleman. I said, “You are not putting in the value of your business. You have a business that generates $100,000 a year or more. In today’s environment, most private businesses are getting, if you were to go to sell it, the value of it would be 3 to 5 times the net earnings. You have a business that’s worth minimally $300,000 to $500,000.” I would probably pay him $500,000 to buy his business out because I know the business. I understand the value and the cashflow.

If I could, I would say, “Here’s a check for $500,000. I will buy your business. Put that on your balance sheet and net worth.” Many people are so guilty of doing this that they don’t look like an entrepreneur. Maybe I haven’t created that much investible assets outside of my business but your business is extremely valuable. I’m not telling you to sell your business. I’m never going to sell mine.

The cashflow and the intrinsic rewards or fulfillment are too great. There’s no price tag that would cause me to sell my business. However, if I’m doing a net worth statement, I certainly got to put my business and the valuation of that private business on my net worth statement. When I do that, it boosts my net worth up tremendously.

Measuring yourself against an ideal is an endless race to nowhere. Share on X

As entrepreneurs, we put so much money, time, energy, and effort into investing in our own business that, a lot of times, we don’t invest in other assets. That is stage 3, stage 4 in the 5-stage strategic plan that I teach you. You got to remember, if you are in stage 2 or 3, you are investing and building something special. You’ve got to make sure that you are counting and looking at that as a gain.

It’s human nature to be in the gap. The gain is the antidote. The gain is what creates immediate happiness. The gain connects you to yourself and your own progress. The gain will transform everything. The gain gives you power over the direction in your life. The gain is the only way that you are going to be able to get out of that awful, terrible gap.

Measuring Against Ideals

You want to look at this in terms of three places. You have the start. The start is where you were 90 days ago, a year ago or a decade ago. For me, many years ago, where did I start? A college student and broke. Maybe $200 in my checking account. I sold my CD collection to get $50 to be able to go put an ad in the local newspaper. Now I can stroke advertising checks for quite a bit more to that. I don’t have to sell anything to be able to do it. You have the achieved. The achieved is what you’ve achieved over the past 90 days, the year, the ten years, or whatever period that you are measuring.

The ideal that’s where you wish that you were. You have this ideal in your mind, and you are measuring yourself, your business, and your finances against your ideal rather than the actual progress that you’ve made. This is why you are unhappy with what you’ve done. It’s why you are unhappy with pretty much everything in your life. You are measuring yourself towards that ideal.

You are measuring yourself in the gap. You are in the gap every time you measure yourself or your situation against an ideal. For example, you are on your way to a concert with your spouse. You have been looking forward to it but you are running late. If you are frustrated and focusing on those 20, 15, 30 minutes that you are held up in traffic, or that you got out the door late, then you are in the gap. You are measuring yourself against your ideal and not living in the moment.

If you focus on the fact that you are having an exciting night, the whole night is a gain. If you look at the whole aggregate, the whole picture, you are in the game. My wife, Cara, makes some great home-cooked meals through HelloFresh. She doesn’t do it from scratch but has to put them all together, and they are great. Sometimes our kids get to the table and complain that the meal isn’t all that good.

INWE 72 | High Earners

High Earners: Measure yourself backward against where you were before and don’t compare yourself to something external. Don’t measure yourself against your ideals.


It’s not their favorite dish. They are in the gap. Instead, what should those little shits say? “Thanks for making dinner, mom.” The truth is they have gained. They just weren’t appreciating the meal in front of them or their lives for that matter. This is what people are when we call them spoiled. They are not appreciating what they are because they are measuring their experience against an ideal at that moment.

Measuring yourself against an ideal is an endless race to nowhere. If you measure yourselves against your net worth, where you are at now, against your ideal of where you want to be, you are going to be disappointed. I hate to break it to you but there’s probably no net worth that’s ever going to be a place where you are going to be like, “I’m perfect here. I’m totally happy with where we are at. I don’t need anything more.” I don’t see that happening for most of us. You probably wouldn’t be reading this if that’s how you thought.

The Quest For More

I remember a few months back. I was showing Cara our net worth. I was disappointed. I was disgruntled. I was bitching about it. She was like, “Why are you not happy?” “Look at this. It’s because I made many mistakes. I should be so much further along.” She gave me a pep talk, maybe a lecture. I needed the lecture. Cara knows when to give me the lectures. Psychology has a term for this. There’s a moving horizon. It’s called hedonic adaptation.

It’s the tendency of humans to quickly adapt to where they are and what they’ve got. It leads to never being satisfied and constantly seeking the next thing. It’s on that famous movie, Wall Street, Gordon Gekko says, “How much is enough? A little bit more.” It’s powerful that no matter how big the change is, you marry your dream girl, double your income, triple your income, achieve all your goals, the thrill wears off, and you quickly revert to that feeling of normal and unfulfilled again.

You’ve moved forward, and the horizon moved with you. Psychologist Dr. Michael Isaac says this term is called the hedonic treadmill. When you are on this treadmill, you are working harder to be happy but stay exactly where you started. The reason this treadmill exists is that people aren’t taught how to be happy. Ideals are meant to provide direction, motivation, and meaning to our lives but they are not the measuring stick.

Society has trained us to measure ourselves against our ideals, which by definition, are unreachable. Our society is driven by continual inflated and unreachable ideals. That’s why we live in this consumer driven culture. It’s why you are trying to keep up with the Joneses. People buy more than they can afford because they are trying to measure up to this cultural ideal. Even religion, which is supposed to bring people hope and healing, can be a reason people go into the gap.

Happiness is where you start. It's not where you finish. Share on X

As one person told me, “I’ve always measured myself against perfection because that’s what I believe God can make me. I’m never measuring up.” Maybe they didn’t get the memo that God is in the gain, not in the gap. The real God doesn’t measure us against, “You are supposed to be here by now.” I don’t believe that at all. He measures us with all that we have been able to accomplish and do in the gain. Being in the gain, here’s what you do. You measure yourself backward against where you were before. You measure your own progress. You don’t compare yourself to something external. You don’t measure yourself against your ideals. I’m thinking about this on this platform.

I have been doing this for almost a year. I have over 70 episodes. This is number 72. I posted a ton on social media. I’ve got an email list. I’ve got a YouTube channel that we have been posting on. I’ve got this platform. I’ve had this sincere desire to build it to make a difference, and yet, here I am, I’m disgruntled about where it’s at. My show downloads are over 12,000 but that’s tiny in terms of overall podcasting. There are shows that do that in an hour. My email list has 400 or 500 people on it. My book, I have been working on that for a few months. It’s not released yet. This lack of what I consider external success in this platform has caused me not to feel so good about it. To be honest, it’s caused me to lose some motivation to keep cranking out the content.

I’ve had to work on myself with this concept of focusing on the gains, looking back and saying, “Damn, dude. Fuck, you’ve got all these other businesses you’ve got to attend to. You’ve got young children that you are coaching their basketball team. You take your family on trips. You are a present father. You work from home. You are always around. You are there for them when they need them. You see them when they wake up. You see them when they come home from school. You’ve got other investments that you got to attend to, and yet, you’ve still managed with all of those distractions, with all of that stuff going on, had toxic mold in your body since 2010 that you have been dealing with that’s rapidly depleted your energy and compromised your immunity.”

Yet through all that, I have been able to crank out tons of social media posts, set up all the email lists and autoresponders, filmed all the videos, pushed all the episodes out, wrote a book, and created two video courses. “What the fuck is wrong with me? Why am I not totally grateful and happy with the progress that I’ve made so far?” I had this expectation of where I would be a year in on this platform. I’m not even close to meeting up to that expectation. That pushes me into the gap.

Be Better Not Bitter

When you are in the gap about any experience, that experience becomes somewhat of a trauma. The word trauma could sound a bit extreme but trauma is an experience you framed as negative, which you avoid, and which creates ongoing dysfunction in your life. When an experience is framed in the gap, you haven’t learned from it. You haven’t taken ownership of it.

Until you actively learn from a gap experience, you are stuck. You won’t be able to move forward until you frame the experience as a game. You embrace failing when you are in the game because you are actively converting every experience into learning and growth. You are grateful for every experience. You are no longer bitter. You become better instead of bitter.

INWE 72 | High Earners

High Earners: When you’re doing something that you genuinely love and you’re doing it for yourself, then you’re intrinsically motivated and you have a healthy passion.


I remember how we got this dream house that we are in now. I remember the moment that it became real and that it was attracted. We were disgruntled with the house that we were in prior. We were looking for and constantly searching for a next-level home. The house that we were in was getting cramped. The floor plan wasn’t what we wanted. The two houses next door were virtually 4 feet away.

Every house in the neighborhood was built close together. It felt constricting. We didn’t have a yard to go play, throw catch in. It wasn’t what we wanted to be. It was great at that time of our life but it was wearing out. I remember being disheartened about where we were at and why we hadn’t gotten to the next dream home yet. I felt we deserved it.

I remember thinking, “You are so off in your thinking now. You have an incredible family that you love and that loves you. You have so much fun. You have laughter, relationships, and love. That’s all that matters in this home.” When we are ready for it and deserving of it, and when it’s according to God’s plan, we will get the next house.

Within a few weeks of that moment, I was searching online. I never searched for houses. Our house came up. We grabbed it right the day before somebody else put an offer in. We grabbed this house at an incredible deal. I look at that moment and think to myself, “You got in the gain without even knowing that that’s what you were doing. You’ve got yourself into the gain.” Happiness is where you start. It’s not where you finish. For you financially, your net worth may be negative. Maybe you’ve made some financial mistakes. In all likelihood, you’ve probably made a lot. I’ve made a ton. If I went back in time, I probably made 200, 300 or 400 financial mistakes along the path.

I’ve lost money on investments. In all likelihood, that’s probably happened to you as well. Those are all gains because of the knowledge that you’ve now accumulated from all of those experiences. Those are making you wiser, stronger, and better financially. Those are making you better in your entrepreneurial life as well. I would suggest that when you are in the gap, you have an unhealthy attachment to something external. You feel that you need something outside of yourself to be whole and happy.

You need to have $ 1 million. You need that person’s approval. You need that position where the next level up, the next promotion. You need to be of a particular size or shape or to look a certain way. When you are driven by need rather than want, you have an urgency and desperation to fulfill that need. The problem is that needs are unresolved, internal pain, not something that you can solve externally.

Building wealth requires you to be thinking about the long game. Think of all the things that you've already done that have really made a big difference for you. Share on X

I go back to the conversation I had with Pastor Mike when I explained to him, “I lost a lot of money on this investment. I feel terrible.” He said, “Jack, here’s the question for you. Where could there potentially be a situation where bad roots produce bad fruits? Are there any bad roots internally going on in your heart that could be producing this outcome?” Bad roots produce bad fruits. I looked at him, and I thought about it.

It came out right away. I said, “All my life, I felt I needed to prove something. I needed to prove that I was good enough. I’ve always felt like I’m average. I needed people to think that I was successful and doing well.” He said, “You got to go work on those roots. The fruits that you have are going to be much more plentiful and bountiful. In all likelihood, you won’t be running into these types of situations once you resolve what’s going on inside.”

In closing, when you are doing something that you genuinely love, and you are doing it for yourself, then you are intrinsically motivated and have a healthy passion. You don’t need to force things or prove yourself. You are playing the long game. You are playing your own game. You don’t need to go out and buy the car to look good. You don’t need to go out and buy expensive purses, clothes or shoes, because you need to look good. You are playing your own game.

You’re not competing with anyone else. You are not measuring yourself against anyone else’s standards. Something that Dan Sullivan, the author of this incredible book, has noticed in coaching tens of thousands of entrepreneurs is that most of them are mentally here but they are wanting to be there. It doesn’t matter where they are now and how great their lives are. They continually wish that they were there. Many high achievers have a hard time being here.

Training Your Subconscious To Win

Although it’s great to have goals and vision and be driven, you are in the gap if you are here but you are wishing that you were there. Focusing on three wins before you go to bed it’s going to put you in the game mode right before you go to sleep. That’s going to create a powerful transition in your life where overnight, your subconscious mind is going to start working on having gratitude for those wins.

That’s going to build your competence and momentum. Those wins that you celebrate for yourself it’s going to create you want more wins. By focusing on the gains, looking backward, and what you have done, you are going to set yourself up for a more powerful future and ideals that you have but you are not measuring yourself against those. Remember, the gap is anything where it’s an unhealthy attachment to something external.

INWE 72 | High Earners

The Gap and The Gain: The High Achievers’ Guide to Happiness, Confidence, and Success

I hope you guys have gotten a lot out of this episode. I highly recommend that you get the book. I feel this is going to speak to all of your souls. It’s going to make a difference for you. I hope that some of the things I authentically shared help you maybe relate to things in your life where you are focused on there instead of being right here. Also, in your financial life when I give you ideas and things that you can do or give you examples of people that have gotten to there, where you want to be.

I hope that you keep in mind that where you are at in the moment, where you are at here, you are perfect, whole, and complete. You don’t need to be there financially to feel happy and respected and justify your own self-worth. You are exactly where you should be. Everything up to this moment, to this point in your life, all the gains that you’ve made, you want to celebrate those.

You are going to move forward with those celebrations of all those wins in a more powerful and constructive way that’s going to serve you over the long haul, overplaying the long game, which building wealth requires you to be thinking about all of the long game and the things that you’ve already done that have made a big difference for you. Thanks for reading. If you found value in my show, I encourage you to give me a five-star review. Share this show with people that you know could benefit from it. Share it on your social media platforms.

The only way that this show grows that I grow it is if I deliver incredible value to you, delivering great content that can help you to change your life. If I’ve done that, then I would encourage you to pay me back by sharing. All I’m asking is that to pay me back by sharing. I’m excited to push out my courses and my book to you. I will be launching those shortly. You would like the announcement in real-time. Please, make sure to subscribe to my Instagram, @IndestructibleWealth, and/or go to my website, and join the email list.

Whenever those new courses and the book are released, you will be the first one to know. I would love to hear your feedback. I’m excited. I have been working on this content for multiple months. I’ve buried myself in my office by myself. It’s a little bit depressing, to be honest, because I’m a social being, and I love commerce. I love making money. I haven’t been able to do that so far but that’s all about the changes I deliver and coming up with these new products that are going to help change people’s lives. Thank you so much. Again, have a great day.


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  Do you feel like you aren’t good enough, smart enough, or rich enough? I get it. High achievers, this episode is for you. Follow me on IG: @indestructiblewealth and visit me at for more resources. — Listen to the podcast here   Mind the Gap: A Reminder for High Earners Think about this […]