Billions of stars in the night sky

The Ultimate Guide to Making Billion Dollar Decisions

If someone offered me a billion dollars, but in exchange I would only have 6 more months to live, I wouldn’t take it. 

I know this scenario sounds weird, but hear me out. 

We’ve won the lottery of life. We get to decide whether we have coffee, water, tea, or strawberry and banana smoothie in the morning. These choices are amazing. Then you get to experience the deliciousness of your choice.

We get to choose what we do every single day. Sometimes it doesn’t seem like a choice because we can feel trapped or on auto-pilot, but that’s the beauty of this game. When we choose to be present and appreciate our options, we are able to make wise decisions. Seeing how valuable each choice is helps us begin to make billion dollar decisions. 

Being able to give my family a billion dollars would probably do more harm than good, especially my boys. The benefit of having the presence of a father who can love them and teach them about life would far outweigh the benefit of a sum of money.

I’ve interviewed billionaires who aren’t happy. These unhappy billionaires are consumed by money, a desire to live forever, drugs, etc. They aren’t free. They are trapped by their desire for more.

We all want great lives, but we have to take risks to make this possible. You come from a long line of survivors, otherwise you wouldn’t be reading this. Most of our ancestors survived out of fear. They didn’t take big risks because they didn’t want to get eaten by a lion or fall into a tar pit.

It’s time to spin this way of thinking. We can’t make decisions out of fear if we want to fly free. We can’t make rash decisions. We must choose wisely. This requires us to develop a process that fits our personality, so we feel comfortable and confident making important decisions in our lives.

Decision Process

“Nobody’s life is ever all balanced. It’s a conscious decision to choose your priorities every day.” – Elisabeth Hasselbeck

We must make better decisions faster in order to optimize for freedom/joy/happiness instead of fear. Scientists estimate that we make 35,000 decisions a day (1). Most of these happen because of our reticular activating system. We make many of our decisions automatically. For example, most of you probably have coffee every morning. That’s a decision that you made years ago and continue to make each morning. When we are aware of our decision-making then we can begin to dig into making better choices. We can’t realistically make 35,000 conscious decisions a day, but we can appreciate how our brains work and figure out how to improve our important decisions so we don’t procrastinate or behave impulsively out of fear.

We might not always make the best decisions, and when that happens it is important to learn from them and then let go of our regret. We tried our best. It didn’t work out. Now we have another opportunity before us and we can make the most of it. This is how you cultivate billion dollar decision making.

This is how I look at my life. Every day is an opportunity to meet someone that I can help or someone who can help me, or even better… we both help each other. It took me many years to cultivate this mindset, but it was worth every moment of practice because I’m happier and living with more purpose than I ever have in my life. I’m not a billionaire. I’m happier and more content than a lot of billionaires. 

I’ve done a lot of deep work to expand my consciousness (journaling, therapy, meditation, Yoga, etc.), so I’m not chasing after things that don’t bring me freedom. In my opinion, billion dollar decisions are optimizing for fulfillment, not cash. It’s about inner wealth. I am truly wealthy when I can stay calm because my low mileage minivan transmission breaks down. Yes, I proudly drive a minivan because I don’t care what other people think of me. I also know that I can afford a new transmission because I’ve been wise with my money.

A healthy person, mind and body, is a result of a series of daily healthy wins, not one big moment. Good health isn’t an event; it’s a habit. When we realize this fact, we make billion dollar decisions because we know that our future self will appreciate our decision making.


“We see the world, not as it is, but as we are──or, as we are conditioned to see it.” – Stephen R. Covey,

There are no perfect choices. This is why we need to embrace mistakes. We can’t be afraid to look like a fool or worry about what we’ll lose. Every choice is an opportunity. This mindset took a long time to cultivate. I still catch myself getting caught up in my ego, hiding from the potential pain of a bad outcome. I’ve been able to make better decisions faster because I take some time to think through my options, understand there will be obstacles, accept them, get excited for the opportunity and take action on it, so I see how my effort is making an impact on myself and others.

This was only possible because I’ve dug into the stories that I tell myself. These stories are guiding most of my choices. I witnessed myself acting out of past recordings, and I decided that I no longer wanted to act out of anger, fear, or sadness. I wanted to open my ability to see the situation for all its beauty. I decided to appreciate the options that I did have and make the most of each opportunity by fully enjoying it.

Over the past few years I’ve held myself back by jumping from shiny objects, to procrastination, back to shiny objects. I spin my wheels and don’t dig into a project long enough to create leverage in my career. I saw this pattern happen again and again. When I was honest with myself, I realized that I suffered from perfectionism. I was afraid to dig deep, put all my energy into something and still possibly fail. If it wasn’t going to be perfect I would avoid it. This caused me to fear the best teacher that I could possible have in my life: mistakes.

Once I understood that I could use different lenses to help navigate my weakness of perfectionism, I could create a plan to take action. A plan that aligned with my personality, values and goals. I had to start with tackling small fears because I knew they were holding me back from being happy and reaching my goals. One thing that felt intimidating to me was the idea of talking to people in an elevator, so I created a hypothesis.

If I could talk to people in elevators, I would feel more free. I used to just lean against the wall and not say anything, look at my phone and count down the seconds until we could exit. That was my lens, but I had to cultivate my new lens of not caring what other people thought of me. In the same way that Elton John would switch glasses between acts to help him bring fresh energy to the second act, I could find a new mental model to help reframe how I viewed the situation. I decided to be curious about the people in the elevator instead of avoiding their potential judgments of me.

I created a list of questions to ask people:

  • What brought you to (insert city name)?
  • How is your trip going? 
  • Where did you get those sneakers?
  • How’s your day going?

These interactions only last 10-20 seconds, but it made the elevator ride much more enjoyable. I made the billion dollar decision to have fun with the situation instead of avoiding it.

Eventually I stopped worrying about what to say in an elevator. I just said whatever would come to my mind. I recently went on a business trip and asked all kinds of questions to different strangers. Out of over 20 people only one person acted like a jerk. They sighed and answered and that was that. I didn’t stop. I was on a mission to work on my fear.

My lens changed so much that I looked forward to getting on an elevator with a stranger and learning one new thing about them. My stress is lower, too. This practice has helped me stop worrying about what people think and focus on making the best of an uncomfortable situation.

Compounding Interest

“Little disciplines compounded over time make a huge difference.” – Orrin Woodward

Every choice I make matters. It’s how I must live my life. I try not to let my ego get too caught up in whether it’s a good or bad choice. It’s the best choice that I could have made given my circumstances. When I make a good choice I can usually see how my past decisions influenced me. This goes for bad choices as well. Our past stories are strong and when we use our metacognition we make better choices. All that means is that we are wise in our decision making. We aren’t just reacting to a situation; we are responding to a situation from a place of calm and curiosity. 

Every decision compounds on the next one. When I take my dog for a walk, it helps me relieve stress and makes my dog happy. He loves his daily walk. I could have made the choice to stay home and work, but that would have been a poor choice for me. There is a consequence when I focus too much on work and forego my health and my dog’s happiness. This one decision could lead to weeks without going for a walk, so that’s why it’s so important. This is a negative (costly) decision.

This is where it starts to add up and become billion dollar decisions. When you are aware of the choices that you have and take action from your values, then it doesn’t matter what other people think. You are making the best choice in that moment and then riding the wave as that decision unfolds.

“I think the most important question facing humanity is, ‘Is the universe a friendly place?’ Albert Einstein

You may be thinking, not every decision matters. You can fight me on this, but you are choosing to not see the value of every choice that you have. You are losing an opportunity to shape the moment with the lens that you are influencing every moment of every day. That’s why every decision matters. It shades your lens a little lighter or darker with every choice.

The best way to change a habit is to care about your desire to change. If you don’t care then you won’t put in the energy to make the change possible. I’m not saying you should deliberate for hours on whether to have coffee in the morning. I’m saying, know that you are making that choice and be aware of how it affects you. Take a half of a moment to appreciate the beauty of this choice. This is a game of improving your self awareness. If you master this game it gets easier to make better decisions. 

The Value of a Good Decision

“When you make the right decision, it doesn’t really matter what anyone else thinks.” Caroline Kennedy

Now let’s zoom out. If you make a choice to drink a glass of sparkling water instead of Coke, then this will affect the next few hours of your life. You might have had more energy from the sugar and caffeine, but there will be an energy crash at some point. You know this, but the immediate gratification of a Coke is very alluring. 

Your past determines many of these choices. You might think of that Coke that helped you get through that tough afternoon when you felt sleepy and you needed to give an important presentation. The past you says, “that Coke is a good idea because it brought more energy to my last presentation.”

You might be thinking that you have a big presentation today and your brain is wired to think that Coke is a good idea. This is a hard habit to break. Now if you choose Coke today then you are deepening this behavior. If you choose to drink a glass of sparkling water and go for a 15 minute walk, then you are starting to rewire your brain for a healthier future life.

This is a billion dollar decision! 

Your future you will thank you. When late afternoon comes and you still have energy because you don’t have that Coke crash then you supported your future self.

We aren’t wired to support our future selves. We are wired for the present moment. We want joy now, not in four days, four weeks or four years.

Your Habits

“You do not rise to the level of your goals. You fall to the level of your systems.” James Clear

So how do we wire our brain for billion dollar decisions? 

Good question. I’m glad you asked.

It starts with appreciating how our future self will feel instead of reacting to our current heightened emotions. Whether it’s joy, fear, anger, etc, we must respond from a place of calm. Our center.

It’s important to make time to reflect on your decisions. One of the biggest changes I’ve made in my life was understanding my decision making process. You can do this with big or small choices. 

I don’t know about you, but there are decisions that I made 10 years ago that still make me cringe. Don’t start with these at first. These memories are usually too painful. Start with the small decisions you regretted like that big bowl of ice cream before bed.

It starts with looking at a decision that you made and understanding how it came to be. Yesterday, you might have chosen a Coke instead of sparkling water, which is fine. You can’t take it back, but you can review the situation and decide how you’ll act next time. When you decide to have that sparkling water next time, then you plant a seed in your brain to help your future self. This seed will help you say no to that Coke next time.

The more aware you become of how each choice affects you, the easier it will be to make better choices. When you do choose sparkling water, you don’t need to throw yourself a party. What you need to do is review whether or not this was a good choice for you. You help yourself understand that if you make this choice again, your “future self” will be happier. Let’s say you gave the presentation but your energy level felt too low, so maybe the adjustment is a cup of green tea because it has less chemicals and sugar than a Coke.

Your hypothesis is that if you drink green tea in the early afternoon, it will help boost your energy for the presentation without causing you to crash too hard later.

You strengthen this memory by reflecting on your choice. This is where it gets fun. You can then make this choice faster next time. You begin to see how green tea helps reduce your late afternoon energy crash and lowers your stress level too, so you decide not to buy Coke anymore, so it’s no longer in your home. You see the pattern and make better choices faster.

This is the effect of compounding interest of a good choice (AKA processing your stress more often). It goes from a million dollar choice to a billion dollar choice.

You are also reducing your medical costs because you start to lose weight and are less stressed. You are happier, healthier and have more energy.

Do you see how this is a billion dollar decision?

You start to make decisions that support your health. You make better choices to support your relationships. You make better decisions to support your future happiness.

I’m going to be candid. I’m working on my patience with my family, business and with myself. I’m not very patient. I get frustrated quickly and it has hurt my relationships, especially with my oldest son. I want him to become a well-rounded adult, but I’m too quick to get after him if he is off track. I’m seeing the value of choosing to be more patient with him and our relationship has improved. This choice to improve our relationship is a billion dollar decision, probably a trillion dollar decision because I want us to have a great relationship. It means the world to me.


“Pay attention to the intricate patterns of your existence that you take for granted.” – Doug Dillon

My billion dollar decision is to focus on being more patient with my loved ones. I know it will help my future self. I can begin to recognize when I’m letting my past stories turn me into the father that bullies his son to stay on task when emptying the dishwasher. Just noticing this is half the battle. Now that I notice this issue, I can put a plan in place to practice making better decisions.

This is not easy work. Habit change is hard, but my relationship with my son is a billion dollar decision. If I continue to act the way that I do, he isn’t going to want to spend time with me when he is an adult. I have to make a choice to be more patient with him, so my future self can enjoy a nice glass of sparkling water with him on the back porch in 10, 30, 50 years.

I’m working on digging into these patterns and creating habits that support my patience. 

This is true for my business as well. I like shiny objects. I say yes to every opportunity and it ends up burning me out. I lose my way and my confidence shrinks.

I’m also working on these patterns so I can be more intentional about what I say “yes” to and what I say “no” to, so my future self can be happier.

This is why every decision matters. Every decision eventually adds up to a billion dollar decision. You are worth more than a billion dollars to your loved ones. You deserve to have the best possible life with them based on your values, while optimizing for joy and health. 


You are priceless. Your life is worth more than a billion dollars. If you try to put the value of your life into perspective, someone who is dying of cancer and has a week to live would probably give a billion dollars to enjoy a quality of life like yours. You’ve won the lottery of life and it’s up to you to find ways to appreciate and grow it.

Are you ready to take the first step toward making billion dollar decisions? I’d like to challenge you to respond to the following journal prompts at the end of every day for the next 30 days. Try to do it before your evening meal. I call it the Rate Your Day Routine.

Answer these three questions: 

  1. What are three things you did well today?
  2. What did you learn about yourself? (No judgment, just curiosity.)
  3. How would you rate your day on a scale of 1 (Terrible) to 10 (Amazing)?

Just add this five minute routine to your calendar. If you end your day at 5pm, then send a meeting invite to yourself for 4:55. You have to build that habit to make lasting change.

After 30 days, you’ll see your strengths and weaknesses more clearly so you can make improvements to your decision making process.

You can get the Rate Your Day Mini Guide by joining the Dig to Fly community. You’ll also get access to a bunch of guides (Dig to Fly Guide, Leadership guide and much more). The guides are all designed  to help you make better decisions faster.

After doing the Rate Your Day routine for just a week, you’ll start to see patterns that will change your life. You’ll begin to make billion dollar decisions instead of costly decisions.

As you continue to make better and better decisions, you’ll notice that you’ll also speed up your decision making process. You’ll know your weaknesses and you will be more likely to utilize your strengths. You’ll use your systems to make better decisions faster. You won’t procrastinate because you will be clear on how each decision will help your future self.

It starts with small steps. You might be at $100 decisions right now, but soon you’ll be at $10k decisions, then $100K and before you know it you will be well on your way to $1 billion decisions that lead you to live a wealthy life filled with gratitude, love and support. A life that allows you to feel comfortable in any situation, eventually being evolved enough to be loving and grateful for any situation that life throws at you because you get to choose how you view it. 


  1. Mindless Eating: The 200 Daily Food Decisions We Overlook. Brian Wansink and Jeffery Sobal. Volume 39, Issue 1.

Images courtesy of Unsplash: @invadingkingdom, Paul Skorupskas, Ameer Basheer, Prophsee Journals, Yun Xu