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What Scares You the Most About Being Rich?

September 9, 2024

This past week I was having a conversation with a new friend when he gave an answer that stunned the rest of us.

“The truth is, I don’t think I’ve earned it.”

We had just invited him on a once-in-a-lifetime, bucket-list vacation, sailing on a catamaran in the British Virgin Islands.

Now, this is a very successful entrepreneur to whom I was talking. He’s spent the last two decades building an empire, including completing a very sizeable acquisition of a competitor this year. You’ll note, as I did, that he didn’t say that he couldn’t afford it, but that he hadn’t earned it.

Sadly, this is an all-too-common story I hear from so many of the founders I talk to.

His statement underscores a universal truth that plagues so many of us:

We will only allow ourselves to be as wealthy as we believe we deserve to be.

Of course, being truly wealthy has nothing to do with the zeros in our bank account. You can be incredibly rich without a lot of money or be a multi-millionaire and still be poor.

Being wealthy starts with owning our value.

If we aren’t able to own our value, we will always limit our earning potential as well as limit our enjoyment of what we do earn.

I know this because I used to have trouble owning my value.

No matter how much money I made, I always found a way to empty my bank account as quickly as I could fill it.

Now, I didn’t realize this was what I was doing. I had a quite elaborate narrative to justify my behavior. It’s not like I was irresponsibly spending; I was investing in my future, or so I told myself. I believed I was putting my money to work, optimizing every dollar for growth.

But the fact remains that every time I would get a windfall, I would find a new investment and redeploy the capital as soon as it came in.

This behavior also served me in a way. By constantly putting my back against the wall, I would be even more motivated to work and earn more.

That is until it all came crashing down.

I had finally flown too close to the sun. I had invested in a distressed company and was hemorrhaging cash to keep it afloat. On top of that, I was building my dream home and cost overruns were mounting rapidly.

I had to face a harsh truth: I was great at making money, but terrible at keeping it.

I knew something had to change. I was no longer willing to live with the constant stress of always having to earn more.

When I dove in to uncover the root of this self-sabotaging behavior, the answer was shocking.

Underneath it all, I didn’t believe that I deserved it.

Why does AI always make me wear a suit, even on a boat?

This deeply rooted belief was not obvious and maybe even unbelievable to the casual observer. By all accounts, I was living an Instagram-worthy life. But my behavior betrayed the carefully crafted veneer of success. I was addicted to risk and, as a result, injecting chaos into my life.

The truth is, we all have insidious subconscious narratives that keep us from living up to our true potential. I call these patterns our Cognitive Financial programming or, more casually, our money stories.

Uncovering these narratives requires us to face uncomfortable truths about ourselves.

My favorite question to reveal the limiting beliefs that keep us stuck:

What scares you the most about being rich?

For some of us, the answer may be that we are afraid that our friends and family may think differently about us or, worse, abandon us altogether. This common limiting belief is known as the fear of success.

Others may fear being rich because we could lose it all, and we are afraid of the pain associated with falling from grace.

One of the most common ways that we limit ourselves is the widespread idea that we should be happy with what we have and that we don’t really need anything more.

While gratitude is an integral part of living a fulfilling life, there is also a particular comfort in telling ourselves that we should be happy with what we have.

When we believe this story, we casually let ourselves off the hook from reaching our true potential.

Imagine the courage it would take to acknowledge and own the idea that we have the true power to create anything we desire.

For most of us, it would be deeply unsettling to actually believe that we can create a life beyond our wildest dreams.

In doing so, we strip away all of the excuses and lies that we tell ourselves on a daily basis. The most common way we do this is by telling ourselves that our dreams require sacrifices that we are not willing to make, and therefore, it is better to stay where we are and be happy with the status quo.

We tell ourselves that we don’t want to scale our business because we don’t want to work 80-hour weeks and sacrifice precious family time.

We allow ourselves to remain unhealthy and out of shape because we don’t want to sacrifice our favorite foods or because we simply don’t have the time in the day to work out.

We remain slaves to our vices, such as alcohol, because we tell ourselves that giving them up would mean giving up fun with our friends.

So we stay small and unfulfilled, all the while telling ourselves that we are doing our best and should just be happy with where we are now.

But ask yourself:

Who or what could you become without these stories?

With this simple yet powerful question, we set ourselves on the path to becoming the best version of ourselves. When we take ultimate responsibility in this way, we acknowledge that the only sacrifice required to reach our dreams is the story of our current limitations.

We can scale our business without working endless hours, but it requires systems and leadership skills that we may not currently possess.

We are only 90 days away from being as healthy and fit as we would like by creating a new identity of a healthy person.

We can give up the vices that hold us back at any time by embracing the fact that we can create fun in any way that we choose.

We can be as wealthy as we want to be and create any life we desire, but we must first own our power.

While giving up the stories that keep us safe can be uncomfortable, I’ve also found that no longer lying to myself brings a feeling of true authenticity.

Instead of writing off my biggest dreams as impossible, I simply acknowledge that I currently lack the skills (or desire) to make them a reality, or else I would already have achieved them.

I now own the fact that I can become or create anything I choose, and you can, too.

What will do you with this secret?

What will you create?

Who will you become?

The answer lies on the other side of our fears.

To our future selves,

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