shutterstock_123579487In the last few months, I’ve had several opportunities to share a meal with some extremely wealthy people.

We’re not talking average millionaires here. We’re talking titans of industry, tech wizards who cashed out big time, and folks who inherited so much money that they’ll never have to work again unless they choose to do so.

I grew up middle class– comfortably middle class, but middle class nonetheless– and while I’ve dined with big-name politicians and highly successful lawyers, celebrities and supermodels, famous musicians and actors over the course of my life, I’ve never before this year dined with outright billionaires.

What has fascinated me about the experience of getting to know people with THIS MUCH MONEY are two things: 1) what they believe about money as a part of how they acquired it or since, and 2) how they have dealt with success.

The answers are as varied as the people themselves, but as I’ve spent some time thinking about what I learned from these conversations and interactions, some common themes have emerged. And the experience has taught me some very important lessons in my own life that have radically shifted the ideas about money with which I was raised and that I have carried around for far too long.

Observation #1: Money is all about perspective.

One of the most critical things I’ve incorporated over the last few months is the idea that feeling wealthy or poor, feeling successful or buried in debt, feeling financially knowledgeable or like a financial dumbass, is all about one thing: perspective.

Some of the folks I’ve encountered who are wealthy into the billions still feel poor. They look at all they’ve acquired– multiple homes, cars, yachts, staff, and caretakers, to name but a few– and feel nothing but weighed down.

Others, however, feel entirely liberated.

In a similar fashion, I’m working with a client right now who earns in the mid-six figures but has over $100,000 in debt. This amount of debt– acquired over many years of education and not-so-careful spending– has tortured him for years. It has played upon his self-worth. It has ruined relationships. And even when he stopped adding to it, he still felt guilty for having “been so stupid” as to run it up in the first place.

When he and I started talking about his views on debt, he realized that the amount of debt was fundamentally nothing when viewed in the perspective of his total earning capacity. But cutting his expenses and carefully minding his budget, he would actually be able to pay down that debt in a year or less.

In other words, his decision to be weighed down by money was a choice.

Say it with me now: your decision to be weighed down by money is a choice. (tweet this)

And no matter the circumstances in which you find yourself, I can guarantee you that if you choose to focus on your burden rather than your potential, your burden will increase and your potential will lessen.


Observation #2: The person you are does not change when you acquire radical success– but it might amplify.

One of the interesting things about working with people as coaching clients who are suddenly wildly successful– and I’ve had a few at this point– is how they adjust to never having to worry about money again should they choose not to (see Lesson #1).

One of my coaching clients who sold a business that netted him hundreds of millions of dollars has remained an incredibly grounded, kind person notwithstanding his success. He contributes all the time to charities, has joined the Board of an organization that is close to his heart, and throws fundraisers that are incredibly successful in their own right, to the benefit of all.

In some sense, he has become kinder, more grounded, and more aware as a result of his success. Wild financial success has amplified the man he already was.

Others experience the same amplification, but in different directions. For instance, I encountered an old friend at a dinner party this summer, someone who’d unexpectedly inherited a large sum of money from a parent she never knew. She had always been somewhat insecure and concerned with her appearance, and her influx of money hadn’t changed that. In fact, it had made it worse. Despite her young age, she’d already undergone several obvious cosmetic procedures, and was so concerned about whether her high-end designer outfit fit properly that she could talk about little else.

Her palpable insecurity was sad and unsteadying, and had alienated her more from other people, not less, as she became wealthy. Her financial success had amplified who she already was, by choice.

The moral of these experiences for me was that you can’t expect that wild financial success will solve what ails you or change your perspective of the world radically.

What you carry inside you follows you for better or worse, no matter how wealthy you become. (tweet this)

In other words, if you’ve got challenges you need to face, money is not a panacea to what ails you.

Observation #3: Financial success and the idea that money is no big deal often go hand in hand.

In a couple of my conversations with super-rich folks this summer, one of the things I observed was that they all seemed to assume that eventually, one way or another, success would find them. Earning money was, in other words, no big deal.

Personally, I’ve always envied people with this outlook, because I was raised to believe that money only comes through struggle, and that you have to work very, very hard, through painful and exhausting circumstances, to achieve financial success.

My clients and the folks I’ve encountered have proven otherwise. Note: this does not mean that they didn’t work hard to get to where they are.

The difference is that in most cases, they didn’t see it as work.

Wild success came to those who followed what they loved. Who created products and services that the world desperately needed. Who leaned in to their talents for the love of it, rather than the effort. Who leapt on opportunities as they arose without doubting their own ability to follow through.

Who went for it, in other words.

Who believed that the money would follow.

Success follows those who leap in pursuit of their dreams. (tweet this)

The lesson I have taken from all of this is that if you believe your success is inevitable, it will be.

Observation #4: Freedom is internal.

Don’t get me wrong, there’s no question that there is a certain kind of freedom that comes from wealth– including, enviably, the ability to travel pretty much whenever you want.

But I’m not talking about that kind of freedom. I’m talking about freedom from fear.

Some of these super-wealthy people I’ve encountered are STILL living in a state of fear that they will one day lose it all and end up homeless, although the prospects of that are exceedingly slim.

And that fear keeps them from connecting with others, from enjoying their success, and from truly feeling free.

Your freedom is internal. No amount of money can give it to you.

And you can choose, in any given moment, to feel free in your pursuit of happiness.


Each of these lessons has taken me to a better place in terms of my own relationship with money, both in terms of the desire/need for it and the experience of it. Hopefully it will for you as well.

In the comments below, I’d love to hear from you about the money lessons you’re putting into place in your own life. Let me know!

Wishing you a week of wealth and abundance in all its forms.

All the best,


PS. This week, I made a radical offer to my mailing list that I’d never made before. Make sure you’re on my list so you don’t miss the next one! Just enter your info above.







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