“I’m not sure this business is for me,” he said.

“Why is that?” I asked.

I’d been mentoring TJ, the son of one of my partners, for about a year. I was helping him develop a small business that I’d started the year before. His initial motivation had flagged a bit in recent weeks. I wanted to know what was bothering him.

“I just don’t see any way it can make me a billionaire.”

“A billionaire? Why do you want to become a billionaire?”

He proffered a few unconvincing answers. Finally, he told me the truth: If he was going to go into the business, he said, he felt he needed to surpass his father’s success. At the time, his dad was worth hundreds of millions of dollars.

“Man,” I said. “That’s a heavy burden.”

Wealthy Is Not a Number 

Self-improvement books and magazines are replete with the same advice: When it comes to setting any goal – especially a “get rich” goal – make it big and make it specific.

When I first began thinking about building wealth, that idea didn’t occur to me. Today, looking back, I’m glad it didn’t. As I see it now, there is only one minor benefit to that kind of goal setting and many major downsides.

First: Really big goals, like “becoming a billionaire,” are statistically as realistic as deciding to become an NBA MVP. If you are amazingly talented, extraordinarily hardworking, and incredibly diligent, you might be able to bring your chances of success up to one in ten thousand.

Second: Since your chances are so infinitesimally small, the likely result is that you will be seen by virtually everyone you share it with – whether it be your family, your friends, your potential partners, or your employees – as a nutter.

Third: You are defining a career of failure. From the moment you set the goal to the moment you give up on it (or die), you will be living as a wannabe. That is not good for the ego.

But it’s not just the bigness of a billion dollars that was wrong with TJ’s goal. Again, I know that most self-improvement pundits say the opposite. But specific numerical goals will give you only the briefest satisfaction if you achieve them, followed by another long, frustrating period of chasing some new, more ambitious number.

Numerical objectives can be very helpful in trying to achieve (or motivating others to achieve) specific short-term objectives. But for the big things – like life satisfaction – they are useless and even counterproductive.

The moment you achieve them, you experience about 24 hours of exhilaration. After that, the good feeling is replaced by an anxiety-ridden ambition to reach a new goal.

When I started to make “decent” money, I set my first specific financial goal: to pay off my mortgage, which was about $150,000. I did that fairly quickly – within 18 months. As soon as it was taken care of, I set another goal: to put aside a million bucks in savings. I achieved that goal the following year. But by that time, I was thinking about selling the house I finally owned free and clear and buying another one that was five times more expensive and would require me to get another mortgage.

Something similar happened every time I set a specific financial goal. Two days of fun – the first day and the day I hit my goal. And in between, months or years of angst and obsession.

Then, sometime before my 50th birthday, I had a conversation with a friend that helped me jump off this vertiginous mental merry-go-round. It led me to a simple idea that changed my life. Maybe it will have the same effect on you.

The idea is this: Don’t strive to attain a certain amount of wealth. Strive, instead, for the feeling of being wealthy. 

It’s a bit trickier than it sounds.

When I say the “feeling” of being wealthy,” I don’t mean the way you might feel when you picture yourself owning the things that are usually associated with being rich – the houses, the cars, the yachts, etc. I mean the way certain experiences make you feel.

For me, the feeling that I had always associated with being rich was having a sense of ease and independence and possibility. And the experiences that gave me that feeling were such simple things as having a drink in the lobby of a beautiful hotel… reading a book on a comfortable chair in a library… or smoking a cigar on a walk on the beach.

Having identified the feelings that I associated with being rich, it was easier to give up the desire to keep hitting higher financial targets.

I realized that I didn’t have to pay off my mortgage to be happy, I just had to be on the way. I didn’t have to have a million or a hundred million in the bank. As long as I had enough to pay the bills, I could have all the relatively inexpensive “rich” moments I wanted.

I wrote a book about this, called (unimaginatively) Living Rich. The premise was that if you pursue the feelings of being rich rather than some specific financial goal, you will find that you will be able to feel rich while you become rich.

As I said, this was an idea that changed my life. It did not change me immediately and 100%, but it gave me a way to think about my life that put everything into focus. Decisions were easier to make. Mistakes were easier to admit to. Urges and impulses were easier to resist – especially those tied to the ambition of making more money.

If you have specific financial goals that are stressing you out, this is something you might want to think about.

Start with the best moments of your life – the times when you felt like “This is what it’s all about.” If, like me, they were about simple experiences, you will probably also associate those experiences with the sorts of feelings I have described. And if that’s so, welcome to the don’t-worry-be-happy club.

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