I’m Rich and Successful. And Unhappy. Now What?

Congratulations! You’ve done it. You have achieved something that most people will spend their lives yearning for and never realizing. You are rich, potentially famous, and well respected in your field. You’re a CEO with a successful company, a founder who made a big exit, a famous actor or musician or author with lots of fans. People have written articles about you and your company. Maybe you’ve picked up an award or two or a prestigious fellowship. You get requests to keynote at big conferences. Perhaps you even found this success through creating a business that has a positive social impact, that helps other people or changes the world for the better. And yet…

When you wake up each morning, you dread your day, the same way you did when you were just starting out, as an inexperienced entry level employee. When you come home to your fancy, well-designed house, each night you begin to realize you have no one to come home to anymore because you placed your work ahead of your relationships. Or you barely know your kids because someone else has been raising them.

You fill your time with meals at the best new restaurants, get tickets to the hottest shows, have box seats to your favorite sporting events. Your Instagram account is filled with envy invoking travelgrams, but when the camera is off you wonder “what is the point of it all?” And then the guilt begins. It’s been a long time since you’ve had to worry about where your next paycheck will come from and whether you’ll be able to pay the bills. You consider how other people live paycheck to paycheck, how a health problem could ruin their financial security in an instant. You wonder, “How can I be so unhappy when I have so much and so many have so little? How can I be so ungrateful?”

This starts a downward spiral of questions like, “What if my success is unsustainable — I was a one trick pony, and that trick is already getting old?” “What if I was never really good in the first place and I just got lucky?” “How will I ever keep up with all the other wealthy, successful friends I’ve made along the way?” “How can I keep my kids humble and teach them good values, when everything is being handed to them?” or perhaps worse, “What if the people in my life only love me for my money/fame/what they think they can get for me?”

In my career I have spent a significant amount of time with some of the most successful people in the world and I have witnessed first hand that there is never enough money or stuff. I was once sitting with two self made billionaires, with one informally pitching the other on investing in his new venture. When asked why he needed to raise so much money, the one doing the fundraising said, “Being a billionaire isn’t what it used to be. It doesn’t even guarantee you a place on the Forbes 500 (richest people in the world) list anymore.” While this is a dramatic example, even those with more limited success succumb to the comparisons to their peers to determine where they stand.

The reality described above is all too common among the intellectual and social elite. It is the result of people being driven by extrinsic motivation rather than intrinsic motivation. As we move farther and father towards having our fulfillment and meaning based on external factors over which we have little or no control, we begin to lose touch with the things that truly make us happy and satisfied (if we ever were in touch with them in the first place). The problem with these extrinsic goal posts is that they are in constant motion — obtaining the thing you want just leads you to want something more.

So how do we get off the hamster wheel? How do we begin to assign meaning to the things that are going to make us truly and sustainably happy and give us purpose in our lives? The answer is different for each of us. Unlike extrinsic motivations that assume “more of everything” is the best motivation for everyone, intrinsic motivations are uniquely ours. In order to find out what yours are, you need to strip away your dependence on external goal posts to tell you where you are, and instead listen to your intuition and instincts.

The Japanese have a concept called “Ikigai,” which loosely translates to, “that which gets you out of bed in the morning.” It is based on 4 elements:

1. That which you love

2. That which you are good at

3. That which the world needs

4. That which you can be paid for

Sometimes it is easy to explain something by demonstrating what the absence of it produces. Below are descriptions of what happens when you are missing one of the Ikigai elements. Do you recognize yourself in any of these?

Without Pay: Volunteer — You love your work, you know you are good at it, the world (or your company or other people) needs it, but no one will pay you for it (or the pay isn’t enough to support you).

Without Need: Job Searcher — You have a strong skill or ability, you love doing it, and it is something that other people get paid for, but unfortunately there is limited demand for it, so you are constantly searching the classifieds or your company’s internal listings to find that rare opening for this role.

Without Skill: Perpetually Entry Level — You like doing the type of work you are doing, there exists a role that you can fill, and you are paid for it. Unfortunately, you probably aren’t being paid very much because if you aren’t good at something, you probably aren’t getting many chances to progress in that field.

Without Love: Uninspired Workhorse — You are good at your job, people need you to do it, and you are being paid very well, but you are unhappy because you simply don’t feel inspired or passionate about what you do.

Usually, people who have tremendous financial success and are still unhappy fall under the “uninspired workhorse” category, and could thus benefit from exploring what they love. Here is a post that includes a list of questions (they are about halfway down the post, if you want to skip straight to the questions) to begin the process of finding your intrinsic motivations, starting with what you are most passionate about.