When Will You Have Enough?

🚀 The pursuit of happiness, success, and wealth - Issue #199

Over the past few weeks, I’ve been asking people questions related to money, success, and happiness. For example:

  • Would you be willing to reduce your lifespan by 10 years to become extremely successful?

  • Would you be willing to reduce your lifespan by 10 years to become extremely wealthy?

  • Would you rather be extremely happy in your personal life, but have a mediocre career, or extremely successful in your career, but have an uninspiring personal life?

As you might imagine, I received a range of answers and clarifying questions (e.g., “When do I get the wealth?”). I wasn’t looking for the right answer. I wanted to have a conversation about pursuing what matters the most; however people define that.

When we discuss success and wealth, we often describe it in terms of prestige. We care about how others view us, and we evaluate our standing relative to them.

I frequently hear a lot of “more than” language, but rarely hear mention of “having enough.” I suppose that’s to be expected when we begin our careers and even later when we have our heads down in the middle.

I remember that feeling of “just getting started” in my life when I was much younger. Of course, I didn’t have enough. How could I? I hadn’t even started my real career, found a life partner, or had children.

I knew that I wanted more.

  • More money.

  • More success.

  • More happiness.

  • Well… more of everything.

More is always better, right?

I don’t think that I ever considered what enough would be, especially at that age. More money, success, and happiness is always better than less. How could you ever have enough?

It was only when I was older and had tasted some success that I realized that there is a tipping point. Too much of a good thing becomes a bad thing. Going beyond having enough introduces new issues.

We also fall into the trap of comparing ourselves to a whole new level of peers. Young me would have been thrilled with my success, income, family, homeownership, and luxury car. But, older me was now comparing my success and wealth against people who had much more than I did.

I was doing OK, but I wasn’t a multimillionaire or billionaire. I had a good home, but I didn’t have a mansion in Palo Alto. I had a nice car, but I didn’t have a Lamborghini. I traveled internationally, but I didn’t fly on my private jet.

I know that this may sound silly. But that’s the kind of crap that happens when you feel like you never have enough. No matter how much you achieve, there is always someone above you on the ladder.

I wasn’t the only one complaining about my lack of immense wealth and success. I was surrounded by people who craved it and pursued it. It’s called the “rat race” for a reason.


The Hedonic Treadmill

The “hedonic treadmill” — also called hedonic adaptation — refers to our tendency to quickly return to a stable level of happiness despite major positive or negative events. That’s why someone is thrilled to receive a promotion, but can be depressed again at work a couple of weeks later.

"Whatever we have, we tend to get used to it. So no matter how awesome our lives might be, or what wonderful things come into our lives, we tend to get used to them over time, and the pleasure that they provide gradually diminishes." — Dr. Elizabeth Dunn, Psychologist

It’s also why more is never enough. The excitement of a big home and fancy car wears off. You look over the fence at your neighbor’s larger home and fancier car and feel envy.

In some fascinating research, psychologists compared major lottery winners with a control group to measure their happiness. You might expect the lottery winners to be happier than the average person. After all, money was no longer an issue!

However, they found that the winners no longer enjoyed the pleasures of ordinary life as much as they had before. Once the spike of joy from winning had faded, they drifted back to their previous level of happiness.

When you are stuck on this treadmill, you are always seeking your next high. You still want more. When you do experience success, the delight is fleeting.

Can you escape the hedonic treadmill? Yes, it does seem possible. It starts with redefining what success means.


What does success mean for you?

It is essential to make your definition of success about what is right for you vs. comparing yourself to others. It’s helpful to learn from a “career hero,” but it is a mistake to try to replicate their path and life.

Comparison is the thief of joy.” — Theodore Roosevelt

You also may not want to live the life that they are forced to live to have what they have. I’ve certainly seen that with some extremely successful people in my life. You may think that it sounds cool, but having a bodyguard follow you around 24x7 kind of sucks.

When I work with clients one-on-one, I ask them to visualize their life 20-30 years from now. They create a detailed description of their ideal lifestyle at the end of a successful career.

I do this so that we can uncover what their vision of success is. For example:

  • What have you accomplished by this point in your career?

  • Are you still working?

  • What are you doing for work?

  • Where are you living?

  • What is your home like?

  • How do you spend your days and nights, accounting for every hour?

  • With whom do you spend your days?

When people are introspective and thoughtful — without resorting to simple comparisons to others — I’ve found that their goals are usually reasonable. Their vision of success is typically modest.

People want to have accomplished something, be respected, have an impact, enjoy the work that they do, and feel a sense of fulfillment. So far, no one has said that they want to be the next Elon Musk or have more money than Jeff Bezos.


How much money is enough?

Poverty is a terrible thing. Being poor is a daily struggle of survival.

When you don’t have enough money, you do suffer. You have no sense of security and safety. The basics of food, shelter, and warmth are never a given.

I wouldn’t write a newsletter about pursuing career success if I thought that we all should lead lives of deprivation. It’s true that I do admire minimalism. But, I see it as a means to end, a way to way to break free of needless consumerism and pursue more freedom in your life.

Lack of money contributes to many problems. But making more and more money doesn’t solve everything. Unfortunately, wealth beyond a certain point introduces a host of new issues and steals joy.

Researchers have examined the correlation between money and happiness. This study, in particular, was based on data from the Gallup World Poll, which is a representative survey sample of more than 1.7 million people from 164 countries. The estimates were averaged based on purchasing power and questions relating to life satisfaction and well-being.

It’s been debated at what point does money no longer change your level of well-being. We found that the ideal income point is $95,000 for life evaluation and $60,000 to $75,000 for emotional well-being.… there was substantial variation across world regions, with satiation occurring later in wealthier regions for life satisfaction.” — Andrew T. Jebb, Ph.D.

The study also found that making even more money beyond that threshold was associated with reduced life satisfaction and a lower level of well-being. Yes, money is essential for meeting basic needs and purchasing some comforts, but only to a point. After that, people start chasing material gains and comparing themselves to others, which negatively impacts happiness and well-being.

We tend to pursue more promotions and raises. We want our income to increase year after year. But, have you ever calculated what enough would be?

Earlier this year, I posted a challenge to find your crossover point. This is the point at which your investment income, retirement, and savings will completely cover your expenses such that you no longer have to work.

That exercise is one way to estimate what “enough money” means for you. But, having enough money doesn’t necessarily mean that you’ll be happy.


When will you be happy?

Too many of us put off full enjoyment of our lives today because we’re waiting to live better lives tomorrow. We suffer from stress, anxiety, and disappointment now because we know — we just know — that we will eventually be happy someday.

However, happiness is elusive. The more you chase it, the less likely you will find it.

Jennifer Aaker is a professor at Stanford who studies the relationships between time, money, and happiness. She has discovered in her research that what people think makes them happy isn’t really what makes them happy. Lately, she has been examining the link between time and happiness.

If we rethink how we spend time, and be more intentional on how we spend time (with whom and on what activities) – that may impact the happiness we feel.” — Jennifer Aaker, Ph.D.

The funny thing is, we often make our happiness vanish when we ask ourselves the question, “Am I happy?” Much like knowing the secret of a magician’s trick or staring directly at a faint star in the evening sky, scrutiny ruins the moment.

It is the very pursuit of happiness that thwarts happiness.” — Viktor E. Frankl

We sometimes think that we can buy moments of joy (e.g., taking an expensive vacation). We assume that we’ll be happy once that we have everything that we always wanted (e.g., that big house on the hill).

But happiness doesn’t work that way.

You can’t force it or fake it. Instead, happiness is the side effect of living a meaningful, fulfilling life. Being grateful for what you do have is a necessary first step.


Be careful what you wish for

I know many successful people who have accomplished great things in their careers. They’ve founded their own companies, become C-level executives, and served on the Boards of well-known corporations.

I also know multimillionaires (some of my friends have done quite well for themselves) and have met a few billionaires. I spend enough time with them — yes, even with one billionaire, in particular — to get a sense of their personal lives.

I have seen how they live day-to-day. We’ve talked about their innermost fears over dinner and drinks. We’ve discussed relationship issues with their spouses and children. Some of them have struggled with severe health problems and addiction.

You may think that achieving success as a senior executive or becoming a billionaire is the pinnacle of fulfillment. How could you not be happy at that point?

But you might be surprised. As Tony Robbins once said on a podcast, some of the unhappiest people he has met were the wealthiest people he knew.

Success without fulfillment is failure.” — Tony Robbins

A new friend of mine confirmed this, too. He’s writing a longer article on this topic, which I can’t wait to share with you.

Having enough money solves many problems. It improves your quality of life and can increase your longevity and health. But, having too much money introduces a host of new issues that many of us have never experienced.

Yeah, yeah. I can hear what some of you might be saying right now. I’ve seen the meme.

However, I do know people who have come into large amounts of money (e.g., an inheritance). I’ve also watched friends slowly accumulate success and wealth over the decades of our relationship. It did change them and — in some ways — not for the better.

What you see from the outside doesn’t reflect the reality on the inside. Sometimes, people with amazing professional lives have disastrous personal lives. You think that they must have it all. But they don’t have the things that matter the most for true happiness.


Happiness and fulfillment

I believe that you can escape the trap of the hedonic treadmill and define the right “level of enough” for your life. It requires:

  1. An understanding of the phenomenon.

  2. Recognizing when you’re stuck in that cycle.

  3. An intentional effort to escape the trap.

  4. Redefining what success means for you.

  5. Defining your “enough” point.

  6. Breaking free of external comparison.

  7. Being able to live in the moment.

  8. Gratitude for what you do have.

  9. Seeking meaning and fulfillment, not happiness.

  10. A commitment to stay out of the trap.

I was on that treadmill, and it was killing me. No matter how hard I worked, I was never satisfied. No matter how much I purchased, it was never enough.

It’s like many other addictions. You’re never completely free of the risk of backsliding. So, like many addictions, you have to change your environment, and you probably have to change your circle of friends if they feed the addiction.

Each of us has our personal definition of what enough means. I only ask that you decide what that is on your own. Don’t look to anyone else as your measure of success.

I don’t wish you great success and wealth.

I wish you enough to find happiness and fulfillment.


Do you have that one friend who is always chasing more, more, more? This newsletter might be helpful. Feel free to share it.

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