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The Paradox of (Financial) Success

success doesn't bring happiness
❝When you chase money, you're going to lose...Even if you get the money, you're not going to be happy.❞ -Gary Vaynerchuk

I'm on my way to the gym listening to a podcast. It's snowing out, and I have to drive a little slower than I usually do. As I'm driving, I'm careful not to come to a complete stop because otherwise, I'll get stuck in the snow. Essentially I'm stuck between not going too fast and not going too slow.

While I'm driving at the appropriate Goldilocks speed, the podcast host talks about the television program, BoJack Horseman. Specifically, he wonders if the show has it right; he wonders if we have to either be a Zoe or a Zelda. He explains that in the show, a character named Zelda is happy, optimistic, and generally likes life in people. Another character is Zoe, who is pessimistic, generally sad, and often in a bad mood. The question they raise in the show is whether or not we are born as a Zoe or a Zelda, or if we can change.

This idea is fascinating to me, and I've heard of the show before, but I haven't watched it. I convince my wife that BoJack Horseman is worth a try. As we're watching it, we find out that the show is about a very successful actor who is unhappy by nature. He's unhappy even though he has all the money he could ever want. He's unhappy even though he has one of the best houses in Hollywood. He's unhappy even though he has many awards, fans, and followers. Throughout the show, he continues to strive for more success, thinking that maybe then he'll be happy, but he never is. Then he starts to think that maybe there's something wrong with him because he should be happy, but he's not.

As I'm watching the show, I start to realize that this is a common phenomenon. Of course, we're not all successful actors, but we are all pursuing something that we feel will make us successful, and many of us hope the happiness will follow when we get there.

The curious paradox is that, in all likelihood, the main character becomes less happy as he gains more success. This is because, before he had the success, there was hope that he would be happy when he became successful. Once he became successful, he realized that there was nothing there.

The way to win this game is to not play it. Instead of pursuing success or money, we ought to pursue happiness. And since everyone is different, we all have the opportunity to play our own game.


Intuitively, it feels like success should make us happy, whatever success means to us. Success could mean career success, marital success, personal success, or financial success. It's intuitive because it follows a formula. If I set a goal, take steps to achieve the goal, and succeed at attaining my goal, I've accomplished what I set out to do. That is, I should be happy.

The paradox is that once we achieve what we set out to achieve, we can sustain the happiness that comes along with our success for only a short time. It is fleeting. Then we find ourselves back at where we started. Then we have to set a new goal, hope to achieve that, only to find out that that didn't bring us lasting happiness either.

Psychologists call this hedonic adaptation, where we adapt to our new surroundings very quickly. We get used to things.

The paradox is that we don't know that we'll get used to our success until we achieve it.

successful people can become unhappy when their success doesn't bring happiness


Therein lies the paradox of success; less successful people can be happier than more successful people even when they have the same goals.

For example, take two people. Person A is more successful than person B, and they have the same life objectives. Person B wants to be successful and puts together a plan to get there. There's a strong belief that achieving the success will make person B happy. Thus, person B has hope that all the work will be worth it.

On the other hand, person A used to have the same hope but found that all the success was there, but the happiness that was expected didn't follow.

Therefore, we have a situation where less successful people can be happier than more successful people, even when they have the same objectives.

less successful people still grind away because they think success will bring them happiness


The obvious question is: what am I supposed to aim at if not success? It's a great question, but it's not a question with a universal answer. Everybody has different values, and so the answer will be different for everybody.

Some people will say that more time with family will bring more happiness. Other people say that time outdoors will bring happiness. Others will have a specific hobby or activity in mind, like biking or writing. The idea, though, is that only you can figure out what you should aim at in order to bring more happiness.

what will bring you happiness? what are your values?


It tends to be difficult for some people to think about the things that will bring happiness because they've been hardwired to think that money and success are what they ought to pursue. It's a common belief that more money will make people's lives better.

In his books Happiness Studies and Happier, No Matter What, happiness expert Tal Ben-Shahar talks about happiness as being defined as whole-person well-being. He breaks down well-being into five different elements, spiritual well-being, physical well-being, intellectual well-being, relational well-being, and emotional well-being. The first letter in each of these elements spells out the acronym SPIRE.

Thinking about happiness in this way helps to break the idea that money is a goal in and of itself.

spire elements of happiness

Instead, money is a tool and nothing more. Money is a tool that can be used to support each of the SPIRE elements.

This is not to say that money isn't important or that financial health isn't necessary. It just simply reminds us that having a healthy financial life allows us to pursue the SPIRE elements that will bring us happiness through the lens of our own values.

money is a tool you can use to find happiness, but it's not a goal and won't bring you happiness by itself


Once we start to view money as a tool, we can ask ourselves, what is our money for? Without understanding what the money is for, it's easy to make financial decisions either blindly or in a reactionary way.

Once you understand what your financial purpose is, you can begin to make your decisions with intention. You use money in a way that supports what's important to you, which has the side benefit of helping you avoid using your money in areas that you don't care about.

your financial purpose is the foundation of all your financial decisions

The paradox of success exists because too many of us default to pursuing money and success instead of happiness. Understanding what happiness means to you, what your values are, and what your aspirations are, helps you use your money as a tool to bring you the best life possible with the money that you have. It helps you live in a way that will give you the fewest regrets as you look back on your life.

You only have one life. Live intentionally.

Until next time,


If you know someone else who would benefit from reading this, please share it with them. Spread the word, if you think there's a word to spread.

Related Money Health® Reading
References and Influences

Ben-Shahar, Tal: Being Happy

Ben-Shahar, Tal: Happier

Ben-Shahar, Tal: Happier, No Matter What

Gilbert, Daniel: Stumbling on Happiness

Klontz, Brad, Edward Horwitz & Ted Klontz: Money Mammoth

Klontz, Brad & Ted Klontz: Mind Over Money

Sinek, Simon: Start With Why

Sinek, Simon, David Mead & Peter Docker: Find Your Why

Note: Above is a list of references that I intentionally looked at while writing this post. It is not meant to be a definitive list of everything that influenced by thinking and writing. It's very likely that I left something out. If you notice something that you think I left out, please let me know; I will be happy to update the list.



About the Author

Derek Hagen, CFA, CFP, FBS, CFT-I, CIPM is a speaker, writer, and coach specializing in financial psychology, meaning and valued living, resilience, and mindfulness.


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