How To Step Away from the Never-Ending Pursuit of Success

Updated: Feb 15



There is a massive problem with success. One "successful" business owner summarized it by saying the following on their multi-million dollar boat:

"I feel dead inside."

Unfortunately, this situation is much more common than you might think. I want to help you avoid feeling dead inside on your (proverbial) boat. I want you to avoid destroying your health, family and marriage in pursuit of "success". I will do this by showing you the difference between success and fulfillment, and how to find fulfillment.

Playing the Wrong Game: The never-ending pursuit of success

What have you noticed about how long the feeling of success lasts?

Think about a significant achievement you've had in the past few years. What was it? I bet it felt great to achieve it. How long did that great feeling last?

For most people and most achievements, the good feeling lasts for less than a week. Your new salary from a promotion, your new car, or your new boat become your NEW NORMAL. After a week, that glow is mostly or entirely faded, and you go back to feeling the way you did before, but with more expenses.

You go back to feeling the way you did before because the feeling of success is ephemeral. Fleeting. Temporary.

The problem is there is always a bigger house or a more expensive car, so your pursuit of success is never truly fulfilled. When your self-worth begins to depend on these dopamine hits of success, you risk chasing them at all costs. You risk sacrificing important (but not urgent) areas of life, such as family and health. You risk ending up feeling dead inside on your sailboat.

It doesn't have to be that way. 

Playing the Right Game: Finding fulfillment in what you do every day

In contrast to the fleeting feeling of success, the feeling of fulfillment is available to you every day. It is possible for you to feel fulfilled every day by doing what you love to do. You don't have to sacrifice the important areas of life like family and health to feel fulfilled.

I'm not saying that you shouldn't pursue success. I'm not saying don't work hard for a promotion, or not to work toward buying a house or a boat.

"Find a job you enjoy doing, and you will never have to work a day in your life." - Mark Twain

Stop using other people's definitions of success.

It's up to you to define success and fulfillment for yourself. Avoid using the definitions of success set by society or by others. You will find that this path leads to less anxiety and more happiness.

Success has traditionally been defined as having money or power. Getting the big promotion; getting the big house; having a nice car. But how many people do you know who have this "traditional" success, but seem miserable?

Success for you is whatever you define it to be. A big step on the way to feeling fulfilled is setting your own definition of success and working towards what you want in life. Below I share an exercise that you can use to start creating or updating your vision for a fulfilling life.

Start to visualize a fulfilling life with this 30-minute exercise

The two key questions that help you find fulfillment are these:

  • What do you really want?

  • What do you love doing?

If the answer to those questions is different than what you have today, then GOOD. You have a starting point for a clear vision of a future state that is different from your current state.

If you feel that the answers to those questions are not inspiring, did you dig deep enough? You can ask yourself, "And What Else?" to go a few layers deeper.

Take those questions a step further and spend at least 30 minutes completing this vision exercise. Ask yourself these deeper questions:

  • Imagine yourself in five years' time. How do you see yourself?

  • Will you be in the same employment or elsewhere?

  • What will you be working on?

  • Will you be living in the same place or not?

  • Who will your friends be?

  • What time will you spend with your family?

Try and be as concrete and realistic as you can. Write the answer as one or two paragraphs.

My advice on making this powerful is to go somewhere with no distractions. Get off the tramlines of your day-to-day and go somewhere where you can think differently.


My wife Julie and I completed this at a seaside cafe on the Meditteranean, on the island of Crete in Greece. We took a few hours to visualize the life we wanted right after moving from Vancouver to Oxford in 2006. It was incredibly powerful.

If you don't have an inspiring seaside cafe handy, think of somewhere local you can walk to, and do this vision exercise with a pad and pen.


Think about more than just your career and money. The major areas of life are things like Health, Family, Career, Wealth, Friends, Fun & Recreation, Community. Think of these as balls that you are constantly juggling. Career and wealth are rubber balls; if you drop one, it bounces and you can pick it up. On the other hand, health and family are glass balls; if you drop them, the impact can be shattering.

It's up to you to define success and fulfillment for yourself. Avoid using the definitions of success set by society or by others. You will find that this path leads to less anxiety and more happiness.