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Does Rich = Successful? What Defines Success?

I have a quick question for you dear reader, and what makes this a good question is that there is no single answer… but in asking it I hope to encourage you to question your goals and your dreams just as it has made me question mine.

What does it mean to be successful?

Is it becoming filthy rich? Achieving fame, glory or notoriety?

Perhaps is it becoming the master of your craft; the expert that everyone turns to, or wishes to be?

Is it to have your art hanging on walls, or for your buildings to stand for years that will far outlive your name?

Do you cure a disease? Nurse a child or counsel a friend?

Money does not equal happiness, of that we are all at least subconsciously aware. Though we collectively tend to desire more of it, I believe that most do not have a clear idea in their head how that money would affect their lives.

So why is it that so many of us would connect the word “success” with money?

I don’t plan on this post becoming a long-winded sermon on the evils of money, nor do I plan to preach to you what you should or shouldn’t desire. Instead I had just hoped to share with you a couple of interesting anecdotes that I have come across recently that have really driven home the fallacy of “money = success”.

Rolf Potts, the author of Vagabonding, brought up a story while chatting with Tim Ferriss on one of his podcasts that perfectly illustrated this dissonance. He spoke of an event which was effectively a retreat for extremely rich individuals, most in the hundreds-of-millions or greater. The long story short is that an organiser of the event made this preposterous statement after speaking with the invitees,

“The billionaires can’t spare a week of course, so they’ll only be attending for 36 hours”

Rolf found this as ridiculous as you or I would, and pondered the question that if having access to literally billions of dollars left these individuals with less freedom than he himself could boast – then what exactly was the purpose of that money?


You may have noticed the beautiful island scene in the featured image for this post. It’s right up there at the top. I’ll give you a moment to refresh your memory… no it’s okay I’ll still be here.

I could have picked any stock photo of a beach for this banner, in reality I just needed that image because it spaces out my front page nicely. That beautiful sandy beach lies not just any tropical island however, that beach is actually on the lovely Necker Island. I wonder if the name rings any bells for most of you? If it does then it’s probably because Necker Island is the personal property of the one and only Sir Richard Branson.

Sir Richard is, in my opinion, and incredibly successful man.

When I think of the reasons for why he could be considered ‘successful’ however, I would never add “owns an island” to the list.

Richard lives an incredible lifestyle that has incorporated both the process building his multitude of economically successful businesses under the Virgin banner, and a huge range of extra-curricular activities fiscally supported by these businesses. Okay so that didn’t come across as clearly as I had hoped, what I mean to say is this:

Richard is a true entrepreneur at heart, and the process of building all of his companies has added value to his life. Perhaps just as importantly however, Richard’s life outside of these businesses (mountain climbing, diving, spelunking, hot-air-ballooning, you name it) has been financed and supported by the financial success he has found in these companies.

He is, in my mind, successful because of the combination of these two things:

  • He followed one of his passions, which was to be an entrepreneur and build a multitude of companies
  • He then took this success, and turned it into personal freedom.

So what, then, is the meaning of freedom?

Once again I don’t believe there is any one, true and final answer… but the following is one possible definition that I have adapted from a point that Rolf made in his interview with Tim Ferriss:

Freedom is to possess the means with which to follow and discover your passions.

Sir Richard does not appear to be bound by the golden chains of his business success, and instead has used his money to achieve personal freedom.

Is that the answer then? Have we cracked the case?

I’ve actually gone on a bit of a journey while writing this post, and now I wonder… could I have just stumble upon MY definition of success?

Success is the combination of the freedom to discover and follow your passions, with the desire, drive and fortitude to actually pursue them to the best of your abilities.

You can’t have one without the other, and the terms freedom and passions are so broad that they could suit just about anyone.


You know what?

I don’t mind that definition one bit.

Let me know what you think!