Chapter 34 – If you could do anything

If you could do anything

Imagine you won the lottery.  You had an exit with a startup, an uncle left you a fortune, or you found a sunken treasure ship worth millions.

You are financially free.  You do not need to work ever again to pay your bills.  Your family, children and their children are set.   Multi-generational wealth and all that jazz.  You are set!

Now what?

Imagine you have a magic wand, and you can do anything.  Sit on a beach with a drink in your hand (with a little umbrella in it), every day.  You can be the president, you can be anything you want.

What is it you want?

What is it you want when you can be anything?


That is an existential question.  It’s your most avoided question, ever.  I have met few people who knew the answer to this question, or asked themselves the question seriously.

Why is that?

Since childhood you were told what to do, where to go, how to behave.  Then, when you became an adult, you find out that you need to work to make a living, pay your bills – so you will not end up homeless.

You are introduced to the game of life, without much fanfare, or thinking about what you are really doing.  You actually don’t realize until its too late that the game is setup against you.  The ability to generate enough wealth that will let you CHOOSE if you want to play the game of life or not – is diametrically opposed to your employer’s desires.

Wait, what?


When you begin working at a company, you usually start from the bottom rung of some “ladder”.  That ladder is represented in the management levels of the organization.  If you started in a business owned by YOUR family, you still are not going to get the profits of the owner.  You are still going to not make the wealth of the owner, right?

If you join a business that is owned by another family, the point is even clearer. 

When you join a startup or a public company, you still need to learn skills, and climb the corporate ladder.  Ces’t la vie.

The worry most businesses have is that if the employees got paid too much, they “could” leave, and there will be no business.  Makes sense, right?

It’s just that only when you get to be wealthy, you see what a fallacy that is.  All your life you thought that once you had enough money, you will retire and “do nothing”.  Sit on the beach… no worries in the world. Right?

The reality is different.  Once you make all the money in the world, you still need to DO something.  You go crazy otherwise.

It does not matter what you choose to do, but there is an end to the glow of doing nothing.  You feel useless, a leach in society, and you cannot relate to others who are toiling and going to work every day.  You are not relatable to them.

It may take a month, a few months, a year – but you will crack, and decide to do something with yourself, with your life.

So what would you choose if you could do anything?



Until you need to face this question – you do not appreciate how hard this existential question is.  You can go through life, from one day to the next, from job to job, from career to career – and never wrestle with it.

If you trace back your life to the very first job you took – you will see that there was little choice you had in taking it.  You may have had to take it, or that was the only job available.  From that moment on, you really just kept going… and if you are like most of us, you are still on a continuum of working to make ends meet.

So, in reality you NEVER had the need to think about this question. 

Try now to think about it, seriously, and see where it leads you.

To help illustrate why this is so difficult to think about, here is an example.

Say that you walk down the street and see an ice cream store.  You step inside, and see that they only have ONE flavor, vanilla.

The clerk asks “Would you like ice cream?”

There is no question of WHICH flavor you want, as there is only one.  So the choice of do you want ice cream, and the choice of do you want vanilla ice cream are the SAME.

Its a binary choice.

Now, imagine you walk into another ice cream store that has 31 flavors of ice cream.  You take your time to explore all the flavors you COULD have.

The clerk asks “Would you like ice cream?”

Now the question is different.  It is no longer binary, as you have all these wonderful options.  To the naked eye, it seems like you are going to choose and WHICH flavor you will have, right?

What if its not the case… what if the thought process you really are going through is WHICH ice cream you are NOT going to have.


You simply can not say “I will have one of each” and avoid this decision all together.  That would be similar to the binary decision of having vanilla or no ice cream at all.

Say that you have an appetite and enough money for three scoops of ice cream.  There are 31 flavors, a few you like and a few you do not like.  You boil it down (after tasting of course) to six flavors you like – they are all yummy.

Now you need to decide which ones to tell the clerk to scoop into your cup or cone, and inversely which ones will NOT be part of your dessert.

It seems like you are only choosing the ones you will have, while you are really thinking about which ones you are not going to have, aka FOMO.  The fear of missing out.

The same thing happens on that day you will really ask yourself the question “What would I do if I could do anything?”

It’s not just about the things you will do, it’s also about what you are actively saying you will NOT do with your life.  Every person has more than one thing they want to do, to experience.  Thus, if you can have it all, you are only limited to the time you have on Earth.  And because of this time limit, you can’t have it all.  You need to DECIDE, you need to CHOOSE, you need to wrestle with what is it that you would do and not do, if you could do anything.


The story of the Mexican Fisherman helps explain this best:

An American investment banker was at the pier of a small coastal Mexican village when a small boat with just one fisherman docked. Inside the small boat were several large yellowfin tuna. The American complimented the Mexican on the quality of his fish and asked how long it took to catch them.

The Mexican replied, “only a little while.”  The American then asked why didn’t he stay out longer and catch more fish? The Mexican said he had enough to support his family’s immediate needs. The American then asked, “but what do you do with the rest of your time?”

The Mexican fisherman said, “I sleep late, fish a little, play with my children, take siestas with my wife, Maria, stroll into the village each evening where I sip wine, and play guitar with my amigos. I have a full and busy life.” The American scoffed, “I am a Harvard MBA and could help you. You should spend more time fishing and with the proceeds, buy a bigger boat. With the proceeds from the bigger boat, you could buy several boats, eventually you would have a fleet of fishing boats. Instead of selling your catch to a middleman you would sell directly to the processor, eventually opening your own cannery. You would control the product, processing, and distribution. You would need to leave this small coastal fishing village and move to Mexico City, then LA and eventually New York City, where you will run your expanding enterprise.”

The Mexican fisherman asked, “But, how long will this all take?”

To which the American replied, “15 – 20 years.”

“But what then?” Asked the Mexican.

The American laughed and said, “That’s the best part. When the time is right you would announce an IPO and sell your company stock to the public and become very rich, you would make millions!”

“Millions – then what?”

The American said, “Then you would retire. Move to a small coastal fishing village where you would sleep late, fish a little, play with your kids, take siestas with your wife, stroll to the village in the evenings where you could sip wine and play your guitar with your amigos.”

Click here for Chapter 35

References and Quotes:

Examples of Existentialism

The Story of the Mexican Fisherman – Courtney Carver

“Having it all doesn’t necessarily mean having it all at once” – Stephanie Luetkehans