4 Questions a Man Must Answer Before He Can Truly Succeed

By phildrolet

Mar 06

Audio version: Reading time: 8 minutes

For most of my 20’s, many people thought I was crazy.

I was always seeking new experiences and having wild adventures around the world.

I was really into comfort zone challenges, from cold showers to salsa dancing and facing bulls in Costa Rica.

From the outside, it looked like I was the typical millennial “experience junkie”, always chasing the next thrill.

But in truth, and everything I did had a greater purpose (yes, even partying in Ibiza and becoming a topless waiter in Australia…).

Underneath the hedonistic appearances, I was using unconventional lifestyle to answer what I believe to be the 4 most important questions in the world.

There was a method to my madness. And now that I’ve entered my 30’s, it’s paying off in a big way:

I live in a beautiful Colorado mountain house with the woman of my dreams.

I’m in the best shape of my life and recently won my first ever Spartan Race.

My business is booming and I get to do work I love with people who inspire me.

I feel extremely blessed, and most of it is directly correlated to answering those 4 questions.

In this article, I want to share these questions with you, and how to best answer them so you too can step into the most powerful iteration of your life.

This will set the perfect foundation to reach your full potential, live a life you love, and make your success appear effortless.

But I must warn you: if you avoid these questions (like most people do) you run a high risk of living what Thoreau called “a life of quiet desperation“.

Needless to say, this is important stuff. Let’s dive in!


Why do most people struggle? 

Before I share the 4 questions, we need to understand one thing:

Why do so many people struggle with their life?

Don’t we live in the most prosperous (and safest) time in history?

Why aren’t people happier? Why is life so hard for most?

It’s a complex issue but here’s what I think it boils down to:

We live in a society that’s in an all-out war with introspection.

In other words, instead of reflecting deeply on our lives, we are constantly distracted by instant gratification.

Social media. Email. TV.

Alcohol. Drugs. Porn.

Text messages. Amazon. Etc.

Those are all easy ways to obtain a quick dopamine hit… but sadly, they take us away from the most important thing we can do:

Understanding who we are, what makes us come alive, and how we can improve our life. 

As a result, most are chronically disconnected from themselves, and are failing to apply the original personal development admonition: “Know Thyself.”

Most people have no idea who they really are. That’s why they struggle, and barely survive rather than live it up.

Is that how life is really meant to be lived?

The Greek philosopher Socrates would have disagreed. As he once said, “The unexamined life is not worth living.

Strong words…. but think about it:

How can you live a life you love if you don’t know who you are, and what makes you tick?

The Reason We Avoid Existential Questions

Answering life’s deepest questions is not easy.

These inquiries are challenging, messy and confusing.

To make matters worse, we’ve never been trained to answer multi-faceted questions.

Remember what school was like? There was always one right answer and everything else was wrong.

What’s 2+2? 4.

Who was the first US president? George Washington.

How many elements on the period table? 118.

And so on.

But when it comes to understanding ourselves, it’s not so simple.

Answers to existential questions don’t come easily.

They can’t be studied or memorized.

They must be contemplated, experienced, and distilled over time.

Most men can’t (or choose not to) handle that.

Instead of trying to figure things out, they crack open a beer, turn on the TV or rub one out on Pornhub.

They choose short-term pleasure at the expense of long-term happiness.

And it’s one of the most destructive decisions one can make.

4 Questions to Live Optimally

How can we do things differently, and live a life that would have made Socrates proud?

I believe there are 4 questions we need to answer to do so.

I’m going to share each one, explain it briefly, and then we’ll look at a simple framework to help you answer then effectively.

  1. Who am I? 

This is the most foundational of all questions, and perhaps the hardest one to answer.

But if you’re going to “Know Thyself“, there’s no avoiding it.

Fundamentally, this question encompasses 3 facets:

a) Your preferences:

What do you love?
What do you dislike?
What makes you come alive?

b) Your strengths:

What are you naturally gifted at?
What valuable skills do you posses?
What is your Zone of Genius?

c) Your shortcomings:

What do you struggle with?
What’s your Achille’s heel?
What mental blackholes do you get caught in?

Understanding this will be deeply helpful in optimizing your decisions, and creating life conditions that allow you to thrive instead of merely surviving.

2. Why am I here? 

Now that you have a better grasp on who you are, it’s time to figure out why you’re here.

I believe that all of us are born with unique talents, interests and gifts, and that our role is to figure out how we can use them to make a difference in the lives of others.

That’s our purpose. Our mission.

My brother, you’re not born to do a boring job just to pay the bills.

You’re born to do the work that only you can do, in service to all humanity.

Here’s are the 2 sub-questions to help you do that:

  1. What am I good at that I love to do? (your zone of genius)
  2. How can I use this to help others?

If you accurately answer these 2 questions, you’ll have the foundation to a successful career that will give you both financial freedom and deep satisfaction.

3. Where do I want to spend my life? 

Now that you have a solid understanding of who you are, and why you’re here, it’s time to choose where you want to build your life.

We live in an extremely fortunate time in history- it’s easier than ever to move to a new city and build a life there. We’re not bound to live in the place we grew up.

In my case, I was born in a small town in Canada but I realized that Boulder, CO was the perfect place for me. I rolled up my sleeves, and put in the work necessary to build a great life here. It’s one of the best things I’ve ever done.

Based on my experience, I sincerely believe that finding a city that aligns with our answers to Questions #1 and #2 radically increases the odds we’ll live a great life and put a dent in the Universe.

Here are some powerful questions to help you figure out what that place might be for you:

a) Do you prefer big cities, small towns or nature?

b) Do you prefer a city that’s more progressive or traditional?

c) What are the top places in the world for your kind of work?

d) What city has always mysteriously called to you?

Once you find the right place for you, your power (and happiness) will increase dramatically, and you’ll be set to answer our fourth and final question.

4. Who do I want to spend my life with? 

Now that we’ve answered the first 3 questions, we’re almost there… but we’re missing a big piece:

Who do you want to spend your life with? And how do you find that person?

This is not an easy question to answer (and one I struggled with for years) but I’ve finally figured it out.

Here 2 sub-questions that will help you:

1) What barriers have you built against love?

The Sufi poet Rumi once said, “Your task is not to seek for love, but merely to seek and find all the barriers within yourself that you have built against it.

This is such a powerful idea. Most of us have been emotionally banged up through our lives, and chances are part of you has become afraid of love.

Part of you wants a relationship more than anything. But chances are, another wants to avoid it like the plague.

When I realized this was happening to me, I went to Bali for 4 months to work with a spiritual teacher who helped me open up my heart, trust again, and let go of my women-related fears.

5 days after coming back to Boulder, I met the woman of my dreams (and have been with her ever since).

2) What do you most love to do?

Most people seeking a relationship nowadays are spending inordinate amounts of time of dating websites/apps.

Personally, I’ve always known deep down that wasn’t how I would meet my life partner.

If you feel the same way, I suggest a change of approach:

Instead of spending your time and energy on Tinder/Bumble/Match.com, challenge yourself to spend more time out in the world doing cool stuff.

Go to interesting events. Attend workshops. Seek spiritual gatherings.

Go outside your normal circle, and meet new people. Sounds simple but so few people do it these days.

If you’re an inspired man, living a life you love, and bring good energy wherever you go.. you’ll naturally attract the right people when you walk into a room, and magic is bound to happen.

The Fastest (and Most Fun) Way to Answer These 4 Questions

As a recap, here are our 4 questions:

  1. Who am I?
  2. Why am I here?
  3. Where do I want to live?
  4. Who do I want to spend my life with?

Inevitably, sitting down and writing your answers will lead to dead-ends.

We can’t think our way to these answers.

I believe we need to figure them out experientially, not intellectually.

Which brings us back to the reason why I was so wild in my 20’s.

I had figured out that the best way to answer these questions… was to try new things, have fun, and pay close attention to the results.

As Ralph Waldo Emerson once said, “all life is an experiment. The more experiments you do, the better.

That’s why I went to all sorts of foreign places.

That’s why I did all these crazy comfort zone challenges.

That’s why I took on projects I didn’t know how to complete.

Because every time, I was learning about myself.

About the world.

About life.

And I was getting closer to answering the 4 questions.

There’s nothing stopping you from doing  the same.

How to Be a “Life Scientist”

Here’s my invitation to you: become the kind of person who sees everything as an experiment.

Because really, it is. When you try something new, it either works (which is awesome) or you learn (which is awesome too).

When you see things this way, fear of failure disappears.

It gets replaced by the trepidation of endless possibilities.

You become bolder, more adventurous, and more attractive to others.

You see life as your playground, as your lab, as an adventure to be experienced.

People might think you’re crazy.

But you’ll be evolving and learning about life 100x faster than them.

Because every day you’ll be acquiring new data points about yourself, your life and the world around you.

That’s how we become wise and capable of showing up at our best in any situation.

So go to new places. Try new activities. Talk to new people.

Experiment, experiment, experiment.

Next thing you know, you’ll be figuring out your life at a radically accelerated rate…

And who knows, you might even find yourself living it up in Ibiza or facing a bull in Costa Rica.

All in the name of knowing thyself, of course.

Much love,

PS. Now I’d love to hear from you: which existential question are you currently stuck on? And what are you doing to find your answer? Let me know in the comments below.

Life is short. Don’t settle.

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