4 Questions a Man Needs to Answer to Achieve ‘True Success’

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

I was really into comfort zone challenges, from cold showers to salsa dancing and endurance races.

From the outside, it looked like I was the typical millennial experience junkie.

But in truth, everything I did had a greater purpose (yes, even surfing in Australia and facing bulls in Costa Rica).

I was using my lifestyle to answer what I believe to be the 4 most important questions in a man’s life.

And now that I’ve entered my 30’s, it’s paying off:

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’m passionate about.

I feel extremely blessed, and most of is the direct result of those 4 questions.

In this article, I want to share these questions with you so you can achieve “true success” and leave your mark on the world.


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?

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.

Those are all easy ways to get a quick dopamine hit… but they take us away from understanding what makes us come alive.

The Reason We Avoid Existential Questions

Answering life’s biggest questions is not easy.

The answers don’t come easily.

They can’t be studied or memorized.

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

It’s a challenging process- but the cost of avoiding it much greater than the effort it takes to actually go through it.

4 Questions to Live Optimally

To build a life that makes us happy, here are the 4 questions we need to answer:

Who am I? 

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

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 black holes 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.

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

What am I good at that I love to do? (your zone of genius)

How can I use this ability to help others?

If you accurately answer these 2 questions, you’ll have the foundation to a rewarding career, both financially and emotionally.

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.

Personally, I was born in a small town in Canada but I realized that Boulder, CO was the perfect place for me.

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 energy (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?

That’s a question I struggled with for years, and 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.

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 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 I wasn’t going to meet my soulmate online.

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

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

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

If you’re an inspired person, living with virtue, you’ll naturally attract the right people when you walk into a situation.

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

As a recap, here are our 4 questions:

Who am I?

Why am I here?

Where do I want to live?

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 explored so “crazy” during my 20’s.

I 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 comfort zone challenges.

That’s why I took on projects that seemed out of my league.

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.

My Invitation to You

I invite you to become the kind of person who sees everything as an experiment.

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

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

It gets replaced by the trepidation of 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 100x faster than they are.

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

Experiment, experiment, experiment.

And who knows, you might even find yourself surfing in Australia or facing bulls in Costa Rica.

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.


Do you want to be part of creating a kinder, more inclusive society?