Strategic Contrarianism: Why Unconventional Choices Can Help You Win At Life

By phildrolet

Jul 27

“Whenever you find yourself on the side of the majority, it is time to pause and reflect.”

Mark Twain

Last week, I did something shocking.

Some would call it social suicide.

But I believe it’s one of the smartest things I’ve ever done.

And today, I hope to inspire you to do the same.

Strategically Contrarian

Over the past few years, I’ve made a habit of experimenting with unconventional life choices.  

At first, I was afraid of standing out, being judged, or making costly mistakes.

But repeatedly, my experiments produced superior results than following the norms.

That’s why today, I want to challenge you to question your assumptions about the world, and start setting up your own experiments in unconventional living.

I believe embracing this philosophy will give you a significant competitive edge over the rest of the world, while helping you enjoy greater freedom and inner peace.

Waking up to the Possibilities

In 2010, I had just left a prestigious but unfulfilling job with a Fortune 500 company.

I decided to move to Australia to do my MBA, and soon began reading Chris Guillebeau’s book The Art of Non-Conformity.

This manuscript was a paradigm-shift of the highest order, and made my head spin for days (in the best way possible).

It gave me FULL permission to say “screw the norms”, and build an extraordinary life on the outskirts of society.

All of a sudden, I started experimenting with all sorts of unconventional mindsets and behaviors, to see what worked and produced the best results.

Before long, I became happier, healthier, and more successful than I’d ever been.

Needless to say, I was onto something…

Doubling Down on Unconventionality

Since returning from Australia, I’ve continued my experiments with great results.

Here are some of the unconventional ways I’m now enjoying life:

  1. I don’t own a TV (haven’t for 5+ years).
  2. I have my own sensory deprivation tank.
  3. I practice “Radical Honesty” (and avoid lying at all cost).
  4. I refuse to eat fast-food (and haven’t for 6+ years).
  5. I do a new Comfort Zone Challenge every week.
  6. I’ve tallied up more than 1200 hours of meditation.
  7. I’ve built a Crossfit gym in my garage.
  8. I take a 30-minute nap every afternoon.
  9. I live in a mountain house (away from the city).
  10. I try to say hi to every stranger I cross on the street.

The Philosophy Behind It

As you read this, you might be thinking “That’s not that hardcore. There are way more unconventional people out there”.

True. I’m not a breatharian, I don’t live in a nudist colony, and I don’t have tattoos on my face.

But here’s an important distinction:

I only engage in behaviors that produce positive results- I am NOT doing this to be a rebel or to give society the middle finger.

There are plenty of people out there who live weird-ass lifestyles but create little to no value to society, are unhappy, unhealthy, and broke.

That’s not my aim. I’m a mission to live life optimally, and inspire others to do the same.

And so far, it’s working out quite well.

I’ve built a successful business doing work I love.

I’m in a fulfilling relationship with the woman of my dreams.

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

And perhaps most importantly, I don’t feel shackled by society anymore.

I live by my own rules… while still feeling love and acceptance for other people’s choices. Life is good.  

Unconventional Leaders

Now here’s the big question:

Does living an unconventional lifestyle really work? Or am I just an exception?

To answer this question, let’s look at 3 of the most famous men of all-time (and how their unusual choices lead to their uncommon success).

Conor McGregor

4 years ago, Conor McGregor was completely unknown and had never fought in the UFC.

Now, he’s the first man to ever simultaneously hold 2 belts in the UFC, a global superstar, and about to compete in the most lucrative fight of all-time.

One of the main reasons for Conor’s unprecedented ascent is the unconventional way he lives his life.

  1. He’s a fervent practitioner of “unusual” training methods.
  2. He puts a tremendous amount of importance on mental warfare.
  3. He’s developed a controversial, larger-than-life media persona.
  4. He’s the first MMA fighter to transition to top-level boxing.

Conor is one of the most unconventional characters you’ll ever encounter. And he’s one of the greatest success stories of our time.

Coincidence? I think not.

Henry David Thoreau

Born in 1817, Henry David Thoreau is arguably the greatest American philosopher of all-time.

To write his seminal book, Walden, he made a highly unconventional choice: he spent 2 years, 2 months and 2 days in a small cabin next to Walden Pond.

This was in the 1840’s so there was no internet, no cell phones. He truly lived in the woods.

And this choice lead to some of the clearest thinking, and most influential writing our world has ever seen.

If he’d decided to play it safe and keep living in Concord, would he have been able to achieve such a feat? I doubt it.

Siddartha Gautama

Our final example is a man by the name of Siddartha who lived 2500 years ago. The son of a King, he had a clear path to the throne.

But something in his heart compelled him to make a radical choice:

He escaped the castle, left his wife and baby behind, and moved to the forest to pursue enlightenment.

He spent years meditating 10+ hours/day, eating only one daily meal, and sleeping under the stars.  

A radical lifestyle, to say the least.

But his effort paid off.

Within 6 years, he achieved full enlightenment, and became known as “The Buddha”.

Why is it so hard to be unconventional?

If stepping outside the norms has the potential to be so effective, why are so few doing it?

There are 3 mental obstacles we need to overcome to enjoy true freedom and exceptional success.

1. The Tribe Mentality

For the vast majority of history, we lived in small tribes (~50-150 people). This allowed us to work effectively as a group and increase our chances of survival.

The problem is, being an outlier in the tribe system was highly frowned upon. It created “disruption in the ranks” and jeopardized the tribe’s ability to survive.

This left our ancestors with two choices: conform to the tribe, or get banished (and die).

This is a big reason why our nervous system evolved in a such a way that we feel uncomfortable standing out. 

2. The Education System

School teachers tend to prefer “good students” who conform to the norms because it makes their job easier (hard to blame them!).

They encourage us to sit down, be quiet, and regurgitate information we’ve been fed. This leaves very little room for originality and creative thinking.

As a result, our ability to challenge the status quo and make unconventional choices gets conditioned out of us, and replaced with a desire to be “well-behaved”.

3. The Negativity Bias

If you do ten things outside the norm, chances are one will backfire. You might get in a bit of trouble, upset someone, or fall flat in your attempt to change things.

Objectively, this is no big deal at all. 9 successes and 1 failure is an excellent ratio.  

But our nervous system remembers the failures WAY more than the successes, and it creates a simple neuro-association: “being different = pain”.

Since we’re wired to avoid pain, this new belief keeps us from being daring… even if it causes us to miss out on tremendous opportunities.

How to Rewrite your Mental Software

As you can see, the deck is stacked against us when it comes to stepping outside the norms.

But thankfully, it is possible to reprogram your mind and liberate yourself from this limiting conditioning.

Here are 3 principles that will help you do so:

1)  “If it makes you happy (and doesn’t hurt others) it’s OK”

If you do something strange (ie, walking downtown barefoot), does it hurt other people? No. Is it against the law? No.

So what’s the big deal?

I invite you to install this belief in your consciousness: it makes you happy and doesn’t hurt others… go for it!

You’ll probably get funny looks but who cares. This is your life, your journey, make the most of it (without being a jerk)!

2)  Don’t take things personally

When you step outside the norm, you will challenge other people’s perception of reality. Sometimes this might upset them.

But here’s what you need to understand: they’re not really upset at you (you’re not doing anything to hurt them, after all)- you’re acting as a reflection of the fact that deep down, they feel shackled and repressed.

When this happens, don’t take it personally, and treat them with love and compassion. And you’re feeling inspired, gently invite them to step outside their own perceived limits.

3) Ask for forgiveness, not for permission

In school, we had to ask for permission for almost everything (even going to the bathroom!)

As we get older, the rules of the game change… but sometimes we forget it. When it comes to stepping outside the norm, I invite you to assume it’s OK- and apologize if needed.

Remember, as long as it doesn’t hurt other people, it’s OK.

Note: Be discerning here- in some situations, asking for consent IS important.. But in many situations, going for it is the superior strategy.

Ready to experiment?

While this all makes for interesting discussion, the real magic comes in the application of these ideas. So let’s make this real.

What is one thing you’ve been wanting to do for a long time…. that you’ve avoided because it’s unusual?

Starting a new, unconventional business?

Taking on a crazy new hobby?

Throwing away social scripts in conversation?

What is ONE THING you want to try out?

Commit to trying it this week, and see what happens.

After taking action, reflect on the following:

Did it work? Was it fun? Did it make you feel more alive?

My latest experiment

Last week, I did something shocking.

Some would call it social suicide.

I quit social media for good.

Bye, bye Facebook. Adios Instagram.

Only time will tell if it turns out to be a successful experiment…

But here’s the bottom line:

Challenging the status quo is fun, and is the foundation to an extraordinary life.

Give it a try,

PS If you want to free yourself from the grips of social media, download my 15-minute audio training “3 Ways to Reclaim Freedom from Social Media”.

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