Why You Should Be Living Your Own Unconventional Life

What it means to be living an unconventional life, why you might want to consider it, and how to make it a success.


What comes to mind when you think about someone who’s living an “unconventional life”?

  • A hippy living in a commune in rural India?
  • A digital nomad like Kim or me who makes money in mysterious ways over the internet?
  • Your cousin who dropped out of school to be a documentary filmmaker and teaches scuba diving to pay the bills?

Whatever your answer is, my goal with this post is to change it.

Because maybe, just maybe, a fresh perception of what it means to be living an “unconventional life” can help you find ways to make more out of yours.

Sleeping on the floor
You don’t have to sleep on the floor to be unconventional. It’s up to you.

What is an “unconventional life”?

Let’s start by giving “unconventional life” a clean and simple definition.

Mashing up the Merriam-Webster and Cambridge dictionaries’ definitions, here’s what we’ll go by:

An unconventional life is a life not bound by what is usual or the way most people do things.

“Not bound” is the pivotal part of this definition.

If most people sleep on beds, you can do the same. Or you may decide to try sleeping on the floor. It’s up to you.

Or if you usually eat steak with a fork and knife, you can keep doing the same. Or you can try eating it with your hands one time. It’s up to you.

It’s up to you.

Independent decision making is the blueprint of an unconventional life. And the quality of those decisions determines whether you build something boring, something extraordinary, or something that crashes down on top of you.

A hungry lion who'd happily eat anyone who decides to do their own thing.
Any ancestor who ventured off to do their own thing would’ve made her day.

The game has changed.

Until recently, independent decision making would have been a losing strategy in the game of life.

Independent-thinking smart-asses were quickly snuffed out in prehistoric, real-life games of Survivor. They ran one way while everyone else ran the other and became saber-toothed tiger meat. Or they dissented with their clan one too many times and ended up alone in the jungle.

But not our ancestors!

They stayed alive by conforming, being risk-averse, and holding strong status quo biases. So we’re wired to want to fit in.

We’re also wired to be competitive. We want our genes to carry on, not some other ape’s, so we feel inclined to prove we’re better and smarter at what everyone else is doing.

But the game has changed.

Life’s no longer a competition. Cheap food and medical, financial, and societal safety nets protect us from the mortal downsides of taking unconventional “risks.” And instead of using sex, money, or power to keep score in the game of life, you can decide on your own measure.

This is great news for anyone willing and able to rewire their thinking.

Personal user manual image
Nobody gets these. (Though I made one for myself.)

Build what only you can build.

Each of us is born with:

  • A unique set of tools (our genes).
  • A collection of materials to start with (our lots in life).

Then we’re told to go make something special.

But nobody’s given an instruction manual.

In a conventional life, you take what seems to be the easiest and safest approach: You see what everyone else is building and try to create something similar, but somehow special.

The problem is there’s zero chance your toolset and materials are perfectly equipped to copy convention. So, at some point, you’ll have to start jerry-rigging to replicate the “success” of others who have more appropriate equipment.

You’ll have to work extra hard to keep up. Or you’ll complain that life isn’t fair and hope someone will give you a hand. Or you’ll brainwash yourself into believing that what you’ve built is good enough.

In an unconventional life, you’re not bound to building what everyone else is.

When you get to the stage where your tools and materials don’t fit the conventional standards, you don’t struggle through. You try something different. You look elsewhere for inspiration and tinker with what you’ve got until the pieces come together. And you do more of that instead.

It’s not easy. You don’t know what you’ll end up creating or how long it’ll take, so it requires risk-taking, hard thinking, intrinsic motivation, and patience.

But if you figure it out you’ll be creating a glorious life only you build given your toolset and materials. There’s nothing more rewarding and fulfilling than that.

Chris walking alone in the desert
An unconventional life doesn’t have to be like this.

Consider the upsides of being an “outsider.”

What about the social downsides of an unconventional life?

As authors Ben Casnocha and Scott Young have written, you miss out on shared experiences, have a harder time finding common ground with others, and feel misunderstood.

I experienced these downsides early in my own attempts to live unconventionally. You probably will, too, if you try.

But think of the upsides. If you persevere at thinking independently to use your toolset and materials to the best of their ability, you will:

  • Find similarly open-minded people whom you can relate to at a deeper level.
  • More easily collaborate with others, since you’re not competing to win at convention.
  • Build something special that will attract people’s attention and desire to help.

I’m experiencing this, now. I feel less alone than I ever did when I was living conventionally.

working out at la cancha in el dorado in envigado
Kim and my headstand workouts attracted new friends in Medellin.

It’s contagious.

When others see your unconventional life working out for you better than a conventional one, it nudges their decision making in riskier, more independent directions. If their decisions pay off, they’ll keep at it. And they’ll inspire others to do the same.

If this continues—and I don’t see any reason why it wouldn’t—it’s only a matter of time before the number of people living unconventionally exceeds the number who aren’t.

At that point, you could say that living unconventionally will have become conventional.

It’s happening.

The bounds of convention are unwinding already.

People are increasingly educating themselves outside of the standard system. They’re trying more careers than ever in pursuit of a purpose that better fits their toolsets. They’re connecting and collaborating with equally independent-minded people more freely than ever. And unconventional success stories are becoming mainstream.

But it’s not all positive.

Some people are escaping one convention only to be sucked into others. Instead of being bound to how most people do things, they get even more tightly tied down to a smaller echo chamber’s identities and beliefs.

Optimistically, I believe these are societal growing pains. It takes time for people to learn how to think for themselves. You can’t just give everyone a dose of psychedelic mushrooms and expect them to unspool their brains.

Some people are indelibly stuck in their ways. And some will only make it partway out before getting stuck again. But many more will learn from their mistakes and keep tinkering to make the most of it with what they’ve got. It’s in their own best interests to do so.

It’s in everyone else’s best interests, too.

Think outside the box quotes cover image of Kim thinking with big open sky


Imagine a world where everyone’s making the most of their toolsets and materials. Wouldn’t that be an extraordinary place?

Or have I become so “unbound from what is usual and the way most people do things” that I’ve lost connection with reality?

Maybe I’m trapped in my own little echo chamber. I invite you to challenge me.

But if I allow you to challenge me, allow me to challenge you back:

What if what I’m saying is true?

What if the world is slowly evolving into a place where it will be conventional to live unconventionally? And what if there are better ways you can be putting your toolset to use?

If so, the questions isn’t, “Should you live an unconventional life or not?” The question becomes, “What are you waiting for?”

Ask yourself again.

Back to my question from the top:

What comes to mind when you think about someone who’s living an “unconventional life”?

I hope by now you’re starting to think of yourself.

Maybe you can imagine your future self who has tinkered with the possibilities of your toolset and materials to create a life more fabulous and fulfilling than you could ever build by copying convention.

Is there any reason you shouldn’t be working in that direction?

I don’t think so.

But that’s just me.

It’s up to you.

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About the author

I'm Chris. Canadian, husband, dad, writer, investor, athlete, and obsessed explorer of the secrets to living a never-boring, always improving, unfollowable life story.

One response to “Why You Should Be Living Your Own Unconventional Life”

  1.  Avatar

    I loved reading this!! Happy to hear I’m not alone. Tying my conventional life w a big beautiful bow signing off in Feb 2024 to pursue being a treasure Hunter. All I can say is it doesn’t happen by accident to work with purpose is a game changer. It’s taken 8 yrs to buy my freedom back. To be done chasing money in my forties is a dream come true. It can be done & best of luck

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