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Outsmart the Hustle

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When I left the corporate world ten years ago, I did it to pursue my truest, most adventurous life.

I wanted to interrupt the pattern of my life and go after more meaning where I could take plane trips and read books and hike in the woods and experience the world without the confines of sales quotas and staying at Marriott’s.

Not that there’s anything wrong with Marriott’s. But my favorite Marriott’s happen to be in places like Maui and Costa Rica, not Denver and San Jose.

And if I’m honest, I wanted to bring my work to Phoenix while seeing my sister for the holidays and then head to Costa Rica for two weeks to do yoga, stare at the ocean, and squish the sand between my toes, and dry off in the warm breeze with a Modelo and a lime, and to go for a for a walk in the jungle and look for monkeys and feel like I’m alive.

This guy would show up to watch us do yoga on our recent visit to Costa Rica

And to do this I needed to win the battle with my own brain.

Because, you know what brains do? Awful, terrible things.

Your brain will tell you that you can’t.

Your brain will tell you that you’re stupid for thinking that way.

Your brain will tell you that you don’t have the time.

Or that you’re not good enough.

That whatever version of work you want to offer to the world will be garbage; that no one will want what you’ve created; that you’re delusional; that you could never replace your corporate salary doing something you care about.

Your brain will try to convince you of all the things you ARE NOT.

That you aren’t creative enough, young enough, old enough, smart enough, cool enough, brave enough, expert enough.

Your brain will tell you you’re off your rocker crazy for even thinking you could coach, write, speak, code, start a podcast …and actually make money with your ideas.

Your brain will gaslight you & abuse you at every turn.

Who do you think you are? it’ll say.

Nobody’s going to pay money for that.

You can’t possibly travel AND work.

You should really go back to doing what you know works: everything you hate.

And you should stop being so self-centered and try really hard to just be happy and grateful for what you’ve got – which, for me, amounted to a treadmill of work travel, rarely sleeping in my own bed, and weekend binges of Netflix because I was too tired to do anything else.

You musn’t be greedy, your brain will advise.

You must stop acting like you are so special. You aren’t special. Why can’t you just be satisfied?

Brains sabotage the sh*t out of our most beautiful ideas.

So, when you ask me: How can I do meaningful work – while also traveling more and enjoying my life and doing yoga with monkeys overhead?

I’ll ask you this:

Can you do what is required?

Can you silence your brain long enough to actually attempt something meaningful?

This is not the same as doing what feels good.

There’s a lot of talk about that, but I’m not interested in pursuing blissful ignorance and living like a hippie.

Giving a damn about your life – that’s the name of this game.

It’s about maximizing for meaning and adventure and, critically, financial security.

Yes to travel. Yes to experiences. Yes to being independent and free and excited by your own existence again.

But also, yes to mature achievements, and a thriving business, and flush retirement accounts, and excellent health insurance, and maybe even an investment property in a mountain town that you rent out and also stay in whenever you feel like it.

Pursuing a better life isn’t about chasing juvenile whims or feeling entitled to things you haven’t worked for.

It’s about being an adult who’s decided to intentionally design a life that works for you, because the modern world has given us some great options, and it’s time to stop listening to the troublemaker inside your head and start analyzing what your options really are.

Your skills are worth money. Your experience is worth money. Your ideas are worth money.

Your ability to be creative and design unique solutions is a very real product in the modern economy.

Here’s a comforting and disturbing fact: 80% of the people who are successful at designing their lives are mediocre.

But they’re great at one thing: EXECUTION.

They move forward without overthinking it, and as a result?

They’re more successful than someone sitting in their living room trying to think their way to a solution.

They aren’t afraid to try new things – to experiment and see what happens.

This is the frustrating flipside of the modern economy: mediocre people find more success because mediocre people aren’t perfectionists.

It’s the people who care too much that get the short end of the stick, because while they’re overthinking every step, someone else is actually taking steps.

Can you do what is required?

What is necessary is doing the work – regardless of what you think about it.

Regardless of how you feel.

Regardless of how harshly you judge yourself.

Regardless of your own opinion as to whether it’s any good.

In a world that endlessly asks us all to trust ourselves, maybe the real thing we need is a new kind of trust.

Not the kind of illusory, delusional trust that most new age gurus pump you up with – “You’re brilliant! You’re magic! Trust the Universe! If anyone can do it, it’s you!”

But rather, the kind of deep, profound trust that comes from showing up to do the work every damn day, disciplined and without fail, in solidarity with yourself, with a sound commitment to move forward in order to honor what you actually want …instead of what you’ve convinced yourself is an acceptable substitute for the life you wished you had, but don’t.

Live bravely,

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