Updated: 02-03-20


Whoa…heavy topic, right? Settle in, this is a longer one, but I feel that someone needs to read this.

I wrote this post shortly after listening to The James Altucher Show Podcast. The episode was called “How To Become A Master Of What You Love” with guest Robert Greene (author of several outstanding books).  You can listen to it here.

It got me thinking.

How did I get here?

I didn’t ask myself this question in the existential sense?

God, are you listening?

I was reflective of the path it took to get here, where I am today, doing work I love. What I do for a living today was not my dream as a child; I wanted to be the starting Point Guard for the Knicks.

When that didn’t pan out, I wanted to do something different; become a world-famous Hollywood Director and make movies that would be remembered throughout time. When that didn’t pan out, I changed course again. I’ve had plenty of failures but as I look back on my life, I was never really, truly, unhappy in my career, and there’s a very good explanation for that.

I have only ever aspired to do work that made me feel fulfilled and happy with my contributions to the world.  

Even when I wasn’t doing work that fed my soul, I never felt trapped. I have always seen everything as a stepping stone to the next thing.  Even now, I’m only on a stepping stone to the next level.  My career never feels final, it’s iterative and always evolving. I have so much more to accomplish, and I plan to play until the clock runs out.

Speaking from “here”

I’d like to pass along some things that I’ve learned about falling in love in every sense of the word.  Though I’m going to write this about falling in love with your career, the exact same principles exist in dating and relationships.

I operate from the belief that the only way a person can die happy, is to live a life of love and a life of purpose.

How To Fall In Love

Step 1: Start With The Voice Inside

Falling in love starts with knowing yourself and you can only know yourself if you listen to yourself.  However, before you can even think about listening to yourself, you must first love yourself. You cannot love another person or the work you do, until you are clear with yourself.

This is YOUR life.

You don’t need to live up to other people’s expectations. Provided you’re not doing anything unethical or immoral, accept the things about yourself that may not fall into other people’s categories of right and wrong, safe or stupid, etc. Until you have that, you’ll never see the path clearly.

This is one of the reasons people fall in love with the “wrong” things. They’re too busy chasing someone else’s dream instead of their own. When they finally catch it, they quickly realize that it doesn’t feel right…they’re not happy.  This is what happens when you go after what seems like the “smart decision.”  When you chase money or status.  When you chase job security (or the illusion of it). When you play it safe.

In relationships, this is why people look for a partner of a certain height, weight, or hair color. They don’t do the work to dig deep so they focus on what’s superficial.  Love doesn’t sit on the top epidermal layer, it’s not colored by melanin…and it can’t be purchased.

So, get all that crap out of the way, look deep inside yourself and listen closely. Listen for the giggle. Look for things that make you feel like a kid freaking out about a movie they want to see. In the midst of all those adult decisions, when you look a little deeper, you’ll find something exciting… you’ll find the magic.

You choice of career should ideally cause that magic, giggling voice inside of you to go absolutely bananas.  

I assure you, falling for magic will beat falling for salary, every time. What’s more, when you can make that salary and believe with every fiber of your soul that you’re in the right role, that’s true love.

Find The Path

Step 2: Go On First Dates

Finding your way to the path is simple, it’s just like dating. Most people don’t expect that the first person that they ever date is going to be their soul mate.  I mean, what are the chances?

But it starts like this:

You start dating someone.

  • Maybe it’s because you’re attracted to them.
  • Maybe it’s because they live next door and it’s convenient.
  • Maybe it’ll piss off your parents.

Whatever the case may be, after the relationship falls apart you learn something about yourself. Then, you do it again. The more of these experiences you can go through and learn from, the higher the likelihood that you’ll see your true love when they come along.

By doing this, you will learn about what’s really important to you. You will see all the places where it didn’t feel right. You will see all the things that actually worked. You will start to be more discerning about who you go out with, where you meet people, and what things are really your dealbreakers.

Date after date, time after time, you get more and more clarity, and then one day you see it, clear as day what you want, what you need to fulfill you in every way.  You know this because you’ve done the work chasing what felt right at the time.  And after disappointment and elation, you have a clear picture of what it is.  This is how you continually move closer to true love.

Now, use this same lens to look at your career.  

Chase the “girl” or “guy” that grabs your attention. The one that makes you tingle inside. If it doesn’t work out, reflect, learn, and move forward.

It’s. A. Process.

Falling Deeper In Love

Step 3: Separate Lust From Love

Thankfully–and occasionally regrettably–my path was never stunted by a desire to make the “smart” decision.  I took every opportunity to listen to the voice inside my heart.

P.S. that voice is a tad bit insane (I mean, at 5’5″ I thought I was going to be the starting point guard for the Knicks.  I’m not saying it couldn’t happen, but it certainly was a long shot)

In any event, after much trial and error, I arrived at a point where I had an MBA and a business of my own. I ran it for 7 years, then it got acquired. Then I leave that business and start a new one.

…and this is where it gets tough.

It’s not enough to fall in love.  

I’ve had multiple careers and multiple businesses and I’ve gotten divorced and remarried. Much like relationships, you don’t just fall in love, walk off into the sunset and everything is rainbows and sunshine.  You have to work at it.

Love isn’t lust. Love is not just passion.

It’s commitment. It’s dedication.

One of the reasons people fail in their careers and in their relationships is because they give up too early. They give up on their relationships when they realize it’s not always easy. They give up on their dreams when they realize they have to confront failure, inadequacy, competition, and all manner of other hardships.

But (sometimes) this is exactly where you have to dig in. Sometimes, yes, it’s time to walk away. Don’t stay in bad jobs, don’t stay in bad relationships, and don’t finish bad books. But, don’t run from those things because they’re hard.

Falling in love with your career, with your work, is so much more than the initial feeling that follows cupid’s arrow piercing you. It’s more than the initial excitement. I’m not at all religious but there’s plenty of truth in this (emphasis mine)…

Love is patient, love is kind. It does not envy, it does not boast, it is not proud. It does not dishonor others, it is not self-seeking, it is not easily angered, it keeps no record of wrongs. Love does not delight in evil but rejoices with the truth. It always protects, always trusts, always hopes, always perseveres.

1 Corinthians 13:4-8

If you want to live a remarkable life, do work that matters, and (eventually) die happy, you need to commit. You need to give it everything you’ve got. You need to be patient. When runner’s talk about the “runner’s high,” it’s not happening in the first half-mile.

Don’t take the first thing that comes along.  Heck, don’t even take the “best” thing that comes along. Go after the RIGHT thing. Be the author of your story, and fall deeply, truly in love with the life you have.  There’s nothing wrong with anything less, but there’s something so much more profound about constructing the life and career you want.

If you truly want to live a remarkable life, and taste the sweetest victories, you need to be doing something with purpose. If you want to die happy, leave it all out on the court. Search high and low for your true love until you find it. Do this in everything you do. Don’t settle for anything less.

If you do this, I promise that one day, when you drift off, you’ll feel at peace with the life you’ve led and you’ll leave behind the legacy of a champion.

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