This is Part II of my essay series about how I figured out what I wanted out of life. Part I is now the highest rated essay we have ever had. If you missed it, click here. 

Yesterday I told you How I Spent A Year Being ‘Strategically Broke’.

The essay talked about how my life changed when I decided “the ordinary life isn’t for me”. 

Those first few years were rough. My life chart basically looked like this: 

Everyone focuses on the big ‘upswing’ of the chart.

But the million dollar question is - how do you survive the 10 years of flat line progress? 

Unless you’re cousins with David Goggins, you probably won’t have the willpower to go through 10-12 years straight of nothing but failures.

The answer is simple: they don’t.

The people that make it through the ‘decade of suck’ are the ones who enjoy the game. They don’t play to win, they play to play.

That’s why they keep going, even when they see all their friends getting promotions and buying houses with nice backyards in Connecticut.

Even when the scoreboard says: “Life 12, You 0” - they keep playing.

They keep playing, until they get so good that the game has no choice but to give them the win.

But I know what you’re thinking. What game should I even play? How do I find a game I love?

Well the simple answer is…I have no clue. I don’t know you. I don’t know your situation. Remember, I’m just a jackass with wifi.

But, ‘not knowing’’ has never stopped me from confidently giving an answer - so I present to you: UNCLE SHAAN’S EAZY-PEEZY 3-STEP PLAN TO FIGURING OUT WHAT YOU WANT TO DO IN LIFE™️

Step 1: Pop The Bubble

Whatever job you THINK you want to do, it’s probably wrong. 

You probably have been saying “I want to be a doctor” or “I love b2b software” because it sounded good to your friends, your parents, and your college counselor.

I’m not saying you’re wrong. I’m saying, you actually have no idea. 

Instead of just talking about it - take it for a 2 week test drive. Try before you buy. 

Don’t let your dream float in a magical theoretical bubble. Pop the bubble and find out what you really love.

I know this because I spent 10 years telling everyone I wanted to be a doctor - sports medicine, to be exact.

One day - I met a guy at a wedding who had the exact job I wanted (orthopedic surgeon for a sports team). I asked him if I could shadow him for 2 weeks. He agreed.

Right away, I realized that I did NOT want to be a doctor. Doctor’s are very noble, but the job has very little creativity. (trust me, you don’t want your doctor ‘getting creative’ on you…)

Turns out, I realized creativity and variety matter a lot to me. This simple decision to shadow a doctor totally slayed the false dream I had been chanting to myself for years.

Those 2 weeks saved me from 8 years of med school… and another 20-30 years doing a job that didn’t light me up. 

If you pop the bubble, you’ll know for certain: 

• YES - this is my thing. I’m down to invest a decade becoming great at this 
• NO - this ain’t it. Glad I found out now. 
• MAYBE? - (see ‘No’... as Derek Sivers once said, “if it’s not a Hell Yes, it’s a No”)

Step 2: Give Yourself Permission To Wander

Marcus Aurelius once said: “To live well, one must first know what is worth wanting." 

The greek philosopher Seneca believed: “True freedom is found not in acquiring much, but in knowing what to desire." 

Actually, they didn’t.

But I told ChatGPT to “take my quote and make it sound like it came from 10 wise philosophers”…

… and it delivered like Stockton to Malone. 

Anyways. It’s true. The most important thing is to figure out what you even want.

You are probably a ‘high achiever’ type. And high achievers get really anxious when they don't have an “answer” for what they’re going to do with their life.

This causes them to prematurely commit to something - anything. 

As Tim Ferriss says, most people would rather be unhappy than uncertain. 

So - the trick here is to name this era and time box it.

People will behave very differently if you give something a name and date. Don’t believe me? Go checkout how people behave during Mardi Gras or Burning Man. 

I call this a season of wandering. This is a season where you’re going to explore options. You’re going to dabble. Try things. 

I call it “wandering” because it let’s you think creatively. There is no ‘wrong path’ when you wander, as long as you’re following your curiosity and excitement.

..but, what are you looking for while you wander? 

Clues, not answers. You see, we all want answers. But like any detective, you don’t seek the answer directly. Answers come from clues.

STEP 3: Look For Clues

What are some examples of clues? Energy & Blueprints. 

ENERGY: Start paying attention to what gives you energy, vs. drains you.

• I get drained at social events. I hate it.
• I get tons of energy from reading books.

But the real clue is to figure out: what feels like play to you, but looks like work to others? That’s the moneymaker. 

For me, that’s writing. The average person hates writing. They dread the blank page. I think they have PTSD from school essays.

But I love writing, so I followed that clue. Which led me to starting Milk Road - a newsletter company. A year later, it grew to 250,000 subscribers and sold for millions of dollars.

The Big Lesson: clues can be very valuable. 

So I’ll ask again - what feels like play for you, but looks like work to others?‍

BLUEPRINTS

Tony Robbins says: “Success leaves clues”.

The fastest shortcut in self improvement is to find someone who already has what he wants and download the blueprint of their habits & mindset.

“Who’s living the life I want?” - this is a simple, yet powerful question. And you need to be specific…

For example, I wanted to be successful. But then I met a bunch of rich guys who were busy, stressed & divorced and their kids resented them.

I didn’t want that.

So I updated my Blueprint. I wanted money AND fun AND a house full of love. So I started looking for people who had that.

Anytime I found someone who fit that profile, I drilled in: 

• What do they do? 
• How did they get started? 

The key is to get outside your bubble. I met a guy who was filthy rich, from selling the conveyor belts that go on treadmills. What?

Then I had a older friend that I played ping-pong with daily. I asked him: “how do you have free time to play during the day? don’t you have a job?” 

He told me he imports fancy soap’s from Italy and resells them to 5-star hotels at a big markup. He said he makes $3M a year as the soap guy. 

The best part? He doesn’t even make the soap! He just saw a gap and filled it.

Turns out there are 10,000x more “ways to win” than you even realized existed. Even if you don’t end up doing those things (I don’t sell soap or treadmills), it simply opened my eyes to the possibilities.

My parents had very normal 9-to-5 jobs, so I only knew that flavor. They could only teach me what they knew.

That’s when I learned you can’t ask someone for directions to a place they’ve never been. 

But instead of complaining about my upbringing, I learned to bring myself up. I moved to SF, because I wanted to be a founder, and that’s where the founders lived. It was simple. Proximity is power. 

Today, I live a life that the younger me wouldn’t believe. I get paid to talk (my podcast). I’ve built and sold multiple companies.

My daily lifestyle is exactly what I want - Wakeup. Workout. Eat meal from private chef. Ride bike to drop off kids at school. Watch the bachelor with my wife at night.

I work on whatever I want, whenever I want, from wherever I want.

Everyone says hard work is the key to success. Bullshit.

Energy is the key to success. My energy comes from loving what I do, not from pushing myself to grind harder.

I get paid a fortune to do what I would do for free (podcasting, writing, investing). And best of all - I get to do it with people I love to hangout with everyday (shoutout to my dawgs Ben & Diego). 

If the 22-year-old-broke-boy-me saw the life I live today, he’d just say: “You lucky bastard. How the heck did you pull this off?”

Of course, everyone’s journey is different. And not everyone ‘makes it’. 

I am extremely fortunate that I rolled the dice and hit a hard six. (a craps reference, for those who haven’t played god’s greatest casino game)

So yea, luck matters. But if you think it’s all luck, you’re just a victim of circumstances. Luck matters, but action matters more.

The actions to figure out what you love to do are simple: 

• Give yourself a “Season of Wandering” - take 3 to 12 months where you experiment & follow your curiosity. Test drive before you buy.
• Look for clues - Ask yourself… “what feels like play to me, but looks like work to others?”
• Find Blueprints - find the people who already have what you want. Study them. Hang with them. 

If you do that, your career will take off. My short definition of a great career is doing things you love, with people you love.

And I know “love” sounds like fluffy woo woo to most, but to me, it’s a competitive advantage.

Why? Because people who love it, do it more. And the more you practice, the better you get. The better you get, the more money you make. 

If you’ve already found it (like me) - welcome to the Lucky Bastards Club™.

If you haven’t yet - don’t count yourself out. You just need to give yourself permission to wander.

Most will say ‘I can’t afford to’. Don’t have the time. The money. The courage. But you only get one ride on this rollercoaster of life. 

So, maybe the question is: can you afford not to? 

-Uncle Shaan

P.S. - this is Part II of my essay series about how I figured out what I wanted out of life. Part I is now the highest rated essay we have ever had. If you missed it, click here.