The great music producer Rick Rubin once said: “Great art divides”.

Well, you’re either going to love this essay, or totally hate it. There’s no middle ground.

This essay has concepts (and pics) I’ve never shared before. And it answers the question: “what do you wish you knew when you were younger?”

It starts with a single decision that changed my life.

That decision was to spend a year “Strategically Broke” — no job, no salary, and no plan.

At the time, it looked stupid. My friends laughed from their desk at JP Morgan.

But I had heard a quote from a guy I met at a casino: “I don’t know much, but I know one thing: the ordinary life isn’t for me”

That line stuck with me for the 16 years since I heard it: The ordinary life isn’t for me.

I wanted to live a life where I could be creative, with my friends, and get filthy rich in the process.

I didn’t know how to do it at the time, but I know now. So if you read this essay, you’ll learn:

1/ How I Spent A Year “Strategically Broke” — my backstory being young, dumb and fearless. (with pics & numbers)

2/ Permission to Wander - The 3-step system I used to answer the big question: “What should I do for my career?”

You in?

Alright, let’s start with this tweet that got me in a bit of trouble:

200,000 views - and my inbox slammed with messages.

The reaction was split:

Older people: “yep, that’s right.”

Younger people: “wtf - how am I supposed to do any of that without money?” 

I hear ya. I never wanted to be “that guy”.

You know, the guy who goes on podcasts after selling his company for $737M dollars and says “money doesn’t really make you happy”.

(Really? Alright bet. Gimme half of your money if it’s not doing much for ya)

It’s like when Bill Gates went on Ellen and she made him guess the price of groceries: 

He thought a bag of Totino’s pizza rolls was $22. (which goes to prove you can be smart and totally out of touch)

So - did I actually do that in my 20’s? Or am I just giving crappy life advice that I didn’t follow myself?  

Short answer, yes. I did. It was the most important 2 years of my life.

PART I: How I Spent A Year “Strategically Broke”

After college - everyone from school went and got jobs. Good jobs, bad jobs…but definitely jobs.

I chose a different path.

I decided to create my own “grad school”. Where I would spend 1 year with no job, working on my own projects, and traveling the world.

Everyone thought the idea was stupid. How will you pay rent? How will you travel with no salary?

Here’s how I did it:

Step 1 - Living “Scrappy”

My two best friends (Trev & Dan) drove to Boulder, Colorado and we rented the worst 2-bedroom apartment you’ve ever seen.

There were 3 of us, so Trevor put his bed (aka air mattress) in the living room.

Boulder is a great city. There’s amazing outdoors, a university party scene, and tons of entrepreneurs (Techstars was based there).

I think our rent was about ~$1,400 a month. Split 3 ways, that was $466 a pop.

We lived cheap - no furniture, craigslist desks (that we got for free), and Target air mattresses.

Oh, and our living room was our bedroom, our office, and our gym.

We also ate cheap. This was our menu: 

• Costco frozen grilled chicken bag ($25 for 10 pounds of chicken) 
• Eggs 
• Avocados (our luxury item)
• Rice 
• Ranch style beans
• Tons (and I mean, tons) of frank’s red hot sauce

It’s not the blueprint diet to live forever (and I’m sure they give out better food in prison), but it was effective to let us live cheaply. 

MONEY - OK so how did we pay for everything?

Instead of trying to figure out how to make the most money, we calculated the minimum money needed to live with max freedom.

I realized I needed about $1,000 a month. So I decided to try to make that in ~5 hours a week of work.

• I met a girl at a bar who needed help with math (yea, I didn’t have much game)… so I offered to tutor her and, eventually, her friends for $35/hour.
• I loved playing basketball, so I became the head basketball coach at a school for autistic children ($35/hour x 2 hrs a week).

At one point - the girl asked if the tutoring would be free if she was my girlfriend. I replied, “I’ll take the $35/hour, thanks”. (Rule #35, you can’t hustle a hustler)

These gigs were fun, easy, and gave me $700/mo - at only 5 hours a week.

Ok. So that was $700/mo. But I hit my 5 hours a week cap. So what do I do? Well, constraints breed creativity. I asked myself “what’s something easy I could do once, that would give me my entire year goal?”

I was already thinking of business ideas - but instead of launching them, I realized there was a shortcut: I could just pitch the idea, and get paid for the pitch (without even doing the business).

There were niche business plan competitions - with decent prizes and low competition. I entered a dozen of them, got paid for 2 of them, and we won $25K+ in prize money. That was ~2 years of living costs.

Our scrappiness had no bounds. 

Instead of a dog, we got a mouse for free as our pet (RIP Marty).

I put these photos here to show you: it’s not glamorous.

Frankly, it’s gross…

‍… but this was the best trade I ever made. “Nice stuff” was cool, but freedom of time was much cooler.

A year of free time in your 20s is worth a decade of free time when you retire at 65. When you’re young, life is a lot more fun.

The relationships and skills you build in your 20s have 20+ years to compound. The travel is more fun. You literally just have more energy.

So, what did we do with the freedom?

Traveled like hell. I road tripped across the States, then went international - China, Bali, & Australia.

Why not just travel later in life? Because when you’re young, traveling is easier, cheaper, and much different than traveling later in life. 

Backpacking through Thailand and sleeping in hostels with strangers is cool when you’re in your 20s, uncomfortable in your 30s, and damn near impossible when you’re in your 40s.

In fact, traveling young deserves a totally different word than traveling when older.

• Young travel is a lightweight spontaneous adventure, like backpacking. 
• Family travel is more like a U-Haul move, with fist-fulls of diapers.

I still travel, but it feels much different with a wife & 3 kids. 

Step #2: Work on projects (not jobs)

Now - the goal was not to be unemployed forever.

The goal was to use my 20’s to figure out what I really love to do. What am I really great at? What do I enjoy?

I wasn’t sure - so I started off by just learning master skills.

Have you ever seen a janitor’s key ring with like 573 keys on it?

Well - they also have 1 key called a master key that unlocks many doors.

That’s a master skill. A skill that unlocks many doors in the future.

So I made a list:

• Skill of making something out of nothing (hustle)
• Skill of selling stuff online (sales/marketing)
• Skill of pitching ideas, get people on board (persuasion)

To be clear - I had no clue how to actually learn this stuff. So I just started “doing projects”.

Pixar says their process of making movies is to start with something that sucks, and then remove the suck.

Every version 1.0 of everything, sucks.  So your job is to edit, and tweak, over and over again until… it no longer sucks. 

That’s what I did with my projects. I’d launch them, but they sucked. Then suck a bit less. Until finally, I didn’t suck much (still suck a little tho). 

Here are some of the projects I worked on that made me ‘suck less’:

• An e-commerce store that sold custom wristbands to frats & sororities. We made $1k in our first weekend. This taught me how to sell things online, find manufacturers on Alibaba, drop ship products, and cold email.
  
• Game Shows: I always wanted to go on a gameshow. So I said, why not? Being young gave me the license to do irrationally dumb things. Me and my buddy Dan got casted onto Wheel of Fortune. Dan almost won a trip to Italy.

• Video editing for real estate. I pitched real estate agents a service that would turn their photos into an animated video for each property. We charged them $500 for, basically, a cheesy slideshow of pics with music - $500 for like 15 minutes of editing.
  
  Agents were hard to sell to. But we learned video editing, more cold email practice, and that I should do things where my earning power ($$) is not tied to my time (like tutoring).
  

• I got obsessed with poker. I even won $10K in a poker tournament one night. We used that money to travel Australia. This taught me a ton about strategy, thinking in probabilities, controlling my mind, and figuring out if others are lying.

• A delivery-only sushi restaurant. This taught me how to make sushi, run a restaurant, negotiate a lease, get financing from a bank, etc. 

To be clear - none of these projects were a big success financially. A few made money. Most went nowhere. 

At the time, I felt like I was striking out. Over and over again. But I was having fun, so I kept going. I didn’t realize that those early skills would pay off so big later, but as Steve Jobs said: You can’t connect the dots looking forward, only looking backwards.

So my job was to just make each project, each ‘dot’ as bold as I could. Having faith that it would connect later.

So - sushi? poker? e-commerce? how did you ultimately figure out what you want to do? 

Great question. I figured out what I wanted to do in life with something I call the Permission to Wander. A 3-step system for figuring out what you really want to do in life.

That’s in Part II (read here). 

Stay thirsty my friends,

-Uncle Shaan

ps. if you loved this essay, let me know. (send me an email in the box below).

I’m fueled by caffeine and compliments.