6 lessons I learned sleeping on the floor for a year

I got kicked out of college when I was 19. My GPA was 0.33. I was broke and too ashamed to ask for help. It was the end of the year and everyone was packing up for the summer. I was packing up forever.

I gave away most of my stuff. I was too lazy to move. I was almost too lazy to be alive. I sold my laptop to some guy from Craigslist for $500 bucks.

I slept in my car the first two nights. I didn’t want anyone to know how badly I fucked up. I was embarrassed. I was scared that people would think I was a loser.

I pulled my car into the back of a hotel parking lot and slept there. I didn’t know where else to go.

Sleeping in your car is pretty challenging. You don’t actually do much sleeping. I played “Brick Attack” on my flip phone and watched cars drive by to pass the time. I snuck into the hotel and ate breakfast from the buffet. I was sort of staying there.

$10 an hour doesn’t go very far, but my web developer job was the best thing I had going for myself. $400 bucks a week, I was scraping by.. even in middle-of-nowhere Rochester, NY.

The commute was pretty easy, though. You just wake up, brush you teeth in the parking lot, and drive to work.

After 2 days of hunting, I finally found a room. $375 a month. Utilities included. I moved in with my new roomie, Mark, the very next day. I was tired of sleeping in the back seat of my Toyota.

I had about $200 left over after my first month’s rent. It was the poorest I’d ever been.

Of course, I spent it all immediately. I bought a really expensive, high-quality air mattress. I slept on it for one night and returned it the next day so I could buy a cheap air mattress and a cheap desk.

Growing up, my dad told me that I had “caviar taste on a peanut butter budget”. I think he meant “be realistic” but I always took it as a compliment— because I had good taste. I didn’t like settling for peanut butter.

I really wanted an Xbox, but it cost $300. There was no way I could afford it. It was 25% of my monthly income and I was broke.

By the way, I didn’t have any credit either. My credit score was something like 520, because I didn’t pay my bills. I had like $10,000 in debt that I hadn’t paid. When the debt collectors called me, I yelled and argued. I called them assholes, but I was the asshole.

There was no way I could afford the Xbox.

I bought a brand new Xbox. And then I sold the brand new Xbox to a pawn shop 6 days later.

Turns out, I was right, I couldn’t afford it. And now I was short $200 on rent. I think the guy gave me $180 for the Xbox. He probably thought I was an idiot. He was right.

Lesson 1: I (finally) took unequivocal responsibility for my situation

This is going to sound ridiculous, but..

I remember the defining moment when I hit rock bottom.

My air mattress popped. Not an exciting, blood-rushing pop, just a slow and mushy deflation. It just stopped.. holding air. It gave up.

My air mattress died.

I rolled up the lifeless body into the corner of my room and started sleeping on top of it.

The old me would have returned it to Wal-Mart and tried to get a new one. But I finally had enough. I didn’t want to live like this anymore.

I slept on the fucking floor for the next year. I was tired of living life like an amateur.

“I slept on the fucking floor for the next year. I was tired of living life like an amateur.”

I realized that it was all my fault. My own mess to relish in. I got myself here and only I could get myself out. It was my fault. I fucked up.

Lesson 2: I taught myself how to sell

College is an expensive waste of time.

I was $70,000 in debt, making $400 bucks a week with a $500 student loan payment. I was only there for 2 years. I didn’t learn much.

There’s ONE thing I wish that I learned in college— how to sell. Nobody told me I’d need to know how to be a salesman.

Everyone said that selling wasn’t important. They said I could just be a programmer. That I didn’t need to sell unless I was going into business. Plus, selling is irky, right? They said “only car salesmen with beige sportcoats and bad toupée’s need to know how to sell.”

They are wrong. “Hey, I need some money, give me a job” isn’t going to get you work. Being persuasive is a skill. Selling things, or more importantly selling yourself, is an invaluable skill. It’s teachable and most people are AWFUL at it. I was.

I’d give up everything I know about programming and computers to be an expert at selling. You’re selling every second of the day— and you’re either good at it or bad at it.

You’re selling every second of the day— and you’re either good at it or bad at it.

Gary Halbert was a direct marketing genius. He went to prison in 1984 for fraud. While incarcerated at the Boron Federal Prison Camp, he wrote letters about marketing to his son— lovingly titled “The Boron Letters”.

The letters contain phenomenal lessons about selling. I read them every month. Some lady on Facebook told me that I should read the bible instead of letters from some guy that went to prison for fraud. She’s wrong. I’ve read the bible and this is better.

Lesson 3: Ask for what you want. Over and over again.

When I got my first salaried job my boss said “We’ll give you 60K”. I said, “Okay! I can’t wait to start!”

I called him back an hour later and told him that I’d prefer 80K. He said “No”, but called me the next day and said “Fine”. My mom told me I was an idiot for negotiating. But I wasn’t negotiating— I was asking, and I had no clue how to ask for what I wanted.

Asking is pre-negotiation. It sets the boundaries. If you ask for 60, you won’t get 80. I didn’t know how to ask.

You have to constantly ask for the things you want. I’m afraid of being annoying. I’m scared of over-staying my welcome, being obnoxious, annoying, and asking too much.

But no one cares what you want. They care about what you want as much as the lady at the DMV. You need to keep asking. Maybe they say “No”. So what? Ask other people— there’s 7 billion of them. Want a promotion? First ask your boss. Then ask other companies.

I went on an interview once and had to take a Javascript programming test. Some guy popped his head into the room and said, “By the way, how much pay were you looking for?”

“No can do”.

By the way, I was living off of kidney beans and buffalo chicken nuggets at this point in my life. I had just turned 20. I was $375 away from being homeless.

I asked if he wanted me to leave. He told me to finish the test. I left anyway because I didn’t know Javascript. They didn’t offer me 100K. But I kept asking and someone else did.

Lesson 4: I ignored “best behavior”

“The risk of insult is the price of clarity.” The Wizard of Ads

My Mom used to tell me to “be on my best behavior”. What she really meant was “be boring and don’t stand out”.

Once, I went out to eat with a new friend. We were going to order sandwiches. She asked me what kind I wanted. I said, “I don’t know, what kind are you going to get?” I was literally afraid I would insult her with my choice of sandwich topping.

I was living life with “best behavior” mode engaged.

Each person has three different lives— the person they pretend to be, the person they are, and the person they can be.

It’s too complicated. Just murder the person that you pretend to be. Plunge a knife right into his heart. Focus your energy on making sure that the person you are is the same as the person you can be.

When you meet someone, treat them like you’ve known them for 10 years. Be overly comfortable. Don’t be on your best behavior. Don’t be formal because you’re worried about offending them. We all hate formality.

Lesson 5: I started writing (and reading) daily

There’s a secret that real writers know that wannabe writers don’t, and the secret is this: It’s not the writing part that’s hard. What’s hard is sitting down to write. Steven Pressfield

There was nothing I hated more than writing. I’d rather go to the dentist and have all my teeth pulled than stare at an empty screen and blinking cursor.

It turns out I didn’t hate writing. I just hated writing like a staunchy jackass— the high school and college formula for writing.

How to be ignored your entire life and bore everyone

  1. Write a long, boring introductions and only talk about yourself
  2. Write exactly how you were taught in school

Everything you’ve learned about writing in school is wrong. It’s stupid. Only boring people write like that. Formal words are boring words.

Read “This book will teach you how to write better” by Neville Medhora. You’ll thank me when you finally stop writing like a jackass and start writing like a real person.

No one wants to hear your story. They don’t care about your passion. All they want to know is how you can fix their problems. Start your next email with that.

By the way, you should read every single night. Even when I was sleeping on the floor, lying on top of my dead, lumpy air mattress, I read everyday. If you want to get better at writing you need to read. It primes the pump.

Lesson 6: I realized that education isn’t the same as learning

“It is one thing to remember, another to know. To remember is to safeguard something entrusted to the memory. But to know is to make each thing one’s own, not depend on the text and always to look back to the teacher.

Zeno said this, Cleanthes said this— Let there be space between you and the book.Seneca

People think you need to go to college to learn, but they’re wrong. Learning and education aren’t the same.

With a natural desire to learn, a formal education is a waste of time. It’s lacking. And for the self-starter, education is boring and rigid.

You can pay $70,000 for a piece of paper that says you’re educated, but it doesn’t mean that you’ve learned a thing. Real learning comes in a different form— it’s a bookshelf with unorganized stacks. It’s blood and sweat. Daily practice. It’s doing the thing over and over again.

Real learning is blood and sweat. Daily practice. It’s doing the thing over and over again.

Learning is a lifestyle. Education gets you in the chair, but it’s up to you to decide whether or not you learn. Pick up a book and start reading. Practice it. Implement it.

College taught me to be rigid instead of flexible. I didn’t learn anything in college that I couldn’t have taught myself, except how to pay off debt.

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