I just moved into my dream condo on the beach: 7 lessons about success

When I graduated from college, I moved into a small, studio apartment.

  • It was the size of a closet.
  • No AC.
  • Heater from the 1970s.

I was making minimum wage working as an entry-level copywriter at an advertising agency in downtown Chicago.

Every morning, I had to run to catch my hour-long train at 7:00 a.m.

And every evening, I had to take the 90-minute train back home at 6:00 p.m.

I could barely afford the train pass. Taking a cab was never an option. And Chipotle every other Friday was considered a treat. I couldn’t afford to date, couldn’t afford to eat at any nice restaurants (or shop anywhere except the discount grocery store), or buy myself new clothes. Every month, after paying my rent (70% of my monthly earnings, since I was living in Chicago) and my utilities, I would move $20 into my savings account. That’s all I could afford to put away.

I didn’t even own Internet.

8 years later, I just moved into my dream condo on the beach

I moved from entry-level copywriter to full-time copywriter.

A copywriter to Editor In Chief for the agency.

Editor In Chief to Associate Creative Director.

Then, when I was 26 years old (with $5,000 in savings), I quit my job to go all-in on becoming a freelance writer and working for myself. 3 months later, and I went from making $50,000 per year to $20,000 per month.

Shortly after, I started my first company, a ghostwriting agency for founders, executives, and investors called Digital Press and grew that to 7 figures in revenue in less than 18 months. To date, I have ghostwritten for more than 300 executives, professional athletes, Silicon Valley investors, Grammy-winning musicians, and more.

Today, I make 100% of my income from writing—for myself and others.
Here’s what I’ve learned about the journey of “success.”

Lesson 1: Your habits in your shitty apartment define your habits in your dream house

I wrote every day in that studio apt.

Even in the summer, 100-degree heat.

I’d sit at my desk in my underwear and take cold showers every 40 min to cool off. I would work out of the Starbucks down the street whenever I needed Internet (I didn’t have Internet in my apartment for 4 years after college). I rarely went out on Friday nights, and instead went to bed early so I could wake up and spend 7:00 am to noon jacked up on espresso, writing.

The only difference between me today and me “back then” is that I have luxuries like Internet and AC.

But the mentality, and the work ethic, is identical.

Lesson 2: All you really need is a bed and a desk

For the first 3 years out of college, I slept on a $79 air mattress from Target.

My desk was $20 from Goodwill.

And still, somehow, I managed to write my first book. I managed to become the #1 most-read writer on all of Quora in 2015 without owning Internet in my apartment. I managed to master my craft to the point where I could quit my job and start working for myself.

When I look at my belongings today, the two things that mean the most to me are my bed and my desk.

That’s all you need.

Lesson 3: Discipline is the leading indicator of success

In my early 20s, I was so determined to become a successful writer, I gave up a lot of social interaction to write my first book.

  • I wrote every single night from 9 pm to midnight, after a full day of work.
  • I wrote every Saturday and Sunday morning for 4+ hours.
  • I wrote during holidays when everyone else took the “day off” from work.

Between the ages of 22 and 27, I didn’t take a single vacation. Even if I had wanted to, I couldn’t afford it. But the truth is, I didn’t want to—I was so dissatisfied with my life and working for someone else, I was determined to get myself out of my current situation and change the direction of my life.

But every time I tried to explain to the people around me why I was making these decisions, they told me I was crazy.

  • “One night off won’t hurt.”
  • “Come on, you can work on it tomorrow.”
  • “It’s not that big of a deal.”

4 years later, I was an author.

And all of them wondered how I did it.

Lesson 4: Money doesn’t fix everything

I was very insecure about my studio apartment in Chicago.

I was ashamed at how poor I was.

I didn’t date because I hated the thought of bringing a girl back to my bare-bones apartment. I didn’t own a couch or a TV. My bed was practically in my kitchen. And the only chair I owned was my desk chair.

It took me years to realize those insecurities weren’t “my apartment’s.”
They were my own. And the money wouldn’t fix them.

Funny enough, I ended up meeting my girlfriend my last few months in that apartment. We’re still together today. And she reminds me often of how much she enjoyed those years visiting me in Chicago, staying in that small, studio apartment together.

Lesson 5: If you can’t do it here, you won’t be able to do it there

After college, I listened to a lot of my peers say: “Once I get to X, THEN I’ll start working on Z.”

But the goalpost kept moving. And they never got “there.”

One of the hardest lessons I learned after quitting my job and becoming a full-time writer was that writing every day wasn’t going to be convenient. I wrote in airports, in cabs, in hotel rooms, at friend’s houses. I wrote at odd hours, I wrote at 5:00 a.m. before my girlfriend woke up when I would visit her in Arizona, and I wrote on Sundays even when I was completely brain dead.

As a result, I grew very quickly as a writer.

Because I didn’t “wait” for the moment to be right to write.

I just wrote.

Lesson 6: The more you achieve, the harder it is to stay disciplined

I am surrounded by 10x more distractions today than I was 8 years ago.

  • I own a TV now.
  • I have disposable income.
  • I can travel.

In my 20s, I didn’t even have those options. As a result, it was a lot easier for me to work, focus, and not get distracted. I didn’t have friends texting me. I didn’t have clients calling me. I didn’t have hundreds of emails to respond to. My life was much simpler back then.

Not having can be a gift too.

This is why, whenever possible, I still try to “not-have” when I can.
Even today, I look to deprive myself of things to stay connected to that feeling of “not-having” and never lose that commitment to my craft.

Lesson 7: “Wanting” is more fun than “Having.”

2 days after I moved into my dream condo, my weekly therapy session rolled around.

“Now what?” I asked him.

I’d spent almost a decade pounding the pavement, trying to get “here.”

Only to get “here” and not know how to enjoy it.

By every definition, where I live today is everything I ever wanted. And yet, I am painfully aware of how much I am still that same kid in the studio apartment downtown Chicago at heart. My work ethic is the same. My inability to care about “things” is the same. I have a better view, a nicer desk, a comfier bed, but I still spend the majority of my time, energy, and focus thinking, working, writing.

Everyone thinks something massive changes once they cross a certain milestone.

I did too.

But that’s far from the case.

Final story

Two years ago, I had the opportunity to ghostwrite for a Grammy-winning producer.

You would know his name.

He flew me out to his home for a work weekend. A massive ranch with a multimillion-dollar home music studio. He owned every keyboard money could buy.

In awe, I said, “Your creative process must be so different today. You have so many options!”

He shook his head and said, “Actually, it’s killing me.”

To make his next album, he was going to rent a studio apartment in the city.

We all think the journey somehow gets easier once we’ve achieved our dreams, or made a certain amount of money

From my own experience, and what I’ve learned ghostwriting for so many successful people, it’s actually the opposite. The journey & creative process gets harder.

So, enjoy wherever it is you are today.

Focus on mastering yourself, your habits, your state of mind, your ability to create no matter how hot the room is, whether you have Internet or not.

Your bed, your desk, and your apartment might change.

But the work won’t.

This article originally appeared in Medium.