My Leap Story: From 9–5 to Freelance Writer to Successful Entrepreneur

To say my life has changed in the past year would be a severe understatement.

In 2016, I left my 9–5 job in advertising to become a freelance writer.

It was September. And the same day I left my job—the office decorated in, “Best of luck, Cole!” banners and balloons—I published my first book, Confessions of a Teenage Gamer.

I had barely slept the night before. As if taking the leap wasn’t daunting enough, I was sharing a piece of artwork in the morning I’d spent 4 years refining. To give you an idea of where that book ranks for me in terms of my general body of work, I hold (and will forever hold) that book above every single article I write online, combined. I didn’t write it to make X amount of money. I didn’t write it to “position myself” in a certain way. This was my story, penned with obsessive meticulousness, with my only measure for success being sharing the thing at all.

As co-workers were saying their goodbyes, I was trying to hide my shaking hands in my pockets, knowing my book was finally off my desk and out into the world.

Before the day was done, one of the managing partners at the agency came up to me and said, “So what are you going to do now? Be a blogger?”

I shrugged my shoulders. Honestly, I didn’t know.

But I was going to figure it out.

During October, November, and December, every aspect of my life changed.

I went from a rigid day-to-day schedule of train rides, office hours, evening workouts and late-night writing sessions, to zero structure.

Five days after I left my job, I was on a plane to Atlanta to visit one of my closest friends, Drew. I had been grinding my face off for 4 years straight, and figured I deserved a week vacation—something I hadn’t taken since I was in college.

From there, I flew directly from Atlanta to Los Angeles—where I worked on helping launch a gaming start-up I had been introduced to a month before my leap. I wasn’t getting paid, and the equity I was given ended up being negligible. But they were renting a mansion in Hollywood Hills, and the hot tub on the terrace was a massive upgrade from my studio apartment in cold Chicago.

I ended up staying there for a month, sleeping on the couch.

When I wasn’t working on the gaming start-up, I was freelancing as a ghostwriter for a handful of accomplished CEOs.

I had been building my personal brand for almost four years before taking the leap. And even though I knew, in theory, the value of what I was doing, I didn’t truly understand until I started having more time to leverage it.

The moment I put myself out there as a writer available for hire, my book of business was packed. I didn’t even have to go out and find clients—most appeared in my inbox, saying, “I’m an avid reader of your material. Would you be willing to help me with my own content?”

My worry that I wouldn’t be able to pay my bills faded away. And by sheer demand, I doubled my prices.

…and then I doubled them again.

…and again.

I had more work than I knew what to do with. I was making real money. I was on planes every week—trips to Arizona to visit my new long-distance girlfriend, trips back to Los Angeles to work at the start-up house, and trips to Atlanta with Drew, where we collaborated on content together and he started debating leaving his own job to join me.

Chicago -> Atlanta -> Arizona -> Los Angeles -> Repeat

By the end of 2016, I had done what I’d spent 4 years of college, and then 4 years of working in advertising trying to prove to myself:

It was possible to earn a healthy living as a writer.

On New Year’s Eve 2016, I took some time to set my intention for the year to come.

For the first time in my entire life, every single minute of every single day was mine.

I didn’t have teachers or bosses telling me what to do. I didn’t have an office to show up to. And while this was, by every definition, a dream come true, it was also extremely daunting. Every single morning, whatever I wanted out of life was on me to make happen. Nobody else.

That responsibility weighed heavy on my shoulders. I suddenly realized why taking the leap isn’t for everyone. I consider myself an extreme case of someone who requires independence in order to be happy and fulfilled—and even I felt the weight of what that really means.

At the start of 2017, I went through a few weeks of staying up late making music instead of working, sleeping in and enjoying slow mornings to myself.

But it didn’t take long before I started asking myself, “Is this it? Am I just going to be a freelance writer for the rest of my life?”

My conversations with Drew started to reveal an opportunity. The idea of “doing our own thing, together” came up multiple times, and it was clear I had gotten pretty good at something in high demand: writing content online that grabbed people’s attention.

I made the conscious decision to take another leap.

Instead of immediately upgrading my lifestyle, taking my new income level and spending it on a nicer apartment, new clothes, etc., I reinvested almost everything I made. Drew decided to take the leap with me, with my promising to make sure we would have enough runway to sustain ourselves for at least a year—while we figured out how to provide for ourselves.

Let me tell you something: earning six-figures while living in a rundown studio apartment with a heater from the 1960s and an air conditioner unit that sounded like it was at war with the elements is a jarring feeling.

But I was playing the long game.

So I kept my expenses low, and my sights set on the future.

Drew helping me move out of my Chicago apartment, July, 2016. Headed to Los Angeles.

For 5 months, we didn’t know what to build.

Our original idea was to create an online course, teaching people how to do what I’ve done for myself: how to write high-performing content, how to go viral, how to leverage Quora and Medium, etc.

I flew back and forth to Atlanta, where Drew (dusting off his camera skills) shot the entire course—beautifully, I might add. We recorded it. We created materials and guides. We set up the Facebook ads.

We hit publish.

And then we waited. And waited. Until finally, three days later sitting on the couch in his apartment, one of us said aloud, “Why isn’t it selling?”

It flopped.

That was a scary feeling. Here I had just convinced one of my best friends to quit his high-paying job to take the leap. Whatever amount of responsibility I felt after my own leap doubled. Now, I wasn’t just concerned with providing for myself. I had to figure out how the both of us were going to eat.

During those 5 months, I was writing the word-count equivalent of a book every 1–2 weeks. It was absurd. And draining. And tested my ability to “get the job done, no matter what” in ways life had never presented me with before. I was writing articles in airport terminals, on the way to Arizona to see my girlfriend. I was writing articles on planes to Atlanta, planes to Los Angeles, planes to Chicago. I was writing in coffee shops, and in restaurants, and in my studio apartment for hours and hours and hours.

By the time May rolled around, I was dead. I couldn’t do it anymore. 5 straight months of 5–8 articles per day, 7 days per week, and my head was spinning. I was getting sick every other week. And sure, while my skill level as a writer in the business world had quadrupled, it was clearly taking a toll.

I called Drew one day and said, “We have to figure this out. I can’t keep doing this.”

He suggested we take exactly what I was doing, and turn it into a service.

I’m not entirely sure why it took us so long to make this pivot.

Maybe it was because we were both still adjusting to our own individual leaps. Maybe it was because we were afraid of being wrong. I guess that’s the thing with obvious ideas: they aren’t obvious, until suddenly they are.

It was clear our video course wasn’t selling because the people we were marking to—Founders, CEOs, consultants and aspiring industry thought leaders—didn’t want to learn how to write. They didn’t have the time to write to begin with (hence why I was in such high demand as a proficient writer).

So, we scrapped the course. And we re-launched as a service company instead.

We called it Digital Press.

Overnight, things clicked.

Within two weeks, we had our first handful of clients.

Within a month, we passed six figures in annual recurring revenue.

Within 3 months, we were ready to hire our first employee.

Fast-forward to today (a mere 8 months later), and we have 11 full-time employees (and growing fast). Everyone has health insurance (that was a huge milestone). And we work exclusively with accomplished CEOs and Founders who want to share what they know, and build themselves as thought leaders in their industry through written content.

In addition to Digital Press, and through its success, I’ve been fortunate to have had a number of really special companies bring me in to advise on their messaging strategies. I’ve gotten to talk to and interview some of my business idols. I’ve written whitepapers for select blockchain projects that have raised a collective $100M+. I’ve consulted a handful of high profile CEOs on their own personal brands.

But most of all, I have a folder of photos on my laptop from the day I moved out of my Chicago studio apartment, packed up, and drove 2,000 miles to Los Angeles.

I look back at those pictures often, to remind myself this is only the beginning.

My advice to every aspiring entrepreneur out there is this:

When I put in my 2-weeks notice and got ready to take the leap, I thought that was it. I thought that was the big leap.

It wasn’t.

That was actually the day I signed myself up for a lifetime of leaps. That was the moment I decided, once and for all, I wasn’t going to wait for someone else to tell me what to pursue, or what my measures of success should be.

Every leap since then has been bigger. And as much as I would love to tell you, “It gets easier,” the truth is, it doesn’t. The gaps get bigger. The ground looks farther and farther away.

You just get more confident. You start to believe in yourself more, and more, and more.

But it’s on you to take the first step.