The moment I graduated from college, I made it my mission become a full-time writer.
I knew if I wanted to turn “what I loved” into a career, then I was going to have to be the one to figure that out for myself. For three years (and a brief stint studying journalism my freshman year of college), I studied fiction writing from professional writers and accomplished authors on the school’s faculty. And yet, none of them had very much insight as to “how” an aspiring writer actually becomes financially successful. They could explain how to engineer a riveting plot, how to describe a memorable scene, or how to create a relatable character. But they could not, step-by-step, explain how to go from barista-working-on-a-novel to full-time professional writer.
So, I went looking for the answers myself.
When I was 23 years old, I was nothing but an entry-level copywriter at an ad agency with a college-level writing portfolio.
And by the time I had turned 26, I had written over 1,000 articles on the internet, had work published in Forbes, TIME, Fortune, Business Insider, CNBC, and more, and I had become one of Inc Magazine’s top 10 most popular columnists. Month over month, I was averaging over a million organic views on my writing. And I had become the #1 most-read writer on all of Quora—a question/answer platform boasting over 200M users.
This was the moment I took the leap from my 9-5, started freelance writing, fell into the world of executive ghostwriting, and six months later started a company of my own, called Digital Press.
In 4 short years—from the moment I received my college degree, to the moment I took the leap—I had successfully figured out how to turn the craft of writing (my “side hustle”) into a full-time career.
Step 1: Question what you think you know—and search for what you “don’t know you don’t know.”
My mentor at the time used to say this to me all the time. “Cole, you don’t know what you don’t know.”
When I first graduated college, I had a very particular image in my head of what being a “full-time writer” looked like. I thought it meant having a book deal with a formal publisher. I thought it meant getting a “big” advance. I thought it meant sitting quietly in a room, by myself, for 18 hours per day, writing. Just writing.
The truth is, that image in my mind was based on very little information. I didn’t know what I didn’t know. For example:
- I didn’t know that a “big advance” for most writers falls in the ballpark of $5,000 – $30,000. Very few writers receive anything more. And even less writers land book deals, period.
- I didn’t know that there were plenty of other ways to make money (in fact, even better money) as a writer than publishing books. I didn’t even know the term “sales copywriter” existed for several years after graduating college.
- I didn’t know that consumers don’t buy “books”—they buy authors they admire and “follow,” and titles that speak to a question they have.
- I didn’t know that ghostwriting was even a viable industry for a writer (or how lucrative, the industry was).
The list goes on. My point is, the decisions I was making (or thought I was making) for my career were based in theory. Projection. Assumption. Instead of being rooted in fact and lived experience.
Which is why Step 1 of turning your side hustle into a full-time career is to rid yourself of these myths, and make sure the future you’re imagining for yourself has merit.
Step 2: Once you set your horizon, start moving toward it relentlessly.
As that same mentor would say, “You can’t steer a stationary ship.”
Most people that come across my writing today have no idea how much time and energy and effort I put into “finding my way” in the beginning. To be perfectly honest, I didn’t know what sort of writer I wanted to become. I wasn’t even sure becoming a writer was a realistic dream for myself. All I knew was, every time I sat down at my computer to play with words, I was happy.
So, I tried a million different things. One of my first writing-related endeavors, actually, was micro-blogging on Instagram about my journey as a bodybuilder in my early 20s. When my co-workers at the agency I was working at found my Instagram, they cracked jokes and failed to understand why I wanted to post pictures of myself on the Internet. But I saw my efforts through a different lens. For me, it was a step toward figuring out how I could write things people wanted to read online. That’s it.
I had over 10,000 followers and loyal readers on my Instagram page a year and a half later.
Fitness writing led me to Quora. Quora introduced me to long-form writing and storytelling online. Consistently writing online caused my work to get republished by nearly every major publication on the Internet, and an exclusive column with Inc Magazine. My column with Inc Magazine led to my first freelance client. One client turned to two. Two turned to four. Four turned to a startup that now employs 15+ people with 50+ clients from all over the world in a wide range of industries.
My point is, “you can’t steer a stationary ship.” So many people want to have the full strategy, the entire map with all the answers clearly laid out in front of them—all before they even start.
But that’s not how the journey goes.
You start, and then the map starts filling itself in as you go.
Step 3: Remove all distractions.
People don’t believe me when I tell this story.
Once I entered the real world and found myself dealing with the stresses and responsibilities of life outside college, I quickly realized how easily years of my life could just fly by. I had to commute an hour to work each day, each way. And I usually didn’t get home (after work and then the gym) until 9:00 p.m. Which meant I really only had two hours per day to move myself closer toward my dream: 9:30 p.m. – 11:30 p.m., before passing out and doing it all over again.
Terrified that I’d squander those two hours (and forfeit my dream) by watching TV or browsing the internet, I removed the option altogether.
Between the ages of 23 and 27, I didn’t allow myself to own internet in my apartment.
That’s right—and no, I’m not exaggerating.
I didn’t own a modem. I didn’t own a TV. I didn’t have an internet connection, period. I lived in a studio apartment on the north side of Chicago. I had a bed (which, for 3 of those 4 years, was an air mattress—because I couldn’t afford a real bed). A desk. And a small table by the window in my kitchen, which was about four steps away from my bed, which was two steps away from my desk.
Every single night, I came home from work.
And every single night, I wrote.
At the time, I knew what I was doing was over the top. I knew my decisions were unconventional and easily misunderstood. But I honestly didn’t see any other option. Sure, maybe I could have owned an internet connection and just moderated myself. But the risk of “accidentally” forgoing my dream outweighed the pro of having instant access to YouTube and Facebook on my laptop. I didn’t want four years to go by and for me to say to myself, “I wonder if I could have done more. I wonder if I could have become a professional writer.”
Most people aren’t willing to go to great lengths to remove the distractions in their life keeping them from achieving their dreams. Instead, they try to add to their To Do list. They say, “I just need to…” and then fill in the blank. But what they fail to realize is that habits and routines are the secret to success, and a habit cannot be formed when another one already exists in its place.
Before you can create a new habit, you must first remove the bad one.
Step 4: Don’t “know in theory.” Know because you practice your craft day, after day, after day.
I can attribute 99% of my success in the writing world to one thing (and sit tight, because it’s going to shock you).
I write. A lot.
When I first started writing on Quora in 2014, I challenged myself to write one Quora answer per day, every day, for a year straight. Where this approach even came from was, when I was 17 years old, I started a gaming blog on one of the first social blogging sites on the internet, called Gameriot. For my entire senior year of high school, I challenged myself to write one new blog post there, per day, every single day—and by the time I graduated high school, I had become one of the Top 5 most popular bloggers on the entire site.
When I started writing on Quora, I decided to take the same approach that had already proven successful at a previous time in my life. And sure enough, after three months of writing on Quora, I had my first answer go viral—accumulating 100,000+ views. A month after that, I had my first answer get republished by Inc Magazine. A month after that, I had my first answer go massively viral—accumulating over 1,000,000+ views and landing on the front page of Reddit. And every month after that, more and more things just started happening.
Today, I have written over 3,000 articles on the internet under my own name, and hundreds more as a ghostwriter for clients and companies.
In short: volume wins.
There is no substitute for practice. There is no way to avoid the thousands upon thousands of hours required in order to master your craft. Which means, if you want to become a professional, if you want to turn your “side hustle” into a long-lasting and successful career for yourself, you need to practice. You need to care. You need to root your knowledge in lived experience—not theory you read in a blog post about marketing, most likely written by a marketer who hasn’t done any of the things they’re recommending you do.
Practice is what separates the people who go on to have incredible careers from freelancers who fall flat on their face.
And practice is what allows you to speak with true authority on your craft, because you aren’t recommending what you “think” works. You’re recommending what you’ve learned through hours and hours spent in the trenches.
Step 5: Find yourself a mentor.
One of the biggest reasons, if not the biggest reason, why I stayed working as a copywriter at this ad agency downtown Chicago was because the creative director was willing to mentor me.
I could have taken a higher paying job somewhere else. I could have made another $20,000 per year being a copywriter at a bigger agency. But the reason why I chose not to pursue those opportunities was because I didn’t want short-term money. An extra $20,000 per year wasn’t going to change my life. It just meant I could buy Chipotle two more times per week, and a nice shirt every once in a while—neither of which were going to help get me from where I was, to where I wanted to be.
Instead of money, I wanted access to information. I wanted to learn how to think like someone who was successful. How to be an entrepreneur. How to take my career and the direction of my life into my own hands—and the creative director, who was also one of the founders, provided that opportunity.
Now, everyone’s first question when it comes to mentorship is always, “So, how do I find someone to mentor me?”
The real answer is: you don’t.
I don’t believe mentors are found by asking them to mentor you. I also don’t believe mentors appear the more you say, “Please, please, give me the answers.”
Mentors present themselves when you are already investing in yourself. Mentors hide in plain sight. There are probably five people around you, right now, that could “mentor” you in some way. The problem, however, is most people don’t ask for help. They see asking questions as a weakness instead of a strength—and so these “mentor figures” never have a chance to reveal themselves.
In my case, I didn’t have any sort of formal conversation where I asked to be mentored. I just showed up to work and asked a lot of questions. I offered to do the bitch work nobody wanted to do—like play assistant and type up emails while my boss and mentor dictated them, pacing around the room. Everyone else saw this work as “beneath” them. I saw it as a way to have a front-row seat next to the very person I wanted to learn from.
Mentors are everywhere, and they will skyrocket your growth as a human being.
But they’re waiting for you to ask the first question.
Step 6: Being great at what you do isn’t enough. You have to learn the business side too.
If you want to turn “what you love” into a career, then you have to figure out how that “thing” is going to make money.
Plain and simple.
This is a skill most people either wait too long to develop, or underestimate entirely. Aspiring writers, for example, think freelance writing is all about the craft, which in reality, it’s actually about the craft and your ability to sell, close, and retain clients. That second part doesn’t just “happen.” You don’t wake up one morning, call yourself a freelance writer on Facebook, and then suddenly have an endless stream of new business.
This means “proving” to yourself that you can do the following:
- Charge for the product or skill set you are offering to the market (for example: people are buying your books, or hiring for your services).
- Consistently bring in revenue performing your side hustle over a long period of time (6+ months is a good gauge).
- Receive positive feedback from customers (you have a problem if people are buying but leaving unhappy and demanding a refund).
And until you can do those 3 things, it’s hard to say whether or not you’re truly ready to “take the leap.”
When I was thinking about leaving my own 9-5, I really doubted whether or not I could execute on the above. I had never landed a freelance writing gig that paid more than $25. I hadn’t increased any other revenue streams (except my bi-weekly paycheck) to any substantial amount. I had all these unknown variables in front of me, and whenever I would think about “taking the leap,” they felt insurmountable.
This is why I stress the importance of testing your hypotheses before leaping. You want to “prove” these things to yourself before you fling yourself off the ledge and into unknown territory. Because if you can “prove” these things prior to leaping, suddenly it doesn’t feel like this big, grand leap anymore.
Leaping feels like the next logical step.
At the beginning of 2016, I challenged myself to start tracking my side-hustle income.
I’ll never forget creating this excel spreadsheet at the office on a Sunday (my mentor gave me a key and said I could work there whenever I wanted on the weekends—which I did often).
At the end of January, 2016, I marked down all of the different places my revenue came from. At the time, it was my paycheck working at the agency, and my very first product that I’d launched online—an online video course teaching people how to write on Quora, which I sold for $37.
In January, I sold 1. So my side-hustle income was $37.
I still have this excel document (and have continued tracking my finances this way ever since), and it’s actually pretty amazing to look back at 2016 as a whole.
- January, I made $37.
- The next month, I got paid to write a guest article for a fitness website, and sold two more courses, so I made ~$200.
- In March, nothing happened. I made $0. But, at the end of March, I officially got my column with Inc Magazine (where they offered to pay me per pageview).
- In April, I wrote 30 (yes, thirty) columns for Inc Magazine, drove over 100,000 page views, and made my first $1,000+ in a month.
- May, I wrote another 30 (yes, thirty) columns and doubled the amount of page views I brought in—with one article going especially viral. Inc had to cut a check that month for several thousand dollars, all of which went directly into my savings account.
- May I also herniated a disc in my spine, so I suddenly had a lot more free time on my hands. I invested every single evening after work into finishing my first book, Confessions of a Teenage Gamer, knowing that finishing the project would 1) elevate my personal brand as an author and professional writer, and 2) create a new revenue stream.
- June and July were back-to-back profitable months writing for Inc. Suddenly, I saw this as a potentially reliable income stream (even though it was 100% based on page views and performance, which is inherently risky). All the money I made writing for Inc went directly toward my “leap fund.”
- In August is when I decided for myself that it was time to take the leap. I had successfully saved up ~$5,000+, which was 3 months of runway based on my current living expenses. I had proven to myself that I could land a few freelance clients and sell them on my services. And I had, month-over-month, come close to matching my full-time monthly income with side-hustle income.
Suddenly, “leaping” didn’t feel so daunting anymore.
It just felt like the next logical step.
Step 7: Once you leap, you’re not on vacation. It’s time to sprint.
I will never, for the rest of my life, forget the day I truly realized what I’d done.
Right after I took the leap, a friend of a friend asked for my help on a startup they were launching in the gaming space. The opportunity was everything a 26-year-old could have asked for: they were renting a former Victoria’s Secret model’s mansion in Hollywood Hills as their “office,” and they offered to let me stay in la-la land rent free—as long as I worked on the company with them (which, coincidentally, is also where I met my girlfriend of the past three years).
Free from my 9-5 and formal work responsibilities, I said, “Absolutely, I’ll book my flight tonight,” and off I went.
Taking the leap was such an exciting time of my life. I felt like four years of ridiculous work ethic had awarded me a level of freedom most people could only dream of. That is, until about a week and a half into the trip, when the 15th of the month rolled around and I opened my bank account. Without even realizing it, somewhere in my subconscious I expected to see my bi-weekly paycheck. And when that wasn’t there, I had a mild anxiety attack. I remember pacing around this house nestled up in the hills thinking I’d made a terrible mistake. That I’d been lying to myself, and I wasn’t actually prepared to take the leap. That I’d miscalculated. That I’d be out of money in no time—and worst of all, I’d have to go back to Chicago and beg for my job back.
That’s when I felt, deep in the pit of my stomach, the reality of my situation.
On the surface, “taking the leap” seems like this big, amazing moment.
Instead, it’s a humbling awakening to the fact that you are now 100% responsible for your own life and wellbeing. Nobody is cutting you a guaranteed paycheck. Nobody is going to hover over your shoulder and say, “Hey, you need to drum up some new business, and fast.” It’s a scary feeling, actually, to admit to yourself that you are the only person who can put food on the table. And unless you go out hunting, you aren’t eating.
For a very, very long time after “taking the leap,” I was driven by fear.
I worked relentlessly. I took on as many clients as I could possibly handle. I was available 7 days per week, 12-14 hours per day. There was a point in time when I was ghostwriting 4-5 articles per day, every single day of the week, for about five months straight. And I did it because I had so much fear of what was right around the corner—would all this work disappear tomorrow?
It took me a while to learn how to balance this feeling of anxiety with the reality of my situation. Unfortunately, there’s also a lot of merit to being driven by fear. I know a lot of people who try their hand at “taking the leap,” don’t prepare themselves accordingly, and then worst of all, treat their “leap” as a vacation. They use their leap fund to travel the world, or hang out at the pool while everyone else is working, only to be right back applying for 9-5 jobs a few months later.
That’s not what you want.
Instead, you want to instill habits, a positive mindset, and very clear goals for yourself prior to taking the leap—so the moment you’re out on your own, you don’t falter or get distracted. Leaping is all about doubling down on your side-hustle, and accelerating it to the point where it’s the only thing you do, all day long.
Not enjoying a 2-3 month vacation and then going back to square one.