Five years ago I resigned from my last 9–5 job to become a full-time freelance copywriter and ghostwriter, turning my lifelong love for writing into a creative career.
The first year was rough to say the least. I barely earned the minimum wage, had to take on a couple side hustles to cover bills, and didn’t know the first thing about running a business.
But my knowledge and situation steadily improved. I learned a lot through books, articles, and just the daily trial and error of running a business. Writing became sustainable.
Less than a year after starting the business…
Both women took a turn with the knife.
One at a time they stabbed the side of their Monster can.
Sleeves rolled up on their arms, the women gave one another a nod, popped open their tabs in unison, and the race was on. They put their mouths against the puncture holes, threw their heads back, and chugged.
The winner raised her hands in triumph a moment later.
This was Vans Warped Tour 2015. And no, these staffers weren’t shotgunning energy drinks — they were drinking water.
It’s risky business giving up a 9–5 job to work for yourself as a freelancer. Instead of relying on a biweekly paycheck, you accept a career that ebbs and flows without a predictable pattern. One moment you’re juggling more work than you can handle and the next you’re staring at an empty calendar — and a draining savings account.
I almost gave up freelancing several times in my first year. One month I had to tell my landlord that rent would be late. Another, I had to borrow money from my brother. Multiple times I had to expense essential bills…
I swore I’d never be an active trader.
I’ve invested regularly and aggressively in the stock market since 2018, always under the same strategy: buy index funds that I plan to hold for decades. If someone told me they actively traded and tried to time the market, I’d silently judge them, thinking about all the stats I’ve read about how rare it is to consistently beat the market.
The truth is, I still swear by index fund investing — and it still makes up almost all of my investing portfolio. But lately, I’ve also decided to try something new. …
Years ago I freelanced as a live event logistics hand, staffing conferences, concerts, and festivals across North America. I formed many good memories during those years. I watched performances from The Cure and Drake respectively from backstage, interviewed filmmakers between showings at a film festival, and got to see world-class motivational speakers in their prime.
One week I helped put on a two-stop business tour in Ontario, Canada. The speaker was Jordan Belfort, the man behind the business memoir that became the movie, The Wolf of Wall Street. The tour took place about a year after his film came out…
In the late 1970s, before Charles Schwab Corporation was a household name in investing and banking, founder Charles Schwab was introduced to a well-known syndicated financial columnist named Dan Dorfman.
They shared a corner table at the Four Seasons in New York City, where Schwab explained to Dorfman about his new company. At the time, high broker fees were standard within the industry of stock market investing. But Schwab saw an opportunity to significantly cut costs: His company would eliminate the expensive research and advisory side of investing to provide a discount brokerage firm.
Let customers do their own investing…
I was only a year out of high school the first time someone asked me to write professionally. A local nonprofit needed a blogger and one of my childhood friends was generous enough to recommend me for the gig.
Months later, a freelance designer saw the work I’d completed for the nonprofit. He asked if I could help him with a few projects as well: a mix of business brochures, website copy, and technical writing. One day I found a writing gig on Craigslist. Friends started referring me to other businesses. …
When someone tells me they stopped freelancing after one year, I can’t help but feel a little bad for them. If their first year was anything like mine, then they endured the absolute hardest aspects of freelancing while enjoying very few of its rewards.
Don’t get me wrong, I have loved freelancing since day one. But at the beginning of 2016, during my first several months as a freelance copywriter, being self-employed felt a lot like being unemployed. My calendar was empty (in a bad way). I often went for several days or even a few weeks between projects. The…
I am a full-time freelance SaaS copywriter. I’m regularly asked how to get started as a copywriter. I created this curation piece as a place to store my thoughts / ideas / tactics for being a successful copywriter.
I plan to update this document regularly as I write new articles about the craft and business of writing. If you want regular writing advice from me, you can also subscribe to my newsletter: The Craft and Business of Writing.
I tried to cover all the big, intimidating subjects I wished someone had taught…
“Think of yourself as an explorer. You cannot find anything new if you are unwilling to leave the shore.” Robert Greene, Mastery
Let’s pretend for a minute that Twitter, Facebook, and LinkedIn suddenly disappeared. These social media sites dissolved in a flash and you were left blinking at the wall behind your computer, jaw agape.
You scramble to Google for answers. It’s confirmed. They’re all gone. Forever.
As reality sets in, you panic thinking about all the photos and distant high school crushes you’ll never see again. …