My senior year, the only path I knew for earning a living as a writer was teaching.
I started tutoring students in the department as a "Writer's Workshop" teacher—with plans of going to grad school.
I learned a lot about my own writing by teaching other students.
6. Self-confidence
A week before submitting all my materials to Iowa's Writer's Workshop (#1 creative writing school in the country), a teacher I respected told me not to go.
"I went there. It killed my love for writing."
She suggested I get some life experience instead.
7. Marketing
Instead of grad school, I took a job as a copywriting intern at a small ad agency downtown Chicago.
I made minimum wage writing social media copy for brands.
My first "ghostwriting" experience was writing for a well-known female gynecologist.
I was 23.
8. Proofreading
My boss (the creative director & co-owner of the agency) became my mentor.
He used to have me proofread his emails, proofread his texts to girls, proofread multimillion-dollar proposals to national brands.
I racked up 2,000+ hours of proofreading.
9. Sales
The agency was small, and eventually there was nowhere for me to go.
When I asked how I could earn more money, my mentor said, "Bring in deals."
I used to watch Wolf of Wall Street & teach myself "how to sell," and after a year, I finally landed my first client.
10. Online Writing
While working at the agency, I didn't want to let go of my dream of becoming a writer.
So I challenged myself to write 1 Quora answer per day, every day.
In 2015, I became the #1 most-read writer on the platform.
Slow & steady wins the race.
11. Columnist Writing
On Quora, Inc Magazine started republishing dozens of my answers.
Eventually, they offered me a column of my own.
There, I wrote another 409 columns for them over the course of 2.5 years.
I mastered the art of the 800-word article
12. Freelance Writing
After working at the agency for 4 years, and seeing success writing on Quora & Inc, I decided to take the leap.
I quit my job & went all-in on freelance writing.
All that practice on Quora & Inc meant I could write an article in 30 minutes.
My income 📈
13. Ghostwriting
Then, I stumbled into ghostwriting.
My first client was a guy in his 60s who had sold his company for $1B.
He wanted help sharing his entrepreneurship advice.
One client led to 2, 2 led to 4, etc.
All of a sudden, I was ghostwriting for 12+ execs at a time.
14. Entrepreneurship
When my bandwidth hit a ceiling, I convinced one of my best friends to quit his job and start a ghostwriting agency with me.
We called it Digital Press.
2 years later, we had 20+ full-time employees, 80+ clients (at a time), and $2M in revenue.
15. Self-publishing
In 2019, we decided to scale the business back.
Ghostwriting is very subjective and hard to scale. The biz was a disaster.
Once things settled down, I spent 4 months writing a book about everything I'd learned about Online Writing.
Branding became the answer to the problem, “We’re indistinguishable. What do we do?"
Instead of creating a DIFFERENT product altogether, big companies opted to change visual attributes with the hopes of convincing customers their "same" product was "better."