The $100K Club | Superpath

One-person writing business earning $120,000/year

Jimmy Daly
December 29, 2020

Welcome to another post in the $100k Club series. You can see the full series here. This is "My Morning Routine" for content marketing folks making six figures. The goal is to shed light on the skills and habits that enable people to achieve lucrative jobs and help get more people in this club.

These will be anonymous and updated regularly. If you make more than $100k/year and want to contribute, email me.

For more info on content marketing salaries, check out our salary report.

If you'd like to see more info on salary by job title, check out these resources: Content Marketing Manager Salary, Content Strategist Salary, Head of Content Salary, and Content Director Salary.

What was your first full-time job in content? What was the salary?

I graduated with a Master's degree in journalism shortly after the 'Great Recession,' and after a 6-week unpaid internship at a major daily newspaper, followed by 8 months of unemployment, I took a job with a content marketing startup without really knowing it. I was told that I was hired for my journalism skills, and my colleagues, all early 20-something poly-sci and journalism grads, were mostly working on a very credible news site at the time, with a few content marketing contracts to help pay the bills. I was hired to help produce journalism-quality content for both the news site and the paying clients.

What I didn't know at the time was that the company had already begun to abandon the news site and pivot towards becoming a full fledged content marketing studio. Over the ensuing months a couple of colleagues quit in protest, a couple were let go, and a few marketing experts were brought in to help with the transition. The CEO knew very little about journalism, or content marketing, but he had a couple of degrees from prestigious Ivy League colleges, which prevented him from taking any feedback from us lowly, entry-level journalism grads seriously.

I was paid $30,000, with the promise of a year-end bonus and a $10,000 raise after my first year, neither of which came to fruition. After I was offered a $1,500 raise I began looking for another job, but in the wake of the 2008 recession there weren't many full time positions available, so I began freelancing to make some extra money on the side.

How much do you earn today? What's your job title?

I am a full-time freelance journalist, public speaker and content marketer, earning roughly $160,000 Canadian, or about $120,000 USD, per year.

What's the single biggest salary jump you've made? (either from job-hopping or a promotion/raise)

My earnings have been trending upwards since the day I quit my full time job and began freelancing. Here's a breakdown of the 8 years that followed:


2013: $40,000 - my first year freelancing, I got that $10k raise that was promised to me, only I did it entirely by myself, and almost entirely through journalism work for major news outlets in Canada.

2014: $50,000 - 27% increase - things were snowballing, editors knew my name and started giving me assignments I didn't ask for. I was able to spend less time networking and hustling, and more time actually doing paid work.

2015: $75,000 - 50% increase - This was the year I made the leap from the Canadian journalism market into the U.S., and moving to New York for three months in order to entrench myself in the American media industry. Once my name became more visible I started getting inbound requests for content marketing opportunities, which had a dramatic impact on my earnings, and resulted in the biggest salary increase of my career. (To be clear I have always kept a clear separation between my journalism and content marketing work, and have never used my journalism contacts to help a client get media coverage. I have also never written about a former client in any news outlet, nor engaged in any activities that might risk my credibility as a journalist.)

2016: $80,000 - 6% increase - That year I felt a little guilty about accepting more content marketing work and decided to balance it out by pursuing freelance assignments for some of the magazines I had always dreamed of writing for, but previously felt were out of my reach. That year my journalism profile improved significantly, with a lot of global journalism brands added to my portfolio, but the content marketing pretty much stayed the same, and as a result my salary did too.

2017: $90,000 - 12.5% increase - In 2017 I began making a name for myself as a content marketer, and started to get more inbound requests. As with journalism I realized there was a significant upfront investment of unpaid work in the form of networking and hustling and proving myself to new clients. Once I made it through that period successfully, however, I started getting referrals and requests from people I had never heard of before, and could again spend more time working than hustling.

2018: $93,000 - 3% increase - At about this time I began to think that I had reached my ceiling and that, despite my best efforts, this was the most I was going to make as a freelancer (which was certainly enough and far more than I ever expected to earn as a journalism student).

2019: $120,000 - 29% increase - This was the year that I decided I had more to offer than the written word, and started doing public speaking engagements based on my journalism writing. I also started doing some media consulting for local startups that had no PR staff but needed some help getting noticed, along with the journalism and content marketing.

2020: $120,000 - 0% increase - 2020 was the first year my salary didn't increase, but I'm thankful I was even able to come close to the previous year's earnings, given that public speaking was out of the question and freelance budgets were drying up across the board. This year I spent a lot of time working on a single project for a major client, which paid about 1/3 of my salary. Without it, I would have taken a huge hit in 2020, but I'm confident things will continue moving forward once the economy improves and I can get back to building my public speaking profile.

What is your most valuable skill?

From the very start of my career I have always said that I am a better hustler/entrepreneur than I am a writer. I graduated alongside some very talented writers and journalists who have struggled throughout their careers despite their talent. The only reason I'm thriving when more talented writers are struggling is my ability to sell myself as a freelancer.

What's the best book you've ever read on writing, marketing, sales, business or productivity?

On Writing: A Memoir of the Craft, by Stephen King (yes, that Stephen King). This is the single most important book for anyone in the writing business.

Have you had a career mentor/coach? If so, how did you find them and what have you learned from them?

I've had many informal mentors and coaches over the year — lots of authors and journalists I've reached out to and have generously offered their time — but I don't believe I've ever used the word "mentor" with them before and it wouldn't be appropriate to start now.

What skills or habits help you thrive at work?

I am meticulously organized, which is vital both as a writer with multiple deadlines on a given day as well as a freelancer running an independent business with accounts receivables and business expenses and lots of other financial stuff I never learned in school.

What advice would you give to someone who wants to join the $100k club?

I can't speak to those who took the more traditional route to the $100k club, but I can speak to the freelancers out there, and my advice to you is two fold; be patient, and never turn down an opportunity.

As you can see from my career progression, so much of my success came from hustling at the outset with little to show for it, sometimes for years, before eventually reaching a tipping point where projects and opportunities came to me, and I could dedicate more of my time to revenue generating activities. Don't quit before you reach that tipping point.

I also made a habit of never turning down work, even when it involved covering subjects I knew little about or doing tasks I hadn't done previously; there are a ton of resources out there (blogs, youtube tutorials, etc.) that can help you get started in any new direction, and as a freelancer you should always be willing to sacrifice this weekend's plans in order to make more money to spend next weekend (within reason).

Be patient, building a six-figure freelance career takes time. And when an opportunity comes your way, say yes first, then figure out how you'll get it done.

What is your gender and ethnicity? Where do you live?

I'm a white male living in Toronto, Ontario.

Cookie Consent

By clicking “Accept”, you agree to the storing of cookies on your device to enhance site navigation, analyze site usage, and assist in our marketing efforts. View our Privacy Policy for more information.