My copywriting salary went up 400%.

It took 5 years. Here’s how I did it.

Kevin Sawyer
8 min readMar 26, 2021
“A piggy bank on a white surface” by Fabian Blank on Unsplash

Copywriting has plenty of perks.

You get to be creative every day. Investigate new clients and industries. Chat with brilliant subject matter experts. On the best days, you can go to bed knowing you’ve removed confusion from the world and filled the gap with humanity. (And also puns. Or at least some subtle alliteration. Because we can’t help ourselves.)

But it’s generally not the surest path to lucrative salaries. If you want to be feted with lavish compensation packages and all-you-can-drink Soylent shakes… try a course in writing code.

However, with a little networking, a long-term career strategy, and plenty of calculated risks, I was able to quadruple my starting income as a copywriter.*

Here are the 5 strategies I used to go from low $30Ks in 2011 to crossing the six-figure line in 2016.

Photo by Hunters Race on Unsplash

1: Start with the job that’s “good enough.”

Just before Christmas 2011, I dropped out of a graduate program at Vanderbilt University.

I was at a professional crossroads: My original plan to earn a teaching degree and settle in Nashville for the next half decade was no longer viable. I needed to pivot. And quickly. I still had 5-figure student loans and a monthly rent check to pay off.

I leaned back into my earlier training in writing and editing and eventually landed a job — my first formal job as a copywriter — at an international book distributor.

It wasn’t glamorous. It wasn’t well-paid. It actually paid less than the job I had left to start my graduate program in the first place. And my cubicle was in the middle of a large, blue-carpeted room with zero windows and questionable coffee. But it covered rent and food and let me add Copywriter to my resume.

Here’s the funny thing about that first job: Even though it was quasi-entry level, it was perfect training for more advanced writing positions down the road. For 40 hours a week I basically did nothing but pare down thousands of book descriptions to fit the word count for my company’s product catalog.

In other words: I got really, really good at editing. My own writing naturally got sharper and more focused as a result.

Don’t ignore the “good enough” jobs. You’ll lose out on valuable career equity waiting for the perfect gig. And once you get your foot in the door, find a practical way to develop specific skills and build the relationships that will become your professional network.

Photo by Gary Lopater on Unsplash

2: Follow the money. Literally.

That first job only lasted six months: After a bit of soul searching, my wife and I decided to leave Nashville and return to Boston.

Our cost of living obviously went up as did my winter coat budget. But my earning potential nearly doubled as soon as the wheels touched the tarmac at Logan Airport. Boston’s more competitive job market was offering rates $20–$30K above what they would have been in Nashville for similar jobs.

A lucky connection with my future sister-in-law (thanks, Kate!) secured my second copywriter job. This time, I was writing travel itineraries and marketing materials for an international adventure travel company.

Writing about exotic locales taught me how to use romance copy to create a sense of place. The job also gave me opportunities to write journalistic features about people and places in far-flung corners. With a few new notches in my copywriting belt, I was rounding out my skills and developing a more diverse portfolio.

Relocating to a larger city with more jobs in my industry required extra effort and upfront expense, but the opportunities it offered were invaluable.

“Iowa man sits at a messy table while holding paint covered pencil and brush” by Alice Achterhof on Unsplash

3: Put your passion into practice.

Employers love authenticity: They want people on their team to have energy, enthusiasm, and a dynamism that can spur innovation.

Spending a season of your career committed to a pursuit of passion—whether it’s a formal job, a general industry, or pet project, side hustle, or volunteer program—can make you a more attractive candidate. It broadens the perspective you bring to the table, shows a commitment to values, and separates you from the stack of similar resumes.

After a couple of years at the travel company, I took my third copywriting job. It was with a well-loved Boston cultural institution. The job was a perfect fit for my passions, considering my lifelong love of learning and belief in the power of curiosity.

And although I made a tough decision to take a strategic pay cut, I believe the experience actually helped me secure higher-paid positions a few years later.

First, having a recognizable name on my resume was helpful as I benefitted from credibility by association. Second, talking about my non-profit experience with authenticity and excitement has been a highlight of every job interview since. It’s no doubt made me more memorable than similarly qualified candidates. Third, I learned the hard way that working at a non-profit wasn’t ultimately sustainable for me—which erased any anxiety about passing over jobs that sounded cool but had dismal salaries.

(Note that I’m not recommending a Machiavellian detour into non-profit work just for your career’s sake. Nor should you fake passion just to appear authentic. But if you have the chance to explore a job that complements your personal interests, by all means, give it a chance.)

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4: Negotiate.

Thanks to a few additional years’ experience under my belt, I had a bit of fresh confidence when I got the offer for my fourth copywriting job. I’d be the first formal copywriter for a music software startup.

So I researched what other positions were paying for similar jobs, quantified the additional value I could bring to the role, and gave them a counter offer that was slightly higher than what they were initially offering. To my great surprise—and relief—they said yes.

My negotiating gave me a significant bump from my non-profit salary; I was also able to add “Senior” to my job title. That small change, and the responsibilities that came with it, made me a contender for better-paying salaries down the road.

“A person's jeans and converse hanging out over the edge of a cliff at Yosemite National Park” by Leio McLaren (@leiomclaren) on Unsplash

5: Step outside your comfort zone.

After a few years working within marketing teams, and networking with more people in the field, I started to see the writing (no pun intended) on the wall. I was hitting the ceiling of what a copywriter could expect to earn.

During the soul searching time, I was promoted to Content Marketing Manager at the music software startup. I started to think more critically about content strategy and how copywriting fits into a larger framework of leads and conversions. While the mechanics of content marketing were fascinating, I was still hungry for a new set of challenges, preferably in a more established company that had greater open space for career advancement.

I had to make a scary choice: 1) Stay put. 2) Pivot to agency work, where I could earn more money but forfeit my quality of life. 3) Build up additional skills for a higher-paying job that valued writing but didn’t rely on it exclusively.

So when a recruiter reached out with an opportunity for long-term contract work within a Fortune 500 UX department, I took another calculated risk. It wasn’t guaranteed to be forever (or even to result in a full-time position). But I knew that sharpening my skills in content strategy, UX writing, and design would open new doors and allow me to make more significant contributions—and therefore earn more robust compensation.

My hourly rate, sustained over a typical workweek, allowed me to finally cross over into six-figure income, effectively increasing my salary 400% from my starting salary 5 years earlier.

Not bad for a guy who once took a freelance gig writing LinkedIn posts that paid about $4/hour, after accounting for all the time I spent.

(Yes, I could have finished faster to move on to my next project, but I just couldn’t live with myself submitting a half-baked job. And I had to spend all that extra time to sneak in some puns.)

I hope these strategies give you inspiration to advocate for your true value. Remember, the respect for writers is only as strong as the outcomes we produce. So keep learning, keep growing, and keep challenging yourself to be the best copywriter in the room—and then, have the courage to find a bigger room.

*My individual story is inseparable from a wider, parallel story: a story of privilege, professional norms, access, and other enabling factors. There is no neutral territory when privilege meets professional prospects; it is either actively helping you or actively harming you. Which is to say — my majority status as a White, heterosexual, cisgender man undoubtedly shaped my career trajectory in a positive way.

My upbringing exposed me to cultural topics, manners of speech, and other invisible fluencies that gave me an undeniable advantage in “culture fit.” My name, my appearance, and my identities guaranteed I’d receive the benefit of the doubt at every corner. And the absence of bias, prejudice, and discrimination in my life has made me never question whether I belonged, which on its own projected an aura of confidence that may not have been in proportion to my skills.

Acknowledging this privilege is one step, and certainly not the final one, in dismantling White supremacy.

If you are an aspiring copywriter/content strategist, I can support you through professional connections, portfolio reviews, and resume/cover letter writing. Please reach out to me at: