We caught up with the brilliant and insightful Kelsey Woods a few weeks ago and have shared our conversation below.

Hi Kelsey, thanks for joining us today. Have you been able to earn a full-time living from your creative work? If so, can you walk us through your journey and how you made it happen? Was it like that from day one? If not, what were some of the major steps and milestones and do you think you could have sped up the process somehow knowing what you know now?

The single question I get asked the most about my career is, “How did you become a copywriter?” When you see someone fully living out their creative passion, it’s easy to think they found their path right away. But I can tell you my journey to becoming a full-time writer was anything but quick, easy or linear.

As a kid, I loved reading and writing. I’d take out 4-6 books from the library and have “who could read them faster” competitions with my bookworm friends. I started my first “novel” in Grade 4 narrating the adventures of my fictional character, Eddy The Raccoon. Then, I went on to write a murder mystery tale, bringing the board game Clue to life, that my Grade 6 teacher then read aloud to the whole class. So there were definitely signs indicating I would end up in a writing profession.

When it was time to go to university, I thought an English degree would bring me closest to my passion for writing. But countless people told me that “it’s tough to make a living writing” or “writers don’t make any money.” However, I knew this was something I was passionate about, and I soon discovered areas like Communications and Marketing, talking about persuasive writing. During my 5 years at university, I changed my focus 3 times to determine where I could make the biggest impact, and earn a living, from writing.

After I graduated, I fell into the popular belief that I needed a 9-5 job, something stable and secure. But instead of finding one main job that checked all the boxes, I found countless part-time contracts looking for writing and marketing support. So I kickstarted my creative journey by working for countless local businesses in my home city of Calgary, Canada — a restaurant, a gym, marketing agencies, barber shops, a comedy festival, a clothing company, you name it.

At this point, I remember thinking “I’ve made it, I’m working full-time as a marketing contractor and content writer. This is it.” And while I did like what I was doing, I reached a point where I was maxed out on time, energy and resources. I knew I could make a bigger difference for the businesses I was supporting, but I didn’t know what I didn’t know.

That’s when a series of events throughout 2020-2021 led me to the creative life I’m living now. I found a business course that opened my eyes to entrepreneurship, a copywriting program that taught me the power of persuasive writing, and a money-mindset program that dispelled a lot of my limiting beliefs about how “writers don’t make money.”

Since 2021, I’ve created my own schedule, found my own clients, and fully embodied the entrepreneurial lifestyle. Relentlessly following my creative passion has allowed me to write every single day, make a good living, and travel the world, simultaneously. And it all started from a deep desire to write, despite what other people said was possible.

Kelsey, before we move on to more of these sorts of questions, can you take some time to bring our readers up to speed on you and what you do?

In 2021, I made the shift from freelancer to entrepreneur. I incorporated my business, Content By Kelsey Inc, and I fully committed to the self-employed lifestyle.

Today, I work as a full-time copywriter and email marketer, helping service-based businesses around the world make a bigger impact. Through persuasive copywriting and powerful marketing strategies, I help them stand out from the online noise, connect more authentically with their audience, and sell more services through relationship-based storytelling.

Because in a world of AI, online scams and pushy marketing tactics, having a clear brand voice and core values is more important than ever. Simply having an offer and promoting it is no longer enough, when there are dozens of similar products on the market.

I’ve worked with a range of business owners — from start-ups and solopreneurs, to marketing agencies and 9-figure companies — and the same principles still apply: People are looking for solutions to their problems. So how well do you know your audience?

Today’s customers are looking for brands that align with their values, speak the truth, and can genuinely help them solve their problems. So if you’re talking to everyone, you’re talking to no one. The more specific you can be in your marketing, the more successful your messaging is.

That’s why I offer my clients a range of services, including: detailed brand voice guides to clarify your messaging, done-for-you sales copy funnels to walk customers through the complete buying journey, email marketing to stay top of mind in the inbox, and marketing strategy to reach more of the right people.

You can see some of the clients I’ve worked with here, and the results they’ve experienced by getting more clear on their audience, their offer and their messaging: https://www.contentbykelsey.com/case-studies

How’d you build such a strong reputation within your market?

Copywriting has really exploded over the last 5-10 years. With more people working from home, increased access to the internet, and the big push to move online in 2020, you can really find professionals to support your business anywhere in the world. So how can you set yourself apart from others who are offering similar services?

By producing your best work, and providing the best client experience. As a creative entrepreneur, your work has to speak for itself. You may not always be able to compete on price or experience, but what you can always control is how you deliver your services.

Over the years, I’ve built my reputation by showing up consistently, implementing feedback, joining like-minded communities, and continually investing in my education. Like any profession, industries change and you need to uplevel your skills. But the single best reputation builder is doing good work, and having happy clients refer you to their network.

We’d love to hear a story of resilience from your journey.

You’ve probably heard people compare running your own business to a rollercoaster — and this couldn’t be more true. Clients come and go, markets increase and decrease, and revenue dips and skyrockets.

In 2022, I doubled my business as I shifted from a solopreneur to a boutique agency owner. In 2023, I 1.5xed my company again, as I took on more clients, hired more contractors and expanded my reach. I did this all in the hopes of serving more businesses and creating a bigger impact in the world. Plus, everything you see online is about making more money, scaling your business and doing more, more, more.

But in 2023, I took a hard look at my business and my day-to-day. I thought I’d wanted to start an agency, but once I did, I realized I wasn’t growing what I truly wanted. I’d turned into a project manager and copyeditor, instead of the copywriter I still wanted to be. So I did the unthinkable, and shut my agency down. This was before I knew my main client at the time was about to shut his business down too.

So rather than comfortably scaling down by business as I let my own team go, I was left with very few clients and little work to do. However I didn’t let this experience scare me into changing my mind. For 9 months, I worked a little while travelling the world, and then came home to recalibrate what I actually wanted my future look like.

2024 was actually my lowest income year since 2020. Which to some would look like a failure. But this year of travelling and realignment was crucial in leading me to my next dream client. I got clear on what I wanted to do, I had space for the right opportunity when it appeared, and I got to check off a lot of fun bucketlist items that weren’t work related. I had the time, energy and space to create the life I wanted to have, not stay stuck in the life I had.

This has to be one of the most beautiful and rewarding parts of entrepreneurship, when you’re following your creative passion. You have the complete freedom to push or pull back, to work more or work less, and to design the business that YOU want — and change it whenever you need to.

Contact Info:

• Website: https://www.contentbykelsey.com/
• Instagram: https://www.instagram.com/contentbykelsey/
• Facebook: https://www.facebook.com/contentbykelsey/
• Linkedin: https://www.linkedin.com/in/kelsey-woods-5b658abb/
• Other: https://www.contentbykelsey.com/case-studies

Image Credits

Valerie Richer Photography