CHA CHA IN THE CITY | Supporting Entrepreneurs In Any City
“When You Support A Local Business, An Actual Person Does A Happy Dance...We Call That The CHA CHA! ”

Real Entrepreneurs. Real Stories.

Learn from someone who has been there. From learning how to find their market to setting prices, and more, here are true entrepreneur stories.

From Burnt-Out to Six-Figures in 18 Months: How One Freelancer Turned Her Soul-Sucking Business into a Fulfilling Career

A Headshot of Rai Cornell - Cornell Copywriting

Written by Rai Cornell, Owner & Senior Copywriter of cornell copywriting

Keep Reading To Learn How She Made Her Success Her Own.


This isn’t your typical rags-to-riches story.

I’m not going to throw around huge numbers and lofty promises of how you can “Be a millionaire by your next birthday!” or “Make money while sipping wine coolers on a beach in the Bahamas!”

No.

I’m going to tell you the real story and share the actual techniques that helped me go from a miserable existence working like a Siberian exile to building a copywriting and content marketing business that is fulfilling, true to my nature (no MLM schemes here!), and pays the bills – and then some.

Ready?

I Bet You’ve Been Here Before

In January 2017, I was burnt out. I was writing from 7 AM to 11 PM every day, breaking only to make dinner for my family and inhale a few bites before returning to the keyboard.

My clients were mediocre, at best. They valued quantity of posts and keywords above quality of writing – and their rates reflected their crappy attitude.

That January, I hit my highest earning month, bringing in a total of $5,563.19. Instead of celebrating what should have been a great milestone, I collapsed into bed and didn’t look at my email or even glance in the direction of my laptop for three days.

I was miserable.

Food didn’t taste good anymore - my mind was always on work and not on what I was putting in my mouth.

I was snippy and impatient with my then-boyfriend (now husband) for no reason other than I hated how I was spending my days.

And despite living with him and working from home, I felt increasingly distant from the man I cherished so much.

All of the research, writing, project management, stress, long hours, and - let’s be frank here - dealing with thankless, demanding clients wasn’t worth the 5 Gs I managed to scrape together.

And it certainly wasn’t worth sacrificing my relationship or my happiness.

Dire Circumstances, Radical Change

As soon as I had the realization that “This isn’t worth it,” the decision was made. I dragged myself to my computer and, with the first smidgen of excitement I had felt in month, I emailed all of my clients:

“I’m writing to let you know that this will be the last month I’ll be able to work on your project. Please let me know what you need from me to finalize our work together.”

Sent. Sent. Sent. Sent.

As soon as I heard the last “woosh,” I felt my heart, chest, and lungs expand. For months, the weight had been building in my body, but I hadn’t realized it until it was gone.

Finally, I was free.

Desperation Drives Results

I gave myself about two weeks to enjoy my freedom before facing the next logical reality: I had no clients...

...and no income.

As us young’uns are known to do, I turned to Google and Facebook for answers. I spent hours searching “how to find great clients” and “high paying freelance writing jobs.” I knew others were doing it and I wasn’t so bitter as to think that there were no great clients in the world.

I just knew it might be harder to find the clients who appreciated high-quality work and a well-crafted content marketing strategy as much as I did.

Thankfully, I had saved up about three month’s worth of minimum salary and expenses in my business account by the time I cut ties with my last client.

But the clock was ticking….


If you're embarking on the adventure of transforming your business, here are the five steps I recommend taking to ensure you have the tools and structure you need for success. While I had to stumble along blindly to find the right path for myself, I hope you can learn from my experience to have an even more successful and enjoyable business transformation for yourself. 

Let's dive in! 


Find the Right Model

In April 2017, I found a mastermind group on Facebook that promised that a six-figure salary as a freelancer wasn’t impossible.

I was sold.

I dedicated nearly $500 per month of my diminishing cash stores to learning everything I could from the mastermind mentors and fellow members. I spent 10 hours a day studying my mentors’ business model and applying it to my own work. I opened my mind to all the lofty mindset magic they told me I had to embrace if I ever wanted wealth to find me. I completely transformed my professional persona.

And the result was shocking.

In June 2017, I landed my first ever retainer client off a cold email pitch. Not only were they letting me launch their company blog from the ground up, but also they were excited to pay me 6 times what I was making per post back in January with my crappy clients.

Prior to finding this mastermind, my client-acquisition strategy consisted of scouring job boards and applying for anything that had the word “writer” in it. I did one-off after one-off and was always stressing about where my next gig would come from.

The mastermind taught me the beauty of retainer clients, how to structure your business and service offerings to support a retainer sale, and how to get clients through cold pitching – all things I had never done before.

In August, I landed another retainer client. In September, another.

I gradually added one new client per month at increasingly higher rates until January 2018, all through cold email pitching and a retainer-based proposal.

Then, after the novelty of the new year died down, my hot streak went cold. My email pitches weren’t landing any new clients and I was beginning to feel burnt out again.

While the mastermind taught me some of the most valuable lessons I’ve learned about finding the right business model for your individual goals, there were certain elements that just didn’t sit right with me.

For one, cold pitching.

When I first registered my domain for my business website, I was bombarded with poorly written cold email pitches from dozens of web developers wanting me to hire them. It wasn’t the words they used or the fact that I could tell none of them spoke English as a first language that bothered me. It was the sheer audacity they had to email me asking me to give them money when I knew nothing about them, their skills, or their business, and didn’t invite them into my inbox.

The realization that I was now doing the same thing to get my own clients made me bristle.

I knew there had to be a better way.

Make It Your Own

Rather than reaching out to people who I had never met to sell them on services I didn’t know if they needed, I decided to focus on building relationships.

Using LinkedIn as my primary platform, I began connecting with CEOs and Marketing Directors of companies that sounded interesting. I would send them connection requests with a genuine message about my interest in their company. Not my interest in selling them something; just my heartfelt enthusiasm about where they worked and what their business did.

For every 50 connection requests I sent, about 48 were accepted.

Every time someone accepted my connection request, I would send them a message thanking them for doing so and offering my expertise if they ever had even the tiniest copywriting-related question.

Instead of offering them a laundry list of services and an invoice to pay, I offered my help. For free.

Whether they just wanted to chat or they wanted an outsider’s perspective on a marketing project they were working on internally, I was happy to help.

Each week, about 25 percent of the people I connected with took me up on my offer.

Not only did I get to help them with whatever they were struggling with at the time, but I also got to practice talking about my business (because they always ask). In many cases, the men and women I talked to were interested in learning more about my services, and about half would end up asking for a proposal.

Now, rather than me barging into people’s inboxes asking for them to spend money on someone they’d never heard of, people were actually asking me for sales information.

This took the sleazy, salesy quality out of my client acquisition process and allowed me to meet some of the most incredible business owners and leaders, many of whom have become clients.

Collaborate with Kindred Spirits

Once I felt like I got everything out of the mastermind I could, I decided to go it alone. As with most things in my life, I found that I did my best when I was flyin’ solo and trusting my instincts to guide me.

I spent a few months honing my skills, fine-tuning my service offerings, and polishing up my internal processes. But every once in a while, I would wish I had a second pair of eyes to review a quote or a proposal before clicking the “send” button.

As the universe tends to do from time to time, it dropped just what I needed right in my lap at the precise moment I needed it.

A former fellow masterminder reached out to me to see if I wanted to start a little group with her and a couple other women who had since left the mastermind group, too.

It was perfect. We all knew each other well and were familiar with everyone’s businesses and goals. Despite the fact that we are all copywriters, we didn’t feel like we were in competition with one another. Instead, we felt like friends trying to help each other succeed.

A Team Putting Their Hands Together

The camaraderie was exactly what I needed.

My little group of supportive freelancing friends filled the void that being a solo business owner often leaves.

We posted questions, proposals, work projects, and helpful resources in a private Facebook group that was the base of operations for our tight-knit 5-person collab. We encouraged each other when things were bleak and directed referrals to one another when a client wasn’t a good fit for one of us but was right up another’s alley.

The camaraderie was exactly what I needed. My little group of supportive freelancing friends filled the void that being a solo business owner often leaves.

On a more business-minded level, joining this group was my life raft. It prevented me from reaching that burnout point again and gave me the hope and encouragement to see my goals through to the next breakthrough.

Always Up-leveling

By February 2018, I had filled up my client roster with a pretty solid list of companies. I was out of the danger zone financially and no longer felt uncomfortable when I looked at my bank statement.

But I wanted more.

In fact, I wanted way more.

After earning a B.S. in psychology, an M.A. in MFT and professional clinical counseling, and an M.S. in criminology, I had amassed quite the hefty sum of student loan debt. I was 28 and had more than $86,000 to pay back to FedLoans.

I decided I wanted to pay off my entire loan before my 31st birthday.  

Doing so would require way more revenue than I was bringing in, however. Plus, I quickly learned that revenue was not the same as take-home pay.

Let me be clear about this: If you’re going to make it as a freelancer and business owner, the money you earn in your business does not all go into your pocket.

In fact, after consulting with a financial advisor and a couple tax experts, I now operate on a 50-20-20-10 model:

  • 20% of what I bring into the business is reserved for expenses

  • 20% is for taxes

  • 10% is for equity

  • 50% is what I actually pay myself

In other words, all those promises of “You can be a six-figure freelancer!” are actually a bit misleading. In order to pay yourself a six-figure salary, you need to be bringing in at least $200,000 in revenue through your business.

With my numbers and goals firmly in place, I set off on the daunting task of up-leveling my business to get me to those higher figures.

I could have kept doing more of the same – more pitching, more LinkedIn networking, more clients, more work.

Ultimately, though, I realized that I wasn’t going to make it to $200,000 in annual revenue with a dozen small retainers.

I needed to figure out a way to create more value for my clients so I could sell larger packages to fewer clients and make more money.

Enter: Maggie Patterson.

The key to up-leveling is to learn from the people who have already done what you want to do.

I sought out a business coach who had done precisely that. Maggie runs the digital marketing agency Scoop Studios, coaches service-based business owners, and creates and sells her own digital products covering everything from productivity to business savvy.

Over the course of three months, I worked with Maggie to strip down and rebuild my service packages, proposals, and processes.

Rather than focusing on just the deliverables I was comfortable creating after 11 years as a writer, Maggie helped me figure out what else clients needed before and after I delivered my copy.

By approaching my services from the perspective of my potential clients, I became the one-stop-shop for all things content marketing. Maggie even helped me see that I should be charging for many of the behind-the-scenes tasks I was already doing.

For example, when previous clients would hire me to write 4 blog posts per month, I would create a content strategy so I knew what direction to take the content to get my client the most results. I wouldn’t send my clients the document, but I would use it as my own tool to make sure I was delivering work that would serve my clients’ goals.

After working with Maggie, I realized my clients could seriously benefit from getting their hands on this tool I had been keeping all to myself – and they would pay good money for it, too!

Maggie also helped me create a funnel that would usher my clients from one-time projects to a retainer-based contract if they weren’t ready to start with such a big commitment.

Together we came up with a couple services—like a website audit or a content strategy—that, once finished, would naturally move the conversation along to ongoing work, like on-demand copywriting and monthly blogging.

Speak Up

Before working with the mastermind mentors, my freelancing friends, and Maggie, I was pretty tight-lipped about my business. I didn’t like to talk about it because I wasn’t proud of the work I was doing or the clients I was working with.

After working with such incredible mentors, coaches, and supportive colleagues, I can’t stop talking about my work.

I love that every day I get to create magic on a page, money out of thin air, and progress for my clients so they can reach their goals, too.

Now, I speak up in online groups, too. I know my situation isn’t unique and what I did to transform it isn’t a unicorn story. These are real techniques that anyone can apply to grow their business and transform their professional life.

A Boy Screaming into a Microphone

Speak up!

Being stingy or selfish with your knowledge does no one any good.

Whenever I hear a fellow writer or service-based business owner talking about how they’re stuck or they don’t know what to do to get to their goals, I share. I give them all the tips and tricks I have and hope they can benefit from them.

Being stingy or selfish with your knowledge does no one any good. Doing the opposite has the potential to enrich someone else’s life and help you continue on your upward trajectory.

In fact, I’ve even received several requests from grateful Facebook group members to do one-on-one coaching with them with me as the coach!

It has always been a dream of mine to teach writing and content marketing to others so they can create massive online movements with just words. Now I get to, all because I finally built a career I’m excited to talk about with techniques that I’ve proven can work.


As you put one foot in front of the other on your start-up journey, remember these key points and you’ll find yourself climbing higher before you know it:

  • Face Your Reality – Check in with yourself. Are you happy? If not, what needs to change?

  • Find the Right Model – Be honest with yourself about what business model will allow you to sustain a healthy business long term. What do you need to feel comfortable? What do you need to cut out to stop feeling unhappy?

  • Make It Your Own – Don’t force yourself into anyone else’s box. Combine all the things that you’ve learned that feel right to you into one harmonious strategy.

  • Collaborate with Kindred Spirits – It doesn’t take much to build your support system: a small circle of 2 or 3 like-minded business owners can keep you focused at the most challenging times.

  • Always Up-leveling – Never settle. Appreciate what you have in the moment and be grateful for how far you’ve come, then aim higher, set your eyes on the next prize, and give it your all.

  • Speak Up – Share your wins, losses, and lessons learned with others. You never know what could help the next person and what you’ll learn about yourself and your potential in return.

If you have specific questions about how to find the right business for you or grow your existing business, post them in the comments below. I respond to each and every one! Or reach out to me on my website at www.cornellcopywriting.com.