How I Leveled Up My Writing Career in 60 Days for Debt Payoff and Long-Term Success

By Rebekah Mays | September 1, 2019

This entry is part 10 of 13 in the series Writing Challenge Winners

PWA Member Rebekah Mays

Congratulations to the 2019 “No Excuses” Writing Challenge Grand Prize Winner, Rebekah Mays!

Rebekah Mays is a writer for the health and lifestyle industries, where her goal is to help people lead healthy, meaningful lives. She lives in the Netherlands with her husband, runs the occasional marathon, and is trying (so far unsuccessfully) to learn Dutch.

You can learn more about Rebekah by visiting her at, reading her AWAI story, or simply reading her winning essay here.


We should all have one goal so big it scares us at least a little bit.

For me, that big, scary goal has been to pay off my $22,000 of student debt before I turn 30 next July.

At the beginning of this summer, I was starting to wonder how I would make it.

After all, as of June 1st, I’d billed my clients a little more than $2,000 in freelance income for 2019. I was certainly gaining momentum, but the reality of freelance life – and how long it can take to get established – was also sinking in.

“It’s taken me six months to earn my first $2,000,” I told myself. “I can’t realistically earn $4,000 in one month any time soon! I guess I should just be happy with my progress so far … take the projects as they come … and maybe push back my debt payoff goal a year or two.”

Do you see what I was doing to myself?

While it’s true that going from $400 to $4,000 a month is a big leap, I was trying to find a way out.

Of course it takes time to get established as a freelance writer. But I was using this truth as an excuse, hiding behind it to shield myself from the scary, and perhaps painful, growth process I had in front of me.

That’s why this “No Excuses” challenge came at the perfect time. I read through the guidelines and knew exactly what I had to do.

I needed to dig deep and get past my excuses – to do everything in my power to land better projects, level up my writing income, and most of all … not let myself give up on my goal. 

The Action Plan: Going for Better Projects

Since I’d been mostly writing blogs so far, I decided to make my main focus landing bigger and better-paying projects. Namely, sales letters.

This was a timely choice, because in May I’d received my first sales letter assignment – and I was getting a peek into what it was like to play for the “big leagues.”

I also considered that most of my freelance income had come from the one client that assigned me that letter. So it seemed obvious that I should build on that relationship, as well as reach out to new prospects.

I made my action plan. And I decided to: 

  • Complete the sales letter for my client to the best of my ability. By doing an excellent job on the letter, I’d prove myself to be a professional writer they’d want to hire again and again.
  • Be ready with ideas to pitch to my client upon completion of the project. Since I wanted to build on my existing client relationship, I’d need to be prepared to keep the momentum going.
  • Submit two Bootcamp specs. I knew I needed to get my foot in the door with a few other direct-response companies. Submitting specs from AWAI’s Bootcamp and Job Fair was a perfect way to do it.

My hope was to line up several sales letters for the months ahead.

What Actually Happened:  (At First, Nothing!)

So what happened?

Well, I managed to do all the things in my action plan, but nothing moved as quickly as I expected.

For instance, I completed the sales letter project – and it went quite well, providing me a great testimonial and sample. But it didn’t immediately lead to the next assignment.

I also submitted an idea to my client, but after a couple weeks of discussion, they concluded it wasn’t quite right for the product.

I submitted the specs, too, but in both cases I didn’t get a response at all, even after some follow-ups.

Two clear themes were emerging that I hadn’t anticipated. One – the bigger the project, the harder it is to land. And two – landing new clients isn’t always easy!

So with a month left in the challenge to keep going, I decided to take my action plan to the next level. Here’s what I did:

  • First of all, I went back to the Bootcamp specs, and I submitted other specs I hadn’t considered initially. This made me find some other potential clients and industries that could be a great fit for me.
  • Second of all, because I was spending so much time marketing myself, I decided to rebrand my business to set me up better for the long-term. I settled on a new niche focus and put together a new website that would speak to my dream clients.
  • After my first idea didn’t get anywhere with my client, I pitched a lead-generation campaign to them. I knew if I was persistent and helpful they would say yes eventually.
  • And finally, I submitted an editorial idea to a new prospective client, since I’d learned from experience it’s easier to start with editorials and work my way up into sales letters. 

The Results: More Possibilities Than I Could Have Expected

After I “leveled up” my action plan, and completed these new activities … what happened?

In the end, a whole lot. Here are my results:

  • First of all, my client expressed interest in my lead-gen idea … and asked me to send over a proposal. We’re still working out the details, but they’ll probably assign me a funnel. This takes our relationship to a new level. Plus, if the project goes well, they’ll probably hire me regularly for services like this.
  • A marketer who received one of my specs got back to me, after some follow-up. She expressed interest in my skills, and may have me do a trial period for an ongoing copywriting job. There’s no offer yet … but if it works out, it would be a huge growth opportunity for me.
  • I’ve set up a discovery call with another potential client who needs a lead-generation campaign. Since I had my new website and niche focus set up, I was confident when responding to her job description and was able to send her my info right away.
  • A new prospect said yes to my editorial pitch. This is a small project, but if it goes well it could lead to many more projects in the future – including sales letters!
  • I’m in a conversation with my main client about ongoing work. After not getting very far with my pitches, I decided to do something a bit forward – and I simply told them I was interested in working for them on a regular basis. Thanks to my efforts over the summer, they see how enthusiastic I am about their company … and they’ve made it clear they’re interested. This could be another huge opportunity for growth and regular income … and would be a very exciting development in my career.

Strengths, Weaknesses, and Opportunities of This Challenge

When I look at everything I accomplished over just two months, and see the opportunities it’s led to, I’m pretty amazed. And it was all thanks to the focus and mindset I adopted over those 60 days.

Will I be able to pay off my debt by next July as I hoped?

It’s not a “done deal” by any means … but I’m a whole lot closer to my goal than I was at the beginning of the summer.

In any case, by having me focus on the number one obstacle preventing me from moving forward, the challenge uncovered the deep, psychological reasons that were at the root of it all.

I realized that my expectations were simply not realistic. I was holding on to a hope that I would be able to cruise into this new lifestyle … and that after a few months of studying copy, I’d be bombarded by clients ready to pay me anything I asked.

The past few months have shown me that’s not how it works for most people. I realize that if I’m truly going to reach my goal of debt pay-off by next summer – and thrive in the long term as well – I’m going to have to take a much more proactive approach.

I need to get creative … be a little ruthless in my persistence … and let myself take advantage of unexpected opportunities.

My strategy certainly wasn’t perfect. For one thing, I learned I need to balance both short and long-term growth.

Focusing almost 100% on big-picture items like large projects, rebranding, and sales letter specs was great for “leveling up,” but not so great for short term bill-paying. If I had to do it over, I might pitch a few small projects earlier on to help with cash flow.

And the biggest opportunity of all this?

For the first time, I’m looking at in-house opportunities. I’ve realized that they’re perhaps the best way for me to level up my skills more quickly, and bring in super-consistent income in this early stage of my career. That realization alone is transforming my income prospects.

Ongoing Shifts: Where to Next?

The challenge opened up many possibilities to me, but there are a few main shifts I’m going to make going forward.

  • Thanks to all the proposals I submitted and discussions I’ve had this summer, my negotiation skills have improved – and it’s something I’ll keep working on. I’ve realized it’s all about being confident in the value I offer, being clear about what I need, and finding that “middle ground” that’s fair for both parties.
  • I’ll prioritize long-term growth, but keep working on balance. I’ve realized that if I had to pick between short and long-term success, I would focus on the latter, since I’m still quite early in my career. But the ideal situation is to balance the two – so I can both pay the bills now and enjoy a great income years down the line.
  • Retainers and in-house! I’m now open to different work situations, and see that being a remote staff member could take me where I want to go in my career much more quickly.

The Bottom Line: Don’t be afraid to go BIG

Above all, the biggest shift I’ll make is to keep tackling the deep, psychological excuses keeping me from achieving my goals.

I believe it’s only by doing this that I can really go BIG with my goals.

Do you want to try this in your own career? It’s tough, but not complicated. Here’s how you can make it work for you:

First, identify your “why” – a goal that’s deeply meaningful to you. If you don’t have something important motivating you, you’re not going to be able to stick with your goals when things get difficult.

Second, identify the psychological excuses holding you back from that goal. Do you need to adjust your expectations about how easy or hard this is going to be?

Be honest with yourself about the reality of your situation. Then, face up to that truth, and decide not to let it hold you back from giving it your very best shot and moving forward at all times.

The third step is to make an initial action plan to move to where you want to go … and then to DO it.

But that’s not all – as you move through your plan, you’ve got to learn from your actions and adjust your strategy as you go. The most successful people are those who keep pushing themselves and trying new things until they reach their goal.

This challenge proved beyond a doubt just how much 60 days of consistent action without excuses can change your situation … your career … maybe even your whole life.

So … are you ready to shake off your excuses?

Try it. If my experience counts for anything, chances are this decision will change everything.