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What If I’m Too Old to Freelance?

When Debbie reached out with a pitch about starting a second freelance career in her 50s, I was hooked.

She said she had a lot of things to share about her progression from the “scared little rabbit” stage to the “jumping in with both feet” stage.
I admired her positive outlook and her determination to make it work.
But most of all, I admired her dedication to being a lifelong learner.
So here is Debbie’s story of how she learned the ropes of freelance writing in her 50s.

What if you’re too old to start freelancing?

You knew this was a trick question, right?

Of course, you’re NEVER too old to start a career in anything your heart desires. Mine just happened to be freelance writing.

I was “one of those kids” who did really well in school. I got straight A’s in almost every class (except math, but I always liked words more than numbers anyway). I always thought I’d be a journalist “when I grew up,” but that plan got derailed by a creative writing teacher who just didn’t think I had the stuff. I’m not sure why I believed her, but she stole my confidence and my would-be career.

Looking back, I know I took the path of least resistance. Getting an Associate’s Degree in Secretarial Science at a two-year college, getting married soon after graduation and jumping into a job as a junior secretary seemed like a good idea at the time, but I could have done so much more.

What About My Dream?

Funny thing about dreams … if you’re really passionate about them, they’ll always find a way to be part of your life.

Writing was definitely my passion, and regardless of what that creative writing teacher told me, I knew I was good at it.

Throughout my career as an administrative assistant (it’s taboo to call me a secretary now), and over the last 30 years working for a home builder (Geez, I’m old!), I’ve ghostwritten hundreds of newspaper editorials, ads, web copy, blog posts and customer letters.

I was pretty sure I was a good writer—my boss would always gush over what he called my “Pulitzer-prize winning” creations. But whenever friends and family would suggest I write that book I’d always talked about, I’d just shrug my shoulders and say, “I’m not smart enough to write a book.”

How My Mindset Changed

I was inspired by my brave, brilliant, jump-in-with-both-feet, Millennial-aged nephew.

Five years ago, he left the comforts of home in suburban Western New York for the potential of greatness in New York City. He threw all he owned into a couple of bags, hopped on a train headed east and never looked back.

On his Christmas visit that year, I couldn’t help but marvel at how he took a leap of faith and just went after his dream. As I was reminiscing about what I’d do if I were 30 years younger, he stopped me mid-thought with, “you’re only too old to pursue your dreams if you’re dead.” (I told you he was brilliant!)

Is There Such a Thing as Too Old to Freelance?

Could he be right?

Was it really possible for me to start a writing career at 50 years old?

I had absolutely no idea where to start, but my nephew had mentioned that he managed to make some money freelancing before he found a full-time job.

I only had a vague idea what that was, so I Googled it.

Imagine my surprise when “freelance writing opportunities” netted over two million search results!

How was I going to sift through all of this information? After all, I still had a full-time day job, a husband and a house to take care of. When was I going to find time to do this too?

What Was I Worried About?

A more accurate question would be, “What wasn’t I worried about?”

I was worried about:

  • My age. I still wasn’t convinced I wasn’t too old to freelance. What if my ideas were out of touch with younger readers?
  • Lack of confidence. It had been a really long time since I learned proper grammar and punctuation. Maybe I wasn’t as good as I thought.
  • Starting a business. Where should I start? How would I avoid getting scammed? Could I do it without spending a lot of money? Could I learn the tech skills I needed? And where was I going to find the time to write with all my other responsibilities? And those were just the initial questions. After that, I’d have to figure out invoicing, tax structure, and a few other things “math related” that I really didn’t want to think about.
  • Using a pen name. Ghostwriting worked great for me because there was no pressure; no one really knew who wrote those articles, so I was safe from criticism or repercussion. What would happen if people knew my opinion differed from theirs? Could I write freely or was I opening myself up to problems?
  • Whom to trust. This was probably the most troubling for me, because the whole concept of working online was all new to me. Was there any way I could become a freelance writer without any risk? What if the people I wrote for didn’t pay me? How would I know if I was getting the best advice?
  • Finding a niche. I didn’t even know what a niche was, not to mention what to write about or where to publish it. I wasn’t an expert in anything, so who would want to read what I had to say?

Pro TIP! Finding a niche is what prevents a lot of people from just getting started. We’ve put together a list of over 200 freelance writing niches that you can pick from when you’re first starting out.

Here are the steps I took to freelance successfully in my 50s:

1. I Did My Research

While I was both overwhelmed and excited about starting my late-in-life career, I knew I had to take things slow at first.

Instead of signing up for a bunch of writing courses or hiring a financial planner, I started out doing research.

I refined my Google search to “entry-level freelance writers” and then “earn money as an entry-level freelance writer.”

Once again, I was amazed at what popped up—over a million search results miraculously appeared for writers, just like me, with little or no experience.

Everything from applying to job board posts to setting up my own blog to creating the perfect LinkedIn profile to writing for content mills. Each of these ideas seemed interesting, but the little voice in my head kept warning me that “there must be a catch.” To silence my skeptical side, I decided to focus on one idea and find out as much as I could about it. I chose content mills first.

A few of the larger content mills kept appearing in my research, so I listed the pros and cons of each. I looked for details on how they chose their writers, if it was subscription or free service, how much they paid, how often and the method of payment, and whether I would be writing “on spec” (writing the entire article hoping someone would buy it) or if orders I chose were guaranteed to earn income.

I also looked for reviews from other writers who had worked with the companies before to filter out those less-reputable organizations.

2. I Tested the Waters

Now, armed with as much information as possible, I decided to launch my freelance writing career. I found a free content mill that was selective about their writers. (I liked that they didn’t accept just anyone.)

I took a writing test to determine my level of expertise. In this case, a star-rating was assigned with the higher number earning a larger per-word payment. Imagine the confidence boost when I achieved the highest-level, 4-star membership on my first try!

You may be unfamiliar with the concept or may have been told to run as fast as you can away from them, but it was the best way for me to test the waters. I was thrilled with the first $5 I earned for a small blog post, and enjoyed the variety of topics I could choose to write about.

In one small step I learned that I wasn’t too old to write, I still knew enough grammar and punctuation to get by (they even had free refresher courses I could take to update by skills), and I eventually started to find a couple of niches that were easy to write because of my previous work and life experiences. Who knew that being “old” would actually come in handy?!

During the first four months, my writing improved, my confidence grew, and I earned over $700. Writing for a content mill was a great experience for launching my freelance writing business.

I continued on to write hundreds of articles for them over the next couple years and used them as a fill-in for easy cash whenever I needed it. However, I realized that my writing skills warranted a greater return for the time I was investing, so I started my search for higher paying, long-term clients.

3. I Picked My Freelance Writing Niche

Writing for the content mill helped me narrow down the subjects I was most familiar with so that I could start to market my expertise in a few specific niches.

I’ve worked in new home construction for most of my life and had hands-on experience with remodeling and home improvement working at my family’s summer resort.

I applied to some job posts in the home improvement and real estate industries and immediately landed a couple of orders. One client is a website designer for several home improvement contractors. They all needed web content and blog posts, so I became the go-to writer for a variety of industries.

I earned many bylines for my work and was able to include them in my ever-growing portfolio.

While I have written for many clients over the years, my very first professional relationship has grown into a partnership. We’ll soon be launching a brand new home renovation website of our own. With my partner’s website and outreach experience and my writing skills, we look forward to a successful and lucrative site.

Not bad for a 50-something writer!

4. I Adopted a Lifelong Learner Attitude

My writing career has evolved because I was committed to learning everything I could about the business.

You have to set goals in order to grow, so I did just that.

I wanted to earn more money, so I had to improve my skills. To do that, I had to find reputable companies with talented people to show me the ropes.

Forget about those “you can make a six-figure income while sipping margaritas on the beach in your first year” pipe dreams. It’s not going to happen.

There are, however, some amazing people out there who can help guide you on the path to freelance writing success, no matter what age you are.

First, I had to learn about blogging. I had no idea just how immense the writing community was until I set up my own blog. I learned about the platform through a client who has also become a mentor. I followed tutorials and lessons on how to set up a free website, write blog posts, link to social media, generate followers, and find writers just like me to share ideas. Best of all, it provided the perfect place to practice my craft.

Then I learned about becoming a freelance writer from the 30 Days or Less to Freelance Writing to Success course. Honestly, I wish I’d found this resource sooner. Make sure you join the Facebook group too. Being a writer can be a little lonely, and Gina’s followers are supportive and fun to hang out with.

5. I Trusted My Instincts and My Life Experience

I’m a firm believer that you don’t have to know everything, as long as you know where to look.

There is no possible way you can know everything there is to know about freelance writing—even if you’re a fearless Millennial, an overly confident Gen-Xer, or a shaky Baby Boomer like me.

At the end of the day (and that’s usually about 2 a.m. for me), I learned to trust my own instincts. One benefit of being over 50 is that I’ve got great life experiences to draw from.

They’ve helped me find my niches. My jobs, my hobbies and my interests all work together when creating articles companies will actually pay you to do.

They’ve helped me recognize when something is a scam or doesn’t feel right. This sixth sense has saved me from spending money foolishly on “get rich quick schemes” and when a potential client wants full “samples” so they can steal your work without paying for it—it happens.

They’ve also helped me see the future. I write under a pen name because I could “see” that using my legal name could restrict free writing. Creating a new persona has allowed me to explore new topics, share my opinions, and recreate myself without fear of repercussions. It’s quite liberating!

They’ve helped me see the importance of being a lifelong learner. No matter how old we are, we should strive to learn something new every day. It’s only by continually seeking knowledge that we can be truly successful.

So, no, you’re never too old to freelance. So, what are you waiting for? I hope I’ve inspired you to take that first step toward fulfilling your dreams. I’d love to hear your story.

Debbie Dey is a married baby boomer, an empty-nester with a full-time day job and the energy of a Gen-Xer. She’s also a professional writer and blogger with over three decades of experience in residential construction. She grew up working in the family summer resort business in Canada and learned firsthand how to handle just about any home improvement project. Her business name, Debbie Dey Writes, tells her story, but her ultimate goal is to give your vision a voice.

















Gina Horkey

Gina Horkey


Gina Horkey is a married, millennial mama from Minnesota. Additionally, she’s the founder of Horkey HandBook and loves helping others find or become a kickass virtual assistant. Gina’s background includes making a living as a professional writer, an online business marketing consultant and a decade of experience in the financial services industry.

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