What If I’m Too Old to Freelance?

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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.

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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.

Ready to Kickstart YOUR
Freelance Writing Biz?
Grab two of our most popular workSheets and get started TODAY!

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.

















16 thoughts on “What If I’m Too Old to Freelance?”

  1. What a great article. The very idea that a 50-year-old is “too old to learn” just boggles my mind.

    I’m 72 and learning and blogging and earning every day. I see people from their 50’s on up almost every day who have lost their jobs or suffered other reverse and fallen on hard times. So many perpetually mona and groan about how hard life is becuase the “don’t know” a better way. Learning didn’t finish with your high school or college back all those years ago folks. Not only _can_ you learn new things, if you let yourself, you might even enjoy it.

    Write on, learn on, earn on ……

    • You’re so right, Dave!

      Learning should be a lifelong adventure we all embrace. I can’t tell you how excited I get when I hear from other “mature writers” who really “get it.” Those that make excuses about being too old to learn something new have no idea just how much they’re missing.

      Thanks for your thoughtful comments. Keep on keepin’ on.


  2. Thank you for sharing your story – filled with inspiration, very encouraging for us “shaky Baby Boomers.”

  3. What a great post!
    It doesn’t matter what age you are when you decide to try freelancing. Anyone can do it! IF you are older and just starting to freelance, know that you have the experience and the brains necessary to do it; you just need to get out there and start doing it.

    • You are so right, Angela! I actually believe that more mature writers produce more valuable content because they have more experiences to share. Never say never. Give it a try. You may just be surprised how much you already know. Thanks for your great comments!

  4. 51 is a few months away, and I am certainly NOT the 50 my mom was! This post has certainly encouraged me to stop making excuses, and move forward. Thank you!

    • Awesome, Deb! So glad I inspired you to even think about doing something. I can’t tell you how great it is to earn your first paycheck doing something that comes naturally. Go get ’em!

  5. A few years ago I was wrestling with a similar question and wondered if I’d failed to do all that I “should.” Thankfully I made the comment to a much wiser person (in age and wisdom) than myself. And she said these words, “It’s not the beginning of a thing that matters, but the end.” I tucked those morsels into my breast and never looked back.

    Now I believe in possibilities, new beginnings, and endings that would blow your mind. All things are possible. Take the limits off and soar. 🙂

    • Sarah, you rock! I’m so happy you found a mentor to give you the push you needed. I’m a few years away from cutting those ties but I have a 5-year plan. It feels great to see the path clearly. Thanks for sharing your experience. ?

  6. I loved your article and like you, I too hope to inspire older men and women to just DO IT! I’m a “Gen-Xer” and after years of corporate misery, I left the “rat race” behind last fall to begin freelancing. I couldn’t be happier! Your nephew’s advice is spot on. (I’ll definitely remember that sound advice). Another piece of sage wisdom that keeps always me going is when we say to ourselves, “I’m too old to start such and such because, by the time I get anywhere, I’ll be 40, 50, 60. Well, whether you go for your dreams or not, you’ll be that old anyway so… you may as well go for it!”

  7. Cicely, I think as we age, many of us tend to take the simpler path in life. I’m so happy my nephew gave me that nudge and that I was able to step outside of my comfort zone to pursue my lifelong passion. It hasn’t been easy, nothing worth having ever is, but it’s very rewarding to see that people are actually interested in what I have to say. Congrats on taking the leap sooner (instead of later.) Good luck in all you do!

  8. Great article Debbie!! So inspiring!! After a couple of rejections my confidence got bruised, sorry to say. I have a lot a want to share, but I need to rid the block. I’m not giving up hope though. Someday…

    • Bev, thanks for your kind words. Like you, I’ve needed encouragement at every step to keep pushing forward. Being a freelance writer can be both lonely and intimidating, but it doesn’t have to. There are so many people out there that are ready to help. All you have to do is ask. You’ll be amazed! You can do this…It’s Never Too Late! 🙂

  9. I just now saw this article, Aug 2, 2018, and wanted to reach out and say how much I enjoyed it. Honesty, integrity and genuine enjoyment is what I read and heard.

    Thanks for listening to your nephew and sharing your dream with us!

  10. I congratulate you Debbie for your encouraging and motivating gem words of advice. I am from Nairobi, Kenya and I’ve just seen your article today, and I mean it from the bottom of my heart that it has started to free me of doubts of starting out as a freelance writer or starting anything that I am passionate about. I have harbored this self-doubt about my age and of immersing myself fully into the waters of freelance writing for so long and I have not even reached the age of forty yet. thanks so much for boosting my confidence.

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