How to Start Freelance Writing at 50 (and Make Money!)

Getting paid to work as a writer when you’re over fifty is easier than you think. I’m 54; my tips for starting a freelance writing career are guaranteed to help you succeed. If not, I’ll give you your money back 🙂

I’m kidding – of course you don’t have to pay money to read my blog post! And that’s one of my first tips for starting a midlife writing career: do not pay money to get into a pool of freelance writers, participate in writing communities, or join groups for 50+ freelancers. When you’re first beginning, those aren’t the best investments in your freelancing career.





A reader’s question inspired me to share these tips. Here’s what he said:

“I am considering pursuing freelance writing, an occupation in which I have little to no experience,” says Craig on Changing Careers at 40: How to Make it Easier. “I’m almost 60 years old so it’s a little late for a ‘midlife career change’ but (like Maria who commented earlier) I want to pursue my writing dreams. Laurie, I understand you worked as a writer for years. How do you recommend one start a writing career in one’s late fifties?”

Since every midlifer is different, I decided to round up a list of the best tips for pivoting into writing for a living. In his comment, Craig didn’t mention whether or not he wants to earn money as a freelance writer. It’s very possible that he’s retired and wants to write out of passion, not financial need. If so, he’s in an enviable position.

How to Start Freelance Writing at 50 - and Make Money

Of all the suggestions I can share, the most important is to work on your writing every single day. Freelance writing – even if you don’t need to make money because you’re a retired midlifer – is a pursuit that takes time, attention and energy.

1. See your age and experience as a strength

As a midlife career changer, you have more to offer than a young freelancer fresh out of journalism school. Your history, experience, education, stories and season of life gives you a valuable perspective that can’t be duplicated. Not even by AI (artificial intelligence)!

I started freelance writing when I was 36 years old. I had just gotten married and moved to Bowen Island, which is a tiny island in British Columbia. My previous jobs included teaching Grade 8 Language Arts at a school for missionaries’ kids in Africa and working as a Mentoring Coordinator for Big Brothers/Big Sisters in Calgary.

I was tired of freelance writing and blogging for “Quips and Tips” (which I rebranded as Midlife Blossoms), so I went back to school for my Master of Social Work (MSW) degree. And then I went right back to blogging. Two six-month practicums in the social services field was enough to send me right back to my beloved writing career!





So while I didn’t start freelance writing at 50+, I know what it’s like to make career changes in the middle half of life. Even better, my history makes me a stronger writer, happier midlifer, and more confident freelancer.

2. Never stop asking HOW

I took an Artist’s Way writing course, and loved meeting fellow authors and aspiring writers who were closer to 100 than 10. One thing that stuck with me was the facilitator’s encouragement it’s never too late to start writing. Even at 50, 60 or even 70.

That was the good news. She shared stories of old-timers starting different careers in their 60s and 70s. She shared the famous story of Grandma Moses who started painting when she was in her 80s and even marathon runners like 92 year old Harriette Thompson who started racing long past middle age.

But she didn’t tell us how to start freelance writing at 50+ or running marathons 90. As I mention in my blog post about changing careers and blossoming when you’re 40+, it’s hard to switch career tracks when you’re a midlifer. We have kids, aging parents, neighbors with trees blocking our view of the ocean, taxes, retirement concerns and health issues that range from bunions to breast cancer.

How do people over fifty start a freelance writing career? These tips are a great starting point for new aspiring midlife writers, but your job is to try different things until you find what works for you. How I started freelancing as a 36 year old writing for the local island newspaper for free won’t be how you do it as a 60 year old with an elderly wife who needs care.

If you don’t feel supported at home, read My Retired Partner Isn’t Motivated. Will He Drag Me Down?

3. Get out of your own way

If you’re searching for tips on how to start a freelance writing career in middle or late life, I suspect you’ve wanted to be a writer for a long time. Perhaps your whole life.

Something or someone is holding you back. Perhaps it’s a buffet of somethings and someones. An ocean of reasons – some real, some in your head – why you can’t start writing for real. But now that you only have a couple decades of good life left, you’re ready to do something about it.

It’s time to get out of your own way.

To get out of your own way, you need to know what you’re putting in your way.







Feel the doubt, fear and insecurity – and write anyway.

4. Go beyond blog posts to actual books or ebooks

The reason I was quickly successful at starting my freelance writing career was because I spent hours reading books about freelancing and starting a business. I learned how to pitch query letters, wrestled with the idea of sending multiple submissions to different editors (writers should definitely submit multiple queries, despite what some books say), and honed my professional entrepreneurial skills.

Book learning is better because print material contains more information, isn’t as distracting as online, and is easier to bookmark.

That said, however, it’s important to remember that there is no one right way to learn how to become a freelance writer when you’re starting a career in midlife and beyond. Even more importantly, writing is a business. As with any business, if you want to succeed you need to become an expert in your niche. That involves learning how a freelancing business operates – but you don’t necessarily need to go to journalism school or get a degree in writing.

You’re already on the road to getting your writing published in magazines! good, because you don’t have time to waste.

5. Think freelance writing career, not hobby

When I first started freelance writing, I called myself The Adventurous Writer. That helped me think of myself as a “real” writer with an actual career. I felt weird starting as a freelance at age 36, but looking back it seems young to me now!

And then my husband Bruce kept talking about my “writing career.” That freaked me out at first, but then I began to think about my writing that way…as a career, not just a dream, goal, or even a way to pay the bills. It changed how I organize my workday, what I focus on, and what types of magazine assignments I accepted.

If you’re serious about starting your freelance writing career, you need to call it your CAREER. Maybe not out loud yet, but definitely in your head. And definitely in your Morning Pages (which you’ll start writing as soon as you start reading The Artist’s Way).

Starting out as a freelance writer at 50+ is serious business. It requires effort, discipline, energy, and an investment of time and money. If you treat your freelance writing career with respect, it will return the favor. If you honor your work, it will honor you.

How to write your family memoir- Mary Karr

If you want to write about your ancestry and history, get The Art of Memoir by Mary Karr.

You might also want to read Writing Your Family Memoirs? 10 Mistakes to Avoid

6. Decide which magazines you want to write for

Here’s a question from a published Christian author who has written 17 books:

“I’d really like to sell to Reader’s Digest. I was encouraged that your first article with them went through the slush pile. That’s the way I sent my first query letter a couple of weeks ago, but I haven’t heard anything. How long would you advise me to wait for a response? I have another high-profile article I’d like to pitch to them, too.”

In 10 Writing Tips from a Reader’s Digest Editor, I explain the importance of knowing the magazine and the editor you’re pitching. Some editors take three months to decide on a piece, others accept immediately. Some editors acknowledge your query letter, while others don’t say a word until they assign the article.

If I was pitching Reader’s Digest from the slush pile today, I’d probably wait three months for a decision from the editor. But, as I said earlier, there is rarely one right answer to any question when you’re learning how to become a freelance writer.

7. Prepare to fail, and to try again and again and again

Part of being a successful freelance writer – and getting out of your own way – is learning how to overcome failure, recover from setbacks, and focus on your long-term vision for your career. At 50+, you know success doesn’t happen overnight. You know you’ll have to struggle to achieve your goals because good things rarely come easily.

You know you’ll be rejected, but you’ll make choices that take you in the right direction. You’ll choose to learn how to start a freelance writing career at 50+ instead of choosing to Like something dumb on Facebook. You’ll choose to practice writing instead of choosing to try out that butterscotch cookie recipe on Pinterest.

8. Decide what type of articles or content you could sell

A reader asked me if he should write full feature length articles with tips or humorous stories about his life. The answer is that it depends on all sorts of different factors – but the most important question is: “What type of freelance writer do you want to become?”

Once you decide that you want to be a tips-based health writer, then you can start aiming in that direction. If you’d rather write humorous stories, then you need to research the freelancing possibilities in that market.

Read 11 Types of Articles to Write for Magazines. I think the only category I didn’t include in that blog post was one on how to write for seniors’ magazines or organizations (that’ll be an upcoming article!).

How to Start Freelance Writing at 50 (and Make Money!)

9. Write for a variety of sources

Here’s another reader’s question:

“I want to eventually make money writing, and I would just love to begin a career. I would even write for free if this meant I could get paid opportunities in the not too distant future. My huge problem is how to start. Should I begin a blog (following the writing tips in your blog) and wait for it to get bigger and bigger until I can earn some money? Or should I try emailing my writing to already existing blogs or online magazines?”

If you’re in your 60s and want to write as a hobby, then start a blog. If you’re a midlifer who wants to start an actual freelance writing career that pays money and allows you to save for retirement, start pitching article ideas to magazines.

You could also do both. Don’t focus solely on blogging or solely on freelance writing for magazines.

10. Learn how to sell your writing

This is the most disappointing tip on how to become a freelance writer: you have to be a salesperson. If you’ve already had a career or two in sales, then this might be easier for you in mid to later life.

As a freelance writer you have to sell your article ideas to editors over and over again, even if you’ve written for the publication dozens of times. Even when you build a great relationship with an editor at a magazine, she might leave. This means you have to start over with the new editor, who is probably bringing her own stable of writers in with her.

I didn’t like constantly pitching articles (or writing for other people, to be honest), so now I blog for my Midlife Blossoms 99% of the time. But when an editor asks me to write an article, I say yes! In fact, just yesterday I got an assignment from alive magazine to write a 1,000 word article on chronic fatigue syndrome. Payment is $500. Sweet.

12 Tips for Midlifers Who Want to Write

That’s the beauty of building good relationships with editors: they start emailing you with article ideas, and asking if you’ll write for them.

Have you heard of Stephen King? He’s a pretty good writer. One of his least famous books is On Writing: A Memoir of the Craft.

11. Use your waiting time wisely

After you pitch an editor, move right along to your next pitch. Don’t just sit around waiting for the magazine to respond! Tweak the slant of your article so you can pitch it to a different magazine. Work on a different feature article idea. Blog. Create a spreadsheet of your “article pitches sent” and your “replies received.”

One of the best things you can do when you’re learning how to become a freelance writer is create a “Pitch Calendar.” Create a plan, set goals, and set yourself up as a professional writer. This will help you succeed as a freelancer because it’ll provide structure to your day.

12. Remember that it takes years to be an overnight success

Most artists and creative types struggle financially. That’s why the majority of writers have another source of income when they’re learning how to become a freelance writer. Either they work part time or they have a job related to writing (freelance editor, blogger, social media expert, etc).

If you’re a retired 60+ year old, financially stable and not writing out of necessity, you’re both blessed and cursed. It’s a blessing because you’re not desperate to make money writing. It’s a curse because you’re not hungry enough to really make a go of freelancing.

All freelance writers have their own journey, their own race, their own road map (which isn’t always obvious until they look back). I can’t tell you if the “best” or “right” way to become a freelance writer or begin a career in writing is by writing articles or short stories, or by blogging or writing for free for online e-zines. I encourage you to seize the opportunities that are in front of you, and make the most of every chance you get to write!

Resources for Aspiring Midlife Freelance Writers

The Elements of Journalism, Revised and Updated 4th Edition: What Newspeople Should Know and the Public Should Expect is the book I’d use if I was teaching journalism to students of all ages today. If you want to pursue more serious reporting as a journalist in your late fifties or sixties, learn how to write for today’s marketplace.

The Writer’s Market Deluxe Edition: The Most Trusted Guide to Getting Published is an essential resource for beginning freelance writers. I always learned from the “how to start a freelance writing career” chapters at the front of the book – they always included tips for pitching articles, invoicing editors, managing financially on a freelancer’s sporadic income, etc.

How to Start Freelance Writing at 50 (and Make Money!)

If I was starting my freelance writing career today, I’d invest in The Essential Guide to Freelance Writing: How to Write, Work, and Thrive on Your Own Terms by Zachary Petit. When I wrote an article for Writer’s Digest, he was the editor I worked with. Now he’s at Print Magazine, I think.

For me, learning how to become a freelance writer was more interesting and fulfilling than actually being successful at freelancing. This is partly what made me a success: my curiosity, willingness to learn, and ability to motivate myself to work even without a boss. Or an immediate paycheck.



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Your thoughts and questions on freelance writing in midlife and beyond are welcome below. Who – or what – is holding you back?



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9 Comments

  1. This was incredibly helpful – thank you. As a complete (43 yo) novice to writing-as-a-career, your site and content is invaluable (and inspiring!).

  2. Writing always poses challenges for people over 50. Add to that the struggle of having a chronic illness or disability, and it’s even harder! I’m housebound, which makes the writing life seem overwhelming. I took a year out to write, but badly injured my back a week after quitting my job! Do you have any writing tips for people who are chronically ill? I want to keep my writing passion alive and would appreciate some support.

    1. I’m sorry you injured your back, Arianna! That’s a difficult way to start a freelance writing career. But, sometimes these setbacks provide new ideas for magazine articles that are more important and valuable for readers.

      I offered a few tips in this blog post:
      Write Through the Pain: 7 Tips for Writing With a Chronic Illness
      https://www.theadventurouswriter.com/blogwriting/7-tips-for-writing-with-a-chronic-illness/

      I hope it helps, and wish you success and good health in your new freelance writing career.

      Warmly,
      Laurie

  3. Hi, Laurie —

    Thanks for the info. I’m a new 62 year old writer, and recently turned down work from a newspaper that was paying 10 cents per word. I was finding that the stories required too much effort for too little compensation. I’ve had some second thoughts about my decision, but perhaps it was the right decision after all. What do you think?

    Thanks again! 🙂

    1. Hi Aimee,

      Welcome to the Midlifers Writing Club! Congratulations on being offered newspaper writing work. I agree that 10 cents per word is too little, depending on the type of writing, research, and background fact checking you have to do.

      I’ve been offered 20 cents a word from the Vancouver Sun, and 50 cents a word from the Globe & Mail. And, I know many people write for their local papers for free, just for the experience.

      So I guess I’d say the ballpark is 20-50 cents a word, depending of course on the newspaper….the rate increases if you’re syndicated, well-known, or a celebrity! I bet the Dog Whisperer Cesar Milan would get far more than $1 a word if he wrote for newspapers.

      I hope this helps, and wish you all the best as you pursue your midlife writing career goals.

      Laurie

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