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How to Start Freelance Writing at 40 – and Make Money

These tips on how to start a freelance writing career at 40 are screaming to get out of me! Why? Because I’m taking this epic Artist’s Way writing course, and the facilitator told us it’s never too late to start writing. Even at 40, or at 50, or 60.

start freelance writing at 40

“Freelance Writing at 40” image via notonmystreet.com

That was the good news. Yes, it’s awesome to know about various writers who didn’t start writing until they were in their 60s and 70s. (By the way, this means you’re well ahead of the game if you’re looking for tips on starting a freelancing career at 40.) The facilitator also told us about painters like Grandma Moses who started painting when they were ancient and marathoners like 92 year old Harriette Thompson who started running when they were even more ancient.

But, the teacher didn’t tell us HOW to start freelance writing at 40, or marathoning at 90. As I mention in Making a Career Change at 40? 10 Things You Need to Know, it is really hard to switch career tracks when you’re in “midlife.” We have kids, aging parents, neighbors with trees blocking our view of the ocean, taxes, and health issues that range from bunions to breast cancer.

We also have fears, insecurities, and the biggest BUT of all: self-doubt. That’s the other thing the Artist’s Way course facilitator talks about. We are our own worst enemies because we let our own stuff stand in the way.

And that’s the focus of my first tip on how to start freelance writing at 40.

But first, let me tell you something. 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.

And I went back to school at 42. I was tired of freelance writing and blogging for “Quips and Tips” (which I rebranded as Blossom), so I got my Master of Social Work (MSW). 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 40, I definitely know what it’s like to make career changes in the middling part of life.

5 Tips on Starting Your Freelance Writing Career at 40

My first suggestion is mostly psychological. The next four suggestions are highly practical and actionable…

1. Get out of your own way

If you’re searching for tips on how to start a freelance writing career at 40, I suspect you’ve wanted to be a writer for a long time. Am I right?

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 a freelance writing career. But now that you’re looking at 40 (or you’ve seen it come and go several times), you’re ready to do something about it. Or, at least you’re ready to search for tips on starting a freelancing career.

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

You want to learn how to make money as a freelance writer. If you don’t do it now, then when? Stop letting your doubts, fears, insecurities, and weaknesses get in your way. All writers and all humans beings are doubtful, scared, insecure, and weak! And yet, we write.

2. Study books on how to start a freelance writing career

For me, learning how to become a writer was the best part of my experience as a freelancer for magazines. I wrote for Reader’s Digest, MSN Health, Flare, and even More. I learned a lot and got a mild kick out of seeing my articles published in magazines…but it wasn’t terribly fulfilling for me. I never cared about seeing my articles or my name in print. I still write for alive magazine – and in fact, I have a feature article in their print issue this very month! They send me assignments about three times a year, and pay me $500 per assignment. It’s sweet.

The reason I was very quickly successful at starting my freelance writing career was because I spent hours reading books about freelancing. I don’t love freelancing so I quit pitching article ideas to editors after a couple of years. I love blogging and I love learning – as evidenced by my two undergraduate degrees and one Master degree. I’m still blogging and learning, but I’m not writing for magazines anymore.

If you want to know how to start a freelance writing career at 40, you need to read books about the business of writing. You don’t need to love learning the way I do, but you do need to know how to learn.

3 quick tips on how to start a freelance writing career at 40:

  1. Don’t bother with getting a journalism degree
  2. Get off the internet
  3. Read print books about the freelance writing business.

You don’t have time to waste. Do you?

4. 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.

How to Start Freelance Writing at 40

How to Start Freelance Writing at 40

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 40 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.

5. Kick failure in the not-so-sweets

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 40, 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 40 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.

One last bonus tip on how to start a freelance writing career at 40

Before you decide to take a writing class, quit your doctoring job, or have another child – ask yourself if that choice moves you towards your long-term career goal or a short-term desire to scratch an itch or please someone.

Choose activities, people, and even memories that take you TOWARDS your goal of freelancing as a career. Everything you add to your life needs to take you one step closer. And, start thinking about what you can delete from your day that takes you one step away from being 50 and ignoring my advice on how to start a freelance writing career at 40.

Resources for You: The Freelance Writer

how to start a writing career at 40Feature and Magazine Writing: Action, Angle, and Anecdotes is the book I used when I taught high school journalism. Perhaps this is why I knew how to start a freelance writing career at 40 – and make money. I’d already learned (and taught) the nuts-and-bolts of journalistic writing, and I had a solid foundation of how to find original ideas, locate expert sources to interview, pitch magazine articles, work with editors, etc.

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.

If I was starting my freelance writing career today, I’d definitely 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.

Question for you

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.

What have you recently learned about becoming a freelance writer at 40? Who – or what – is holding you back from giving it your 100%?


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3 thoughts on “How to Start Freelance Writing at 40 – and Make Money”

  1. It’s never too late to fulfill a dream, even being a writer after the age of 40! Really inspiring post. People should never give up their dreams 🙂

  2. This was a very helpful and inspiring read. I extra double appreciate the list of book recommendations. I ordered them all! It feels good to get started on a new, more independent path doing something I actually care about and enjoy. Thanks!

  3. I think the tip about looking at freelance writing as a career rather than a short-term job is huge. It’s hard for a lot of people, if they make the move to work at home, to respect their own business.

    A few things that have really helped me and the writers I’ve coached are:

    – Have a plan for each day. Don’t just dive in and put out fires all day – set a few goals so by the end of the day, you know you’ve accomplished something.

    – Work on your business consistently. No matter what it is, every business needs marketing – and that should be done every day… even if you’re busy.

    – Build systems so you’re not constantly reinventing the wheel. If there’s a task you expect to have to do more than once, document how you do it. Ultimately you may be able to outsource it – and by having the documentation done, it’s a lot easier to train someone to help you.

    Thanks for a great post.