“What it Takes to be a Freelance Writer” Keynote at Penn State’s “Freelance-a-thon” Conference

Who Am I?


I’m really an artist masquerading around like a writer. Or at least if you look at my formal education, over 4 years of learning as a fine arts-painter, attending Indiana U of PA and  the Pennsylvania Academy of Art in Philadelphia, the oldest art school and one of the most prestigious in the country.

But before I could try to make a living as a painter, I went and had a life changing experience. I backpacked the 2,100-mile National Scenic Appalachian Trail. I kept a journal and sketched along the way and because there were few female long distance hikers  in the early 80’s, let alone ones who could draw, I was able to publish my first book, entitled A Woman’s Journey on the Appalachian Trail, written in calligraphy with 125 drawings illustrating it.  It has been in print for 33 consecutive years and has become a classic.

I was fearful that if I took off 6 months off to backpack and not paint, I would lose it. But my art instructors told me, if you don’t go out and live your life, have experiences, especially life-changing ones, you work will grow stale. On the trail, you will paint with your eyes and when the time comes to put brush to canvas, you will have grown, as an artist and as a person. The same goes for writing or any creative endeavor

Henry David Thoreau, author of Walden, wrote, “If a man advances confidently in the direction of his dreams, and endeavors to live the life he has imagined, he will be met with a success unexpected in common hours.”  Reaching Mount Katahdin in Maine, the end of that long trail and getting a book published that I wrote and illustrated, proved that.

I had one writing class in college and got a C. Pretty mediocre, but keeping a journal on the trail, made me fall in love with writing. My success buoyed me to go on to hike the 2,600-mile Pacific Crest Trail (the one Cheryl Strayed of the book and film “Wild” attempted.) I wrote and illustrated a book about that long distance trail. In fact I had three books published before I ever wrote my first magazine article, which is not the normal route a writer takes.


I am not the normal writer.

I will soon have  7 published books, get about 50 magazine articles published a year and have made a successful living as a writer for over 30 years.

I do have some wisdom to share with you that I have gleaned from all these words.

Your life does not have to look like anyone elses. The route you choose to take to become a successful writer can be completely different than the norm. You do not need a degree in journalism or writing or English. You don’t need any degree. You don’t even need a single class in writing.


These are the things that you DO need in order to be a successful writer.

You must love to read and love to write. These have  to be in the top 3 things you love to do in your life. If you love them, if you are impassioned about expressing yourself in words,  telling stories, communicating, you will already be writing. You won’t be able to help yourself.  It’s what you do, it’s who you are. It can be as simple as keeping a journal. JUST KEEPING A JOURNAL can make you into a writer.

My girlfriend’s husband was helping edit my second book, Journey on the Crest.  He earned his Bachelors at Temple U in Communications/Journalism, but he was working full time as a mailman. He came to resent me because I was getting my second book published. I was an artist, for God’s sake.  He was the writer.

So I told him. “The definition of a writer is ONE WHO WRITES. That’s’ it.” He did not write anything. That was what stopped him from being a writer.    


So if writing is not something you adore and do because you can’t NOT do it, change your major, because the life of a freelance writer is even harder.

If you want to be a freelance writer, Money cannot matter. You cannot be in love with material things, aim for the high life, seek creature comforts. Sometimes the money comes in, sometimes it does not. It is a very unpredictable risky lifestyle.  If you are someone who needs security, switch your major.

You must get out of debt if you are in debt and it has to be top priority. Then you can relax and strive to live a rich, full and exciting life. Because that is what you need to do to be a successful freelance writer.

There are stories everywhere. Orson Scott Card said, “Everyone walks past a 1000 story ideas every day. The good writers are the ones who see 5 or 6 of them. Most people don’t see any.”  WE ARE THE STORY TELLERS. It is the most important work we can do.

Why? Because we are the voice of our people. We speak for them. We share what is inside them, what is inside us, creating connection. It is one of the fundamental needs of a human being- to connect and as writers, we are the conduit.

My daughter Sierra first enrolled in Journalism at Temple U and her professor told the students in the very first class, “I don’t know why you are here. Journalism is dead.”

I do not believe that. I can sell a story to almost any editor if I can get them on the phone. That is because I have the most amazing story ideas. With amazing stories, you can find outlets for your work. You will be passionate and enthusiastic about your story and the editor will be more easily convinced to allow you to tell it. You will be able to sell and make a living from your work.

You can’t be a meek shy introverted writer and be a freelancerIf you are, practice being assertive, develop your other side. It is a jungle out there and some editors want to eat you alive. Cultivate a very healthy positive belief in yourself and what you have to share with readers. This affirmation will help grow you and toughen your skin.

But you have to be willing to do things like hike the Appalachian Trail, take home a homeless person, ask the fire department if you can be a Ride Along on fires, captain a houseboat down the Mississippi River, buy a motorcycle and travel on it, learn to fly fish, volunteer to build a house with Habitat for Humanity, become a part time rafting guide, jump out of an airplane, deliver Meals on Wheels, snow tube with a double amputee Wounded Warrior. LIVE YOUR LIFE. DO SOMETHING. Every person you meet has a story to share and every experience you have is yours to write about. You have to leave your house, push past your comfort zone, engage, scare yourself, stretch. These will be your best stories and be your best writing. And when you find something you love to do (besides reading and writing) be the best you can be at it. I became a writer because I loved to backpack and hike and began to write about it. I was good at hiking so I got good at writing about hiking.

I want to tell you a story about my friend Corey Rich, one of the most successful and prestigious photographers in the outdoor world. He recently documented the historic first free ascent of El Capitan’s Dawn Wall, a climb of 19 days. Corey did not take a class in photography. He began as a climber who started to take photos of his fellow climbers on the wall. Everyone else was too busy climbing, Corey managed to do both and got so good at it, he is a world famous climbing photographer. He was just following his bliss and wanted to communicate what he saw.

There is one life philosophy that tells folks to figure out what the world is missing and give that to them, be the one to fill that need, even if it means creating a job. But another philosophy of Howard Thurman says, “Don’t ask what the world needs. Ask what makes you come alive and do it. Because what the world needs is more people who have come alive.”

As writers, if you strive to be that kind of person, to live that kind of rich full life, there will always be stories to tell and stories to sell.

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19 thoughts on ““What it Takes to be a Freelance Writer” Keynote at Penn State’s “Freelance-a-thon” Conference Leave a comment

  1. Truer words have hardly ever been spoken. To get good at anything, you have to do it – over and over again. In addition, as a writer, you have to do things about which to write. What a concept! What a life!!

  2. Very nice piece. I hope to hear more about your adventures at our upcoming IUP reunion in July!

    1. hi there- yes, will look forward to seeing everyone- told Val to get us a hotel room- have to go speak at a hiking conf in VA that same afternoon so will arrive win time for dinner Sat night- thank you!

  3. Thanks again Cindy. I’ve passed this along to Anne. I suspect she will share with her faculty. This entire week of at Penn State with StartUp type themes – we’ve heard over and over from many, many speakers, to live your passion. That the money will come – but it can’t matter first. You are a prime example. Thanks so much for sharing your time and your passion with Penn State students this week.

  4. Thanks again for a great essay (or should I say speech)! I was intrigued by this:

    ‘My daughter Sierra first enrolled in Journalism at Temple U and her professor told the students in the very first class, “I don’t know why you are here. Journalism is dead.”’

    My response: Journalism as that professor knows or may have knew it, is dead! But the reality is that It’s not dead! Just like everything, it has changed!

    I’m not much of writer, but I do read a lot. I only go C’s in my English classes in college. (I was a math/physics major) I don’t have the interest in being a writer. But I love to read.

    And of course as I tell everyone I know: . LIVE YOUR LIFE. DO SOMETHING!!!

    I’ve done more than my share and am continuing to do more. (heading out for a 12 day raft/hiking trip through the Grand Canyon a week from now).

    Again thanks for posting!

    P.S. I’m gonna re-read you AT book again! Need to get inspirited and hopefully get back on the AT next year for a section hike! I know it will bring back those memoires of when I was hiking parts of trail in southwest VA and Shenandoah when I was in college (Concord College ’72) and the trail in PA/NJ/NY when I lived in NJ. I am curious to see how the trail has changed.

    1. you MUST come see us Earl dear when you get close by and let me know ahead of time so we are home!!! have fun on the river- one of my dreams too! i used to drool over dories ion the canyon but think not now! too woosie! let me know how it goes

      1. I sure hope I can get back on the AT next year. I have many more sections to complete. I surely will stop in if I am in the area. I surely post some of my experiences from my GC raft trip when I return. It has been a big dream of mine to do the whole canyon and I am going to get it done! Keep on traveling! Later!

  5. Someone from the Women of the PCT facebook group posted this link saying it was about hiking as much as writing. I saw the name and thought, hmmn seems familiar. Your post helped me remember reading your book back when it came out. I hiked the PCT 30 years ago, back when you/I/we rarely saw anyone on the trail, and even more rare to see another woman! Great to read that you are still writing and successfully freelancing. I wrote a novel about my experience but did not follow up on the several big name publishers who were interested in it –I was going to “revise” it. Mostly I was scared. This year I’m on the CA PCT again–I hope to complete the PCT in 1987.

    1. hi there- thank you for writing- yep, still around doing my thing, having fun. Best of luck on the trail this year. Gotta do it while we can! Lots of good examples out there for us.

  6. Cindy, You are a writer! I have always envied your ability to capture the reader. Great inspirational essay. -Lila

    1. that’s my sweet friends , who I admire and respect so much- I will finally get to pay back you in this next book about raising and educating our kids- you guys are in it multiple times ! (building house too)!

  7. WOW. Thank you very much for sharing this article, Cindy. What an inspiration you are. I am thrilled that I stumbled across it by way of a fellow thruhiker’s Facebook post. I was highly criticized for taking time out of my “normal” life to attempt the AT or be part of a crew on a sailboat and other non-conventional decisions I’ve made over the last few years. I believe in everything you wrote here and really needed this reminder right NOW. As in, today! My life looks nothing like the lives of my peers from college. “DO SOMETHING” was on a post-it note on my bedroom door for the longest time. I also believe there are stories & paintings everywhere. You are amazing and I will be certain to follow this page now that I know it is here! I love it when I find exactly what I need exactly when I need it. That whole synchronicity thing. Thank you. Happy Trails.

    1. hey Cheryl- thank you very much for the affirmation message- the universe/God is working for you! it always feels goo d when that happens- check out my books – google Amazon- have a few new ones coming out- I am a Triple Crown author and will be traveling next year when my “Scraping Heaven- A Family’s Adventure Across the Continental Divide” about our family’s 3,100 mile traverse of the Rockies with llamas is brought back into print- where do you live? maybe I can get a speaking engagement nearby and meet.
      The new book I am working on is about alternatively raising and educating my children using the whole and natural world- lots of good stuff in there about following your own drumbeat in life.

  8. Your article is excellent. It gets to the point of life and fulfillment-do what you love. The Howard Thurman quote has been hanging on my fridge for years-in the hopes my children do this very thing!!

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