Writing Inspiration: What’s Your Best Holiday Gig as a Freelancer?

Evan Jensen

Writing Inspiration During the Holidays. Makealivingwriting.comNeed some writing inspiration during the holidays?

It’s a crazy time of year for a lot of freelance writers.

You’re hustling to work ahead. You’re thinking about how to move up and earn more in 2020. Maybe you’re feeling a little worn out since the holiday march began last month.

Sound familiar? How about a little writing inspiration to give you a boost during the holidays?

Believe it or not, you can still connect with clients and prospects during the holidays, land assignments, get paid well, and enjoy your work.

It happens all the time. Editors respond to queries and pitches during the holidays. A client asks for a rush job and pays extra. Or by taking some time off, your mind works out a smart way to earn more.

What’s your best or most unusual gig as a freelance writer during the holidays?

Here’s a little writing inspiration, a few laughs, and reminders of what’s possible. Grab a cup of coffee or hot chocolate and enjoy…

The business of being a freelance writer during the holidays

What’s your best story about freelancing during the holidays?

First, the non-writing related stories…

  • Sample the candy. Freelance writer Mary Rosewood once sampled everything See’s Candy sells during the holidays.
  • Wake up…Happy New Year! When writer Diane Helentjaris was a medical intern, she walked through the pediatrics unit with the chief medical officer and woke up all the kids to wish them a Happy New Year.
  • Miser or merry? Journalist Melinda Rizzo once received advance tickets to see a local theater performance of A Christmas Carol, which included a memorable scene with the Ghost of Jacob Marley rising up from a trap door in the floor of that stage.
  • Chanukah kickoff. And then there’s kicking off the first night of the holidays with a Chanukah parody video, recommended by Carol Tice.

We also heard from freelance writers about landing assignments, getting ahead, and making extra money during the holidays…

Holiday hustle pays off with $1,500 assignment

Holiday Writing Inspiration: Carol Tice

Carol Tice

Carol Tice carved out a niche as a business reporter when she worked for the Puget Sound Business Journal. It paved the way to help her create Make a Living Writing, and land freelance assignments like this one during the holidays.

“I used to write for a Nation’s Restaurant News special section that comes out mid-January, where you had to talk to restaurant owners during one of their busiest seasons,” says Tice. “But it was a fairly reliable $1,500 or so to start the year!”


‘Bah humbug’ Upwork: It’s time for better-paying freelance work

Holiday Writing Inspiration: Beth Casey

Beth Casey

What if you were getting paid a pittance and working yourself to the bone during the holidays like the Charles Dickens Jacob Marley?

That’s where freelance writer Beth Casey found herself during the holidays a year ago, and it wasn’t pretty. At first, it was 500-word articles for a dollar. She moved up to getting paid $50 to $75.

And then she gave herself a gift that will change everything.

“I stopped searching for jobs on Upwork this year,” says Casey. “I’m currently finishing out the last two contracts and then I’m outta there!”

Now she’s writing for clients on ClearVoice, earning $110 to $300 per assignment, and a steady stream of work.

“This is one more step in the right direction for me.,” says Casey. “I know it’ll only get better from here.”

The $20,000 holiday-rush assignment

Holiday Writing Inspiration: Maddie Osman

Maddie Osman

“I got a $20,000 SEO content writing project for an education nonprofit a couple years ago,” says freelance writer Maddie Osman. “I had three months to use up that budget to produce the long-form content deliverables they hired me for.”

The challenge? This time frame encompassed every major winter holiday…Thanksgiving, Christmas, and New Year’s.

What would you do with an assignment like that during the holidays? Osman worked like crazy to get the work done, in between celebrating the holidays.

“Those months involved some of my longest work days as a freelancer,” says Osman. “But I made it my mission to make this client happy with their decision to work with me and executed the full contract by the first few days of January.”

Long-term marketing efforts make the holidays merry

Writing Inspiration: Lori DeMilto

Lori DeMilto

A few days after Thanksgiving, Lori DeMilto got one of those unexpected emails.

It was from an editor she pitched about a year ago. No response…nothing…until now.

The editor asked DeMilto to write four articles about health-related topics for consumers. The perfect niche assignment. DeMilto delivered, landed more work and a long-term client.

If you want to give yourself a gift as a freelance writer, keep marketing, follow up, and leverage online search and networking opportunities.

“More clients will hire you, if you develop a client-focused LinkedIn profile and website, build a strong network, and do outreach to clients throughout the year,” says DeMilto.

The chill-out freelance assignment for Make a Living Writing

Holiday Writing Inspiration: Maria Veres

Maria Veres

“One of my most unusual and memorable holiday freelance stories involved a piece for Make a Living Writing,” says freelancer Maria Veres.

Here’s the scoop. One late December, she went to the library to work so her family wouldn’t bug her.

The task: Verify 150+ links in a monster list of writing jobs. It took longer than she thought.

“By the time I left, it was pitch dark and there was ice on my car,” says Veres. “Northerners can laugh all they want, but Oklahoma is the land of winter weather wimps. And I’m the queen wimp.”

After shivering and panicking for awhile, Veres realized two things:

  1. There was nothing falling from the sky anymore, and the ground wasn’t even very slippery.
  2. There was at least a 50 percent chance she would make it home alive.

Unprepared for icy conditions, Veres used her credit card, a pocket comb, and her car keys to try and clear the windshield.

“I made the drive home without any slipping or sliding,” says Veres. “And I survived to turn in my article on time.”

Feast on freelance success during the holidays

Writing Inspiration: Kaitlin Morrison

Kaitlin Morrison

Just about every freelance writer has a family member or friend who raises an eyebrow at writing for a living. Right?

It can come up in conversation during the holidays. One Thanksgiving, Kaitlin Morrison served up a little freelance success at the dinner table. Here’s what happened:

First, she replied to a post from the Junk-Free Job Board inside the Freelance Writers Den. She landed an assignment to write a blog post, along with $100 worth of desserts including a cheesecake, chocolates, for photos to go with the post.

“After the project, I served the food at my Thanksgiving,” says Morrison. “And it helped to finally convince the family that I was a real freelance writer.”

Celebrate the freelance life

If you’re new to freelance writing or you’ve been at it for years, the holidays can be a great time to celebrate your wins, land some well-paying work, and refocus your efforts to move up and earn more. The secret to success is simple…Keep going. Happy holidays!

What’s your best gig as a writer during the holidays? Share in the comments below.

Evan Jensen is the blog editor for Make a Living Writing. When he’s not on a writing deadline or catching up on emails, he’s training to run another 100-mile ultra-marathon.

300+ Hours of Trainings. One Affordable Price. Freelancewritersden.com


  1. Michelle Kaplan

    Love it! Just the boost I need to start over in 2020! Thanks, Carol!

    • Carol Tice

      You’re welcome! See you ’round the 2X Grads’ Slack. 😉

  2. Tracey Stepanchuk

    For the past 7 years I graded MBA student assignments for a university in the Netherlands over the holidays. It was easy work that earned me around $5k to $7k each time. Now they have restructured and no longer need the grading help, so I’m getting a break for the first time in many years. I’m missing the easy work and could use a bit more income over this period, but I don’t want to spend the holidays writing so I’m focusing on my marketing for next year instead.

    • Carol Tice

      Love it, Tracey!

  3. Glenn Eidson

    I am just excited to get started at something I am comfortable doing. I am glad I found you and your site. Looking forward to a long relationship.

    • Carol Tice

      Me too, Glenn!

  4. Wendy Meyeroff

    I’m more of a writer then an editing person. I mean true editing, not acting as a magazine editor or developmental book editor. I know AP style, but the APA (for psychological association) hadn’t handled 4 yrs. But last week of Xmas last year, suddenly get a call for supposedly a 3-hr review of someone’s case study with tables, et al.

    I started and did a few more than three hours, then contacted client. Told her this was a true mess (said it more politely!), showed her the before and my after. She realized it would indeed need more than 3 hrs. I asked her how many hours would be her limit? “As many as it takes,” she replied. “What if it’s 40 hrs?” I said sort of jokingly. “Whatever it takes,” her email emphasized. Well, it took 40 hrs and so I brought home about $1500 instead of $100!

    • Carol Tice

      Love it, Wendy! For years, I used to earn about $1500 around the holidays, writing for a trade magazine’s annual special section. Their staffers of course wanted the time off, so if you were willing to try to buttonhole restaurant owners during one of their busy times for interviews, you could earn nicely. That was like my Christmas bonus for years!

  5. Allen Taylor

    These are all great stories.

    Heading into December this year, I wondered where my next assignment was coming from after my largest client–a $1,200/month residual client who’d been with me for four years–decided he needed my services no longer. Then, last week, I closed a $5,000 white paper on the state of private lending and a $10,000 book editing gig. On top of that, the white paper client, for whom I write several blog posts each month, wants to double up the blog post production. Then, two days ago I closed a $3,000 gig to write summaries for several white papers for an international telecom association.

    I’m definitely working through the holidays, and put in two hours yesterday morning. It’s been a very merry Christmas. And I’m looking forward to the new year.

    • Carol Tice

      Loooove this story Allen! I’m hearing from many 2X coaching students about taking meetings or getting multiple pitch responses in this holiday week. #keeppitching

      And hey — come back to your 2X grads group for support, we miss you!

Submit a Comment

Your email address will not be published.

Related Posts

You CAN Write a Query Letter That Gets a “Yes”: 5 Resources

Freelance writer getting a gig after learning to write a query letter.

Love them or hate them, queries are one of the most important marketing tools for any freelancer who wants to write for magazines. And the skills you learn from writing a good query letter also help business writers and copywriters pitch their potential clients.

If you’ve been sending queries off into space and never getting a reply, you may think it’s impossible to break into new magazines. But it’s not true! Editors are always looking for new talent.

To help you learn to write a query letter that will get you the gig, we’ve pulled together a collection of five of our best posts on pitching:

Can’t Write? Try These 9 Ideas for Writing Motivation

It’s the bane of every freelance writer’s life: You know you need to sit yourself down and get some writing done, but nothing happens. The writing motivation just isn’t there. Sometimes, you can't even make yourself sit down with the computer -- even if you...