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How to Make the Most of the Holidays If You’re a Freelancer

Being in business for yourself doesn't have to mean flying solo during the holidays

November 18, 2019

Feat image_holidays

It’s almost the holiday season. Work-wise, this means something entirely differently if you’re a full-time salaried worker versus a freelancer.

If you’re full-time and work in the creative industries, you probably have the annual holiday party to look forward to (if you love your coworkers, and the company knows how to throw a party) or dread (if you see your coworkers all the time and it’s one of those two-drink-tickets-per-person-everyone-home-by-9 p.m. affairs).

If it’s been a good year for the company, you might have a holiday bonus or even profit-sharing in your near future, which can more than offset the costs of holiday travel and gift giving. And chances are you’ll have extra time off too. If you work at a design firm or advertising agency, for instance, you might be looking at a paid vacation the entire week between Christmas and New Year’s. Depending on which day of the week those holidays land, this relatively new unofficial-but-assumed holiday time can mean nine, ten, even eleven days off while the checks keep rolling in.

Even day-to-day business as usual around the office is a little less usual come December. There are the holiday decorations, assorted baked goods on countertops, gift-shopping trips during lunch — maybe even an all-department game of White Elephant.

For freelancers, the holidays feel a little different. For starters, there’s no work-holiday party, unless you call realizing that the last job you’ll work this year just ended and sitting down for how-long-can-I go-without-more-work accounting a party. Plus, the only holiday bonus you’ll get is the one you mentally subtract from the rest of your income and give back to yourself.

And while you might very well have the same nine, ten, or eleven days off as your clients, there’s a chance it’ll be more like fifteen or twenty days. The holidays are a notoriously slow time for freelancers, and the days we’re not working are unpaid, making any travel or gift-giving a double whammy of outgoing cash without any coming in.

So, in the spirit of giving, here are a few ideas to make your holiday season a little brighter if you’re a fellow freelancer.

Spreading cheer

First, remember it’s better to give than to receive. Right about now is a perfect time to start thinking about who made your year a success. Which clients did you really enjoy working with, and who brought you projects or paychecks you’re thankful for? Or, put another way, which clients would you really like to work for again in 2020? What about collaborators or colleagues you had a fruitful partnership with or who referred you for the big three-month gig that was the difference between a good and an outstanding year?

If you’re a creative freelancer, why not extend some creativity to your gift-giving too?


Give those folks a gift! Sure, you can get them wine, whiskey, or a basket of fruit, but if you’re a creative freelancer, why not extend some creativity to your gift-giving too? For instance, if you’re sending gifts to out-of-town clients, give them a taste of unique, locally made offerings. (Bonus! You’ll also be boosting the local economy.) A curated box of local hot sauce like this one by Wieden + Kennedy director of creative operations Robin Rosenberg, artisanal socks (yes, I just wrote artisanal socks — it’s a thing), local chocolates infused with something else made local, and so on not only feels more personal, but it’s a way to support and promote the makers where you live.

And if you really want to go the extra mile, remember what every adult told you to do when you were a kid: Pair it with something homemade. Of course, you can make your own hot sauce, but unless you’ve got a secret recipe you’ve been honing for years, stick with your strengths.

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If you’re a designer, design something! A poster, card, or holiday zine. If you’re a writer, draft a card or an ode to great clients. If you’re a filmmaker, how about a moving image holiday card thanking all your best clients by name? And if you’re songwriter or composer? Time to record the holiday song to end all holiday songs. If you’re a photographer, put together a bound book of your best images from the year.

If I’m a client and I hired you back in February, I’ll be honest. I’m not expecting a gift. I may have even forgotten if we worked together in 2019 or the year before.

But if I get a gorgeous book of your photos, not only do I appreciate your thoughtfulness, you’ve also given me a portfolio that showcases your personal work just before the new year, when I might be gearing up to hire photographers. And If there are fancy socks in my package, you’re near the top of my hiring list in the new year — assuming you did a great job for me back in February, naturally.

Yes, it’s work to put these gifts together, but it’s a nice gesture and good for your freelance business moving forward. Clients tend to have new budgets and grand ambitions come January. Early December is a great time to get back on their radar and remind them you appreciate their support.

So, get your packages in the mail and aim to have them arrive before December 20, when folks start leaving early for skiing trips.

Charities need gifts too

Remember to give back to the nonprofits working to create the world you want to live in. There are so many organizations devoted to building a better world. Perhaps you’ve even helped some out pro bono or worked at a reduced rate, but we all know cash is what they need most.

So choose companies with values that align with your own and donate. Charitable giving is necessary now more than ever, feels good, and is . . . tax deductible! You can give throughout the year, but towards the end of the year, there are often incentives, like matching opportunities, where a major donor offers to match gifts up to a certain dollar amount. Here in Portland, one of the weekly papers selects worthy groups and coordinates with local shops and companies to give anyone who donates through the paper’s site a gift basket as thanks. Win, win, win!

Avoiding a blue, blue Christmas

That takes care of the giving part of the holidays, but there’s still the social side.

Freelancing can be inherently lonely. Even if you’re working around other people all day long, you still work for yourself and have to figure out the business aspects of your venture all on your own. Add the stress of obligatory holiday visits to see relatives and all the gifts to buy at a time when you’re potentially not making much money and, well . . . you need to fraternize with people who can relate to such worries.

The cure? Host a holiday party for your community of freelancers! If you love to entertain, invite your fellow directors, editors, or fellow designers over. If that’s not your bag, enlist a friend or two to help organize a party and hold it at a restaurant or bar. You’ll no doubt be invited to other holiday parties by friends, family, or clients, but this is your chance to bond, vent, and make plans to collaborate with likeminded folk.

It’ll probably be a blast and necessary — I bet you’ll want to get together with these folks more often. Maybe the holiday party becomes a monthly brunch, which becomes an even bigger holiday party next year.

Treat yo self

Finally, give yourself a gift. As a freelancer, you’re simultaneously the boss and the employee, not to mention accounts payable, IT support, and everything else a freelancer needs to run their own business.

Be a good boss and give the employee part of yourself a gift. You’ve worked hard. You’ve done good work. You’ve taken risks. You’ve probably made a few mistakes and learned from them.

Maybe the gift is a new toy that’ll lead to creative discoveries and expressions. Or maybe it’s a trip that’ll give you much needed downtime in the new year. Or, heck, maybe you invest in tax-deductible training or education like the Mt. Freelance course I co-created to help freelancers like you.

I know, I know — I couldn’t help a bit of self-promotion.

But the idea is to invest in yourself. You’re worth it. You can and should do everything you can to ensure you have a fantastic and profitable year ahead.

Andrew Dickson is a freelance copywriter who works for clients like Apple, Ikea, and Adidas. He likes freelancing so much he co-created Mt. Freelance, an online course and community designed to help creative freelancers freelance better. Before going out on his own, he spent seven years at Wieden+Kennedy Portland writing ads for brands like Old Spice and running the WK12 ad school. Before that, he was a freelance set dresser, performer, and eBay PowerSeller. Besides freelancing and writing about freelancing, he also performs regularly, hosting storytelling events for The Moth and auctioneering events for schools and nonprofits.
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