My favorite anchor client is a dream to work with. They promptly pay me a monthly fee, which made up more than half my earnings in 2020.

This steady cash flow certainly helps take the edge off occasional dry spells and keeps me afloat when unforeseen personal situations arise. So to show my appreciation last year, I contemplated sending this top client a holiday gift.

However, my heartfelt gesture quickly turned into a stressful endeavor. After all, I’d never done this before. Should I buy or make something? If I send food, do they have any allergies? Is this even appropriate?

In the end, I didn’t send anything but a season’s greeting and a silent vow to be better prepared next time.

Still, my indecisiveness got me thinking. To see what others were doing, I queried four fellow freelancers from various content verticals about the dos and don’ts of sending holiday gifts to clients.

To gift or not to gift

Michelle Seitzer, a health writer and founder of Caregiving Advice, a content hub for caregivers, believes the art of gift-giving is all about building bonds with her most treasured clients. “Rapport is vital to me, so I’m intentional in the way I develop that with a client—especially if it’s one I work with often,” she said. “As I build relationships through friendly interactions while maintaining professionalism, I’m able to get a sense of what a meaningful gift would be.”

“I enjoy gift-giving in general,” she added. “Choosing something unique, meaningful, and that really makes a client happy makes me happy, too.”

“Choosing something unique, meaningful, and that really makes a client happy makes me happy, too.”

On the flip side, freelance screenwriter and translator Alexis Plossignac thinks it’s not a good idea to give clients gifts at all. “I wouldn’t want my client to feel obligated to reciprocate,” he explained. “I’d rather show my cherished clients gratitude for their continued collaboration by doing my best to be a consummate professional.”

Opt for originality

For those who do opt to give gifts, the question turns to what’s appropriate—and where to send something. Most freelancers work remotely, and it can be challenging to spread holiday cheer without the office Secret Santa to fall back on.

So, some freelancers get creative.

Writer, editor, and content marketer Wendy Ramunno said she tries to send thoughtful gifts to her star clients. “I personalize my gifts somewhat—like a gift card for an independent bookstore or restaurant in [a client’s] city,” she said.

Adding a personal touch is often better than sending something expensive but generic. “I’ve heard of fruit baskets sitting uneaten and attracting fruit flies in offices… that doesn’t leave a great impression,” Ramunno said.

Seitzer agreed that it’s best to send something personal whenever possible. In one case, she’d been working with a client for nearly a decade, which made giving a meaningful gift much easier. “I knew she loved Dunkin’ Donuts, so a gift card there wasn’t random; it was something I knew she would use,” she said.

How much should freelancers spend on client gifts?

Although the IRS limits the amount of client gift write-offs to $25 per person, freelancers tend to be more concerned with sentiment over cost. As a general rule of thumb, Seitzer gives cards to smaller clients and gifts to those that provide the majority of her freelance work. “For me, it’s more about the quality of the gift than the amount, and also what my budget is for gifts that year,” she said.

“It’s more about the quality of the gift than the amount [I spend].”

For Ramunno, what she spends depends on factors like how close she is to her clients and how much work she does for them. “I typically send most clients similar gifts, but this year, I’m thinking of sending a bigger (read: more expensive) item to an old friend who ended up getting me a ton of work at her company,” she said. “I really appreciated the referral.”

Jennifer Billock, a journalist and author whose book “Historic Chicago Bakeries” was published last September, treats all her clients equally, regardless of pay rates or relationship history. “I’ve only ever sent holiday cards to clients, and although I reserve the nicer or funnier cards for big clients, all of them are personalized,” she said. “I think it’s important to show [every client] they aren’t just another step on my ladder.”

Remote work makes sending gifts more challenging

According to statistics gathered by DDIY, a small business consultancy site, freelancers will make up the majority (50.9 percent) of the U.S. workforce by 2027. Of those currently freelancing, 86 percent work from home. This likely means in the future, most business interactions will be virtual. It may become more challenging to build relationships with clients, let alone decipher if and how to send gifts.

“Always striving to do great work may very well be the best gift of all.”

Ramunno has figured out a way to continue to give seasonal gifts despite the logistical complications. “Before the pandemic, if I knew the client well enough, I would send food or booze to the office,” she said, “Now that most people are working from home, I’ll send e-gift cards since I don’t want to have to ask for their personal address.”

Billock, on the other hand, stopped sending cards when remote work became the norm. “People loved them, but once everyone started working from home, it was too difficult to track down addresses,” she explained. “I’d do it again if I could easily figure out where to send them.”

And while Plossignac’s holiday gifting veto may make him the Scrooge in this group, he does echo one sentiment most dutiful freelancers feel: “Always striving to do great work so my clients look good in the eyes of their customers may very well be the best gift of all.”

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Author: Jessica Benavides Canepa