What NOT to Give Your Boss for Christmas, Hanukkah, Kwanzaa, Winter Solstice, etc.

What NOT to Get Your Boss for Christmas, Hanukkah, Kwanzaa, Winter Solstice, etc. Ready to Torpedo Your Career? Fire Away!

Ready to Torpedo Your Career? Fire Away!

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Ah, office holiday gift-giving: a heart-warming annual tradition fraught with awkwardness, anxiety, and overthinking.

If you’re lucky, you can bypass all the weirdness through an office-wide “Secret Santa” exercise or something. Just kidding! Those are full of weirdness too. I personally once received a bright blue “banana bunker” at an office white-elephant party.

Anyway, at some point you’ll have to decide what to get your boss for… whatever holiday you celebrate. Here are some landmines to avoid in the gift selection process.

The Expensive Gift

As a boss, I did NOT want my staff to buy me an expensive holiday present. Your boss knows if you live in a group house with six other people and “shop” for your family’s holiday gifts in the office swag pile. (Branded koozies for everyone this year!!) Please do not spend your hard-earned money on me.

Plus, no matter how classy the gift, there’s no way to make a high-dollar purchase look like anything but a blatant attempt at brown-nosing.

Without further ado, here are some expensive holiday presents that you should definitely NOT get your boss:

Black-and-white diamond cocktail ring, $3800

Black-and-white diamond cocktail ring, $3800

65-inch Ultra HD TV, $1100

65-inch Ultra HD TV, $1100

nternational Cheese of the Month Club, $340 for 6 months

International Cheese of the Month Club, $340 for 6 months







You are welcome to send them to your favorite blog author, however!

No? Moving on…

The Humorous Gift

I know, I know. You and your boss have the EXACT same sense of humor! You two are totally vibing! She is going to love this hilarious t-shirt you picked out for her!

Just no.

Even if, by some rare miracle, your boss does find it funny, you can be sure that someone, somewhere in your office will be offended. Especially if you pick one of these major no-nos:

My Food Poops on Your Food t-shirt, $17

My Food Poops on Your Food t-shirt, $17


See also: Zombies Eat Brains t-shirt, If You Jingle My Bells t-shirt





Have a Nice Day Coffee Mug, $10

Have a Nice Day Coffee Mug, $10


See also: Addicted to Pot mug, Show Me Your Kitties mug





This Meeting Is BS socks, $13

This Meeting Is BS socks, $13



See also: Carpe the F*** Out of This Diem socks, Kick This Day in Its Sunshiney A$$ socks

Who knew there were so many profanity-laced sock choices out there??



I’m Running Out of Options Here…

Yes, there are plenty of ways to go wrong when picking a holiday gift for the person who approves your paychecks. But, luckily for you, there’s a foolproof formula for the perfect present for your boss.

Part 1: Homemade Food

Your boss will be touched that you spent your precious non-working time on him, and you don’t have to be Laura Vitale to pull together a delicious plate of homemade holiday cheer. Sign up for my email list below to get my holiday “crack cookie” recipe, which is SUPER easy, and SO good that my coworkers demanded them every year!

You can stop here, if you like. But if you’d like to add something more to your boss’s gift, move on to:

Part 2 (optional): Beautiful Coffee-Table Book

Pick a gorgeously photographed/illustrated book related to the work you do together. Write a brief note of appreciation inside, wrap it up, and you’re done! Here are some ideas:

Destinations of a Lifetime: 225 of the World's Most Amazing Places, $27

Destinations of a Lifetime: 225 of the World’s Most Amazing Places, $27

1000 Record Covers, $16

1000 Record Covers, $16

Building Chicago: The Architectural Masterworks, $55

Building Chicago: The Architectural Masterworks, $55







Bonus Tip: Give New Year’s Presents!

Avoid awkwardness when you and your boss may not celebrate the same year-end religious/cultural holidays by making your present a New Year’s gift.

Happy New Year, everyone!

What was your most (or least) successful office holiday gift? What are you getting your boss this year? Share in the comments!

*Note: This post contains affiliate links. If you click on one of my affiliate links and make a purchase, I receive a commission for referring you. This comes at no extra cost to you. I’m grateful for your support!


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Want more holiday shopping help?

The Brainy Business Babe Feel-Good Gift Guide, Part 1


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