National Boss Day: How to Celebrate Your Boss Like a Boss

At some point in October, you might be planning the perfect Halloween costume and stocking up on all the best sweets. But don't forget the other big autumnal holiday: National Boss Day, celebrated annually on or around October 16. This holiday was officially proclaimed in 1958. Reportedly, National Boss Day began with 1 State Farm insurance company employee in Deerfield, Illinois. Now it is celebrated by workplaces nationwide. Will yours be among them this year? If so, you don't have to give the same tired gifts that employees gave more than half a century ago. Want to ditch the fountain pens and coffee mugs and modernize your gifting options? We've come up with a list of top things you can do to show your boss appreciation while bringing your gift giving into the 21st century.

Top ways to celebrate your boss on National Boss Day

You have a great boss, and you're lucky. (Some people work with a bad boss.) So, what can you do? Here are some top-notch ideas for showing appreciation.

1. Share a meal. As in most areas of life, when celebrating your boss, you can hardly go wrong with food. Have employees each bring something for a potluck lunch, a power breakfast, or a home-baked snack. You might even take your boss out for a group happy hour or dinner after work. Enjoying a delicious meal allows your team to participate and bond. It will also make great bosses feel appreciated.
2. Decorate the workspace. Sneak into the boss's office (you might need some admin help) and decorate it for National Boss's Day. Streamers, balloons, and jars of treats on the desk are a nice little surprise and a wonderful way to start the day.
3. Handwrite a note. Telling your boss you're grateful for the leadership with a handwritten note is a classic way to show you care. Try to be as specific as possible. "You're a great boss!" doesn't always sound genuine. Instead, thank your boss for a time when you were helped out of a bind. Or maybe comment on a unique leadership style that you find effective.
4. Give a Boss Day card. If a handwritten note isn't your style, there's a card for that. A Boss Day card will be just as effective. (It might also make all the other bosses jealous.)
5. Throw a surprise party. Get together with your coworkers and plan a surprise party for the end of the day. It's a fun way to express your gratitude. Have the admin schedule a meeting, or some other diversion, for your boss for the last hour of the day. Then spring a surprise celebration in that location. You can even feature a theme. For example, honoring "The Boss" with a Bruce Springsteen-themed party. Play his music, and have all the employees wear jeans with bandanas sticking out the back pockets. Hang a sign reading, " Was 'Born to Run' This Team!" You get the idea.
6. Run it up the ladder. Unless your boss is the company's CEO, chances are they have a boss too. Email that superior or human resources to say what a great leader your boss is. And be specific about how so.
7. Buy tickets to an event. Have all the employees chip in to buy your boss tickets to an event you know they'd enjoy. Perhaps theater tickets, a sports game, or a concert. The gift of a special experience can be relived again and again in memory.
8. Make a donation. Find a cause your boss is passionate about and donate in their name. This shows that you pay attention to what's important. It also allows you all to help others, which makes everyone feel good.
9. Give gift certificates. As with food, you probably can't go wrong with gift cards or certificates. But instead of sticking with the typical coffee shop gift card, try to find something more personal. For example, get a gift certificate from that restaurant your boss has been dying to try but hasn't gotten to yet. Or how about that fro-yo place down the street where they go on break? This way, you give something useful while demonstrating attentiveness.
10. Bring "life" to the office. Give your boss something living for the workspace. No, you probably shouldn't buy your boss a puppy. But you can add a little spice to the space by buying a succulent, a miniature terrarium, or a small desk plant. This is something nice to look at and care for that requires minimal effort.
11. Support your boss's hobbies. Contributing to your boss's enjoyment of a hobby or interest keeps the gift personal without being inappropriate. For example, for a hiker, you can get a book on the best trails in the country. Maybe the passion is for yogi; get a new yoga mat. If you're unsure what your boss likes to do outside of work, get something that's useful on the job. For example, if your boss travels, consider a "survival pack" with sleeping mask, earplugs, and a guide to tipping policies abroad. These items will mean more to them than a fountain pen or paperweight, being both personal and practical.

Ultimately, your Boss's Day gift shouldn't be an exercise in sucking up. If your boss has genuinely been a great asset to you, your work, and your career, take the time to do something personal. Let the boss know you appreciate them. If you aren't that close to your boss, consider going in for a group gift.

Self-employed? Treat yourself!

If you're self-employed, you are your boss. Don't think that Boss's Day is not for you. Turn National Boss Day into a treat-yourself day. Go out to lunch, splurge on a special coffee drink, and reflect on all the good things you do. Because you don't work with other employees, do something nice for yourself on this day. If you'd like company, extend an invitation to a favorite client or customer who makes running a business a pleasure.

When you're the boss, spread the thanks

If you are the head honcho, even though the day may be about you, be sure to make it about your employees, too. It's important to appreciate their work (and their thanks), so return the favor whenever possible. Most importantly, everyone should have fun with this national holiday. Make it about team accomplishments and what good bosses bring to the table. Highlight your boss's uniqueness, and keep this special day fresh and positive to celebrate like a boss. Learn and do more with ongoing news, tips, tools, and resources for HR and business management from TriNet.