When is Boss’s Day and the Best Ways for You to Celebrate in 2019

What is Boss’s Day?

A day that has been set aside to show our bosses a little love. Nobody wants to be the person making the hard decisions and nobody wants to be the bad guy, but sometimes someone has to fire people and take one for the team. Those responsibilities often fall on the boss’s shoulders. Bosses are villainized in movies and on tv shows. Sure some of them aren’t great (or are even terrible), but most of us have good bosses who are doing a hard job. With that in mind, let’s be sure to take (at least) one day a year to remind them that we know what they’re doing is difficult. 

A woman wearing a green sweater is standing, holding a white mug that has the words "Like a Boss" on the side

So, when is Boss’s Day?

Boss’s Day is Wednesday, October 16th. Are you ready? Have no fear, we’re here to help get your mind buzzing with ideas.

How to Celebrate:

Whether you’re looking for a last-minute gift or are planning ahead, we’ve put together a list of the best ways to show your boss how much you appreciate them and all they do. 
The more you can get the whole team’s involvement, the better. So keep in mind that when we say a card we mean a card that everyone has signed, not just one that you pick up on the way to work the morning of.

That morning, have their favorite coffee (or tea) drink sitting on their desk along with a small treat (like a pastry or box of chocolates) and a card. (Again, ideally you’ll get everyone to sign the card to make it more meaningful.)

Two cupcakes and a mug of coffee are sitting on a desk, along with reading material, a plate, a fork and knife, and a pair of glasses.

A fruit arrangement, a plant / flowers, or a goody basket designed around something they love. There are many stores that have pre-made baskets to choose from and ones that you can customize.

A gift that the team pools together on, such as gift cards (which are nice but certainly less personal that other options), an espresso machine, tickets to a show, game or concert, or even a personalized gift such as a desk name plate, cufflinks, a watch, laptop bag or purse, wallet, or more.

A present simply wrapped in plain brown gift paper is tied up neatly and prettily with a red ribbon

A video in which everyone is recorded thanking, sharing a memory, or telling a favorite story involving the boss. This one will definitely require more work than the other ideas mentioned here, but it would be a particularly sweet gift for a boss who has announced they’ll be retiring or leaving the company soon.

Have everyone write on a slip of paper (bonus points if you choose something a little more festive than plain white printer paper) a thanks, memory with, or inspirational quote for the boss. Collect all of these memories and place them inside a new (and fun) mug. Or clip them to pretty thread and string them along the walls of their office as a Boss’s Day decoration! This is a much simpler, and easier to execute, version of the video idea above but is no less sweet. It’s also a great idea to pair with a treat or coffee bundle!

A hand is holding up a white notecard against a plain wall - the index card reads "a rising tide lifts all boats"

A subscription box, whether it is to a coffee club, wine, snacks, crafts, or books. Choose something they love and it’ll be a gift they can enjoy for months to come.

A quick surprise party, complete with treats and small decorations. If this isn’t feasible, may we also recommend something like a potluck style lunch for the whole office where you all present your boss with a card and/or gift?

Cookie bar desserts are displayed on a neutral speckled plate. The treats have a thick layer of white icing and are decorated with rainbow sprinkles

This Boss’s Day grab an idea, shape it into your own, and let your boss know what you really think of ’em.

-Apple Pie Painting