Ali + Julie
Co-Founders, GroupTogether.
Life’s busy. That’s why we’re here to make it easy for you to collect money from a group. Less wasted time, less packaging waste, and spending a little less but giving a lot better!
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Boss’s Day is coming up, and whether you adore your boss (or just want to stay in their good books), we’ve got you. From the when to the what to the what-on-earth-do-I-write-in-this-card panic, consider this your no-stress guide.
By Ali + Julie
September 28, 2025
Boss’s Day 2025 falls on Thursday, October 16.
Mark it in your calendar, set a reminder, tie a string around your finger...whatever works.
Technically, it’s Boss’s Day - apostrophe, double “s,” because we’re honouring your boss (not just any old boss). But don’t stress, “Boss Day” still works - celebration over perfection, right?
You don’t have to hire a marching band (but hey, that’d be memorable). Here are a few fun, thoughtful ways to celebrate:
Organise a group card that the whole team can sign online:
Choose a Boss's Day card from GroupTogether, then share a link with the team. Everyone can leave a personal message (hopefully not too personal), a fun GIF or photo, heartfelt notes, inside jokes, etc. You can print or send digitally. It’s super easy and the most appreciated thing!
Bring treats:
Coffee run, breakfast bagels or cake in the break room...food is the universal love language.
Plan a mini-celebration:
Even a 15-minute team huddle with a toast can go a long way.
Give a gift:
Big or small, thoughtful over expensive every time. If you're creating a group card with GroupTogether, there’s also an option to let everyone chip in some money for a gift. Withdraw it or choose from eGift Cards, hampers, flowers & more.
If you're after more ideas, here's 12 ways to make your boss feel appreciated on Boss's Day.
You know them best - are they the “tickets to a game” type, or more of a “please-just-give-me-wine” type?
Check out our roundup of 20 gift ideas your boss will actually like, but here’s a teaser list:
Need something to write in the card? Cue the what-do-I-say panic. Don’t worry, we’ve got you covered.
By the way, if you go down the GroupTogether group card route, there’s a built-in AI message writer to help you write exactly what you mean to say, but better. We even have an option to write it “in the style of” e.g. Shakespeare, Dr Seuss, Donald Trump or just something professional and nice. Whether you’re a word smith or tongue-tied, it helps a lot!
Here are some amazing boss quotes and ideas for your message for Boss’s Day:
Celebrating doesn’t have to cost a fortune. Thoughtfulness beats dollars every time:
Small gestures can make a big impact - it’s about appreciation, not extravagance.
Short answer: nope. There’s no HR law saying you must celebrate. But if your boss is supportive and you genuinely appreciate them, it’s a nice moment to say “thanks.”
Celebrating Boss’s Day can also be good for morale. It reminds everyone that leadership is noticed and appreciated. If your workplace culture doesn’t do gifts, even a quick Boss's Day card from the team or group Slack message can be enough.
Ali + Julie
Co-Founders, GroupTogether.
Life’s busy. That’s why we’re here to make it easy for you to collect money from a group. Less wasted time, less packaging waste, and spending a little less but giving a lot better!
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Cool! You can create a Group Card. You just can’t do collections or eGift Cards.
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