National Boss’s Day rolls around every year on October 16, and every time it does, people fall into two camps. Camp One: The “I actually like my boss and want to do something thoughtful.” Camp Two: The “my boss once emailed me at 11 PM asking if I saw his earlier email from 10:58 PM.”

Wherever you land, one thing is true. A good boss can change the entire trajectory of your work life. They can open doors, cheer you on, protect you from chaos, or if they are the wrong kind of boss make you daydream about winning the lottery just so you can resign in poetic fashion.

But let’s assume we are celebrating the good ones today. The mentors. The encouragers. The franchise owners leading small teams. The corporate leaders trying to keep everyone sane. The managers figuring it out one Zoom call at a time.

This article is your simple, not-too-corny guide on how to make National Boss’s Day meaningful without being awkward, cheesy, or forced.

So… where did National Boss’s Day even come from?

Fun fact. National Boss’s Day was created in 1958 by a secretary named Patricia Bays Haroski, who plot twist worked for her father at State Farm Insurance. She thought bosses had a rough gig. Employees got appreciation days. Teachers got appreciation days. Mothers and fathers got appreciation days. Why not the people who carry the financial anxiety of keeping the company alive? Fair point.

She registered the holiday with the U.S. Chamber of Commerce. It became nationally recognized in 1979. And despite jokes about it being invented by HR departments, it stuck.

Do bosses actually want to be celebrated?

I’ll be honest. Depends on the boss.

Some secretly love recognition but pretend they do not. Some pretend to love it but immediately throw your gift card into a drawer next to expired coupons. Some get visibly uncomfortable when thanked in public. Others will cry if you hand them a handwritten note.

But after talking to a few managers I know, one thing came through clearly.

“I don’t want expensive gifts. I just want to know my team sees me trying.”

That right there is the key.

What makes a good Boss's Day gesture?

Forget generic balloons and last-minute cupcakes from the grocery store. If you want to make it count, focus on three things:

1. Authenticity over perfection
   A simple handwritten note > A corporate-looking Hallmark card that sounds like it was written by a legal team.
2. Specific over vague
   “Thanks for everything” is fine. “Thanks for backing me up when that client went off-script on the call last week” is unforgettable.
3. Shared appreciation over awkward spotlighting
   Instead of singing “For He’s a Jolly Good Fellow” in the conference room at 8 AM (please don’t), try a team message thread where everyone drops a quick one-liner about something they appreciate.

Practical (Non-Cringe) Ideas to Celebrate National Boss’s Day

Here’s a menu. Pick one. No pressure.

• The Collective Card with Personality
  Pass around a physical or digital card and let everyone write something real. Not “You rock” (unless they really do rock). Something like “You didn’t fire me when I accidentally replied-all to the entire company. You’re a hero.”
• Desk Upgrade Survival Kit
  Coffee lovers? Get them high-quality beans. Desk always a mess? A cable organizer. They snack all day? Build them a “Boss Fuel Basket.”
• Nominate Them for a Local or Industry Recognition
  If your company or franchise network offers awards, submit them. Bosses rarely nominate themselves. It hits hard when someone else does.
• A Team Lunch They Do Not Have to Plan
  Key rule. They are not allowed to organize it or do the fake “Whatever you want is fine” thing. You pick. You schedule. They simply show up.
• Video Message Compilation
  Short clips of team members saying specific thank-you. Canva or CapCut can handle the editing if you want to score extra brownie points.

What if your boss is not great… or you barely know them?

Okay. Real talk. Some bosses are harder to celebrate. Maybe they are distant. Maybe they are overwhelmed. Maybe you have no idea what they even do. In that case, play it safe.

• A polite email or message like:
  “Happy Boss’s Day! Appreciate all your leadership and support across the team this year.”
• Or skip it entirely. Honestly, no one is forcing anything.

This holiday is about genuine gratitude, not forced enthusiasm.

For Franchise Owners and Small Business Leaders

Let’s shift focus for a moment. If you are the boss or you run a franchise or small team, you might be thinking:

“Wait, am I supposed to celebrate myself?”

Absolutely not. But you can flip the holiday into something meaningful:

• Thank your team instead
  Send them a message saying, “Boss’s Day is cool and all, but let’s be honest, this place runs because of you.” Instant respect.
• Host a “Team Wins Day” instead of “Boss Day”
  Nobody hates a pizza party when it’s not weirdly self-congratulatory.

Final Thought: Leadership is Lonely. Gratitude Makes It Less So.

Here’s something most people don’t know unless they have been in management.

Leaders get less feedback than everyone else. When you’re at the top of the org chart, your wins are assumed, but your mistakes are magnified. A single sentence of encouragement can power someone through a long month of stressful decisions.

National Boss’s Day is not about brown-nosing. It is not about pretending your workplace is perfect. It is simply a chance to acknowledge that good leadership is hard and kindness is free.

So go ahead. Write the note. Buy the coffee. Tell your boss that one thing they did this year that mattered.

Even if they blush awkwardly, trust me. They will remember.

Happy National Boss’s Day to every leader trying their best even on days when they feel like they are winging it.