Funny Retirement Messages That Stay Kind

A funny retirement message does a useful job. It lets a room full of people who are a little sad laugh instead, and it tells the retiree they were liked, not just respected. The trouble is that retirement jokes drift easily toward age, health and being glad to see someone go, which is exactly where they stop being funny to the person they are aimed at.

The messages here stay on the safe side of that line. They joke about retirement, about work and about the rest of us being left behind, and never about the person’s age or body. They are sorted by how well you know the retiree, because the same joke that delights a close friend can fall flat coming from an acquaintance.

Four rules for a retirement joke

1. Joke about the situation, not the person. Alarm clocks, meetings, Mondays and the office coffee are all fair game.
2. Leave out age, health and money. None of them is as funny to the retiree as it is to the writer.
3. Do not say you are glad to be rid of them, unless they would say it first and louder.
4. Make yourself the loser. “What will we do without you” is always safer than “what will you do with yourself.”

A quick test: would you be comfortable reading it aloud with their family standing next to you? If yes, write it.

Safe for anyone

For a retiree you know a little, a senior colleague, or a card that the whole building will sign.

• Congratulations on your promotion to full-time weekend.
• May your only deadlines be dinner reservations.
• You have been upgraded to unlimited vacation.
• Welcome to the one job where nobody checks your timesheet.
• Your new performance target is zero.
• Enjoy the meeting-free lifestyle; the rest of us are jealous.
• I looked for your replacement and found that we need three.
• You are now free to ignore every email with a clear conscience.
• The parking spot is the only thing here that will not miss you.
• From now on, “I will get to it Monday” is optional.
• Your calendar has never looked better.
• Congratulations on graduating from work.
• May your coffee always be hot and never drunk standing up.
• You have officially run out of weekdays.
• Retirement: the only project you are allowed to finish late.
• Please accept this card in place of the forty reports you will no longer receive.

For a coworker you know well

You share a history, so you can joke about the work itself.

• Who is going to explain the filing system now? Asking for everyone.
• You are leaving just when I had finally learned to do things your way.
• I assume you have left instructions, because nobody else knows how any of this works.
• We have agreed to blame you for everything that goes wrong for at least a year.
• I will miss you every time the printer jams, which is to say constantly.
• You survived the open-plan office, and for that alone you deserve a medal.
• The break room gossip will suffer a loss it cannot recover from.
• Do not worry about us. We will only call when it is urgent, so most mornings.
• Your chair has already been claimed, and there was a fight.
• I have forwarded you all my problems as a parting gift.
• You taught me everything I know, so whatever happens next is technically your fault.
• The day shift will be both quieter and worse.
• Thank you for leaving before you could see what we do to your spreadsheet.
• We promise to keep your plant alive for at least a little while.
• I never did find out what you kept in that bottom drawer, and now I never will.
• You are abandoning us in our hour of need, also known as the busy season.
• I plan to tell the new hire that you were a legend, and they will have no way to check.

For a close friend at work

Here you can tease, because they will tease back.

• I am not crying, I am calculating how long until I can join you.
• You are leaving me here alone with these people. I will remember this.
• Do not post photographs before noon; some of us are still in meetings.
• I expect a full report on what daytime looks like.
• You always did know when to leave a party.
• Save me a chair wherever you end up. I am right behind you, give or take a decade.
• I hope you get bored enough to visit, but not so bored you come back.
• Without you here, my lunch break is just eating.
• You were my favorite distraction, and productivity is about to go up, sadly.
• First you take the good stapler, now this.
• I will be thinking of you every Monday, with mixed feelings.
• Who will I roll my eyes at across the table now?
• You are the only reason I knew what was going on around here.
• I have decided to take your retirement personally.
• Go on, then. Leave. See if I learn the new system without you.
• Promise me you will do nothing productive for at least a month.
• Text me from somewhere sunny so I can pretend to be happy for you.

Funny, then sincere

The strongest funny messages turn at the end. One joke, then one true sentence. The joke earns the laugh and the last line is the one they keep.

I have checked, and it turns out nobody else here knows how to do your job, including me.
That is the best compliment I can give a colleague. Thank you for everything, and enjoy it.

You are leaving us with a broken copier, a full inbox and no idea where the spare keys are.
You are also leaving us with everything you taught us. We will manage. We will miss you.

For messages that are sincere all the way through, see retirement wishes for a coworker; for one-line versions, what to write in a retirement card.

Jokes to retire

These turn up on every list, and each one has gone wrong at a party.

• Anything about being old. The retiree has heard them all and did not enjoy the first one.
• Anything about health or memory. You do not know what they or their family are dealing with.
• Anything about their partner dreading having them at home. It is a joke about someone who did not sign up for it.
• Anything about drinking the days away. Easy to write, uncomfortable to receive.
• “We thought you would never leave.” Only works between people who are certain of each other.

Where the joke goes, and where it does not

Humor belongs in the card, the toast and the slide show. It rarely belongs on the award. A plaque is read for years by people who were not at the party, and a line that got a laugh in the room can look odd on a wall. If the team wants one piece of each, give a funny card and a sincere plaque. Retirement plaque wording has a short section on light-hearted lines that do hold up, and retirement plaques covers the piece itself.

For a party where the whole team gets a joke award, work superlatives and funny award ideas have lists built on the same kind rules.

Frequently Asked Questions

What is a funny thing to write in a retirement card?

A joke about retirement itself is safest: no more alarms, meetings or Mondays. For example, “Congratulations on your promotion to full-time weekend.”

What retirement jokes should I avoid?

Jokes about age, health, memory, money, drinking, or a partner dreading having them home. Also avoid saying you are glad they are going unless you are very close.

Is it appropriate to be funny in a message to a retiring boss?

Usually, if the joke is gentle and about the situation. Follow it with a sincere line of thanks so the message reads as respect with a smile.

How do I make a funny message feel sincere too?

Use one joke and then one true sentence. The turn from funny to honest is what people remember and keep.

Should a retirement plaque be funny?

Rarely. A plaque stays on display for years and is read by people who were not there. Put the humor in the card and keep the plaque sincere.