All Play and No Work: 30 Funny Retirement Wishes

Retirement is a solemn affair that should always be treated with the utmost sensitivity. Just kidding! Retirement can bring out mixed emotions, but in general, it’s a joyous milestone in a person’s life. After decades of clocking in and operating according to someone else’s schedule, the lucky retiree finally gets to call the shots – and that’s an occasion worth celebrating.

It’s also an occasion that calls for some levity. If you know someone who’s retiring – whether it’s a friend or coworker – one of the best ways to send them off is with a joke. To help you come up with the right words, here’s a list of funny retirement wishes that will leave them laughing when they go.

For a Friend

To start, here are some funny retirement messages you can send to friends.

Retirement is when you stop kissing the boss’s ass and invite him to kiss yours goodbye.

I heard you lost your job and have no plans of ever finding it again. Happy Retirement!
When “I’m too old for this shit” becomes your daily mantra, you know it’s time to retire. Hope you enjoy all the adventures you have ahead of you.
Can you say Senior Discount? Hope you enjoy all the perks of retirement.
Enjoy your permanent weekend.

Prepare yourself for years of hearing: “You look too young to be retired!”
Now it’s time to stop fawning over your boss and start fawning over your grandkids.
Enjoy your new job doing nothing. I know you’re well qualified for it.
You can’t teach an old dog new tricks, but you can put new tires on an old car. That’s why they call it re-tirement.

Now your only job is having fun – and I know you’re a real pro at that.
Retirement doesn’t make you an old fart, but it does mean you no longer give a shit.

Now is the time to throw professionalism out the window once and for all.
Your retirement brings out a lot of emotions in me, but I’d have to say the biggest one is envy.

Uh oh. Someone’s about to have too much free time on [his/her] hands.
I hate to tell you, but the Honey Do List gets a lot longer when you’re retired.
Now that you’re retired, you can start enjoy Mondays again. Of course, you probably won’t even know what day of the week it is anymore.
Now that you’re retiring, you can slack off all day. Just like when you had a job, except you don’t have to worry about getting in trouble for it.

For a Colleague

Here are some hilarious messages for a retiring coworker.

Just wanted to say Happy Retirement. Also, please take me with you!

Without you around, I’ll never be able to stay awake for status meetings.
Your retirement will leave an empty space in our hearts, not to mention the break room fridge.
My job is going to be a lot harder without you around. Fortunately you’re not busy anymore, so I can call you any time, day or night, with questions.

Congrats on making it out of this place without a security escort.
This place won’t be the same without you. In case you’re wondering, that’s a compliment.
You might want to change your number. Once management realizes everything you did here, they’ll be begging you to come back.
I’m losing you as a coworker, but I better be keeping you as a lunch buddy.

For a Boss

Finally, here are some funny retirement wishes for a boss.

Your days of herding cats are finally over. Happy Retirement!

Now that you’re retiring, I can tell you how I really feel about you. And how I really feel is, you’re awesome. Best wishes!
Happy Retirement to an amazing boss. I hope you appreciate how lucky you are that you no longer have to deal with me.
Do you think you could give me a raise on your way out the door? 🙂
Happy Retirement! Looks like the inmates will be running the asylum now.