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97 Funny Retirement Wishes & Messages Signed With Humor

Retirement is a solemn and often sad affair that should be treated with the utmost respect…just kidding! This is an exciting new chapter in someone’s life, and although they might have bittersweet feelings about this milestone, a bit of humor will definitely be appreciated. 

Don’t let this important milestone go unnoticed. To you, it might feel like just another day, but to the person retiring, this is perhaps the biggest change ever in their lives. 

Even when you had a fantastic relationship with the person retiring, finding the right words isn’t always easy. We are taking care of that problem with our 97 funny retirement wishes for everyone, from your dad to your boss.

35 Funny retirement wishes for any type of retiree

  • There is no better excuse to spend your entire life savings than retirement. I hope you enjoy every second of it.
  • Put on your party hat and grab those dancing shoes – you’ve worked hard, but now it’s time to party! Congrats on reaching this milestone.
  • Retirement is a vacation that never ends, so enjoy it! 
  • I can’t believe you are retiring before me! Can we please swap places?
  • I hope your new boss will be less strict! It’s your partner, in case you haven’t realized that yet!
  • Goodbye early morning shifts, and hello senior discounts!
  • I can’t believe you beat me to retirement! Can we swap places, please?
  • Enjoy the new chapter in your life where every day is Saturday. 
  • What do you call a happy person on a Monday morning? A retired one!
  • Congrats on your retirement! I’ve been told the pay isn’t great, but the hours sure are.
  • No more hitting that annoying snooze button in the morning: you’ve now uncovered the forever retirement button. 
  • I’m jealous: you never have to set an early alarm again before going to bed at night. Congrats on reaching this milestone.
  • Enjoy working at living instead of living at work. You deserve this time of rest and relaxation! 
  • Welcome to happy Mondays! 
  • Enjoy the things you always wanted to do… as long as you’re not too old to remember them!
  • It only took God six days to create the heavens and the earth and then retire. What took you so long?
  • Congrats on reaching this momentous milestone! Now it doesn’t matter anymore if the government increases the retirement age.
  • Congrats on getting two new best friends upon your retirement. Their names are Bed and Couch. You will be spending a lot of time with them.
  • Now your only job is having fun – and I know you’re an expert at that already.
  • Oh no, someone is about to have way too much time on their hands! Enjoy every moment – you completely deserve it.
  • Now you’ve finally earned that retirement discount that you’ve been claiming!
  • Can you say senior discount? Enjoy all the perks that come with this new chapter.
  • They say you can’t teach an old dog new tricks. Well, you can put brand new tires on an old car. That’s exactly what you are doing: re-tiring. 
  • Prepare yourself for years of being told, “You look too way young to be retired!”
  • Your retirement is stirring a lot of emotions in me, but I’d have to say envy is the biggest one.
  • Retirement is the phase where you realize that getting showered and dressed in the morning is now entirely optional. Enjoy this new freedom!
  • In retirement, you are going to discover how much you can actually get done without wearing pants!
  • We know you are ready for retirement because you’ve been practicing for the past 10 years. Enjoy the real thing now!
  • Congrats on finally being retired and having free time! Although I’ve been told your schedule is already packed with babysitting dates.
  • Finally – an excuse to spend all your life savings!
  • You are living proof that we can all get out of our jobs alive!
  • Tired of adulting? It’s finally time to retire.
  • How do you make yourself love Monday mornings? That’s super easy – just retire!
  • When you retire, you finally escape the rat race, but you need to learn to survive on less cheese.
  • Let’s say it together: “No more Monday Meetings!”

13 Funny retirement wishes for your dad

You’ve probably seen your day enjoy the highs and lows of working life. But now you and your family can finally celebrate this special new chapter with him.

  • You’ve finally made it to retirement! Here’s to planning travels with us instead of meetings with your team.
  • Dear dad, Retirement will make you realize that you spent so many years trying to mature into an adult just so you can go back to being a kid in the end. Enjoy your retirement.
  • Goodbye tension and hi there pension! You deserve it, dad!
  • Retirement is like a never-ending weekend party, except you can’t drink, dance, or stay up late. Enjoy!
  • Congrats on your retirement… it’s kind of like a six-month holiday, twice a year.
  • Retirement is like a lifelong vacation, except you’re not in good enough shape to enjoy its many perks.
  • Warning: Retired person in the vicinity. Knows everything and has plenty of time to tell it!
  • Congrats, dad. Time to say goodbye to tension and hello to pension.
  • Congrats on reaching retirement! Now it’s time to stop lying about your age and start lying around the house!
  • Guess what you just did? You took all the meaning out of the weekend!
  • Enjoy the future of your permanent seven-day weekends!
  • It doesn’t matter if you behave like a grumpy retiree or not because people will assume that regardless. Good luck dealing with that.
  • Enjoy the new chapter in your life where every day is Saturday. You deserve it!

16 Funny retirement wishes For your friend

No doubt you and your friend have complained about the ups and downs of working life. If they retired before you, you might even be a little jealous. In that case, one of our funny retirement wishes is a perfect pick for you.

  • I hate to break it to you, but the “weekend” as you know it has now lost all meaning. Okay, I’ll admit it – I’m just jealous.
  • I’ve been told retirement isn’t as wonderful as it sounds. No deadlines and no angry clients – how will you survive? Let’s just switch places!
  • A wise person once said that the retirement years are like a long vacation in Las Vegas. You should enjoy it to the fullest, but not so much that you run out of money!
  • Now you can finally sit back and give advice to everyone around you, even though you never followed it in your own life. Enjoy it!
  • Congrats on extending your weekends every week by 5 days!
  • The illusion of retirement is just that – your partner will take over, and your grandkids will become your unruly colleagues.
  • There will be a change in dress code from suits and shirts to flannels and blankies. Enjoy the time with your partner and grandkids!
  • Congrats on becoming the master of doing absolutely nothing.
  • Remember, retirement is an adventure! This is especially true if you count trekking out of bed, climbing on sofas, and eating takeaways. Have fun.
  • Congrats on your retirement. I hope you enjoy living off your savings. Let me know what you do after the second month…
  • Retirement is just fantastic – you can finally do nothing without being worried about getting caught by your boss. 
  • Congrats on retiring, dad. We are going to have to start a support group for mom!
  • People say that retirement marks the end of all of life’s tension, but that’s true only if you have a handsome pension.
  • Retirement to-do list: wake up, coffee, eat, sleep, repeat. You worked hard for it my friend – enjoy every second of your retirement.
  • I can’t believe that you actually beat me to retirement! Can we swap places, please?
  • Goodbye tension and hello beautiful pension. Congrats on reaching this important milestone.

19 Funny retirement wishes For your colleague

Without a doubt, you and your colleague have experienced a lot of highs and lows together. After all, spending 40 hours a week with someone really creates a powerful bond. Don’t let this moment go unnoticed, and let them know what your relationship meant with one of our handpicked retirement wishes for a colleague. 

  • Finally, you can say: goodbye to all your work apps and hello to cat naps. You deserve it!
  • I have one really important question for you: Can you please take me with you?
  • The secret to a happy life? Never having to use a single cringe-worthy work acronym again.
  • I’ve got bad news for you…but you need to learn how to make your own coffee from now! Enjoy this second chapter.
  • Congrats on your retirement! Although, if I’m honest, I could have sworn you stopped working years ago.
  • There’s no deadline and early morning shifts in retirement. I’m not sure you are going to like it, so let’s just switch places.
  • The whole team thought you were going to be fired first, but somehow you made it!
  • Do you know what the best part of retirement is? Never having to laugh at the boss’ jokes anymore. 
  • In spite of how much everyone is congratulating you on your retirement, we are all relieved you’ll be gone soon. Just kidding – we will all secretly miss you
  • Finally – you can browse the internet without being caught by the boss again!
  • All the best in retirement. The team and I are going to miss doing your work for you.
  • Good idea to retire – you better go quickly before the boss finds all your mistakes. 
  • We want you to know that we’ll miss having you in the office. Too bad the feeling isn’t mutual. Enjoy your new chapter.
  • Of all the people I’ve worked with. Well, I can honestly say that you were one of them.
  • My dearest colleague, retirement is the time to finally stop being angry and grumpy – there are no more deadlines and angry customers around!
  • I recommend you change your number. Once management finally finds out everything you did here, they’ll be begging you to come to fix it.
  • We are still amazed that you didn’t get fired first. I guess you are an inspiration to all of us for achieving that.
  • I’m going to really miss doing all your work! Now get out of here and go enjoy retirement.
  • In a vote, we decided that what you’re doing doesn’t help anyone. So go enjoy your retirement.

14 Funny retirement wishes For your boss

If you and your boss had a good relationship and even shared the occasional banter, then you are definitely in the right place. One of our funny retirement wishes will be the perfect cherry on the cake as you bid them farewell from working life.

  • Here’s to finally getting a boss of your own (your spouse!).
  • Retirement is just a polite way for the company to tell you that they have found a more youthful and skilled person to take over your role. 
  • The team and I are all going to really miss doing your work for you.
  • Life has finally given you permission to relax! Kick back and enjoy every moment of retirement. 
  • We know you’ll miss all the crazy deadlines and late nights. So why don’t we just switch places?
  • Your bossing times are over – your partner is now making the rules!
  • Please congratulate your partner on getting double the spouse, but only half the income.
  • Your retirement will leave an empty space in the office and our hearts and not to mention the break room fridge.
  • Now that you’re finally retiring, I can tell you how I really feel about you. And how I really feel is…you are wonderful. Enjoy retirement!
  • Don’t forget that retirement is like a never-ending holiday, so don’t put targets for yourself at home too!
  • Now it looks like the asylum will be run by the inmates. Enjoy retirement!
  • Do you think you could give me a raise as you are leaving?
  • I’m so happy that retirement is not optional but mandatory, or the team and I will be stuck with you forever. 
  • I hate to break it to you, but now it’s time to learn how to make your own coffee, boss! Enjoy retirement.