85 Great Retirement Wishes For Your Boss

Your boss is retiring, and you would like to wish him/ her the best in retirement. But you’re probably looking for some inspiration on what to say or write.

The goal of a good retirement wish is that your boss feels appreciated. You want to congratulate your boss on their retirement and wish them all the best in the future. You can express that their hard work didn’t go unnoticed and thank them if they helped you in any way or for opportunities you’ve had. And don’t be afraid to add some humor as well.

In this article, I share 85 retirement wishes you can use for your boss to wish him/ her a happy retirement. At the end of this article, I’ll share the best retirement gift ideas for your boss. If you can’t wait, jump to Retirement Gift Ideas For Your Boss right now!

Just a heads up, this post contains some affiliate links. As an Amazon Associate, I earn from qualifying purchases. Purchases you make through these links may earn us a small commission, at no extra cost to you.

Retirement Wishes For Your Boss

1. Congrats Boss. I hope you will have a great time in retirement! We are going to miss you, but we will never forget you. You’ve done so much for all of us. And I wish you nothing but the very best for this new chapter in your life!

2. Best wishes for a happy retirement. Thank you for everything you’ve done for me over the years. I appreciate it very much, and I shall miss working with you. Enjoy your retirement!

3. Congratulation on your retirement. Thanks for all the great memories. Your contributions to the company will never be forgotten. Happy retirement!

4. Dear Boss, I wish you a wonderful future with lots of time to enjoy with your family, friends, and hobbies. Congratulations and enjoy your well-deserved retirement.

5. Thank you for bringing so much joy and dedication. You made work a fun hobby for me. I’m going to miss your energy and positivity at the office. (Company Name) will never be the same without you. Have fun with all the adventures in your retirement!

Best Retirement Gift For Your Boss

Give your boss a Personalized Crystal Award to say thank you for all his or her hard work and dedication. You can personalize this award with a custom text either serious or funny. Get FREE shipping and FREE personalization at Crystal Plus. And use their 48-hour express service if you’re in a hurry.

Prestige Diamond (M)

6. Congrats Boss. Your retirement doesn’t mean that you will stop hanging out with us. Right? Drop by for coffee once in a while. I love to hear about your adventures. Happy Retirement!

7. Congratulations Boss! I hope all your future dreams come true and your retirement is filled with joy and happiness. You deserve it! Happy retirement!

8. Congrats Boss, there comes a time that you’re going to miss all of us bastards. I have to admit; the highlight of our days are the times when we really annoy you. We will miss you, because who are else are we going to annoy? Enjoy your retirement!

9. Dear Boss, I just wanted to say that your ideas were inspiring. And you really taught me valuable lessons in life and I want to thank you for that. I can’t imagine our workplace without you. I hope retirement will be even better then you imagined. All the best to you and your family. Congratulation and have fun with your retirement!

10. Dear boss, I am wishing you a long, happy, and healthy retirement. Enjoy it to the fullest.

11. If there’s one person in the company who deserves a retirement; it’s you. You dedicated so much of your time and energy to make this company successful. I don’t know how we are ever going to replace you. You deserve the best retirement ever. Congratulations and enjoy all the new adventures in your life.

12. Wishing you the most exciting and stress-free retirement ever.

13. Sorry Boss, after tomorrow you’re not a boss anymore. Your wife is ;). Happy retirement!

14. Best wishes and good luck with your well-deserved retirement.

15. Retirement is extending your weekend with five days. Cheers to this very loooooong weekend! Happy retirement!

16. Congratulation to my favorite person at the office. No, I’m not sucking up to the boss, because after tomorrow that doesn’t help me anymore. I just loved working for you and I am going to miss. Have fun with all the plans you have in retirement!

17. Congratulations you’ve been promoted to one of the best roles in your life. Enjoy it to the fullest!

18. Dear boss, I am pretty sure you will miss having someone do everything for you. So try not to make your wife you’re new secretary 😉 Cheers to you and congratulations on your hard-earned retirement!

19. Congratulation boss on your retirement. Thank you for being you. You have set a great example to everyone at work. Your graciousness, friendliness, and teamwork are going to be missed. Thank you for being someone we can look up to. Enjoy your this new journey in life!

20. Welcome to the time of your freedom. Happy Retirement!

21. Congratulations on retiring. Life has officially given you permission to relax, sit back and enjoy.

22. Congrats boss! Remember that no matter how much everyone wishes you well for your retirement, deep down inside they’re just happy that you’re leaving 😉 Enjoy your retirement!

23. Your bossy times are over. Your wife lays all the rules at home. So congratulation on becoming a working slave just like us. Wish you a happy retirement!

24. Congratulation on your retirement. You’ve accomplished many challenges with this company… You can be very proud of all your career’s success and achievements. But the biggest challenge of your retired life is about to begin – finding something challenging to do. Good luck. Make your retirement a retirement of a lifetime! And if you need tips for your bucket list don’t hesitate to contact me or just go skydiving together 😉

25. Happy retirement! Your ideas, perspectives, and your guidance have always inspired us. You were not just a boss to us, but a mentor and a friend. Thank you for all the life lessons. I hope you’ll have a wonderful time in retirement.

26. Congrats boss. You were our leader, mentor, and enthusiast. Thank you for your guidance and inspirational speeches. Enjoy your well-earned retirement.

27. Congratulation to your new-found freedom. Make sure you use your time with all the things you always wanted to do. Enjoy your retirement!

28. You are a one-of-a-kind boss. We will miss you! I wish you a long and healthy retirement.

29. Boss… retirement is when you can finally stop being angry and grumpy. Congratulations.

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30. Anyone can be a boss but it takes someone special to be a leader. Thanks for being such a great leader for us. You inspired us, encouraged us and gave us direction. We will miss you. Congratulations and I wish you the best on your retirement. May all your dreams come true!

31. Congratulations! You’re spouse, children and grandchildren will be delighted with your retirement. Enjoy spending time with your family. We will miss you at the office but wish nothing but the best for your retirement.

32. Congratulations boss. Now you can get rid of the tie and put on your pajama’s.

33. Boss. You’re awesome! We wish you wouldn’t retire so we can learn more from you but we are very happy for you. You deserve it. Enjoy your retirement!

34. Thanks for being such a great boss. I am so happy we became friends over the years. It won’t be the same without you at the office every day. But I am glad I can see you on the weekends 😉 May you enjoy your retirement to the fullest. Cheers to you friend!

35. It has been truly a pleasure working with you these years. We will miss you. Enjoy every second of your retirement.

36. Even though you’re done with work, we both know you’ll be busier than ever. Enjoy all the plans you have in retirement. Congratulation on this milestone in your life!

37. To the best boss that the company has ever had. What are we going to do with you? Congratulations on your retirement!

38. You were a great boss because of your leadership and vision, but you are an even greater person because of your kindness, respect, and positivity. We will miss you. Happy retirement!

39. No days have gone by without a dull moment when you were here. Your spirit and energy were the best. And we’re going to miss you being our boss. Happy retirement!

40. You’re a wonderful boss and even greater person. Thank you for your kindness, life lessons, and honesty over the years. I appreciate everything you’ve done for me directly and for all the members of our team. You will be missed, but never forgotten. Enjoy all the new adventures life is giving you after you close this door. Congratulations on your retirement!

41. Teamwork makes the dream work. And we made so many dreams work with you being our boss, leader, and team coach. Thank you for these fun years. I will cherish all the great memories forever. Congratulations on your retirement. Now it’s time to make your dreams work. Enjoy and make the most of your retirement!

42. Retirement is freedom. I hope you enjoy doing the things that you didn’t have time for before. Congratulations Boss! Enjoy your retirement!

43. Dear boss. I am wishing you good health, happiness, and success as you move forward to this next chapter in your life! Congrats!

44. You are a hard worker and optimist. Thank you for bringing so much joy, positivity, and dedication to the office. We will miss you! Have fun with your retirement!

45. Dear Boss, all your hard work has finally paid off. Enjoy having your retirement time filled with all the things you’ve always wanted to do. Happy Retirement!

46. Dear Boss. Close this door and explore the beautiful world out there. May your retirement be filled with awesome adventures. Happy retirement!

47. Congratulations on your retirement. I wish you lots of success and happiness in this new journey of your life. Go and do what your heart desires!

48. Congrats boss. You can finally stop working and start living. Enjoy!

49. Congratulation on your retirement, now the fun really begins!

50. Best wishes for an awesome retirement. Keep staying busy, and make the most of your retirement!

51. I wish your retirement will be filled with many new adventures, meaningful moments, and lots of happiness. Happy retirement Boss!

52. Congratulations! May you enjoy the very best that life has to offer you in retirement!

53. What do you call, someone, who is happy on Mondays? Retired! Congratulations on your retirement Boss. Enjoy your happy Mondays, Tuesdays, Wednesdays, Thursdays, Fridays, Saturdays and Sundays!

54. When ‘I’m too old for this shit’ becomes your daily mantra, you know it’s time to retire. I wish you all the best in your retirement and enjoy all the adventures you have ahead of you. Happy Retirement!

55. Dear boss. Look at retirement this way: it’s like a long vacation in Las Vegas. The goal is to enjoy it to the fullest, but not so fully that you run out of money. Have fun in Las Vegas! Happy retirement!

56. Congratulations boss. The opportunities and possibilities are endless in retirement. Have fun and enjoy everything life has to offer. 

57. Happy retirement Boss… think of it as a six month holiday, but twice a year.

58. Happy retirement Boss. If you ever feel bored and think about the fun times in the office. Just come by and give us your unsolicited advice. We know you love doing that! And maybe by then, we will listen to you.

59. After climbing the mountain, you finally can enjoy the view. Congratulations on your retirement! Enjoy the amazing view!

60. Don’t worry boss. Retirement is not the end of the road; it’s the beginning of the open high way! Get in your RV and hit the road. Congratulations and enjoy your road trip!

61. Congratulations! Welcome to a new beginning of your life. Enjoy it as long as possible.

62. You’re finally freeeeeee! Happy retirement Boss!

63. Congratulations on your upcoming retirement. You’ve had a brilliant career and now it’s time for you to enjoy a fantastic retirement!

64. The countdown has officially ended! You made it! Congratulations on this major milestone in life.

65. I can’t believe the time has come to say goodbye. You’re one of a kind and we’re going to miss you very much. It’s going to be hard replacing you! But that’s not your problem anymore. Enjoy you retirement. Make it a good one.

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66. Congratulations boss. You made every day in this place so much brighter. Thank you for all of your wit and wisdom. You will be greatly missed.

67. I am so glad you are getting out of this place! Wishing you nothing but the best on your future endeavors!

68. Happy retirement! I hope that your retirement day will be everything you’ve ever dreamed it would be.

69. Have fun! Don’t stress! And rock your retirement!

70. Have an awesome retirement! You deserve it!

71. Dear boss, you’ve worked very hard for this. Enjoy it and make it the best time of your life!

72. Bravo Boss. Your time to enjoy life to the fullest has finally come. Congratulation on this milestone. Wish you fun, stress-free and enjoyable days in retirement!

73. You have earned every bit of happiness coming your way. Wish you all the best in retirement!

74. A new day, a new start, give it your best, and do it with all your heart. Happy retirement!

75. May success and happiness find you in all your future endeavors. Congratulations and best wishes to you.

76. Dear boss, may your future be prosperous, may your life be filled with a lot of happiness, adventures, good friends and family and a nice cold beer. Wishing you the very best in retirement!

77. Congratulations Boss, may tomorrow hold more blessings than your yesterdays. 

78. Congrats on your retirement. You hold the pen that writes the next chapter of your life. Use all the ink there is and make this chapter the best one in your book!

79. Best wishes on your next adventure that is retirement. May you enjoy every moment.

80. You only retire once, so make it count!

81. I wish you health.
I wish you wealth.
I wish only the best. 
May your life be blessed.

82. As you start each day, 
may only good things come your way.
Best wishes to you
in everything you do.

83. I wish you nothing but the best,
In whatever comes your way.
For life is filled with ups and downs,
Luckily for you today is your retirement day!

84. I love to hear you so happy,
Your future looks so bright.
May you find yourself succeeding,
And may you continue to be a delight.

85. Wishing you many loving moments, happy times and amazing adventures in retirement. These will be the best times of your life so don’t forget to cherish every one!

Retirement Gift Ideas For Your Boss

If you know your boss well or you have a nice relationship with your boss you can celebrate their retirement by giving a thoughtful gift personally. Or you can decide to give an awesome retirement gift with a group of coworkers.

I’ve researched many hours to find the best retirement gifts for your boss to make things easier for you.

Best Retirement Gifts For Your Boss Under $200

One of the best retirement gifts is the gift of MasterClass. Let me explain more about the MasterClass platform.

The masterClass platform is a streaming platform that makes it possible for anyone to watch or listen to hundreds of video lessons taught by the World’s Greatest. And you can gift your boss an Annual Membership to all the Masterclasses on the platform.

You want to make sure the retiree has the best time in retirement. And having something fun to do and learning new things from the best in the world is an excellent way to live a happy retired life. And the best part is they can learn anywhere, at any time, and their own pace.

Just to name a few classes: Aaron Franklin teaches Texas-Style BBQMartin Scorsese teaches FilmmakingDr. Jane Goodall teaches ConservationChristina Aguilera teaches SingingRon Finley teaches Gardening, Jimmy Chin teaches Adventure PhotographySerena Williams teaches TennisDan Brown teaches Writing, and so many more fun classes (for any skill level). Give an Annual Membership for Masterclass to your Boss, get it here.

Best Retirement Gifts For Your Boss Under $100

Coffee Gift Box

Give your boss the ultimate retired feeling with a Coffee Gift Box. Because enjoying a gourmet cup of coffee without having to rush to work is the ultimate retired feeling. At Beanbox, they have all sorts of Coffee Gifts, but one of the best boxes is the Coffee World Tour Gift Box. You’ll send your boss on a world tour with this retirement gift.

Retirement Gift Basket For Men

Retirement is all about relaxing but also enjoying fun activities. Golfing is a popular activity among retirees. So with a golfing gift basket, you can’t go wrong! This golfing gift basket has everything for an enthusiastic golfer!

The Gift Basket includes:

  • American Gourmet Seasoned Pretzels
  • Sheila G’s Salted Caramel Brownie Brittle
  • 4 Yards More Golf Tees
  • Tee Holder Plus
  • Stinger Golf Tees
  • Ballzee Ball Cleaner
  • First Aid Kit
  • Neoprene Koozie
  • Callaway Golf Balls
  • Golf Ball Themed Photo Frame
I’d Rather be Golfing - Golf Gift Basket

Retirement Gift Basket For Women

Champagne and Truffle pairing is the ideal gift to give to your boss when she loves to drink a bottle of quality champagne with a lovely snack. This gift basket from Gourmet Gift Basket has combined the best champagne and truffles for you so that you can easily give it as a gift. Giving a champagne gift basket is always a good idea!

Best Retirement Gifts For Your Boss Under $50

Craft Beer Gift Box

Is your boss a beer lover? Then there is no better gift than a Craft Beer Gift Box from the Craft Beer Club. You gift your boss exceptional craft beers from small artisan breweries from around the country. A great retirement gift for someone who loves beer.

CraftBeerClub.com-The Finest Craft Beers from America’s Best Micro Breweries- 300x250 banner

Artisan Wine Gift Box

Is your boss a wine-lover? Then there is no better gift than a Wine Gift Box from the California Wine Club. You give your boss handcrafted and award-winning wines from small California wineries. An awesome retirement gift for a boss who loves wine.

Best Retirement Gifts For Your Boss Under $25

Travel Books

Is your boss planning on traveling in retirement? Then the book 50 States, 5,000 Ideas is one of the best books you can give him or her for retirement. On Amazon you can find many more inspiring travel books, below you’ll find my favorite picks:

Retirement T-shirt or Mug

Does your boss have a great sense of humor and you want to have a bit of fun? You can give a funny retirement t-shirt or a cool retirement coffee mug. Here are some of my favorite picks on Amazon:

For Women the best retirement gift basket is a SPA Gift Basket from Design It Yourself Gift Baskets. With this gift she can really start her retirement in the most relax way.

Spa Treausres – Spa Gift Basket

How To Celebrate Your Boss Retirement

You can make the retirement of your boss even more special if you organize something memorable. When it comes to celebrating someone’s retirement, you have one goal: celebrate this milestone in their life so they feel loved and appreciated. And there are different ways to do that.

How you want to celebrate someone’s retirement depends on what you like to do, what other people have planned, your relationship with them and most importantly what you think they will appreciate.

A retirement celebration can be small or big. How big or small is totally up to you. You can just organize a gourmet lunch, drinks after work or an office party on the last day.

Retirement Celebration Ideas:

  • Organize a retirement party
  • Organize a gourmet lunch
  • Organize an after-work drink
  • Do a toast
  • Order a cake or bake a retirement cake
  • Give a speech
  • Create a (funny/ sincere) video
  • Make a scrapbook
  • Make a photobook
  • Create a bucket list
  • Give a service award
  • Organize a flash mob
  • Organize a roast
  • Organize a quiz
  • Pull out one last prank

Read more: 30 Ideas How To Make A Retirement Party Extra Special

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Kirsten Veldman

I'm Kirsten. In 2017, my husband Léon, and I decided to retire from the rat race to travel the world and work and live location independently. In the last couple of years, I wrote over 100+ articles about retirement and did extensive research to help people prepare, enjoy and celebrate retirement in the best way possible.

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