Is Your Boss Retiring? 65 Retirement Messages To Say Goodbye With Style

A good boss sets the tone for a positive experience at work.

When your favorite boss decides to retire, you want to take a moment and offer thanks and good wishes. 

You have plenty of feelings to express but wonder, “What can I say instead of happy retirement?”

You need something more thoughtful. 

There are some good retirement sayings out there that you can use, but an exceptional leader deserves something special beyond a congratulatory cliche.

What Do You Say to Your Boss When They Retire?

When your boss retires, your job will never quite be the same again. Someone who has shaped the work environment and mentored you is leaving forever.

You need to mark the moment in some special way and say a proper goodbye. 

At a minimum, you could find retirement quotes for your boss on the internet and include one card. But you’ll need to write something personal as well.

Retirement is a major life transition when the retiree will have time for themselves and follow their dreams.

You can write about your boss’s more relaxed future, but your relationship with them should also guide what you write.

When composing retirement wishes to a boss, consider these strategies:

  • Use humor – If your boss has a good sense of humor, play to this with some lighthearted wit.
  • Share your feelings – Express gratitude for the guidance and support your boss has given you over the years.
  • Be short and sweet – You don’t need to use an abundance of words to write a nice retirement congrats. Just choose your few words thoughtfully.

65 Retirement Messages to Your Boss

Something on this list of happy retirement messages is sure to be a good fit for your boss. Feel free to use these suggestions verbatim or treat one as a template and change the words to make it extra meaningful for you and your retiring boss.

Funny Retirement Messages for Your Boss

You know if your boss can take a joke or not. If so, here’s your chance to make a playful jab or share a humorous moment from your time working together.

1. Retirement is the season of life when you finally enjoy the rewards of your hard work. The only problem for you is that you’ll be SO bored without my stupid mistakes to fix.

retirement message to boss 

2. Your family will be so happy with your home all day to micromanage their lives and keep things running smoothly.

3. Performance will nosedive around this place without you at the helm. You were always so much more inspiring than our paychecks.

4. On your final day at the office, I want to let you know what my opinion of you really is. The fact is – you were the best boss I’ve ever had.

5. Before you pass the reins of power to our new boss, I humbly request that you approve a 20% raise for me on your way out the door. Of course, if you want to go higher, that’s fine too.

6. Soon, you’ll look back fondly on your days managing me. You’ll realize that getting the best work out of me was your most outstanding achievement.

7. I see that you’ve finally done the best thing for your mental health and fired yourself. May you flourish in your next job of enjoying your life to the fullest.

8. Please think of me when you’re lounging in bed in the morning trying to choose between going golfing or playing with your grandkids. Best wishes on your retirement.

9. You’ve served your time and have been released from the workhouse! But you certainly didn’t get let out for good behavior. What happens in Vegas stays in Vegas! Congratulations.

10. Your retirement is here. The time to relax and not stress over work awaits you. So chill and know you don’t have to worry that I’ll ruin everything at the office without you to watch over me.

11. I wish you the very best retirement. I’m sure you’ll experience great satisfaction knowing that everything at the company will fall apart without you.

12. So many adventures await you in retirement. You’ll have the time to be on hold at the Social Security office and tell long stories to service workers.

13. I’m in a panic at the thought of you retiring. Who’s going to protect us from upper management? Could you have a word with them to go easy on us before you go?

14. May you enjoy a long and comfortable retirement. Now I can finally set the office thermostat to a reasonable temperature.

15. You’ve always been a creative boss. The way you’ve spun job termination into a retirement party is just another example of your ingenuity.

16. You may be wondering what retired people do. The answer is hassling people who still have jobs by sending them links to all of your travel destinations.

17. On the occasion of your retirement, I feel it’s important to apologize for all the stress I’ve caused you over the years. I see now that it was too much and left you unable to work.

18. I wish we had gotten more chances to know each other, but I’ll admit I was hiding from you most of the time. Happy retirement!

19. I extend my condolences to your family that will now have to endure your incoherent demands and unrealistic deadlines full time. Have a great retirement!

20. You’ve taught me so much about succeeding at work, like covering my butt, shifting blame, and gobbling up budget money.

21. Should you miss the routine and fulfillment of the workplace, just think of me. I’m sure you’ll be glad to be at home instead of dealing with my annoying attitude.

22. I can see that you’re excited about retirement. I assure you that I’m even more excited about it than you.

Short Retirement Wishes for Your Boss

Brevity is the soul of wit. If there’s not much space on a crowded retirement card, squeeze in one of these short messages.

23. Goodbye responsibility and hello possibility.

24. Wiggle your toes in the sand and soak up the sunshine every day of retirement.

25. No one can replace you as our leader. You’ve left shoes too big to fill.

26. I was lucky to have you as a boss. May you enjoy your well-deserved retirement.

27. I bet I’ll miss you more than you miss the gang at work.

28. Don’t worry about having too much time on your hands as a retiree. You’ll get used to it!

29. This is a sad day for the company, but a bright day for your future.

30. Everything in retirement should be about your happiness. Savor every minute of it.

31. Retirement means you can do what you want when you want. Do it all!

32. You deserve to have the most extraordinary retirement ever.

retirement message to boss 

33. I hope in retirement you discover new and joyful ways to be alive.

34. Life is about to be a lot more fun and a lot less stressful! 

35. Happy retirement to the best boss I’ve ever had.

36. As your work-life is behind you, keep your eyes on the prize of a well-deserved retirement.

37. Congrats on the culmination of a great career. You’ve been an inspiration every day.

38. Time is one of the most valuable luxuries in life. May each moment of retirement enrich you.

39. May all of your dreams to come true now that you can focus on yourself and your family.

40. Here’s to many years of health and happiness during your retirement.

41. Happy retirement! You’ve earned the ultimate promotion to a life with few responsibilities.

42. Don’t forget us because you will always be part of our work family.

43. The best days of your life are now before you.

44. We will miss you every single day.

Emotional Retirement Messages for Your Boss

A good boss is as rare as rain in the desert. It’s fine to get a little mushy when you say farewell to a great leader.

45. You helped me through my first day on the job when I was so nervous. Now I’m anxious to see you retire because you’ve been my inspiration and mentor.

46. Not everyone gets a chance to be mentored by such a talented and caring person. Thank you so much for being so extraordinary.

47. I’m a better person because you taught me so many things, like diplomacy and patience. I’m in your debt forever.

48. I learned so much from you by working at your side. You’ve made me better at my job while treating me with dignity. 

49. You were a rare gem among bosses. I will remember you as one of the most influential people in my life.

50. Work just won’t be the same without your cheerfulness and confidence. You were the best person I’ve ever worked for.

51. You got me through some tough times when I thought I would fail. I appreciate everything you did to make me a success.

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51. I’m happy to know that you’ll be resting and relaxing every day. No one deserves a permanent break from stress more than you.

52. You’re the first person in my professional life who took the time to help me build my skills and confidence. Thank you!

53. Your dedication to doing good work served as an example to everyone at work. I’m honored to have worked for you.

54. Going to work just won’t be the same without your sense of humor to brighten my day.

55. I appreciate how you always had my back during the tough times. I hope retirement is everything you want it to be.

56. I’m really pleased to know that a hard-working person like you will get to enjoy the peace and freedom of retirement.

retirement message to boss 

57. We work in an emotionally demanding industry, and I’m grateful for the example of resilience and gratitude that you provided.

58. You were the most trustworthy and dependable person who I’ve ever worked for. If everyone were like you, the world would be a better place.

59. I’m so sad to see you go, but I know that retirement will treat you well.

60. You knew how to motivate me to do my best work. I wouldn’t have known what I was capable of without you pushing me. 

61. I never dreaded coming to work after I started working for you. You deserve to have a fantastic retirement.

62. You were my leader at work, but most importantly, you were my friend. Thank you for valuing me as a person.

63. I was lucky to have the opportunity to learn from you. I credit you for helping my career move forward.

64. You’re a wonderful person, and I’m pleased that you can now spend your days doing what matters most to you.

65. You’re proof that “boss” isn’t a four-letter word! It’s a seven-letter word: amazing! I’m deeply grateful for the kindness and trust you showed me all these years.

Hopefully, this list provided you with the right words to answer the question, “How do you thank a retiring boss?” 

Your departing boss will treasure the words you share and remember you fondly for many years. Your thoughtfulness and kind words are part of the ritual that helps a new retiree begin the next chapter on a positive note.

Saying goodbye to a spectacular person does not have to be sad. Instead, you can say your retirement messages to your boss in a classy and a fun way.

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