60+ Best Retirement Wishes & Messages for Your Boss

If your boss is retiring, you might be wondering how to wish them a happy retirement in just the right way—and we can help! Writing a retirement message for your boss isn’t so hard if you know what you want to say, from wishing them well to expressing gratitude for all their hard work and even cracking a joke (if that’s something your boss would enjoy). Read on for a comprehensive guide to writing a message for a retired boss, complete with an extensive compilation of example messages and more.

Section 1 of 11:

Simple Retirement Messages

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Write a simple, general message for a boss you’re not as familiar with. If you and your boss aren’t super close and you’re not totally sure what to write (or how to personalize your message), there’s nothing wrong with keeping things simple! A polite, pleasant message is the way to go; simply congratulate them and wish them well. ^{[1]
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- Wishing you discovery, relaxation, and joy in the years ahead. Best wishes for your retirement!
- Congratulations on your retirement! I’m so excited and happy for you.
- We’ll miss your guidance and jokes around the office. I hope you enjoy your retirement, boss!
- Sending heartfelt congratulations and best wishes on your retirement. I hope every moment is a happy one!
- Congratulations on a long and illustrious career! You deserve a fulfilling, prosperous retirement to match.
- I’m so honored and grateful to have gotten the chance to work with you. Congratulations, and I hope to hear from you again soon.

Section 2 of 11:

Sincere Retirement Messages

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Be sincere so your boss knows you truly wish them the best. Sincerity and authenticity can show the reader that your message is coming from the heart (and that you really mean what you say). If you want to send your boss a meaningful retirement message, the best way to do it is to be sincere and speak from the heart. ^{[2]
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- The first one in and the last one out! You never had to aim for success because you hit the target every time, and we’ll truly miss your leadership here.
- A truly great boss is hard to come by; we’ll miss you here, but you deserve a wonderful retirement. Congratulations!
- I never thought the day would come when I’d walk into the office and not see you. I hate to see you go, but I’m so happy for you and wish you the best.
- Thank you for being not just a boss, but a mentor and a friend. We were lucky to have you here and will never forget the legacy you’re leaving behind. Best wishes!
- It was a real pleasure to work with you, boss. I’ve always admired your work ethic and perseverance in overcoming any challenge. Congratulations!
- Dear boss: may your retirement be the start of a time filled with joy, health, and fulfillment. I’m sure the retired life will look great on you!

Section 3 of 11:

Funny Retirement Messages

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Craft a funny message to lift your boss’s mood. If your boss has a good sense of humor, try adding a good-natured joke to your retirement message. The prospect of retirement can be stressful to some people—and laughter is a great way to alleviate stress! Just remember to keep your jokes lighthearted, playful, and appropriate; don’t write anything you wouldn’t say in the workplace. ^{[3]
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- As you move on to retirement, we’re still here to pick up where you left off. Just one thing—can you finally tell us where the office candy stash is?!
- Congratulations on escaping the daily grind! You’ve spent your career putting out fires at work, but now it’s time to roast marshmallows by the fireside.
- Enjoy retirement, boss! We promise not to call you for help on your first day of retirement…unless it’s an emergency, like figuring out how to restock the water cooler!
- Congratulations on retirement—or, as some call it, the world’s longest coffee break.
- What do you call a person who’s happy on a Monday morning? Retired, naturally! Congratulations, boss.
- Now that you’re retired think of all the fun (and naps) you can have! Enjoy your retirement, boss!
- Happy retirement! After all, retirement is the only time you can drink at 10 a.m. without getting called out by HR.

Section 4 of 11:

Appreciative Retirement Messages

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Express gratitude for your boss’s leadership and contributions. If your boss was a good manager or role model while working together, ensure they know how much you appreciate them. Specify what you’re grateful for (or why you admire them), then give them an earnest thank you. Gratitude can help you end your working relationship on a positive note! ^{[4]
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- Congratulations on your incredible professional journey, boss. I’m thankful I got the chance to work with you and learn from you over the years.
- Your mentorship has helped me excel and find continued success in my career. I am so grateful and wish you endless happiness in your retirement.
- Thank you for always giving your best to this team and the company. In return, you deserve nothing but the best in your retirement!
- Congratulations on your retirement, boss. Your leadership has been a guiding light, and your wisdom is much appreciated by us all.
- Thank you for all these years of guidance, inspiration, and dedication. Everyone here adores and appreciates you!
- You taught me so much, including how to improve myself as an employee and navigate the industry as a whole. I will always be grateful for your leadership!

Section 5 of 11:

Reflective Retirement Messages

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Reminisce about the highlights of your boss’s career. Retirement marks the end of your boss’s career, which means it’s the perfect time to remind them of their accomplishments and the legacy they’ll leave behind. Acknowledge the longevity of their career (which is probably decades long) and a few of the major successes they’ve had. ^{[5]
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- You’ve left a mark on this company—and industry—so profound it can’t be summarized in a single note. Enjoy your well-deserved retirement!
- Reflecting on your career, I hope you know what an inspiration you’ve been to everyone who has worked with you. Take pride in your legacy and all your accomplishments!
- In your long and distinguished time with this company, you’ve made a lasting impact on this team and so many others. You will be missed, but we wish you all the best!
- Your career has been a masterclass in dedication, excellence, and integrity. I wish you a peaceful and joyous retirement.
- Congratulations on your retirement, boss. Your impressive legacy is an inspiration to me and the rest of the team!
- Thank you for guiding this company to success through hard work and positivity. Congratulations on all you’ve achieved!

Section 6 of 11:

Inspirational Retirement Messages

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Encourage your boss by reminding them how great retirement can be. Sometimes, retirement can be daunting. Sure, the freedom is great, but it may feel strange to have no commitments or daily schedule all of a sudden. So, include a few lines wishing your boss the best and reminding them that retirement is full of new possibilities.
- Retirement is so many things: it’s an end to one era but the beginning of another. May your new era be filled with adventure and purpose!
- May your retirement be joyful and full of adventures, boss. Live every moment to the fullest!
- Retirement is the perfect time to find a new passion or resurrect an old one. Enjoy the many possibilities, boss!
- Congratulations on your retirement, boss. My hope is that you thrive and enjoy every moment of it.
- May your retirement be the key to a world of new opportunities and passions to explore. Best wishes to you!
- Here’s to a retirement filled with new horizons to explore and journeys to travel. All the best, boss!
- Here’s to many new beginnings and opportunities in your retirement. Best wishes and congratulations!
- Wishing you a happy, healthy future filled with exciting adventures and rewarding experiences. Congratulations!
- Enjoy your retirement! Wishing you endless days of peace, fun, discovery, and new opportunities.
- Your new journey is just beginning, and I believe it’ll be wonderful! Here’s to a retirement filled with contentment and joy.
- Cheers to retirement and a life of leisure. Congratulations, boss! May retirement be everything you dreamed it would be.

Section 7 of 11:

Casual Retirement Messages

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Write a warm, casual message if you’re on good terms with your boss. Being on good terms means you can chat and banter with your boss in a friendly way. You likely know each other pretty well and have an easy working relationship. If you have this type of relationship with your boss, a light-hearted and playful message might be the way to go!
- Congratulations on making it to the promised land: retirement, where every day is a weekend!
- No more meetings for you, boss—just brunch meet-ups, freedom, and lots of sleeping in. Congratulations!
- Here’s to leaving office life behind and starting a new adventure! I can’t wait to hear all about it. Best of luck, boss!
- Now that you’re retired, I have to admit I’m jealous. You don’t have to deal with a Monday ever again! Congratulations, boss.
- Happy relaxing, boss! Congratulations on your retirement; I hope it’s everything you want it to be!
- Are you ready to trade your business suits for flip-flops and swimsuits? Enjoy your retirement, boss!

Section 8 of 11:

Formal Retirement Messages

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Keep your message formal to show deep respect for your boss. By taking a more formal tone (even if you have a good relationship with your boss), you’re showing deference to your boss and making it clear you take this message seriously. Consider writing a formal message if your boss is someone you admire and look to for inspiration.
- Congratulations on your impressive career. I wish you a wonderful retirement filled with peace and prosperity.
- As you prepare for retirement, we recognize and celebrate the many years of hard work you’ve given to this company and the success you’ve brought us. Thank you and best wishes.
- I wish you all the best for your retirement. Please accept my deepest thanks for your guidance and leadership over the years.
- In recognition of your distinguished and successful career, I wish you a joyful, fulfilling retirement.
- Congratulations on your upcoming retirement. May it be as rewarding as your career has always been.
- Your expertise, integrity, and commitment to your work have always inspired me and many others at this company. Best wishes for a prosperous retirement.

Section 9 of 11:

Retirement Quotes

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Share a quote that emphasizes the perks of retirement. Sometimes, another person’s words of wisdom are just what you need to complete the perfect message. So, consider quoting a well-known public figure or author in your message. Use it to highlight the many ways to embrace retirement and enjoy it to the fullest!
- “Retirement is a blank sheet of paper. It is a chance to redesign your life into something new and different.” —Patrick Foley
- "Retirement, a time to enjoy all the things you never had time to do when you worked." —Catherine Pulsifer
- “The joy of retirement comes in those everyday pursuits that embrace the joy of life; to experience them with new eyes is to open the door to a whole new world of wonder.” —Michelle Hall
- “Retire from work, but not from life.” —M.K. Soni
- "There is a whole new kind of life ahead, full of experiences just waiting to happen. Some call it 'retirement.' I call it bliss." —Betty Sullivan
- “Retirement is the opportunity to do nothing without worrying about getting caught at it.” —Evan Esar
- "I see retirement as just another of these reinventions, another chance to do new things and be a new version of myself." —Walt Mossberg
- “If you look at what you have in life, you'll always have more. If you look at what you don't have in life, you'll never have enough.” —Oprah Winfrey