Skip to Content

21 Signs to Trade Your Briefcase for a Suitcase

(Last Updated On: )

Identifying these signs is an essential exercise in self-awareness that invites us to consider if the time has come to retire. From the complexity of managing a tea round to becoming the unofficial office archivist, each sign suggests a moment where professional life has perhaps reached its culmination. Whether it’s finding more pleasure in the commute than the work itself or dreaming more about retirement than current projects, these indicators serve as a nudge towards embracing a new phase of life. This list provides a look at those moments that may suggest it’s time to transition from career to retirement.

1. The Tea Round is More Complex Than Your Job

shutterstock 2091957562

Image Credit: Shutterstock / Elnur

When orchestrating the office tea round presents a greater challenge than your daily tasks, replete with an array of bespoke requests from oat milk to herbal infusions, it’s perhaps time to consider whether your skills could be better appreciated in the leisurely pace of retirement.

2. You’re the Unofficial Office Archivist

1 shutterstock 2021639234

Image Credit: Shutterstock / Ground Picture

If your colleagues are more likely to approach you for a firsthand account of the ’80s office decor than for a briefing on current projects, it might be an indication that your tenure, while impressive, has reached its natural denouement.

3. The Commute is the Best Part of Your Day

shutterstock 2196741669

Image Credit: Shutterstock / PV productions

Finding more joy in the pages of a quietly enjoyed book on the train than in the office could signal that the journeys you ought to be planning are those of a more personal and exploratory nature, free from the confines of peak travel times.

4. Professional Development Days Feel Redundant

shutterstock 741581971

Image Credit: Shutterstock / goodluz

When workshops on the latest industry innovations leave you pondering retirement plans instead of professional growth, it’s a clear sign that your aspirations may lie beyond the corporate ladder.

5. Your Retirement Plan is More Detailed Than Your Work Plan

shutterstock 2300468707

Image Credit: Shutterstock / larisa Stefanjuk

If you find yourself spending more time mapping out potential retirement activities than actual work projects, consider this a nudge towards making those daydreams a reality.

6. You’ve Mastered the Art of the ‘Tactical Sickie’

shutterstock 142504801 1

Image Credit: Shutterstock / wavebreakmedia

The strategic deployment of sick days to avoid particularly mundane meetings or tasks is a craft in itself, but one that suggests your engagement with work is waning in favour of longing for a less structured existence.

7. The Phrase “Back in My Day” Becomes a Mantra

shutterstock 1043108527 1

Image Credit: Shutterstock / fizkes

Catching yourself starting sentences with “Back in my day” more frequently is a humorous yet telling indication that the generational gap in the workplace might hint at your readiness for a new chapter.

8. The Office Youngsters Discuss Shows You’ve Never Heard Of

shutterstock 421484053 1

Image Credit: Shutterstock / SFIO CRACHO

When the water cooler conversation turns to the latest streaming phenomenon, and you’re left wondering when television became so complicated, retirement beckons as a chance to catch up on decades of missed programming at your own pace.

9. Your Office Jargon Predates Email

shutterstock 1780245680

Image Credit: Shutterstock / Jacob Lund

If “cc” to you still means carbon copy in the most literal sense, and “streaming” is what your kettle does, the digital age suggests it might be time to press ‘eject’ on your professional career.

10. You Begin to Philosophise About Staplers

shutterstock 2326947285

Image Credit: Shutterstock / Elnur

Finding deep, existential meaning in the click of a stapler or the glide of a highlighter across paper? This level of contemplation is a sign that your mind is ready for broader horizons beyond the office desk.

11. Annual Leave Is Spent on Hobby Courses

shutterstock 1663480357 1

Image Credit: Shutterstock / Altrendo Images

If your idea of a holiday is a week-long deep dive into pottery or Renaissance art rather than a beach getaway, retirement could offer the expansive canvas you crave for your burgeoning interests.

12. You’re Unfazed by Office Politics

shutterstock 1013579443

Image Credit: Shutterstock / Roman Samborskyi

The drama of who said what in the break room passes by you like a gentle breeze. Indifference to the office soap opera suggests it’s time for more fulfilling narratives.

13. The Pension Pot Becomes Your Favourite Topic

shutterstock 1032426211

Image Credit: Shutterstock / fizkes

When discussions about your pension pot become the highlight of your social exchanges, it’s a wink from the universe that perhaps those funds are ready to be put to their intended use.

14. You Mistake a TikTok for a New Time Management Tool

shutterstock 570396454

Image Credit: Shutterstock / Rocketclips, Inc.

Hearing “TikTok” and thinking it’s the latest in productivity apps rather than a social media platform is a humorous nudge that the office may no longer be your natural habitat.

15. You’ve Perfected the Art of the Power Nap

shutterstock 47064208

Image Credit: Shutterstock / foto ARts

Mastering the discreet office power nap, whether behind closed eyelids during conference calls or the perfected lean in your chair, suggests your body is voting for retirement.

16. Your Work Anecdotes Are Historical Artefacts

shutterstock 2063155889

Image Credit: Shutterstock / fizkes

When your best work stories involve fax machines and Rolodexes, and your audience responds with amused bewilderment, it’s a sign your tales—and perhaps you—are ready for new settings.

17. Your Desk Gadgets Are Museum-Worthy

shutterstock 1013579443

Image Credit: Shutterstock / Roman Samborskyi

If your desk accessories include a paper diary, a desk calculator, and a landline telephone with actual buttons, the modern office may have outpaced you, gently hinting at retirement.

18. Lunch Breaks Feel Like Brief Holidays

shutterstock 1032685384

Image Credit: Shutterstock / fizkes

When your lunch break becomes the day’s highlight, offering a blissful escape to the outside world, it might be time to consider making every hour your own.

19. You’re the Go-To for Obsolete Skills

shutterstock 2021639270

Image Credit: Shutterstock / Ground Picture

Being the resident expert on merging documents in WordPerfect or creating transparencies for the overhead projector has its charms, but it also suggests your skill set may enjoy a more appreciative audience in retirement.

20. Health and Safety Briefings Are Nostalgic

2 shutterstock 2025930416

Image Credit: Shutterstock / Ground Picture

If the mention of ‘health and safety’ conjures images of simpler times when a computer screen filter for eye strain was the height of workplace well-being, retirement might offer a welcome respite from an ever-evolving office landscape.

21. The Future Is Now

shutterstock 1926215849

Image Credit: Shutterstock / fizkes

When you realise that the ‘future’ you’ve been working towards all these years is actually now, it’s perhaps the most profound sign that the moment to embrace retirement has arrived. Stepping away from the workforce doesn’t mean stepping away from purpose or passion but rather stepping into a new phase of life with the freedom to explore, learn, and grow.

A Graceful Bow

shutterstock 2319461013

Image Credit: Shutterstock / fizkes

Recognising these signs is not an admission of obsolescence but an acknowledgment of a career well-played and a life well-lived, with the promise of more to come. Retirement isn’t the end of the road; it’s merely a change of direction, an opportunity to pursue interests and passions with the wisdom of experience as your guide. Here’s to the next adventure, may it be as rewarding as the last.

More Articles Like This…

Barcelona: Discover the Top 10 Beach Clubs

2024 Global City Travel Guide – Your Passport to the World’s Top Destination Cities

Exploring Khao Yai 2024 – A Hidden Gem of Thailand

The post 21 Signs to Trade Your Briefcase for a Suitcase republished on Passing Thru with permission from The Green Voyage.

Featured Image Credit: Shutterstock / Vlada Karpovich.

For transparency, this content was partly developed with AI assistance and carefully curated by an experienced editor to be informative and ensure accuracy.


Tips for Trip Success

Book Your Flight
Find an inexpensive flight by using Kayak, a favorite of ours because it regularly returns less expensive flight options from a variety of airlines.

Book Your Hotel or Special Accommodation
We are big fans of We like their review system and photos. If we want to see more reviews and additional booking options, we go to Expedia.

You Need Travel Insurance!
Good travel insurance means having total peace of mind. Travel insurance protects you when your medical insurance often will not and better than what you get from your credit card. It will provide comprehensive coverage should you need medical treatment or return to the United States, compensation for trip interruption, baggage loss, and other situations.Find the Perfect Insurance Plan for Your Tripimage 9133145 14418597

PassingThru is a participant in the Amazon Services LLC Associates Program. As an Amazon Associate I earn from qualifying purchases.

To view PassingThru’s privacy policy, click here.

+ posts

This site uses Akismet to reduce spam. Learn how your comment data is processed.

This site uses Akismet to reduce spam. Learn how your comment data is processed.