by Spencer Wilson, Employco
Retirement is a word that evokes mixed emotions—excitement for freedom, fear of the unknown, relief from long hours, or worry about leaving behind an identity built over decades. For many professionals, the decision is not as simple as reaching a certain age or savings goal. It’s deeply personal and requires reflection on timing, purpose, and practicalities.
Below, we explore some of the central questions: When do you know it’s time to retire? Should you retire? What are the key considerations before making the leap? What common misconceptions might cloud your judgment?
When Do You Know It’s Time?
There is rarely a single moment when a person suddenly knows it’s time to retire. Instead, the decision often comes after subtle shifts in energy, priorities, and motivation.
A few signals include:
- Physical or mental fatigue: If the demands of your work—long hours, travel, or complex responsibilities—consistently drain rather than energize you, it may be time to reassess.
- Loss of passion: Work once felt exciting, but now the challenges don’t spark joy. Instead, they feel like obligations you’d rather avoid.
- Changing priorities: Family, health, and personal goals may begin to outweigh professional ambitions. You might notice yourself regretting missed events or feeling more pulled toward what lies outside the office.
- Financial readiness: Practical matters count. If your savings, pensions, or investments are aligned with your desired lifestyle, you’ve cleared one of the biggest hurdles.
- Succession in place: When you’ve trained successors, delegated responsibilities, or sold your business, you may feel freer to step away.
Recognizing these indicators is not about weakness—it’s about understanding that every career has a natural arc.
Should You Retire?
Just because you can retire doesn’t always mean you should. For some, continuing to work well past traditional retirement age provides fulfillment, structure, and purpose. For others, retirement opens the door to new forms of engagement and personal growth.
Why you might retire:
- More time for hobbies, family, and personal pursuits
- Opportunity to leave on your own terms, shaping your legacy
- Relief from stress, travel, or physical demands
- Space to reinvent yourself—through volunteering, mentoring, consulting, or creative projects
Why you might not be ready:
- Fear of losing identity or relevance
- Unfinished goals you still want to achieve professionally
- Financial uncertainty, especially regarding healthcare costs or market fluctuations
- Deep enjoyment of your daily work and the relationships it provides
The question isn’t only whether you can retire, but whether doing so will add meaning and satisfaction to your life.
Things to Consider Before Retiring
A thoughtful transition is far smoother than an abrupt exit. Before making the decision, it helps to examine several key areas:
- Financial Stability: Build a clear picture of your income sources (savings, Social Security, pensions, investments) and anticipated expenses. Factor in healthcare, travel, and unexpected costs. A financial advisor can help stress-test your plan against inflation and market shifts.
- Healthcare Coverage: Medical needs often rise with age. If you retire before qualifying for government programs like Medicare, make sure you have adequate insurance in place. Even afterward, supplemental plans can be essential.
- Succession Planning: If you run a company or hold a leadership role, ensure continuity for those who depend on you. Develop a clear succession plan, transfer knowledge, and reassure clients, colleagues, or employees about the transition.
- Lifestyle Vision: Ask yourself: What will your days look like? Having a clear sense of how you’ll spend your time—whether it’s travel, community involvement, or family activities—helps prevent the feeling of “What now?” that sometimes follows retirement.
- Gradual Transitions: Retirement doesn’t have to be all-or-nothing. A phased retirement—reducing hours, shifting to consulting, or serving in advisory roles—can soften the adjustment both financially and emotionally.
- Family and Relationships: Retirement affects more than just the retiree. Talk openly with your partner or family about expectations for time, finances, and lifestyle changes. Alignment reduces potential conflicts later.
Common Misconceptions About Retirement
“Retirement means doing nothing.” In reality, many retirees find themselves busier than ever—just in ways they choose, not ways dictated by a job.
“I’ll lose my purpose.” While work provides structure, purpose can also come from volunteering, mentoring, travel, or creative projects. Retirement can be a shift, not a loss.
“I can’t afford to retire until I hit a certain age.” With thoughtful planning, some people retire earlier than they expected. Conversely, others realize they want to keep working, even if they don’t need to financially.
“Retirement is permanent.” Many professionals ‘unretire,’ returning part-time or as consultants. The transition can be flexible.
“It’s too late to plan.” Even if retirement is imminent, small adjustments—downsizing expenses, rebalancing investments, or planning post-retirement activities—can make a big difference.
Final Thoughts
Retirement is not a finish line; it’s a transition into a new chapter. Knowing when to retire, deciding if you should, and preparing for what comes next are highly individual decisions. They require honesty about your physical energy, financial readiness, emotional needs, and life goals.
Rather than viewing retirement as an end, it can be helpful to see it as a redesign. What does the next stage of life look like for you? Is it freedom from deadlines, time with family, or a chance to try something entirely new? With careful planning and an open mindset, retirement can be less about stepping away from work and more about stepping toward the life you’ve been waiting to create.
Image credit: Adobe Stock
This story originally appeared in the Q1 2026 issue of Exhibit City News, p. 46. For original layout, visit https://issuu.com/exhibitcitynews/docs/exhibit_city_news_-_jan_feb_mar_2026/46.
