7 Key Considerations for Getting Your Retirement Timing Right

When it comes to retirement, timing can have a significant impact on your well-being.

A man looks at his watch while exercising outside.
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Despite receiving high ratings and a lucrative offer of $5 million per episode, comedian Jerry Seinfeld chose to retire Seinfeld after its ninth season. Citing that it was “all about timing,” he explained at the time, “I wanted the end to be from a point of strength. I wanted the end to be graceful.”

Likewise, many aspire for a graceful transition from their careers. When it comes to retirement, timing can have a significant impact on our well-being. A study from the Center for Retirement Research at Boston College revealed that individuals who opted for retirement felt happier than those who involuntarily left their jobs.

Timing retirement “just right” is a nuanced decision and varies for each individual. However, several general principles can guide individuals in making an informed decision. Here’s a compilation of key considerations for getting the timing right.

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1. Consider your financial readiness

The most evident consideration for retirement is financial preparedness. Clearly, one can’t think of retiring if they can't afford it. But what’s the magic number?

According to Northwestern Mutual’s 2023 Planning & Progress Study, working Americans believe they need an average of $1.27 million to retire. However, many can lead a comfortable retired life with less. The ideal savings benchmark varies based on individual circumstances. Fidelity recommends targeting 10 times your pre-retirement income by age 67 to sustain your current lifestyle in retirement. 

2. Age matters in deciding when to retire

Retirement isn’t solely about savings; age matters, too. For penalty-free withdrawals from traditional retirement accounts, you need to be at least 59 ½. However, the rule of 55 allows those leaving their job at 55 or older to withdraw from their current employer’s plan without penalties.

Given most retirees describe Social Security as a major income source, it's vital to plan this aspect of your retirement thoughtfully. The full retirement age is 67 for those born after 1960. By delaying until 70, you boost your benefit, though you’ll have to lean on other funds in the meantime. Starting claims early at 62 reduces your benefit, but you’ll get more checks over time.

If you’re lucky enough to receive a pension, keep in mind it might also be curtailed if age and service requirements aren't met.

3. How your health plays into retirement timing

Your health can dictate the right time to retire. If work strains your well-being or if retirement offers better health prospects, it might be time to reconsider your career. According to the 2023 Transamerica Annual Retirement Survey, health concerns prompted 45% of retirees to retire earlier than planned.

Healthcare coverage is vital in this equation. With Medicare only starting at 65, ensure you’re protected. If you plan on retiring before this age, look into alternatives like securing a policy through the marketplace or opting into your spouse’s plan, if possible. 

4. How is your career satisfaction?

A woman sitting at a computer monitor with a notebook looks into the distance.

(Image credit: Getty Images)

If you love your job and derive satisfaction and purpose from it, delaying retirement might be appealing. Transamerica reports that 56% of those who retired later than planned did so because they enjoyed their work and wanted to stay active and mentally sharp.

Conversely, if work-related stress is detrimental, an earlier retirement or career change might be beneficial. A report from the National Bureau of Economic Research found that retirement often leads to immediate and sustained boosts in life satisfaction and overall well-being.  

5. Looking at market and economic conditions

While it’s hard to predict market movements, you may want to tread carefully if you’re thinking of retiring during a major downturn. Significant losses or depletions to savings early in retirement – known as sequence risk – could derail your retirement plans by diminishing the longevity of your nest egg.

A poor economy may also be reason to think twice about your timing. Although, economic pressures may force some companies to offer appealing packages that make it better to retire sooner than later. These factors might be beyond your control, but they can present challenges or opportunities worth planning around.

6. Did you forget to plan activities for retirement?

Many retirees, according to a survey from Retire with Possibilities, said the biggest challenge of retirement was the loss of daily structure and routine. The transition to retirement often means a shift from established routines and social engagements. 

To make this transition smoother, it’s essential to have a clear vision for your post-retirement life. Without concrete plans, retirement can feel overwhelming – or boring. Before you take the step, ensure you have activities and goals to pursue. Embrace new experiences, volunteer and remain open to various pursuits to keep retirement fulfilling and vibrant. 

7. The company you keep can determine retirement timing

What value do retirement activities hold if you’re experiencing them alone? According to a Merrill Lynch/Age Wave study, a majority of retirees (61%) value the company they keep over the activities they do (39%).

While you shouldn’t rush into retirement just because your peers are, their decisions can influence your considerations. Notably, spouses play a significant role in each other’s retirement decisions. However, synchronizing retirement dates, even among spouses, isn’t always the best approach, given factors like age differences and financial needs.

But given our inherent desire for social connections, it’s apt to say that in retirement, teamwork really does make the dream work. Perhaps the central question isn't solely “When should I retire?” but rather “When should we retire?” 

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Jacob Schroeder
Contributor

Jacob Schroeder is a financial writer covering topics related to personal finance and retirement. Over the course of a decade in the financial services industry, he has written materials to educate people on saving, investing and life in retirement.

With the love of telling a good story, his work has appeared in publications including Yahoo Finance, Wealth Management magazine, The Detroit News and, as a short-story writer, various literary journals. He is also the creator of the finance newsletter The Root of All (https://rootofall.substack.com/), exploring how money shapes the world around us. Drawing from research and personal experiences, he relates lessons that readers can apply to make more informed financial decisions and live happier lives.