Apr 6, 2026
Many people can’t wait to retire. They dream of finally having free time to pursue passions and spend their days as they choose and, in some cases, they jump at the first opportunity to make that happen.
Sometimes the trigger is a layoff, health issues, or the need to care for someone. Other times, it may be a difficult period at work or a simple yearning to live a little.
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Taking the plunge early can be a blessing — but not always. Surveys suggest that a notable share of early retirees later regret the decision, and not just for financial reasons (1).
Here are six of the most common regrets retirees report after leaving the workforce early.
1. Not saving enough
Having more free time can lose its appeal if it comes with constant financial stress. A common complaint among early retirees is that their savings and other income sources don’t stretch as far as they expected.
According to John Hancock’s Financial Stress Survey, 75% of people who retired earlier than planned said they wished they had saved more before leaving the workforce, compared with 57% of those who retired later (2).
Retiring early increases the number of years your savings must support you while also reducing the time you have to keep contributing to those savings.
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2. Underestimating costs
Many retirees assume their spending habits will remain similar when they retire, but they may underestimate inflation and one major expense that tends to rise with age: healthcare.
Fidelity’s 2025 Retiree Health Care Cost Estimate projects that a 65-year-old retiring today may spend about $172,500 on healthcare, including premiums, co-pays and prescription drugs. This estimate does not include long-term care, dental, or vision costs (3).
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Early retirees may face additional cost pressures, as leaving work before 65 often means losing employer-subsidized health insurance and paying full premiums until Medicare eligibility begins.
3. Claiming Social Security too early
Social Security is the main source of retirement income for most households, and the amount you receive can drop significantly if you claim as early as possible.
Claiming benefits at the earliest eligible age of 62 instead of waiting until full retirement age — 67 for those born in 1960 or later — permanently reduces monthly payments by about 30%. This reduction can have a lasting impact on lifetime income.
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4. Skipping long-term care insurance
Another common regret is not purchasing long-term care insurance while premiums are lower and coverage is generally easier to obtain. A 2023 working paper from the National Bureau of Economic Research found that over a quarter of retirees cited this as a financial regret (4).
The stakes are high. According to New York Life’s 2023 Cost of Care Survey, a private nursing home room costs about $116,000 per year, ****while ****spending three years in assisted living and two years in a nursing home can exceed more than $365,000 (5).
Without insurance, these expenses can quickly erode savings that are already stretched by an extended retirement.
5. Missing structure, purpose and social interaction
Money isn’t the only source of regret. Some people find they miss the routine, sense of purpose, and social connections their job offers.
Academic research shows that leaving the workforce early is often accompanied by a reduction in social networks and mental engagement, both of which are associated with overall well-being (6).
6. Difficulty re-entering the workforce
Some early retirees assume they can return to work if retirement doesn’t work out financially or emotionally. But it’s not always that simple.
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According to AARP, 64% of workers aged 50+ have experienced or witnessed age discrimination, and 74% believe their age could be a barrier to being hired (7)(8).
Meanwhile, CWI Labs reports that 46% of older job seekers have been looking for at least one year, and only 21% feel optimistic about finding a job within the next six months (9).
What to consider before leaving work too early
Early retirement can be rewarding, but without adequate planning, the excitement of leaving the workforce may later turn into regret. Before stepping away, consider the following:
- Estimate retirement needs: Calculate how much money you’ll realistically need each year in retirement, factoring in not only essentials like housing, food and transportation but also healthcare, inflation, unexpected costs and additional spending that may come with increased leisure time. Then multiply this amount by a timeline that could extend into your 90s or beyond. It’s better to overestimate than underestimate.
- Stress-test your retirement income: Evaluate how different market, inflation and economic scenarios could affect your finances to make sure your plan can withstand downturns or higher costs.
- Plan for healthcare: Account for expenses before Medicare eligibility at 65. Explore private coverage or health savings accounts to bridge potential gaps, and consider long-term care insurance while premiums are lower and coverage typically easier to obtain.
- Strategize Social Security claiming: Delaying Social Security can significantly increase monthly payments, which may improve long-term income security.
- Maintain purpose and social engagement: Identify ways to stay active, connected and mentally engaged, such as through part-time work, volunteering or hobbies.
- Consider phased or partial retirement: Gradually reducing work hours can ease the transition, providing continued income, social interaction and structure — while still allowing more freedom to enjoy life.
Taking time to evaluate these factors can help ensure that early retirement is a sustainable and fulfilling decision rather than one you later wish you had approached differently.
Careful planning may not eliminate every risk, but it can significantly increase the odds that your retirement years match the lifestyle you envision.
Article sources
We rely only on vetted sources and credible third-party reporting. For details, see our editorial ethics and guidelines.
Newsweek (1); John Hancock’s Financial Stress Survey (2); Fidelity’s 2025 Retiree Health Care Cost Estimate (3); National Bureau of Economic Research (4); New York Life (5); Oxford Academic (6); AARP (7, 8); CWI Labs (9)
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Daniel Liberto is a financial journalist with over 10 years of experience covering markets, investing, and the economy. He writes for global publications and specializes in making complex financial topics clear and accessible to all readers.
