Retirement is often associated with security and careful planning, but some individuals have taken daring risks. Rather than playing it safe, they embraced bold financial or lifestyle decisions that defied expectations.
Some individuals have taken bold, high-risk approaches that defy conventional wisdom. Here are ten retirees who took a chance and saw it play off:
1. Investing Retirement Savings in High-Yield Stocks

Hank, a retiree from the Midwest, faced retirement with just $100,000 in savings. Instead of opting for conservative investments, he rolled his 401(k) into an IRA and invested in monthly dividend-paying stocks. Over three years, his portfolio grew to over $160,000, providing about $3,000 monthly income. This strategy, while risky, allowed Hank and his wife to enjoy a comfortable retirement. MarketWatchNerd’s Eye View | Kitces.com+1MarketWatch+1
2. Retiring Abroad for Lower Living Costs

Billy and Akaisha Kaderli retired at 38 and chose to live in various countries with lower living costs. By doing so, they stretched their retirement savings significantly, enjoying a fulfilling lifestyle that would have been financially unattainable in the U.S. The US Sun
3. Early Retirement with Minimal Savings

Some individuals have chosen to retire early despite having minimal savings, relying on frugal living and part-time work to sustain themselves. This approach requires significant lifestyle adjustments but has allowed them to enjoy more years of leisure.
4. Betting on a Pension Over a 401(k)

Some retirees have chosen to rely solely on pensions rather than diversifying with 401(k) plans. This decision can be risky, especially if the pension is not inflation-adjusted, but for some, it has provided a stable and sufficient income throughout retirement. WSJ
5. Investing in High-Risk, High-Return Assets

Some retirees have allocated a portion of their portfolio to high-risk assets like cryptocurrencies or emerging markets. While volatile, these investments have the potential for substantial returns, bolstering retirement funds when successful. Investopedia
6. Starting a Business Post-Retirement

Launching a business after retiring is a gamble that has paid off for some. By turning hobbies or passions into income-generating ventures, these retirees have found both financial and personal fulfillment.
7. Delaying Social Security Benefits

Choosing to delay Social Security benefits until age 70 increases monthly payments. Some retirees take this risk, using personal savings in the interim, to maximize future income. Nerd’s Eye View | Kitces.com
8. Investing in Real Estate Ventures

Some retirees invest in rental properties or real estate developments. While requiring active management, successful ventures provide steady income and asset appreciation.
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9. Pursuing Aggressive Investment Strategies

Adopting aggressive investment strategies, such as high equity exposure, can lead to higher returns. This approach carries significant risk but has rewarded some retirees with substantial portfolio growth.
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10. Relocating to Economically Vibrant Areas

Moving to areas with better economic opportunities allows retirees to engage in part-time work or consulting, supplementing their income and staying active.
While these high-risk retirement strategies have worked for some, they are not universally advisable. Thorough research, careful planning, and consultation with financial advisors are essential before considering similar approaches.
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