1. The Most Common Regrets in Retirement
Nearly 8 out of 10 retirees say they wish they had saved more. Sixty-three percent regret not having a detailed financial plan. And 54% say they never planned properly for inflation. Healthcare is another pain point—many underestimate medical expenses or skip supplemental policies like Medigap, only to regret it later. Social Security is also a frequent misstep. Claiming early can permanently reduce your monthly benefit by 25–30%. And 40% of retirees regret entering retirement with high-interest debt like credit cards and car loans, which erode fixed incomes.

2. Financial Planning: The Cure for Regret
Regret often comes from not planning. That’s why calculating your net worth, tracking your cash flow, and projecting your monthly needs is so critical. Joe and Big Al stress maximizing 401(k) contributions—especially the catch-up option if you’re over 50—and diversifying your savings buckets. Relying only on tax-deferred accounts can backfire in retirement. And don’t ignore inflation: $50,000 in annual expenses today may cost $90,000 in 20 years.

3. Social Security: Timing Is Everything
Most people claim Social Security at 64, but delaying until age 70 can increase your benefit by 8% annually after full retirement age. That can mean a 70% higher check compared to claiming at 62. Waiting may not be ideal for everyone, but building Social Security into your broader strategy—alongside your other income sources—can help you avoid lifelong regrets.

4. Don’t Rush Into Housing Changes
Selling your house or moving away from your social network might sound smart financially—but it often leads to regret. Retirees have shared that leaving too quickly led to isolation and logistical headaches. Joe and Big Al suggest “test-driving” new locations with short-term rentals before making big decisions. Compatibility with your lifestyle matters more than property values.

5. The Role of Passive Income
Many retirees wish they had built more passive income streams—dividends, real estate, bond ladders, and synthetic dividends through ETFs or mutual funds. These assets create reliable income without the need to withdraw principal. But diversification still matters. Chasing yield can increase risk or tax liability. A balanced portfolio helps smooth the ride.

6. The Debt Problem
Debt is a major regret—especially credit card balances, auto loans, and even student debt. Joe and Big Al recommend organizing all debts and creating a payoff strategy like the snowball or avalanche method. It’s not just about entering retirement debt-free—it’s about managing the debt you have with a clear plan and low stress.

7. What Retirees Say About Their Lifestyle
Some retirees wish they had spent more on experiences and less on things. Others found that retirement left them bored or struggling to find purpose. The transition from work to retirement is harder than most expect. Even spending more time with your spouse can create new tension after decades of work-life separation. Be intentional about filling your days with meaning, not just leisure.

8. Health and Longevity: The New Retirement Frontier
As Mickey Mantle once said, “If I knew I was going to live this long, I’d have taken better care of myself.” That line hits hard in retirement. Today’s retirees are more health-conscious, and it pays off. A healthy lifestyle doesn’t just reduce costs—it boosts energy and longevity. Make exercise, nutrition, and mental well-being part of your retirement plan.

9. The Retirement Curveball: Early Exits
Over half of retirees leave work earlier than planned—due to health issues, caregiving needs, or workplace dissatisfaction. And for 1 in 5, the emotional adjustment is tougher than expected. That’s why financial freedom alone isn’t enough. You need purpose, connection, and routine to thrive.

Final Thoughts
Regret doesn’t have to be part of your retirement story. Learn from those who’ve been there—build a strategy that includes flexibility, health planning, social connection, and real income. With the right plan, retirement can be everything you dreamed—minus the “should haves.”

Intended for educational purposes only. Opinions expressed are not intended as investment advice or to predict future performance. Past performance does not guarantee future results. Neither the information presented, nor any opinion expressed constitutes a solicitation for the purchase or sale of any security. Consult your financial professional before making any investment decisions. Opinions expressed are subject to change without notice.

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• Investment Advisory and Financial Planning Services are offered through Pure Financial Advisors, LLC. A Registered Investment Advisor.

• Pure Financial Advisors, LLC. does not offer tax or legal advice. Consult with a tax advisor or attorney regarding specific situations.

• Opinions expressed are subject to change without notice and are not intended as investment advice or to predict future performance.

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• Intended for educational purposes only and are not intended as individualized advice or a guarantee that you will achieve a desired result. Before implementing any strategies discussed you should consult your tax and financial advisors.

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