Checklist: 10 Things to Review 5 Years Before Retirement

Thinking about retirement often brings both excitement and questions. Five years before reaching your retirement age is the perfect time to pause and look at a few essentials. This short window can make a big difference in how smooth the transition will feel.

1. Adjust Any Outstanding Debts

Carrying debt into retirement can add unnecessary stress. Even a small credit card balance or lingering loan can eat into monthly income. Did you know that according to the Federal Reserve, nearly 40% of adults over 65 still carry some form of debt? Tackling it early gives you more flexibility once your paycheck stops.

2. Review Life and Health Insurance Policies

Life and health coverage often shift after you leave the workforce. Medicare begins at age 65, but gaps can remain. Looking into supplemental health insurance or long-term care options before retiring can prevent unexpected costs. Many retirees also revisit life insurance needs to see if the policy still matches family responsibilities.

3. Strategies to Maximize Social Security and Pensions

Timing matters when it comes to Social Security. Waiting until full retirement age—or even later—can mean a higher monthly benefit. For those with pensions, it’s worth understanding the payout options and how they align with your retirement income needs. Small adjustments in timing and choice of benefits can add up over the years.

4. Understand Retirement Communities and Housing Options

Some people picture a retirement home or retirement communities near me searches, while others prefer staying put. Exploring options now helps avoid rushed decisions later. Touring retirement communities or learning about the requirements of a reverse mortgage can be part of preparing a secure and comfortable living arrangement.

5. Run a Retirement Calculator Check

A retirement calculator is a simple tool that gives clarity. It can estimate income, expenses, and how long savings may last. Using one five years before retirement provides a reality check and highlights areas to adjust—whether it’s paying off debt, reviewing housing costs, or making sure insurance needs are covered.

6. Explore Retirement Solutions for Lifestyle Goals

Some retirees dream of travel, while others want to stay close to family. Understanding your likely expenses for hobbies, healthcare, or even moving into retirement communities helps connect the numbers with real life. This is where retirement strategies go beyond paperwork—they support the life you want to live.

7. Double-Check Legal Documents

It’s not the most exciting task, but reviewing wills, powers of attorney, and healthcare directives avoids confusion later. Having these in place ensures your preferences are respected and your loved ones have clear guidance.

8. Prepare for Healthcare Beyond Insurance

Medical expenses are one of the biggest retirement costs. The average couple retiring at 65 may need hundreds of thousands of dollars for healthcare over a lifetime. Looking into preventive care, wellness habits, and options for covering long-term care needs can make a real difference.

9. Evaluate Your Retirement Age Flexibility

Some people plan to retire at 62, others at 67, and many choose to keep working part-time. Being clear about your options five years out helps align expectations with reality. Even adjusting your retirement age by one or two years can influence Social Security, healthcare coverage, and overall lifestyle.

10. Map Out Everyday Routines

Retirement isn’t only about finances. It’s also about how you’ll spend your time each day. Exploring volunteering, part-time work, or hobbies now makes the transition less abrupt and more fulfilling.

Retirement isn’t one-size-fits-all. From understanding reverse mortgage requirements to exploring retirement communities, the steps you take five years before can help you navigate this stage with greater confidence. At Penny Lane Financial, we offer retirement support and guidance that fits your unique path—helping you move forward with clarity and peace of mind.

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