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The Ultimate Pre-Retirement Checklist: Everything to Do in the 5 Years Before You Retire

August 25, 2025 · Personal Finance

Photo-realistic, senior-friendly scene that visually introduces the section titled 'The Last 6 Months: Fine-Tuning and Paperwork'.

The Last 6 Months: Fine-Tuning and Paperwork

The home stretch is all about execution. You’ve made the big decisions, and now it’s time to file the paperwork and tie up any loose ends. Attention to detail now will prevent headaches later.

Submit Your Applications

You can apply for Social Security benefits up to four months before you want them to begin. The process can be done online at SSA.gov and is relatively straightforward. Similarly, you will need to submit the final paperwork to your company to start your pension payments. Give yourself plenty of lead time for these processes.

If you are turning 65, be sure to complete your Medicare enrollment. Missing your deadline can result in lifelong penalties, so mark your calendar carefully.

Update Your Estate Plan

A major life change like retirement is the perfect time to review and update your estate planning documents. Make sure your will or trust reflects your current wishes. Check the beneficiaries listed on your 401(k)s, IRAs, and life insurance policies. These beneficiary designations override what’s written in your will, so it’s critical that they are up to date. You should also review your powers of attorney for both healthcare and finances.

Consolidate and Simplify

Over a long career, it’s easy to accumulate multiple old 401(k)s and IRAs at different financial institutions. Now might be a good time to consolidate them by rolling them over into a single IRA. This makes your portfolio much easier to manage and track. It simplifies paperwork, reduces the number of statements you receive, and gives you a clearer picture of your overall asset allocation.

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