21 Things to Do Before You Retire (Part 2)

Nov 12, 2025

Discover critical retirement strategies you might be missing! Learn how to build a healthcare plan to combat rising costs and effectively cover the pre-Medicare gap. Find out why creating a cash buffer is essential for financial security during market downturns. Explore the benefits of entering retirement debt-free and maximizing your HSA for tax advantages. Delve into estate planning to protect your legacy and how to prepare for inflation impacts. Plus, consider a phased retirement strategy for ultimate control!

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INSIGHT

Healthcare Is Retirement’s Biggest Wildcard

Healthcare is the biggest wildcard in retirement because costs and long-term care needs are unpredictable.
Planning converts that uncertainty into a fortified plan that protects both finances and peace of mind.

ADVICE

Master Medicare Parts And Options

Learn Medicare parts A, B, D, Medigap, and Medicare Advantage and how premiums and coverage differ.
Build a plan for which parts you'll use rather than assuming coverage will be straightforward.

ADVICE

Cover The Pre‑Medicare Gap Intentionally

If you retire before 65, plan coverage for the pre-Medicare gap using COBRA, the ACA marketplace, or a spouse's employer plan.
Shop widely and get multiple quotes or use an independent agent to save potentially thousands annually.

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In this episode of The Personal Finance Podcast, Andrew continues with Part 2 of 21 Things to Do Before You Retire revealing 11 more critical milestones most people miss including building a healthcare plan to protect against rising medical costs, creating a 2-3 year cash buffer to survive market crashes, entering retirement debt-free for maximum flexibility, maxing out your HSA for triple tax-advantaged savings, stress-testing your retirement number against inflation and longevity, developing a housing strategy that fits your lifestyle and budget, building guaranteed income beyond Social Security, creating an estate plan to protect your family, planning for Required Minimum Distributions to minimize taxes, and designing a phased retirement to work on your terms, giving you the complete playbook to retire with security and control.

Listen to The Business Show here.

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Watch the 21 Things to Do Before You Retire Part 1 here.

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