Five Key Retirement Challenges (and Solutions), Ep #393

Most people focus on saving for retirement, but what happens when you actually get there? Retirement isn’t just about having enough money—it’s about managing risks that can threaten your financial security and lifestyle. 

In this episode, we explore Five Key Retirement Challenges (and Solutions), inspired by a Kiplinger’s Personal Finance article by Walt West. From unexpected market downturns to rising healthcare costs, these challenges can catch retirees off guard if they’re not prepared.

We break down each challenge—financial instability, healthcare expenses, taxes, inflation, and estate planning oversights—and discuss practical strategies to navigate them. Learn how to structure a flexible withdrawal plan, prepare for long-term care costs, use tax-efficient strategies like Roth conversions, and ensure your estate plan protects your loved ones. 

Plus, we tackle a listener question about using a MIGA ladder strategy to bridge the gap until Social Security—offering insights into the pros and cons of annuities in a retirement portfolio.

If you want to retire with confidence and avoid costly missteps, this episode is a must-listen. Whether you're years away from retirement or already in it, understanding these key challenges and their solutions can help you make smarter financial decisions for the road ahead.

Outline of This Episode

• (0:00) 5 Key Retirement Challenges (and Solutions)
• (1:17) Retirement headline: Kiplinger’s article on retirement challenges
• (1:42) Challenge #1: Financial instability
• (4:09) Challenge #2: Healthcare and long-term care costs
• (6:33) Challenge #3: Taxes in retirement
• (7:33) Challenge #4: Inflation’s impact on retirement income
• (8:32) Challenge #5: Estate planning oversights
• (10:25) Listener question: MIGA ladder strategy for retirement income

Resources & People Mentioned

• The Retirement Podcast Network
• Kiplinger’s Personal Finance “Five Key Retirement Challenges” by Walt West
• Fidelity’s Healthcare in Retirement Report

Connect with Benjamin Brandt

• Get the Retire-Ready Toolkit: http://retirementstartstodayradio.com
• Subscribe to the newsletter: https://retirementstartstodayradio.com/newsletter
• Work with Benjamin: https://retirementstartstoday.com/start

Get the book - out now!Retirement Starts Today: Your Non-financial Guide to an Even Better Retirement

Follow Retirement Starts Today inApple Podcasts, Spotify, Overcast, Pocket Casts,