THE ROTH GUY

5 Ways Wishful Thinking Can Damage Your Retirement (Part 2)
May 29, 2025

Wishful thinking feels comforting, but in retirement planning, it can quietly sabotage your future. In this second installment, Jude breaks down five more dangerous assumptions people make when planning for their golden years. From relying too much on Social Security to assuming Medicare will handle long-term care, this episode challenges listeners to face financial realities with clarity and strategy.

You’ll also hear why banking on your kids to support you, postponing retirement with unrealistic expectations, or planning to sell your house and “make it work” could all backfire. Jude unpacks real-life stories and offers practical steps to help you move from simply hoping to a sound, adaptable plan. If you’ve ever thought, “I’ll figure it out later,” this episode is your reality check.

📌 Here’s some of what we discuss in this episode:

🚫 Common planning mistakes and false beliefs

🏠 Downsizing might not free up the cash you expect

👨‍👩‍👧 Counting on your kids? Think again

💵 Social Security might not stretch far enough

🧯 Putting out fires before it’s too late

0:00 – Intro

0:45 – “Social Security will be enough”

2:53 – “I’ll just keep working”

5:23 – “Healthcare costs will improve on Medicare”

6:58 – “My kids will take care of me”

9:34 – “I’ll just sell the house”

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Episode Transcript

Note: This transcript was produced using AI, so please excuse any typos and inaccuracies…

00:00

We’re going to do part two of ways that wishful thinking can maybe not be the best way to go into financial planning or retirement again this week here on the Roth guy. So let’s get it started flying high above the metropolis. It’s the Roth Guy with holistic wealth advisor, Jude Wilson.

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