The Retirement Tax Trap No One Warned You About

Money Wisdom

Most people go into retirement assuming their taxes will drop, but what if that assumption sets you up for a nasty surprise? In this episode, Jake and Nick unpack the “tax trap” that catches countless retirees off guard. It’s a hidden pitfall that turns decades of diligent saving into unexpected tax bills when you finally tap into your nest egg.

They will reveal how common retirement strategies, like deferring taxes through 401(k)s and IRAs, might backfire if not planned for properly. They also break down why general financial advice may not serve you well once you're within 10 years of retirement, and what to consider instead. You’ll hear practical discussion about Social Security taxation, Roth conversions, and how legacy goals shape tax strategy. This episode doesn’t just teach you how to avoid mistakes, it urges you to ask better questions about how and when to pay Uncle Sam.

Here’s what we discuss in this episode:

💥 The myth of lower taxes in retirement

📉 Social Security surprise tax bills

🧾 Timing your “tax check” for maximum savings

🏛️ Roth conversions and smarter legacy planning

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