Mailbag: Disney Trips, $500K Decisions & Quitting Your Job at 50
Retirement InvestingListen:
On This Episode
Major life decisions (like taking a big trip or starting a business) can all have lasting effects on your financial future. The impact isn’t always obvious upfront, but without a solid plan, even a well-intentioned move can throw retirement off course. In this episode, Mark talks about making smart choices before money becomes a source of stress. It’s not just about cutting back or saying no, it’s about understanding how each decision fits into the bigger picture.
This week, Mark answers three very real—and very different—listener questions, all tied together by one key theme: you need a plan. From a big family trip to Disney World to launching a photography business in your 50s, Mark breaks down how to think through major financial decisions before they disrupt your retirement goals. Big decisions don’t have to derail your plans, but only if you plan first.
Here’s what we discuss in today’s show:
💰 Turning $500K into reliable income
📉 The annuity pitch and why to think twice
🧾 Health insurance after leaving a full-time job
⚠️ Why entrepreneurship in your 50s requires extra caution
🏰 Can you afford Disney before you retire?
Thanks for joining us! We’ll be back for another show every other Thursday.
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