Mailbag: How Do I Stop Going in Circles and Make Financial Decisions?


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Mar 13 2024 17 mins  

We’ve got a mailbag edition of the show today! We’ve gathered some great questions over the last several weeks that we’re excited to share with you. From the tax implications of financial gifts to navigating retirement spending and overcoming indecision, Lee is here to shed light on a range of real-world topics.

Dorothy asks for advice on how to financially support her daughter, who wants to take time off work to be with her newborn baby in the hospital, and what the tax implications might look like. Rose asks how to break the cycle of indecision and make confident financial decisions.

We love hearing from you, our listeners! No question is too basic, so if there’s something on your mind that you’d like Lee to answer, be sure to send it our way for your chance to be featured on the show.

Here are the questions we answer in today’s show:

  • “I’m a police officer and have been given medical retirement at 53, but I feel like I need to still be earning money at my age. Any thoughts on how to approach this?”
  • “My daughter wants to take time off work to be with her new baby who is in the hospital. We want to help financially but are unsure about the tax implications and how this might impact our retirement.”
  • “Every time I need to make a financial decision, I end up talking myself in circles. How do I stop this?”
  • “I’m 79 and don’t worry about us running out of money anymore. We don’t have kids and I have regrets about not traveling much in the last decade. Should I start spending to make up for previous years of pinching pennies?”
  • “At 60, I've been offered two work options: stay on for 5-6 years for a pension or retire now with a severance package and pension buyout. How should I decide?”
  • “I'm retiring soon with 18 weeks of vacation and sick leave payout. If I retire in December, it'll be taxed this year. Should I wait until January for a different tax year?”

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