HeyJaredRetirement Starts Today
Do you want to spend more money in retirement, while paying less taxes? Great news, you're in the right place! I'll also teach you the benefits of retiring TO something, while most retirees only solve half the equation by retiring FROM something.
- Indexed episodes, last 90 days
- 12
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- Sep 21, 2026
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- Jul 6, 2026
Latest episodes
Using IRAs To Reduce Estimated Tax Penalties (opens the original)
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Did you receive a windfall late in the year and then get penalized for not paying estimated taxes on it earlier? It doesn't seem fair, but the IRS might levy a penalty for that. There is a way to fix it - and similarly for RMDs you might take out in December too. That's the main focus on today's Retirement Headline - and it fits in nicely with our Listener Question as well. Resources: Article by Jeff Levine on the Nerd's Eye View Blog: Using Retirement Accounts To Reduce Estimated Tax Penalties
6 Cases When a Roth IRA Conversion Isn't a Smart Move (opens the original)
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A Barron's piece from Jonathan Shenkman shares 6 reasons to think twice before you convert a Roth IRA. I agree with some of them - but strongly disagree with others because they apply to Super Savers - listeners of this show - differently. We will go through all six with my additions for a Super Saver like you. Then we answer a listener question from a 62 year old who is about to retire and wants to bridge the gap until he begins pulling in Social Security at age 70. And you know we have a great
Why I Object to 'Hitting a Number' for Retirement (opens the original)
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Christine Benz got a text from a friend the other day. A mutual friend from college was retiring because he'd "hit his number in the stock market". Most people would read that and think, good for him. Benz says all her alarm bells went off. Not out of envy. In her experience, "I hit my number" is usually a sign that the plan behind it isn't much of a plan. Today we discuss two different ways Christine says people gets this wrong. We also tackle a listener question asking if $1,000,000 is enough
The 'Open Sandwich' Generation (opens the original)
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The term "Sandwich Generation" has been around since the 80s. You're the one in the middle - with aging parents on one side and dependent kids on the other. Dan Haylett shared an article he calls The "Open Sandwich" Generation, which is after your parents pass away. We will discuss Dan's article on what happens when the slices come off. In our Listener Question segment, I'm asked "How do you do estate planning when you don't have anybody to name?" And we wrap it up with a story that hits true to
Your $135,000 Retirement Risk (opens the original)
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The 2025 Milliman Long-Term Care Index put a number on long-term care: $135,000, the lump-sum amount an average 65-year-old would need to set aside today to cover the expected lifetime cost of long-term care. But there are some details you need to know that make up that number. About half of those who need paid long-term care only do so for less than a year (averaging $30,000 in total cost). The other half need care for more than 5 years at an average of $665,000. $135,000 is just the average. W
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