HeyJaredRamp Up to Retirement
You’re nearing your Ramp Up to Retirement, where work will be optional. How do you make the best decisions to set yourself up for success?
- Indexed episodes, last 90 days
- 6
- Latest publication
- Sep 23, 2026
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- Jul 8, 2026
Latest episodes
What Your Parents’ Retirement Can Teach You About Planning Your Own (Ep. 38) (opens the original)
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Your parents’ retirement experience can reveal lessons that are difficult to see while you’re still working. What has changed between their generation and yours, and which financial habits still hold up? In this episode, Dan Reese, CFP®, explains how retirement planning has changed across generations and what you can learn by asking your parents thoughtful questions. He covers the shift from pensions to personal savings, the healthcare gap before Medicare, longer life expectancies, lifestyle cre
Roth vs. Pre-Tax 401(k): Choosing When to Pay Taxes for Retirement (Ep. 37) (opens the original)
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Choosing between Roth and pre-tax retirement savings can feel simple until taxes, healthcare costs, income changes, and future withdrawals enter the picture. In this episode, Dan Reese, CFP®, explains how Roth and pre-tax 401(k) contributions affect when you pay taxes and why the more appropriate choice may change throughout your career. He covers why lower-income years may favor Roth contributions, when pre-tax savings may become useful, and how Roth assets can provide added flexibility in reti
When Should You Claim Social Security? (Ep. 36) (opens the original)
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When should you claim Social Security, at 62, full retirement age, or 70? The answer can affect more than your first monthly payment, including your future income, taxes, portfolio withdrawals, and the benefit available to a surviving spouse. In this episode, Dan Reese, CFP®, explains how Social Security benefits differ when claimed at age 62, full retirement age, or age 70. He examines break-even calculations, annual cost-of-living adjustments, life expectancy, earnings limits, and household cl
Do Roth Conversions Still Make Sense After Tax Law Changes? (Ep. 35) (opens the original)
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If you’re approaching retirement with a large traditional IRA, deciding whether to convert to a Roth account can affect your future taxes, Medicare costs, and what your heirs receive. How do taxes, Medicare costs, retirement income, and estate planning all connect when making this decision? The right decision depends on your situation, not just what tax rates are doing. In this episode, Dan Reese, CFP®, explains how recent tax law changes have shifted the reasons people may evaluate Roth convers
How to Know If Your Financial Advisor Is Really Helping You Plan for Retirement (Ep. 34) (opens the original)
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Are you getting financial advice, or are you simply getting investment updates? Many people build strong relationships with their financial advisor, but that doesn’t always mean every part of their retirement plan is being addressed. Knowing what questions to ask can make a meaningful difference before small planning gaps become bigger problems. In this episode, Dan Reese, CFP®, explains how to evaluate whether your financial plan is covering the areas that matter most. He shares the 3-lane plan
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