HeyJaredRetire With Confidence
Retire With Confidence is the podcast designed to help you move beyond the fear of the complexity of finances so you can be financially free to achieve personal significance. Tune in with Josh Duncan each week to turn fear into fuel that drives you into Freedom & Significance.
- Indexed episodes, last 90 days
- 13
- Latest publication
- Sep 30, 2026
- Audience
- Checking…
- Earliest in this view
- Jul 8, 2026
Latest episodes
No Tax on Social Security? Here's What the Law Really Says (opens the original)
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No tax on Social Security never became law. What passed is a $6,000 deduction for people 65 and older, and your income decides whether you see a dollar of it. Josh Duncan explains how the deduction works when you file: $6,000 per person 65 or older, $12,000 for a couple who both qualify, claimed on the new Schedule 1-A whether you itemize or take the standard deduction, and stacked on the extra standard deduction you already had at 65. This episode covers: How combined income decides the taxable
Step-Up in Basis: Should You Gift Assets Now or Wait? (opens the original)
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Gifted stock carries your cost basis to your children, tax bill included. Josh explains why that is still no reason to hold everything until you're gone. Josh Duncan, partner at F5 Financial Planning, a fee-only fiduciary firm, treats the tax cost as one input among several: how much you can afford to give, what your children need right now, and how appreciated the asset is. A gift you can't comfortably afford isn't generous. It's a risk to your own plan. Cash carries no capital gains question a
Should You Pay Medical Bills Out of Pocket to Grow Your HSA? (opens the original)
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Letting your health savings account grow is the right move for some people and the wrong move for others, and the difference is cash flow, not discipline. An HSA is the only account in the tax code where money goes in untaxed, grows untaxed, and comes out untaxed for qualified medical expenses. Most people collect two of the three and treat the account like a coupon for this year’s doctor visits. Josh Duncan, fee-only fiduciary and partner at F5 Financial Planning, names the one condition that h
Writing a Check to Charity Got More Expensive in 2026 (opens the original)
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Two changes to the charitable deduction take effect in 2026, and a qualified charitable distribution from your IRA sidesteps both of them. Starting in 2026, itemized charitable gifts only count once they exceed half a percent of adjusted gross income, and the top value of any itemized deduction falls from 37 cents on the dollar to 35 cents. Required distributions push a retiree’s income higher every year, so the people who give the most absorb the biggest hit. Josh Duncan, partner at F5 Financia
Will Medicare Pay for a Nursing Home? (opens the original)
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Medicare will not pay for most long-term care. The costs land on you, and there are exactly three ways to cover them. Josh Duncan puts numbers on the risk a 65-year-old actually faces: about a 70% chance of needing care someday, paid help at home near $80,000 a year, a private nursing-home room near $130,000. The dangerous cases are the long ones, and they land late in retirement, when a plan has the least room to recover. F5 is a fee-only firm—we sell no insurance and earn no commissions, so th
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