Rollover the old 401(k) the week you quit?
You can lose three things an IRA never has: NUA on employer stock, unlimited ERISA creditor protection, and Rule of 55 withdrawals.
IRA wins on QCDs and Roth conversions.
Have you checked those three before you sign?
The QCD shows on Form 1099-R. Box 2a is often the full distribution. The exclusion is on the return, not the 1099.
Send IRA dollars to a DAF and it is not a QCD. Public charity only (or the one-time CRT/CGA path).
Have you matched the 1099-R to the 1040, or only the receipt?
A $40k RMD plus a $40k check to charity still lands $40k in AGI if you take the standard deduction.
A QCD at 70Β½+ sends the IRA dollars straight to the charity. 2026 cap: $111k per owner. Counts toward the RMD. Stays out of MAGI.
Have you paired next year's RMD with a QCD?
Gift appreciated stock now and your kids inherit your $80k basis on a $400k lot.
Die holding it and IRC 1014 resets basis to date-of-death value. Same sale. Far less capital-gains tax.
IRAs do not step up. Brokerage lots do.
Which lots are you still planning to gift?
Side hustle at $30k net?
SEP-IRA max is ~$5,580.
Solo 401(k): $23,500 employee deferral plus employer profit-share. Same income. About $19k more shelter.
W-2 already maxed? You still get the employer slice on the side income.
Have you compared the two plans?
IRMAA is a cliff, not a slope.
$1 of MAGI over the tier and the full surcharge hits for the year. Not just the dollar over.
2024 income sets 2026 Part B/D premiums. That Roth conversion or big RMD shows up 24 months later.
Have you mapped MAGI two years before Medicare?
HSA: deduct now, grow tax-free, withdraw tax-free for qualified medical.
Pay cash, invest the HSA, reimburse years later with receipts. Same dollars, three tax wins.
Triple-tax stack only works if you keep the receipts.
Are you investing the HSA or spending it?
Inherited traditional IRA + your own Roth conversions in the same year is how heirs jump a bracket.
SECURE 2.0 already forces the inherited account empty in 10 years.
Convert your IRA in a low-income year. Empty the inherited IRA in a different year.
Have you split those two?
Holding heavily appreciated employer stock in a 401(k)?
Rolling to an IRA could be a $50k+ tax mistake.
NUA rule (IRC 402(e)(4)):
1. Move stock in-kind to brokerage
2. Pay ordinary tax ONLY on basis
3. Growth taxed at LTCG (20% vs 37%)
Have you checked your 401(k) basis?
You inherited an IRA. No annual RMDs required.
Wrong.
Under SECURE 2.0, non-spouse beneficiaries must:
- Empty the account in 10 years
- Take annual RMDs in years 1-9 if the owner had started distributions
Missing a year: 25% penalty.
Have you modeled the tax impact?
High-yield bond funds fall with equities. Correlation ~0.65.
When they do, harvest the loss. Swap to a different HY fund for 30 days to avoid wash-sale.
That capital loss offsets gains elsewhere at ordinary income rates.
Are you harvesting losses in your fixed income?
Medicare Advantage: $0 premium. Network restrictions. $8,000+ OOP max.
Medigap Plan G: $150-$220/mo premium. No network. Covers ~100% of costs.
In a healthy year, MA saves you $1,800-$2,600.
One major hospitalization, Medigap pays for itself 3x over.
Which are you modeling?
Roth conversions before 70 aren't about tax today.
They're about Social Security tax later.
Every $1k of pre-tax RMD can make $850 of SS taxable at 73.
Convert $30k at 22% at 65 to avoid SS taxed at 24%+ later.
Have you modeled provisional income?
Early retirees lose employer coverage. Medicare starts at 65. Gap: up to 10 years.
ACA bridges it, but cross the subsidy cliff by $1 and you lose $15,000+ in premium credits.
Roth vs. taxable sequencing determines which side you're on.
Are you modeling MAGI?
Medicare premiums are income-based.
Cross $106K MAGI: +$74/month.
Cross $167K: +$185/month.
Cross $200K: +$296/month.
Based on income from 2 years prior.
That Roth conversion in 2024 shows up in your 2026 Medicare bill.
Are you modeling this?
Your spouse claimed at 70. Monthly benefit: $3,200.
If they die first, you inherit their full benefit. Not your smaller one.
That's $1,500+/month more than claiming on your own record.
Is your retirement plan modeling both lifetimes?
A GRAT moves appreciation to heirs without gift tax.
Transfer the asset. Annuity payments return to you. Remaining growth passes tax-free.
Underperforms? Trust unwinds. You get everything back.
Estate tax savings. No real downside.
Have you modeled this?
In early retirement, taxable income often drops to the lowest level since your 20s.
Before Social Security and RMDs, it's the cheapest time to convert IRA dollars to Roth.
Fill the 12% bracket now. Pay 22%+ later when RMDs force it.
Are you converting?
Roth conversion ladder: retire early, access pre-tax money before 59Β½.
Convert IRA to Roth. Wait 5 years. Withdraw that principal penalty-free.
Repeat annually. Each conversion starts a fresh 5-year clock.
Are you staging conversions now for access in 5 years?