Tax Guides

148 guides, built from the primary documents. Pick a topic to filter.

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• Roth conversionsJun 14, 20264 min

  Reverse Rollover Trap: Trapping $250k in a Bad 401(k)

  Every tax season, high-earning clients sit across my desk and say the same thing: "My financial advisor told me I need to do a Backdoor Roth."When I point out they...

• Roth conversionsJun 14, 20267 min

  When Is a Roth Conversion NOT Worth It? Seven Times to Skip It

  Almost everything written about Roth conversions is a sales pitch — convert, convert, convert. The truth is more boring: a conversion is just prepaying a tax bill, and prepaying only...

• Roth conversionsJun 14, 20264 min

  Can You Contribute to a Roth IRA if You Are Married Filing Separately?

  You are married, you both work, and you decided on married filing separately for your taxes this year. Usually, I see this happen for one of two reasons: you want...

• Roth conversionsJun 14, 20266 min

  RSU Roth Income Limit: Are You Locked Out After Vesting?

  You checked your paycheck, and the numbers finally look the way you've always wanted them to. Your company just released a massive block of Restricted Stock Units (RSUs), and your...

• Roth conversionsJun 14, 20265 min

  What Is a 72(t)? The SEPP, Explained & - and Why You'd Even Want One

  A 72(t) is one of those tax terms that sounds impossible until you see the problem it solves — and then it’s simple. So let’s do it backwards. Instead of...

• Roth conversionsJun 14, 20268 min

  Roth Conversion Ladder vs. 72(t): Two Ways to Reach Your IRA Before 59 1/2

  Retire in your early 50s and you run straight into a wall: most of your money is locked in a traditional IRA or 401(k), and pulling it out before 59½...

• Roth conversionsJun 13, 20267 min

  How the Spousal Backdoor Roth Works, Step by Step (Funding a Roth for a Non-Working Spouse)

  A spouse with no paycheck can still put money into a Roth IRA every year. Most one-income households never realize it, so the non-working spouse’s retirement account sits empty while...

• Roth conversionsJun 13, 20267 min

  Backdoor Roth Mistake Fix: A Triage Guide to Every Common Error

  Most backdoor Roth “disasters” are fixable. The catch is that the right fix to a backdoor Roth mistake depends entirely on which mistake you made — and two of them...

• Roth conversionsJun 13, 20269 min

  Will a Roth Conversion Spike My Medicare (IRMAA) Premiums? What Higher-Income Retirees Need to Know Before Converting

  You are 63, still working, and you have finally decided to start moving some of that large traditional IRA into a Roth before you retire. The logic is sound: convert...

• Roth conversionsJun 11, 20268 min

  When to Stop Backdoor Roth: Is It Still Worth Doing?

  You set this up four years ago. Every January you move the money into the Traditional IRA, convert it to the Roth a few days later, and file the Form...

• Roth conversionsJun 11, 20268 min

  Roth Conversion ACA Subsidy Cliff: How Much Can I Convert Without Losing It?

  You retired at 57. You are living off a brokerage account and some cash, your taxable income is low on purpose, and that low income is buying you a heavily...

• Roth conversionsJun 9, 20268 min

  Backdoor Roth Pro Rata Rule: How It Can Ambush Your First Conversion

  This is the first year a direct Roth IRA contribution is off the table for you. You got the raise, or the bonus, or the promotion, and now your income...