Tax Planning
13 articles on this topic.
The 0% Long-Term Capital Gains Bracket: Who Gets It and How to Use It
Long-term capital gains can be taxed at zero percent at the federal level. The income threshold is wider than most people realize, and the planning value is significant for early retirees and lower-income years.
The Roth Conversion Decade: Why the Years Between Retirement and RMDs Matter Most
The years between retirement and required minimum distributions are often the highest-leverage tax-planning window of a lifetime. Here's how to think about Roth conversions during it.
Asset Location: The Quiet Tax Win Most Investors Miss
Holding the same portfolio in the wrong account types can cost real money over a lifetime. The principle is simple — the execution is where most plans go wrong.
The Concentrated Stock Position Problem: Five Ways to Solve It
Holding too much of one company — typically your employer or an inherited holding — is one of the most common sources of avoidable risk in HNW portfolios. The unwind is harder than it looks.
Donor-Advised Funds: The Most Underused HNW Strategy
A donor-advised fund decouples the timing of your tax deduction from the timing of your charitable giving. For most high earners doing meaningful giving, it's the right tool — and it's nearly free.
Tax-Loss Harvesting: What It Is and When It Actually Helps
The mechanics of tax-loss harvesting — and an honest look at when the tax savings are real, when they're overstated, and when it doesn't apply at all.
QCDs: The Tax Move Every Charitable Retiree Over 70½ Should Know
Qualified charitable distributions let you give from your IRA tax-free, satisfy your RMD, and preserve other deductions. For charitable retirees, it's almost always the most efficient way to give.
Bunching Charitable Deductions: How TCJA Made an Old Strategy New Again
The 2017 doubling of the standard deduction made annual charitable giving tax-invisible for most households. Bunching multiple years of giving into one tax year solves it.
The Backdoor Roth and Mega-Backdoor Roth, Explained
Two legal strategies that let high earners put meaningful dollars into Roth accounts despite income limits. The mechanics, the traps, and when they're worth doing.
The Step-Up in Basis at Death: A Tax Cliff Worth Planning Around
Holding appreciated assets until death wipes out the embedded capital gains tax for your heirs. Most people know that. The planning question is which assets to hold, which to sell, and when.
When a Pilot Should Consider a Roth Conversion
Airline pilots often have an unusually clean Roth conversion window — if they know when it opens and when it closes. The planning rules that matter most for Age 65 retirees.
When a Pilot Should Actually Move States (and When They Shouldn't)
Many pilots have meaningful flexibility on where to live. Over a 25-year career, the difference between a no-tax state and a high-tax state can run into seven figures. Here's the realistic framework.
The SWA 401(k) Decision: Pre-Tax, Roth, or After-Tax?
Southwest Airlines pilots and employees with access to all three contribution buckets face a real planning question every year. The right mix depends on age, income, marginal bracket, and what comes next.
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