The 457(b) “Cheat Code” for Early Retirees
If you want to retire before 59½, one of the most useful accounts you can have is also one of
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Part 3: Build Your Own Roth Conversion NPV Model
This is Part 3 in a series on Roth conversions. If you haven’t read Part 1 and Part 2, you
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Five Things I Do Choose to Optimize (Even Though I Value Sleep)
In a recent post, I listed five things I choose not to optimize in favor of sleeping well at night
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The Risks Nobody Talks About: Fraud, Fees, and Financial Decisions as You Age
When people think about financial risk, they are usually picturing market volatility. They worry about a concentrated stock position that
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Part 2: When Roth Conversions Win Big
When do Roth conversions pay off? Explore the impact of lower tax brackets today, higher future tax rates, ACA subsidies, and RMD planning.
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Roth Conversions Using a Discounted Cash Flows (DCF) Framework
Part 1: When Should You Do Roth Conversions and Why do Most Calculators Get the Analysis Wrong? There is no
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How to Rebalance Your Portfolio Without Creating Unanticipated Tax Problems (Plus a Rebalancing Calculator)
Rebalancing triggers taxes if you’re not careful. Here’s a framework for rebalancing across taxable, pre-tax, and Roth accounts without the tax hit.
Putting It All Together — The Ben & Leslie Case Study
The final post in our series examines how early retirees Ben and Leslie navigate ACA subsidies and college aid with a graduating senior and a $2.5M net worth
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Coloring Outside the Lines: Tax Strategies that are clearly Not allowed
Financial independence is about working within the rules, not gaming the system. In this article, we explore five financial red lines that early retirees should never cross, from the “audit lottery” and fake business deductions to FAFSA asset hiding, offshore accounts, and Medicaid transfer schemes. We also examine the legal alternatives that can help you achieve the same goals without risking audits, penalties, or fraud allegations.
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The Ethics of Optimization: Tax Credits, Safety Nets, and Social Contracts
Is accessing means-tested public subsidies as a wealthy early retiree legal, moral, or both? Part 6 explores the ethics of FIRE optimization, and offers three practical tests to determine where to draw your personal ethical line.
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