Retirement tax planning doesn’t happen in April; it happens throughout the year. Learn how to monitor your MAGI, manage Roth conversions, harvest capital gains and losses, and avoid costly ACA subsidy surprises with this annual income review checklist.
The Annual MAGI Review: A Year-End Checklist for Early Retirees Read Post »
In a recent post, I wrote about how people pursuing early retirement constantly face a choice between two competing financial
Five Things I Choose Not to Optimize (For My Own Sanity) Read Post »
What is the best withdrawal strategy for early retirement? Learn the ideal order of operations for accessing your brokerage account, Roth IRA, traditional IRA, Roth conversion ladder, and 457(b) plan while minimizing taxes, maximizing ACA subsidies, and avoiding early withdrawal penalties before age 59½.
The Early Retirement Order of Operations Read Post »
Locked out of a Roth IRA because of your income? Learn how the Backdoor Roth works, when it makes sense, and how to avoid common tax mistakes.
Backdoor Roth 101: What It Is, Who Needs It, and Where It Breaks Read Post »
Should you maximize every dollar or maximize your peace of mind? This post looks at the fundamental clash between financial optimization and the “Sleep Well At Night” (SWAN) philosophy across cash buffers, Roth conversions, college savings, and paying off a mortgage early.
Sleeping Well at Night (SWAN) vs. Optimization: Choose Your Early Retirement Philosophy Read Post »
Standard financial education teaches us how to build wealth, but completely ignores how to defend it. When dealing with high-pressure wealth managers and complex products, survival requires mastering one crucial skill: looking a pro in the eye and realizing “No” is a complete sentence.
No is a Complete Sentence: Playing Financial Defense Against Financial Pros Read Post »
Does asset location actually matter? In Part 2, we add a realistic wrinkle to the math: ongoing contributions. Find out how a simple organizational tweak can save over $76,000 in retirement taxes, why a smaller pre-tax balance is secretly awesome, and why you officially have permission to ignore all of it if you want to.
Part 2: Does Asset Location Actually Matter? Read Post »
Every “three-fund portfolio” investor has heard the standard advice to put bonds in pre-tax and stocks in Roth. It sounds good, but what is the actual dollar value of that organization? We put two identical $500,000 portfolios head-to-head for 20 years to quantify the exact after-tax impact.
How Much Does Asset Location and Tax Drag Actually Matter? Read Post »
When the market drops and stays down, you don’t need another lecture on portfolio risk. You need a factual, step-by-step response plan. This post breaks down four levers you can actually pull in a bear market to protect your cash flow and preserve your wealth for the recovery.
What Happens When Markets Drop? Your Response Playbook Read Post »
Everyone has a plan until they get punched in the mouth.” This post looks at why early retirement strategies often fail during a market crash, and why you need an Investment Policy Statement, including the specific sections, including asset targets, investment philosophies, and glidepaths you should include
