Planning
22 viewpoints on this topic.← All viewpoints
Planning is the through-line of this site. Most of the essays below are about decisions that look optional in your forties and become irreversible in your sixties: when to do Roth conversions, whether your beneficiary forms still match your will, how to think about sequence-of-returns risk before retirement actually starts. Each one is a long-form answer to a question I've been asked repeatedly across two decades of practice.
Have you run the RMD calculation most pre-retirees skip?
The IRS starts forcing withdrawals from your pre-tax accounts at 73. Most people have never projected what that does to their tax bracket.
Which tax moves only work before you retire?
The highest-leverage tax moves in retirement are set up before you retire. Here's what the window looks like and what happens when it closes.
Is your retirement plan budgeting for the IRMAA surcharge?
One number changes your Medicare costs permanently. Most retirees find out what IRMAA is after they get the bill.
Is chasing dividend income in retirement a mistake?
Most retirees chasing dividend income are solving for the wrong problem. Here's what that costs them in taxes and returns.
What is your beneficiary designation doing to your estate plan?
The beneficiary form you filled out in 2009 still controls your retirement account. Here's what that's quietly costing your estate.
Does your average return determine whether your retirement lasts?
Everyone focuses on average returns. Nobody runs the scenario where the bad years arrive first. Here's why sequence of returns risk is the variable that actually determines whether your retirement holds.
Which retirement spending assumption quietly breaks most plans?
Your retirement projection assumes spending drops when you stop working. Some does. The parts you forgot about tend to spike. Here's what the real spending curve looks like.
Is the cash in your retirement account actually costing you money?
Cash in a retirement account feels safe. But every dollar of it carries a locked-in tax liability and a compounding opportunity cost. Here's what it's costing you.
What does delaying Social Security actually cost you?
Delaying Social Security sounds smart until you run the math nobody does. Here's how to know if it actually pays off for you.
Why does a "good enough" portfolio usually beat your best one?
Optimization is seductive, but the portfolio you'll actually stick with through three bad quarters beats the one that looks perfect on paper. A practical case for boring, durable allocation choices.
Should you do a Roth conversion in your sixties?
Half the Roth-conversion advice on the internet is built for the wrong client. Before you convert a single dollar, here are the four questions that decide whether the math actually works for you.
Do you actually have a financial plan, or just investments?
Most people I meet have a portfolio, a 401(k) statement, and a vague feeling that things are probably fine. None of those is a plan. Here's the simple verbal test I run with prospective clients in the first ten minutes, and what every "no, but…" answer is really telling you.
What net worth number actually signals financial independence?
Net worth is the wrong number. The one that actually tells you when you can retire is one most people have never calculated.
Is private school quietly derailing your retirement?
Private school gets treated as a parenting decision. The $500,000 to $1,000,000 K-12 commitment is also a financial planning decision. Most families never model both.
Where do people get financial timing wrong?
The strategy might be right. The timing of it might be all wrong. Here's where getting the sequence backwards costs people the most money.
What deferred tax bill is hiding inside your retirement accounts?
Your retirement account statement shows you the gross balance. The net balance, what you actually own after the deferred tax bill, is a different number.
What does the lake house really cost once you run the math?
The lake house is affordable. What it actually costs over its lifetime, almost nobody runs. Here's the math.
What identity trap drains new wealth after a liquidity event?
The liquidity event was supposed to bring clarity. Instead it brought a new set of questions nobody prepared you for. That gap is expensive.
Is "pay off the mortgage or invest" actually the wrong question?
The pay-off-the-mortgage vs. invest debate is one of the most argued questions in personal finance. It's also one of the most misframed.
Which number matters more than your investment returns?
Everyone obsesses over returns. The number that actually determines whether you retire on time isn't in your portfolio statement.
Is the 4% rule actually a rule?
The most widely cited number in retirement planning came from one study, one time period, and one set of assumptions. None of which describe your situation.
Why are high earners often the worst at building wealth?
High income feels like it solves financial problems. It solves the cash flow ones. The wealth-building ones, it tends to make worse.
Planning isn't a binder — it's a habit. The viewpoints here are the questions worth revisiting every few years as your income, family, and goals change, because a plan that fit ten years ago is rarely the plan that fits today.