Retirement Income Planning

Accumulating wealth and distributing it are two different problems — and most financial planning is built around the first one. When you stop working, the rules change. The decisions you make in the first few years of retirement carry consequences that compound for decades. I build retirement income plans around that reality, not around a rule of thumb that was never designed for your situation.

A Single Probability Score Isn't a Plan

Most retirement software will hand you a number: 83% chance of success, 91% chance of success. It sounds precise. It isn't especially useful — because a re-run doesn't fix that.

Come back in a year and that number has usually moved. Maybe your accounts had a rough stretch and it dropped from 86% to 72%. Or maybe your accounts did nothing unusual at all, and the number moved anyway because a firm somewhere quietly updated its long-term market assumptions. From your seat, those two situations feel identical. One is a real change in your life. The other is a spreadsheet getting revised in a back office. A static score can't tell you which one just happened to you — and I've sat across the table watching clients try to guess.

Either way, a score isn't an instruction. It tells you that things look better or worse. It doesn't tell you what to actually do about it — spend less, and by how much, starting when?

I plan around guardrails instead: specific portfolio thresholds, set in advance, that trigger a defined spending adjustment before a problem becomes irreversible. If your portfolio grows meaningfully above plan, spending can increase. If it falls meaningfully below plan, a modest, planned trim now protects you far better than a large, panicked one later. You're not waiting for a mysterious new percentage to show up next year. You already know, today, what happens at the thresholds that matter to you.



The same dynamic approach applies to the tax side of retirement income, not just the spending side. Instead of a static projection, I model your income year by year to work around the cliffs that actually cost people money — staying beneath an IRMAA threshold that would otherwise raise your Medicare premiums, or sizing a Roth conversion to fill a bracket without spilling into the next one. Those decisions change every year as your income, accounts, and the tax law itself shift. A plan built once and left alone can't see them coming. A plan that's re-modeled around your actual numbers, every year, can.

Social Security Optimization Is Worth More Than Most Clients Expect

For most pre-retirees, the Social Security claiming decision is the single highest-dollar planning choice in the entire retirement transition — and it is permanent. Claiming at 62 versus 70 can mean a difference of hundreds of thousands of dollars in lifetime income, depending on health, longevity, and how other income sources are sequenced around it.

Every year you delay claiming past full retirement age, your benefit grows by 8%. That is a guaranteed, inflation-adjusted return on a decision that most people treat as a form to file rather than an optimization problem with a right answer. I model the break-even analysis, coordinate spousal benefit strategy, and integrate the claiming timeline with your other income sources so the decision is made with the full picture in front of you — not after the fact.

Income Sequencing: Which Account You Touch First Is a Tax Decision

Most retirees have income coming from multiple sources — a brokerage account, trust distributions, an IRA, passive income, a Roth, Social Security, possibly a pension. The order in which you draw from those accounts is not obvious, and it is not arbitrary. It is a tax decision that determines your effective rate for the rest of your life.



Withdrawal sequencing coordinates account types, tax brackets, Roth conversion windows, and required minimum distribution timing across your entire income picture. Done deliberately, it can reduce your lifetime tax burden significantly. Done without a plan, it can push you into higher brackets, accelerate RMDs, and eliminate Roth conversion opportunities that close permanently once income thresholds are crossed.

• Taxable brokerage accounts, tax-deferred accounts, and Roth accounts are taxed differently — and the order of depletion changes your bracket exposure every year
• Roth conversions during low-income years before Social Security and RMDs begin are among the most valuable windows in retirement planning
• RMD timing and sizing can be managed proactively — but only if the strategy is in place before distributions are required

Healthcare Costs Before 65 Belong in the Income Plan

If you retire before Medicare eligibility at 65, healthcare coverage is a retirement income planning issue — not a separate conversation. COBRA, ACA marketplace plans, and HSA depletion strategy all carry real cost and tax implications that need to be modeled alongside your withdrawal plan.

I work through the healthcare bridge as part of the full retirement income planning process for any client retiring before 65. This includes projecting ACA premium costs based on your expected income (which directly affects subsidy eligibility), coordinating HSA drawdown strategy, and accounting for healthcare expenses as a line item in your income model — not an afterthought. For clients with significant equity compensation income in early retirement years, this coordination is particularly consequential.

Common Questions About Retirement Income Planning