Pre-Retirees and Retirees
The ten years either side of retiring are the ones that decide how the rest of it goes.
Almost everything written about retirement is about getting to it. Save more, start earlier, stay invested. That advice is fine, and by the time most people reach us they have already followed it. The harder part is what happens next, and it gets far less attention.
The decade around retirement is different in kind, not just degree. During your working years, a mistake has time to recover. Afterwards, the paycheck stops, the portfolio has to produce the income instead, and several irreversible decisions land within a few years of each other. Most of them are tax decisions wearing investment clothing.
Roughly five years out. This is when it becomes worth knowing whether you can actually retire when you want to, rather than assuming. It is also the last comfortable window to change the shape of your savings: how much sits in tax-deferred accounts versus Roth versus taxable, and whether your investment mix still suits someone who will start spending it soon rather than someone still accumulating.
The year you stop working. Income drops, often sharply, and that is not purely bad news. The gap between your last salary and the start of required minimum distributions is frequently the lowest-tax stretch of your adult life, and it is the natural window for Roth conversions. It is a window that closes, and people routinely spend it doing nothing because nobody told them it was open.
The first few years of retirement. Now the questions are practical: which account does this month’s income come from, what does that do to your bracket, and how does it interact with Social Security taxation and Medicare surcharges. These are decisions you make repeatedly rather than once, which is why they are better handled by someone who sees both the portfolio and the tax return.
Later. Required distributions begin, income becomes less flexible, and attention shifts to what passes on. Pennsylvania applies an inheritance tax to transfers to children and other heirs, which regularly surprises families who assumed the federal exemption settled the question. Our estate and gift strategies page covers that side.
Who this tends to suit. People within five to ten years either side of retiring, with meaningful balances in a 401(k) or IRA, who want the tax consequences of their decisions understood before the decisions are made rather than reported afterwards. If you are still early in accumulating, our financial planning and wealth management pages are the better starting point.
For the detail of how the withdrawal sequencing, conversion, and Social Security timing work, see our retirement planning page.
What you get
A straight answer on whether you can retire. Modelled on your actual accounts and spending, not a rule of thumb.
The low-tax window used, not wasted. The years between your last paycheck and required distributions are planned deliberately.
One person for the portfolio and the tax return. You work directly with Kevin Dodgson, CPA, CFA, CFP®, so the investment decision and the tax decision are the same conversation.