This is a map, not a recommendation. It shows when each choice arrives, what it touches, and where the quiet opportunities sit. Move the settings further down and watch the pieces respond.
Some of these dates are fixed by your employer, the tax code, or Medicare. Others are yours to choose. Select any point to see what it decides and what it sets in motion two or three years later.
Each setting below is a real decision in front of you. The four figures underneath update immediately, and compare against the plan as it stands today.
Working years lean on one source. Retirement years usually lean on four or five at once, and the mix is what drives your tax bill. Every figure on this page is in today's dollars, so later years are comparable with this one.
The bands are today's federal brackets, and income is shown in today's dollars. Empty space inside a band is room you can use on purpose, by converting savings to Roth or by selling stock, rather than leaving it unused.
The goal is not only a larger total. It is a healthier mix, so that later withdrawals, Medicare premiums and whatever passes to Hannah and Luke are not all decided by the tax code.
Medicare looks back two years at your income. A large conversion or stock sale in one year quietly raises your premiums in a later one. Each square is one year.
Most of your planning life is steady. A few specific years are not, either because income is unusually low, unusually high, or because a door closes permanently.
Medicare looks back two years. Because Peter enrolls in April 2029, your 2027 income already counts. This year is the final one where a deliberate spike, such as funding several years of giving at once, costs nothing in future premiums, and it lands in your highest bracket, where a deduction is worth the most.
Closes December 31Both of you have stopped working, Social Security may not have started, and nothing is required out of your retirement accounts yet. Income is the lowest it will be for the rest of your lives, which makes it the cheapest time to move money out of tax deferred accounts on your terms.
Ends when withdrawals become mandatoryRoughly a third of Peter's company stock becomes sellable in each window. The position is roughly an eighth of your investable savings and its value depends on the same employer your career did. Each window is also a large taxable gain, so the sale competes for the same bracket room as a conversion.
One window a year, then doneNo single one of these is urgent this month. Together they set your income, your tax bill and your Medicare premiums for the next thirty years, so we will take them in order and revisit each as the date approaches.
The pension pays $2,750 a month for life, continuing at 75% for Joanna, or $460,000 once. The monthly amount never rises, so its purchasing power falls by close to 40% over twenty years of 2.5% inflation. The lump sum can be rolled over, invested, converted to Roth over time and left to your children, but it also carries the market risk the pension would have absorbed.
How much guaranteed income you want underneath your essential spending, and whether the lump sum adds usefully to the conversion window. Due at retirement, mid 2027.
Peter's benefit grows from about $2,400 a month at 62 to $4,300 at 70. Joanna's is the smaller of the two, which makes her claim mostly a question of bridging income, while Peter's sets the survivor benefit that continues for whichever of you lives longer. Every year Peter waits also keeps taxable income low inside the conversion window.
Longevity, the value of a larger inflation adjusted survivor benefit, and how much low bracket room you want to protect between 2028 and 2038.
About nine in ten of your retirement dollars have never been taxed. Left alone, they grow until withdrawals become mandatory, then arrive as income whether you need them or not, at whatever rates apply then. Converting in low income years pays the tax early and deliberately, at a rate you choose, and leaves a tax free account for your later years and for Hannah and Luke.
Employer coverage ends with Peter's last day. COBRA runs eighteen months at about $1,800 a month, then Peter moves to Medicare in April 2029 and Joanna needs individual coverage for almost three more years. Marketplace subsidies stop at $84,600 of income for a couple, which your plan sits well above, so this is a known cost rather than something to optimize around, and that is what frees the conversion window.
Whether COBRA's network and deductible are worth its premium for eighteen months, and how Joanna's individual policy is chosen for 2029 through 2031.
Around $700,000 sits in one privately held company, with a gain of roughly $530,000 built in. Selling as each window opens reduces the concentration soonest and spreads the gain across three tax years. Holding for later keeps the gain in one place and stacks it into a single year, where more of it is taxed at the higher long term rate plus the investment surtax.
Your view of the company, how much of your net worth should depend on one holding, and the gain you are willing to recognize in any one year.
Your $22,000 a year of giving is worth more as a deduction while you are still in a high bracket, and after Peter turns 70 and a half it can come straight from an IRA, which lowers income rather than needing a deduction at all. Gifts to your children and grandchildren are limited only by what your own plan can spare. Your 2019 documents still direct everything to the survivor and then equally to Hannah and Luke.
Timing that pairs your highest bracket years with your largest deductions, and a review of the 2019 trust and beneficiary designations before retirement.
Nothing here needs a decision today. The pension election and the first stock window arrive together in the first half of 2027, so those are the two we will work through first, then the conversion plan each autumn once the year's income is known.