Greg and Maria: Planning a Flexible Transition Into Their Next Chapter
Two careers winding down on different timelines, and a plan that had to hold up either way.
Greg has spent the better part of thirty years in education, and Maria runs a small design practice she built from scratch. Neither one is in a hurry to stop working entirely. What they wanted was room to breathe - maybe Maria cuts back to three days a week before Greg steps away completely, maybe not. They weren't chasing a dramatic change. They wanted to know what a phased transition would actually look like, and whether it would put anything at risk.
- 01
“Can one of us step back from work before the other fully retires?”
- 02
“How do we pay for bigger plans without taking more from retirement accounts than we need to?”
- 03
“What should we be doing now to keep taxes and future distributions manageable?”
They were doing many things right. Savings habits, diversified investments, estate documents already in place, a clear sense of the tradeoffs ahead. What was missing wasn't discipline - it was coordination. A change in work income could ripple into taxes, Social Security timing, Medicare planning, and how distributions get sequenced. And a few near-term plans - a kitchen renovation, more time with their grandkids out of state - needed to fit inside all of that without draining the cash reserves that exist for exactly this kind of flexibility.
Retirement Income
We started with the numbers as they stand today - current spending, the shape of their retirement accounts, and what work income might look like if one of them steps back first. From there, we modeled a handful of transition scenarios: Maria going part-time for a couple of years, Greg retiring on schedule, or both scaling back around the same time. Each version showed a different picture of how much the portfolio would need to cover, and when.
Tax Planning
The timing question mattered more than either of them expected. If Maria's income dropped while Greg kept working, that shift alone could change what made sense for retirement account withdrawals - pull too early and you're creating taxable income you didn't need to create. We reviewed the windows where Roth conversions made sense, looked ahead to required distributions, and factored in how Medicare-related income thresholds could shift depending on the year.
Investments
Because retirement might happen in stages rather than all at once, we treated liquidity as its own priority, not just growth. That meant looking across every account, managed and outside, and finding the overlap and the gaps. We increased global diversification, kept a meaningful bond position to support future withdrawals, and made sure the portfolio wouldn't need to be sold into a bad year just to fund everyday expenses.
Estate Planning
Their estate documents were already in place, which put them ahead of where a lot of people are at this stage. Still, we wanted the financial plan and the legal documents to actually agree with each other. We checked the trustee provisions, confirmed the beneficiary designations lined up with the rest of the plan, and flagged a couple of accounts that still needed to be retitled into the trust.
This is a hypothetical composite based on situations we commonly encounter. It does not represent an actual client and is not indicative of future results.