WHO WE HELP
Planning the retirement chapter
Most of what I do sits in the five to ten years on either side of a retirement transition. The work is figuring out, in coordinated fashion, how the savings you've built turn into a life that doesn't run out of room.
What this typically looks like
The clients I help in this stage have usually done the saving part well. They have IRAs, 401(k)s, maybe a Roth, maybe deferred comp, maybe a pension election still to make. The question they're working through isn't whether they saved enough. The question is the order in which to draw it down, when to convert what to a Roth, what to do with the brokerage account, when to claim Social Security, how to think about Medicare brackets, and how all of that interacts with the tax bracket they live in for the rest of their life.
The withdrawal sequence determines your tax bracket. Convert too much to a Roth in one year and you bump into a higher Medicare premium for two years. Pull income from the wrong account in the first decade of retirement and you lose a tax bracket window you can't get back. None of this is reactive work. The plan needs to drive the decisions, year by year, before the year happens.
Keystone is the six-month engagement where we work all of this out and put it into motion. Most retirement-focused clients fit the Personal tier ($6,000).
The planning windows that open and close in this decade
There's a specific set of tax-planning windows that open between the year you stop working and the year you start Required Minimum Distributions. Most of them close again after they've been missed. A few that come up most often:
- The gap years between the end of a W-2 paycheck and the start of Social Security or pension income. These are often the lowest-tax-rate years you'll ever have, which makes them the right years for Roth conversions, or for harvesting long-term capital gains at the 0% bracket.
- The IRMAA brackets that determine Medicare Part B and Part D premiums. They're based on your income from two years ago, so the planning has to run on a two-year delay. If I convert too much in 2027, you pay a higher Medicare premium in 2029. Not a disaster, but a real cost that needs to be priced into the decision.
- The Social Security claiming decision, which interacts with spousal benefits, ongoing work, and every other income decision sitting around it. Claiming at 62, at Full Retirement Age, or at 70 are three different financial lives.
- The sequence in which you pull from taxable, traditional, and Roth accounts during the first decade of retirement. This usually has the largest cumulative tax impact of any decision in retirement, and it's the one most often made by default rather than by plan.
These don't sit in one spreadsheet. They sit across a handful of decisions made in different years, and the order matters.
What the Personal Keystone engagement actually looks like for retirement planning
When a retirement-focused client engages Keystone, the six months usually flows like this.
The first meeting is a working session where we lay out the complete picture. Accounts, balances, pensions, Social Security statements, expected income, the non-portfolio parts of the financial life (house, debts, insurance, long-term care). Nothing gets decided in this meeting. The point is to have the whole situation visible.
The second meeting is where I come back with the modeling. Multiple scenarios for retirement timing, Roth conversion sequences, withdrawal order, Social Security claiming, Medicare planning, and the tax projections that tie them together. We talk through trade-offs. You don't need to make calls in this meeting either. You leave with a view of what the numbers actually show.
The third and fourth meetings are where decisions get made and actions start getting implemented. This might be initiating the first Roth conversion, rebalancing a 401(k) rollover, filing for Social Security, restructuring the taxable account, or aligning the estate documents. We also start coordination with the CPA so the tax return reflects what we just put in motion.
The fifth meeting, if needed, is cleanup. Loose ends. Things that needed another conversation.
At the end of the six months you have a coordinated plan in place and a clear picture of which moves are scheduled for each year over the next decade. From there we move into an ongoing relationship (the fee structure for that is on the Pricing page), or we don't. That's a call you make in the last meeting.
Questions you're probably already asking yourself
- When should I claim Social Security and how does it interact with my spouse's claim?
- Do I convert to Roth, and if so, how much per year and for how many years?
- What's the order I draw from my brokerage, IRA, and Roth?
- How do I think about long-term care insurance now versus self-insuring?
- Do I delay Medicare or take it on schedule, and what does that do to my premiums?
How this overlaps with tax prep
A lot of what retirement planning looks like in practice is tax planning that spans multiple years. I run Talley Tax on the same engagement model as the planning work, and for most retirement clients the planning and the tax prep end up in the same conversation. If your CPA currently handles the return and you want to keep that relationship, we coordinate. If you'd rather have both sides handled in the same engagement, that's also a clean option. We figure out which makes sense on the Explore Call.
You don't need to have the answers to bring any of this to an Explore Call. The point of the call is to figure out whether Keystone is the right structure for sorting it out together, and to give you an honest read on whether your situation fits the Personal tier or is pointing toward one of the others.