Tax Planning
Forward-Looking Tax Planning for Retirees and High-Net-Worth Households
Tax planning at Compound Advisory is multi-year, IRMAA-aware, and integrated with retirement income, investment management, and estate decisions. We do not prepare returns — we plan around them.
Most households get tax advice at the wrong end of the year. By April, the only moves left are the ones the IRS already lets you make. Real tax planning happens before December 31. Ideally before October. And across a 10-to-20-year window, not one filing year at a time.
We coordinate Roth conversions, capital gain harvesting, charitable strategy, Qualified Charitable Distributions, Net Unrealized Appreciation on employer stock, business-exit structuring, and asset location across taxable, tax-deferred, and tax-free accounts. Each move is sized against your projected bracket, your IRMAA tier, your RMD pressure, and your estate plan. Single-year tax moves are easy. The decisions that move the needle are 5-to-20-year decisions, and they have to be modeled together.
What We Plan
- Roth conversion windows — how much, what year, at what marginal rate
- Capital gain harvesting and loss harvesting across tax years
- IRMAA bracket management (Medicare Part B & D premium planning)
- Qualified Charitable Distributions (QCDs) and Donor-Advised Funds (DAFs)
- Net Unrealized Appreciation (NUA) on employer stock
- Business owner exit structuring — installment sales, QSBS, asset vs. stock sales
- Asset location: which accounts hold which asset classes for maximum after-tax compounding
Coordination With Your CPA
Your CPA prepares the return that already happened. We plan the return that has not happened yet. The two jobs are different, both seats matter, and we coordinate directly with whoever fills the CPA chair.
Each year we deliver a multi-year tax projection: projected marginal brackets, IRMAA tier two years ahead, Roth conversion capacity, and the recommended actions before year-end. We send it to your CPA before fall planning meetings, so the filing reflects the year that was planned, not just the year that was reported.
Why Multi-Year
How much Roth space to claim in the low-income years before Social Security and RMDs. How much capital gain to realize before stepped-up basis dynamics shift. When to fund a Donor-Advised Fund to bunch deductions. How to position assets across taxable, tax-deferred, and Roth so the next decade of withdrawals lands in the most favorable place. These are the decisions that move the needle. None of them are single-year decisions.
We model them explicitly and we revisit the model every year. Tax law changes. Household income changes. Goals change. The plan changes with them.
Related Reading
Frequently Asked Questions
Do you prepare tax returns?
No. We are not a CPA firm. We plan around your tax situation across a multi-year window, and we coordinate the actual filing with your CPA or recommend one if you do not have a relationship.
What is IRMAA and why does it matter for retirees?
IRMAA is the Income-Related Monthly Adjustment Amount — the surcharge on Medicare Part B and Part D premiums when household income crosses certain thresholds. For 2026, the first threshold for single filers is around $109,000 of modified adjusted gross income. Crossing an IRMAA bracket by one dollar can cost thousands per person, per year, two years later. We plan around it explicitly.
When does a Roth conversion make sense?
When your current marginal tax rate is meaningfully lower than the rate you expect to pay (or your heirs expect to pay) on the same dollars later — and when you have non-IRA cash to pay the conversion tax. Early retirement years before Social Security and RMDs are often the best window. We size each conversion against your IRMAA bracket and your full multi-year plan.