Hi, I’m Devin Choules, founder and CEO of Choules Financial.
And on this week’s Key to Yes, we’re talking about one of the most common traps facing retirees today: the Tax Time Bomb.
Today’s story is about Carl. Carl was a successful business owner. He sold his business for a healthy sum—enough to fully fund his retirement. But along the way, he did what many people do: he saved diligently in his IRA and 401(k), deferring taxes just like his accountant told him.
The issue? When Carl learned about Required Minimum Distributions (RMDs), he realized something important—Uncle Sam had a bill to collect. Whether he needed the income or not, those RMDs were going to force massive taxable withdrawals, year after year.
That’s when Carl came to us.
The Problem
Carl had:
A large IRA and 401(k) with no tax strategy
No Roth accounts or plan to shift assets
No idea how much of his Social Security would be taxed
No coordinated approach between his different income sources
He didn’t want to tip Uncle Sam one more dollar than required. And he didn’t want his family burdened with a giant tax bill later on.
The Plan
So we built a custom strategy using what we call The Tax Triangle.
Always Taxable: Interest, dividends, 1099 income—money you pay tax on every year, even if you never touch it.
Tax Later: Traditional retirement accounts like IRAs and 401(k)s—where taxes are deferred until withdrawal (or RMDs hit at 73).
Never Again: The Roth zone—where money grows tax-free, and comes out tax-free, even for your heirs.
We helped Carl gradually convert portions of his IRA into Roth accounts over several years. That way, he paid taxes on his terms, not the IRS’s.
We also coordinated his business sale proceeds (non-qualified assets) and his IRA to optimize his Social Security tax situation. For Carl, that meant reducing his provisional income to minimize the amount of his benefit that was taxable.
The Outcome
Carl didn’t just walk away with lower taxes.
He walked away with clarity. With control. With a flexible income plan that:
Showed him exactly which accounts to pull from and when
Allowed him to say yes to more of what he wanted in retirement
Preserved more of his wealth for future generations
The Process
We do this through our Key to Yes™ process:
Envision Your Yes™ Discovery Meeting
A first date—no pressure. We explore what you have, what’s working, and what’s missing across all five areas: income, investments, taxes, healthcare, and estate.
Unlock Your Yes™ Plan Presentation
You get a rough-draft plan showing risk, fees, income strategy, tax projections, and even a Social Security roadmap.
Engage with Choules Financial
We implement the plan, consolidate accounts, optimize income flows, and—just like Carl—we reduce tax drag wherever possible.
Ongoing Yes™ Review Meetings
Because life changes, markets shift, and plans evolve. We meet regularly, update your binder, and make sure everything stays aligned to your goals.
