Frequently Asked Questions
Is it really possible to save $122,000 in taxes on the same income?
Yes, and the example in this post reflects a real pattern seen consistently at executive income levels. The gap is not the result of aggressive strategies or gray-area moves. It comes from a coordinated multi-year system: deferred comp elections made before the year starts, equity decisions mapped against a full income projection, charitable giving timed to high-income years, and accounts organized by tax efficiency.
Run together before the year starts rather than reacted to in April, the cumulative impact at $500,000 to $2,000,000 in household income commonly ranges from $50,000 to $150,000 annually. Subject to your specific income composition, employer plan options, and state tax situation.
What is the difference between a CPA filing a return and having a tax strategy?
A CPA who files your return is accounting for what happened. A tax strategy is a forward-looking, multi-year system that shapes what happens before it does. By the time April arrives, the tax year is closed. Every decision that could have reduced your bill, the deferred comp election, the DAF contribution, the RSU timing, the Roth conversion, had to be made months earlier.
A real tax strategy for W-2 executives starts in the fall, runs projections before year-end, and coordinates every lever simultaneously. Most executives have never experienced this. Once they do, the difference is measurable in five to six figures per year.
How do I know if my 401(k) supports the mega backdoor Roth?
Check your Summary Plan Description or contact your plan administrator directly. Ask whether the plan allows after-tax contributions beyond the standard employee deferral limit, and whether it permits in-service distributions or in-plan Roth conversions of those after-tax amounts. Not all plans offer this, but the number that do has grown significantly.
If your plan does support it and you are not using it, you are missing one of the few tax-advantaged savings vehicles available to high earners beyond the standard 401(k) limit. Subject to annual IRS limits and your plan's specific rules.
When should I make my non-qualified deferred compensation election?
Generally, NQDC elections must be made before the start of the calendar year in which you will earn the compensation. For performance-based bonuses, there may be a later deadline, typically at least six months before the end of the performance period, subject to IRS rules and your specific plan terms. Missing the election window means you cannot defer that compensation for that period.
This is why deferred comp planning belongs in the fall, not in April. Confirm the exact deadlines with your plan documents and a qualified tax advisor before the window closes.
How does Tailored Wealth approach W-2 tax strategy differently from a traditional CPA?
A traditional CPA relationship is typically organized around filing: gathering documents, preparing the return, submitting it accurately. Tailored Wealth builds a coordinated multi-year tax system integrated with your equity compensation calendar, your deferred comp elections, your charitable giving plan, your asset location across account types, and your retirement timeline.
The goal is not a better return in April. The goal is a system that reduces lifetime tax drag by coordinating every lever before the year starts, and updating that system as your situation changes.
