Tax Strategy Blog
Actionable strategies for real estate investors, business owners, and high earners — written by the Roadmap Tax team.
Laid Off Mid-Year: Tax Deadlines and Decisions to Settle First
Facing a mid-year tech layoff? Review critical tax deadlines for severance withholding, stock option windows, and estimated payments to avoid April surprises.
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Timing a Move Out of California: RSU Vests vs Stock Sales
Planning a move from California? Learn how the timing of an RSU vest versus a stock sale changes your state tax liability and why sourcing rules apply.
Still a Sole Proprietor: Signs It Is Time to Ask About an S Corp
Explore key signs that indicate when a business owner should evaluate an S corp election, self-employment tax impact, and reasonable salary.
Selling Company Stock Over Several Years: Key Tax Trade-Offs
Should you sell concentrated company stock all at once or over several years? Explore the tax brackets, market risk trade-offs, and multi-year tax planning.
Promoted With a Large RSU Grant: Tax Planning Before Your Shares Vest
Got a tech promotion with another large RSU grant? Learn how stacking vest schedules trigger tax withholding shortfalls and how to plan before vesting.
A Gap Year After a Layoff: Why a Low-Income Year Is a Tax Planning Window
Taking a career break after a tech layoff? Learn why a low-income year creates a strategic planning window for Roth conversions and capital gains.
Leaving California: What the State Checks to Confirm You Left
Leaving California for Texas or Florida? Discover how the Franchise Tax Board uses the closest connection test and what records prove you actually left.
One Stock Is Most of Your Net Worth: Where the Tax Conversation Starts
Holding one large company stock position creates serious tax exposure. Learn how California rates, holding periods, and multi-year timing shape your plan.
Severance and a Big Vest in the Same Year: Why April Can Surprise You
Severance and a big RSU vest in the same calendar year stack statutory withholding shortfalls, triggering a surprise tax bill in April. Here is why.
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