Tax Strategy Blog
Actionable strategies for real estate investors, business owners, and high earners — written by the Roadmap Tax team.
Your RSUs After a Layoff: Tax Deadlines You Can't Miss
What happens to your RSUs and stock options when you're laid off in 2026? Here are the key tax deadlines and what to do about them.
Why Your RSU Withholding Didn't Cover the Tax Bill (And What to Do About It)
Your RSUs are withheld at 22% federal, but your real rate is likely higher. Here is why the gap happens and how to fix it before next April.
Why the 401(k) Catch-Up at 50 Isn't Enough for High Earners
The over-50 401(k) catch-up for 2026 lets you save $32,500 a year. For a high earner in San Diego, that still falls short.
Tax Strategy for Law Firm Owners: Retirement Plans and Entity Moves That Actually Move the Needle
A practical look at how law firm owners can use cash balance plans, solo 401(k)s, and entity structuring to shelter more income before 2026 deadlines.
You Crossed $400K. Has Your Business Entity Kept Up?
Most business owners keep their original LLC or sole prop long after outgrowing it. When an S corp election changes the math and how to make the switch.
Planning Your Move Out of California: A Tax Timing Playbook for Tech Executives
How senior tech executives can time their move from California to minimize tax on RSUs, defend against FTB audits, and plan around equity vesting schedules.
What Happens When You Sell a Property After a Cost Segregation Study? Understanding Depreciation Recapture
Selling after a cost segregation study? Learn how depreciation recapture is calculated, what rate applies, and how a 1031 exchange can defer the tax.
When Your Tax Strategy Needs More Than One Calendar Year
Most high earners plan taxes one year at a time. Real savings come from timing income and deductions across multiple years. Here is how it works.
LLC, S Corp, or Sole Proprietor: Which Retirement Plan Fits Your Business
Your entity type decides which retirement plans you qualify for. See how solo 401k, SEP IRA, and cash balance plans work for LLCs, S corps.
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