Tax Strategy Blog
Actionable strategies for real estate investors, business owners, and high earners — written by the Roadmap Tax team.
Consulting Between Jobs: What Changes for Your Taxes
Transitioning to 1099 consulting between tech jobs? Learn how self-employment tax, prior W-2 wages, and quarterly estimates affect your California tax bill.
Two Employers in One Year: Why Your Tax Withholding Falls Short
Switched jobs mid-year? Learn why having two employers creates withholding shortfalls across federal brackets, Additional Medicare Tax, and California rates.
California vs Federal Depreciation: Why State Taxes Differ
California does not conform to federal bonus depreciation. Learn how state depreciation adjustments work and what to review with a tax strategist.
Between Jobs on Marketplace Health Insurance: The Tax Question to Ask Early
Using marketplace health insurance between jobs? Learn how 2026 tax changes remove repayment caps on advance premium tax credits before April surprises you.
Laid Off With Unvested RSUs: What to Review Before Your Last Day
Facing a layoff with unvested RSUs? Learn key tax considerations, vesting negotiation points, and withholding rules before signing your separation agreement.
Why Your RSU Cost Basis Looks Wrong on Form 1099-B
See why your 1099-B may show zero RSU basis, how vest-date value affects your tax basis, and what to review on Form 8949 before filing.
Your 401(k) After a Tech Layoff: Rollover, Cash Out, or Net Unrealized Appreciation
Laid off with employer stock in your 401(k)? Leave it, roll it over, cash it out, or use net unrealized appreciation. Here are the tax rules for each path.
California RSU Tax Rate: How Your Vested Shares Are Taxed
See how California taxes RSU vest income, why flat withholding may fall short, and what can remain taxable after a move out of state.
Incentive Stock Options, AMT, and the 83(b) Election Explained
How ISOs trigger AMT bills before you sell a share. A guide to incentive stock options, the alternative minimum tax, and the 83(b) election.
Ready to build your tax strategy?
Reading is a start. A call with the Roadmap Tax team turns these strategies into a plan built around your entities, income, and goals.
Talk to a strategist