At Tailored Wealth, we help busy high-earning professionals design and live their version of a rich life by turning complex cash flow, compensation, and tax decisions into a clear, living financial plan. That plan connects directly to your portfolio through our Life Driven Investing framework so your money is structured around what matters most to you.
This guide helps you run taxes like a system by forecasting income and equity events, fixing withholding gaps, and aligning investing decisions so you get fewer surprises, cleaner decision-making, and better after-tax results.
TL;DR Answer Box Benchmarks don’t fund your life—cash flow does. If your portfolio isn’t mapped to when you’ll need money (1, 5, 10+ years), it’s not a plan—it’s hope. The fix is a four time-band system that assigns every dollar a purpose and a date: (1) 0–2 years cash safety, (2) 3–5 years conservative income […]
TL;DR Answer Box If your pay includes bonuses, RSUs, ESPP, or options, payroll withholding often under-withholds. The fix is simple: build a one-page 12-month income + equity calendar that maps every bonus, vest, purchase, exercise window, blackout, and estimated-tax deadline—then attach a tax action to each event (increase W-2 withholding, make an estimated payment, or […]
TL;DR Answer Box Your bonus is not fully taxed yet. If your household income is north of ~$400,000 and you’re receiving bonuses and/or RSU vests, the default 22% federal “supplemental withholding” is often below your true marginal rate. That mismatch is why April surprises happen. Fix it with three levers: (1) increase W-4 withholding on […]
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