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 Most high earners optimize salary, equity, and promotions—but never define what they actually want the next 10 years to look like. A decade plan turns “more money” into more choice by aligning your purpose, milestones, portfolio timeline, tax strategy, and quarterly decision rhythm. Use the Five P Framework (Purpose, Plan, Portfolio, Paycheck […]
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 […]
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