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 If you have a comp plan but no 10-year financial plan, you are optimizing income without designing outcomes. A decade plan starts with a clear picture of your life in ten years, then connects equity decisions, taxes, spending, and investing to that target. The goal is not prediction. The goal is a […]
TL;DR Answer Box If your portfolio is built to beat a benchmark, but your life is built around college, a second home, and work becoming optional, you have a mismatch. Life-driven investing gives every dollar a job description tied to a date and a purpose, so you are less likely to become a forced seller […]
TL;DR Answer Box If you get RSUs, a bonus, ESPP purchases, or stock option windows, you need a 12-month income and equity calendar before you need another tax strategy. The goal is simple: map every income spike and equity event for the next 12 months, then attach one of three tax moves to each event […]
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