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 your “plan” is a portfolio pie chart, a Monte Carlo percentage, and a net worth snapshot, you may not have a plan. You may have an investment proposal. A real financial plan is a living model across six phases that helps you quantify trade-offs (taxes, equity comp, goals, work optional timing) […]
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 […]
Subscribe to Our Free Wealth Building Newsletter
You Won't Regret It!
Become part of our free community of successful leaders using clear, actionable content—delivered via newsletter, videos, and podcast—to master their finances.
