Life Transitions

Retirement isn't a date — it's a redesign of your entire financial life.

The income side flips. The tax side gets more complex. Healthcare arrives early. We help you design the next 30 years across cash flow, taxes, and the parts that aren't on a spreadsheet.

Recommended advisor: Hannah Liang, CFP
The situation

What this moment actually looks like.

Most people approach retirement as a date. The math is more interesting than that. The day you stop earning a W-2, the income side of your balance sheet inverts — and the tax side gets considerably more interesting, not less.

The decisions made in the five years before and the five years after retirement determine the next thirty. Roth conversions, drawdown sequencing, Medicare elections, Social Security timing, and the order in which accounts get tapped — these compound, in both directions.

We help you redesign the financial system around the new reality: where each year's income comes from, what the tax bracket looks like by decade, and how the plan absorbs the things you can't predict.

What to think about

The financial considerations, specifically.

A starting checklist. Not exhaustive — a place to begin.

  • Retirement income sourcing across taxable, tax-deferred, and Roth
  • Roth conversion strategy in the 5-year pre-RMD window
  • Social Security claiming strategy — single and joint
  • Medicare enrollment timing and IRMAA bracket awareness
  • Healthcare bridge planning if retiring before 65
  • Concentrated stock and deferred comp distribution scheduling
  • Long-term care funding decisions
  • Estate plan refresh for the retirement balance sheet
  • Charitable strategy — QCDs, DAFs, and bunching
  • Withdrawal-rate stress testing across 25+ scenarios
  • Empty-nest spending realism (travel, sabbaticals, second homes)
  • 529 windup and intergenerational gifting decisions
How we help

Three things we do, repeatedly, well.

01

We model the income side

A year-by-year income map across every account, optimized for tax brackets and Medicare premiums for the next 30 years.

02

We plan the tax bracket arc

The decade between retirement and RMDs is the most valuable tax window of your life. We use it deliberately.

03

We pressure-test the plan

Sequence-of-returns risk, healthcare shocks, and longevity — modeled across 25+ scenarios so the plan holds when reality doesn't cooperate.

Who you'd work with

You'd work directly with Hannah.

HL
San Diego

Hannah Liang

Lead Advisor · CFP
Tech Equity & Empty-Nest

Late-career W-2 households at tech companies — RSU schedules, 10b5-1 plans, and a concentrated single-stock position that has to coexist with a real retirement date.

Free guide

Retirement Cash-Flow Planning Guide

How to think about year-by-year retirement income across taxable, tax-deferred, and Roth accounts — without leaving five-figure tax savings on the table.

  • The drawdown sequence most people get wrong
  • Roth conversion windows that disappear at 73
  • How IRMAA brackets reshape Medicare costs for years
PDF · ~10 minutes

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Common questions

Four things people ask.

Related practice

Tech Equity & Empty-Nest Retirement — the practice

Visit the practice page

Five years out is the right time to start.

30 minutes with Hannah will tell you whether the current trajectory gets you where you actually want to be.