01 · Enjoy today · Retiring on your own
She had saved for retirement. She needed a plan for spending it.
Building a Roth bucket was one part of the work. Making the next paycheck fit her life was another.
Read the case →Retirement Approaching · Be prepared.
Your retirement needs more than a market forecast.
Four households. Different concerns. Real decisions about taxes, spending and what happens when markets change.
Start with the purpose of the money: enjoying retirement, protecting future choices or providing for others. Find the situation that feels familiar. See the choices, the tradeoffs and the work that continues after a recommendation.
02 · Enjoy today · Turning savings into a paycheck
Their Roth had grown. Their spending cash felt tight.
A retired couple discovered that building another tax bucket and feeling comfortable using it are different parts of the same plan.
Read the case →03 · Protect tomorrow · Employer stock & NUA
Before rolling over employer stock, look at the tax choice.
One household’s plan used two different tools—and still needed decisions about concentration, spending and taxes afterward.
Read the case →04 · Protect tomorrow · Conversion tradeoffs
A bigger Roth. But was the next conversion worth the cost?
A couple’s questions about healthcare costs and cash reserves brought the whole household back into the calculation.
Read the case →Thinking about the next generation?
Money intended for family raises a different question: whose retirement is it really funding?
Explore the legacy decision →Take the questions with you.
The companion casebook adds teaching examples and a worksheet to help you connect these decisions to your own plan.
Download the casebook →Names and identifying details changed. Selected ongoing cases illustrate planning decisions, not typical outcomes or guaranteed tax savings. Review edition · September 2026.