01 · Early career
Maya — 27
A software engineer four years in: a good salary, stock that vests on a cliff, and every savings account her paycheck can reach — the 401(k) with its match, after-tax dollars swept to Roth, an HSA, a Roth IRA. She rents now, buys her first place in year five, and wants to know what maxing everything actually buys her.
- RSU grants vesting into a brokerage account
- Employer match, mega-backdoor Roth, and HSA in one paycheck
- A home purchase five years out, paid from the brokerage
- Leftover cash swept to investments above a six-month reserve
- Net worth
- $150,000
- Annual income
- $165,000
- Real estate
- $0
- Annual expenses
- $86,400
- Household
- Retirement year / age
- 2059 / 60
02 · The family years
The Nguyens — 38 & 36
A product manager and a nurse with a mortgage, an eight-year-old and a five-year-old. The question is the one every family asks: can we pay for two childhoods, two college educations, and a retirement, in that order, without one of them quietly eating another. Each child's college years are paid from their own 529.
- Two salaries, two 401(k)s, a mortgage in a high-tax state
- Each child costed birth-to-18, then four college years
- College stages drawn from each child's own 529
- A four-month reserve, the rest swept to the brokerage
- Net worth
- $658,000
- Annual income
- $233,000
- Real estate
- $620,000
- Annual expenses
- $94,000
- Household
- Retirement year / age
- 2053 / 652055 / 65
03 · Retiring early
Sam — 34
A high saver with eleven working years left on their own schedule. The brokerage account is the bridge to 59½, a Roth conversion ladder starts the year the paycheck stops, marketplace cover fills the years before Medicare, and a guardrails rule bends spending with the portfolio instead of pretending the market cooperates.
- A taxable bridge account for the years before 59½
- A Roth conversion ladder from retirement to 65
- ACA marketplace premiums until Medicare, optimized for credits
- Guardrails spending: cuts and raises with the portfolio
- Net worth
- $690,000
- Annual income
- $175,000
- Real estate
- $0
- Annual expenses
- $45,000
- Household
- Retirement year / age
- 2037 / 45
04 · The last stretch
David & Elena — 57 & 54
An engineering director and a teacher at the top of their earning years. Everything is catch-up contributions now; her salary is earning a defined-benefit pension, both Social Security claims are estimated from their records, and the window between the last paycheck and required distributions is spoken for — sixty thousand a year of Roth conversions, before the RMDs and IRMAA arrive.
- Catch-up contributions across 401(k), 403(b), Roth IRA and HSA
- A teacher's pension computed from the salary that earns it
- Roth conversions filling the retirement-to-RMD window
- Estimated Social Security for both, claimed at 67
- Net worth
- $3,710,000
- Annual income
- $355,000
- Real estate
- $1,450,000
- Annual expenses
- $110,000
- Household
- Retirement year / age
- 2031 / 622032 / 60
05 · Already retired
Frank & Rose — 70 & 68
Five years into retirement, the accumulation questions are over and the sequencing ones have arrived: which account pays for each year, what the IRA's required distributions do to the tax bill when they start at 73, and what giving to charity straight from the IRA saves. Two Social Security checks, a small pension with a survivor benefit, and a paid-off house.
- Drawdown across brokerage, IRA and Roth — no paychecks
- RMDs arriving at 73, visible before they land
- Charitable giving as QCDs out of the IRA
- A pension that keeps paying half to the survivor
- Net worth
- $2,080,000
- Annual income
- $81,600
- Real estate
- $480,000
- Annual expenses
- $88,000
- Household
- Retired year / age
- 2021 / 652023 / 65
06 · Rental property
Priya — 45
A dentist with her own practice, a home, and two rentals carrying mortgages, depreciation schedules and tenants. One rental is slated for sale in year twenty — the proceeds, after depreciation recapture, are routed straight into the brokerage account rather than left as loose cash.
- Self-employment payroll on the practice income
- Two rentals through Schedule E: depreciation and carryforwards
- A planned sale in year 20, recapture included
- Sale proceeds routed to the brokerage by a cash-flow rule
- Net worth
- $1,460,000
- Annual income
- $260,800
- Real estate
- $1,640,000
- Annual expenses
- $60,000
- Household
- Retirement year / age
- 2041 / 60