Every dollar you own lives in one of three buckets
Before you optimize anything, know where your money sits. Most people are stuffed into buckets 1 and 2 and barely touch bucket 3 — which is the only one the IRS eventually stops taxing.
Taxed Now
Checking, savings, brokerage. You pay tax every year on interest, dividends, and gains — whether you spent a dime of it or not.
Leaks a little every April.
Taxed Later
401(k), traditional IRA, SEP. You get the deduction today, and the IRS becomes a silent partner in your retirement.
A tax bill with a delayed due date.
Never Taxed Again
Roth accounts and the HSA. Money goes in after tax, grows tax-free, and comes out tax-free when the rules are followed.
This is the bucket you want to fill.
Three ways into the never-taxed-again bucket
Roth IRA
The simplest path — a direct Roth contribution.
Backdoor Roth
Make a nondeductible IRA contribution, then convert it to Roth. The direct-Roth income limit doesn't block this path.
Mega Backdoor Roth
Some 401(k) plans allow after-tax contributions plus an in-plan Roth conversion — the largest door of the three, and the one most people never ask about.
The HSA — the only triple-tax-advantaged account
Most people treat it like a spending account. Used well, it is the best tax-free growth vehicle in the code.
Contributions reduce your taxable income.
Earnings compound with no annual tax drag.
Qualified medical costs come out tax-free.
Requires enrollment in a qualifying high-deductible health plan.
Ask these before you write another retirement check
Tick them off as you get answers. Three sentences can be worth thousands.
Print it. Stick it on the wall.
One page, no jargon: the three buckets, the three doors, the HSA, and the three questions. Great for your desk, your team, or your next meeting with your advisor.
⬇ Download the one-page PDF
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Educational summary based on The Tax Playbook presentation. It is not tax, legal, accounting, investment, or insurance advice. Tax rules and individual circumstances vary; consult your own qualified professionals.