Retirement Unpacked

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How these accounts work, in plain English

Taxes are the single biggest drag on long-term investing. Losing a slice of your gains to the IRS every year quietly costs you decades of compounding along the way. The accounts here exist to fix exactly that: they let your money grow without being taxed every single year, the way a regular savings or brokerage account would be.

Contributions have to be made in cash, so you can't deposit stock you already own directly into most of them. Once the money is in, most retirement accounts grow tax-deferred, meaning the IRS doesn't touch the investment gains until you take the money out.

Every account offers its own mix of tax benefits at three separate points in time: when you put money in, while it sits and grows, and when you finally take it out. Those are the three things worth checking whenever you size up an account. The specific rules change from one account to the next, but the questions stay the same.

The tax benefit going in

Some accounts give you a tax break right away. The contribution comes out of your income before tax is calculated on it, which lowers what you owe for that year. That's what “pre-tax” or “tax-deductible” means (Traditional 401(k), Traditional IRA, HSA).

The tax benefit while it grows

Nearly every account here shelters your investment growth from tax, year after year. In a regular brokerage account, dividends, interest, and capital gains are typically taxed annually. Inside these accounts, that growth is left alone until the money comes out, or in some cases forever. That's what “tax-deferred growth” means.

The tax benefit taking it out

Certain accounts save their best tax benefit for this exact moment. A “qualified” withdrawal from a Roth 401(k) or Roth IRA is entirely tax-free, growth included, so decades of investment gains never get taxed at all. A few accounts go further and offer tax-free withdrawals for a specific purpose like education or healthcare, as long as the money is spent that way (529 plans, Coverdell ESAs, HSAs).

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