The Gap Years

Know what income to take now—and what to delay.

Learn what income to take now, what to delay, and how Roth conversions or withdrawals can affect taxes and health-insurance costs.

Who this is for: My paycheck has stopped, and I'm living from savings. I don't know when to start Social Security, whether I should move money to Roth, or how much income I should take without raising my taxes or health-insurance costs.

After work ends, you may have a few years before Social Security, pension income, and required withdrawals add more taxable income each year. During those years, you may have more control over how much taxable income shows up on your return.

You decide whether to take money from a traditional IRA or 401(k). You might choose to convert some of that money to Roth. Or decide to start Social Security now or wait.

Those choices can create an opportunity.

If your taxable income is lower than it was while you were working, it may make sense to pay tax on some retirement money now instead of waiting until later.

But more income isn’t always better. Before Medicare, extra taxable income can reduce the help you receive for Marketplace health insurance.

Later, higher income can also raise Medicare premiums. And once required minimum distributions begin, you may have to take taxable money from certain retirement accounts each year whether you need it or not.

So the goal isn’t simply to keep this year’s tax bill as low as possible. It’s to ask: “How much income should I take now, what should I leave for later, and what could that decision make more expensive?”

Decide what income should start now

You may have several ways to pay the bills: cash, investment accounts, retirement accounts, Social Security, or a pension.

The timing matters. Starting one source of income can change how much room you have for another tax move that year.

Decide whether paying some tax now could help later

A Roth conversion means paying tax today on money that would otherwise remain in a pre-tax retirement account. That can make sense in a lower-income year if it helps reduce the amount of taxable money you’ll have to take later.

But the right amount matters. Converting too much can push your income higher than you planned and increase another cost.

Know where the limits are

Before 65, one limit may be the income level that affects Marketplace help. A few years later, Medicare becomes part of the equation.

Medicare can charge higher premiums based on income from an earlier tax return. And eventually, required minimum distributions can add taxable income even if you would rather leave the money invested.

The opportunity isn’t to create as much income as possible. It’s to use the room you have without crossing a line that costs you somewhere else.

Make sure the taxes get paid

Your paycheck used to handle tax withholding automatically. Once the paycheck stops, you may need to decide whether taxes should be withheld from retirement withdrawals or paid another way.

That’s a small detail compared with a Roth conversion or Social Security decision—but ignoring it can lead to a surprise tax bill.

Use the window while you have it

The guides here help you decide what income to take now, what to delay, whether paying some tax now could help later, and where higher income could raise another cost.

More detailed guides for this section are on the way.

Not sure where to start?

Answer a few short questions and we’ll help you see which decisions deserve attention first.

Get started