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Can You Withdraw From a Roth IRA Without Paying Tax?

Sep 16, 2026

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11 min read

Can You Withdraw From a Roth IRA Without Paying Tax?

Your contributions come out at any age with no tax and no penalty, because you already paid the tax. It is not a loophole, it is how the account is built, and most people never learn it.

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Can You Take Money From a 401(k) Without Retiring?

Sep 16, 2026

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11 min read

Can You Take Money From a 401(k) Without Retiring?

Five doors exist, and four of them are optional features your employer either included or left out. The difference between a loan and a hardship withdrawal can be six figures over a career.

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Can You Roll After-Tax 401(k) Money Into a Roth IRA?

Sep 16, 2026

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11 min read

Can You Roll After-Tax 401(k) Money Into a Roth IRA?

Your 401(k) has two limits and almost everyone only knows the smaller one. The gap between them is the largest Roth opportunity most employees will ever have, and it comes down to two questions nobody thinks to ask.

Penny Brief

What Happens to Employer Stock Inside a 401(k)?

Sep 16, 2026

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11 min read

What Happens to Employer Stock Inside a 401(k)?

One click on a rollover form can permanently destroy a tax provision worth tens of thousands of dollars. It applies only to company stock inside your plan, and most people have never checked whether they own any.

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Can You Move Money From an IRA Back Into a 401(k)?

Sep 16, 2026

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12 min read

Can You Move Money From an IRA Back Into a 401(k)?

Everyone rolls a 401(k) into an IRA. Almost nobody knows the road runs both directions, or that going back is what makes a clean backdoor Roth possible.

Penny Brief

Sep 16, 2026

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11 min read

Can You Reverse a Roth Conversion?

No. Recharacterization of conversions ended in 2018 and the undo button is gone for good. Which means every safeguard now has to happen before you convert, not after, and most people are still converting at the wrong time of year.

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Roth IRA 5-Year Rule: Which Five Years Actually Matter?

Sep 16, 2026

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11 min read

Roth IRA 5-Year Rule: Which Five Years Actually Matter?

There is no single five-year rule. There are three, they start on different dates, and one of them resets when you roll a Roth 401(k) into a Roth IRA you just opened.

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Inherited IRA Rules: What Beneficiaries Need to Know

Sep 16, 2026

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11 min read

Inherited IRA Rules: What Beneficiaries Need to Know

One box on a custodian form can turn a $300,000 inheritance into a single enormous taxable year with no way back. Ten years sounds like plenty of time, and it is, if you start planning in year one.

Penny Brief

What Happens to Your Retirement Accounts After You Die?

Sep 16, 2026

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11 min read

What Happens to Your Retirement Accounts After You Die?

Your will does not control your retirement accounts. A beneficiary form does, and it has not been updated since you filled it in. Workplace plans protect your spouse by default. IRAs do not.

Penny Brief