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Dive into a collection of past posts and rediscover timeless content.
Can You Sell Investments in an IRA Without Paying Capital Gains Tax?

Sep 17, 2026

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12 min read

Can You Sell Investments in an IRA Without Paying Capital Gains Tax?

Yes, and it is the most underused permission in personal finance. Most people who need to fix a portfolio are sitting on the one account where fixing it is free.

Penny Brief
Penny Brief
What Is an In-Kind IRA Transfer?

Sep 17, 2026

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12 min read

What Is an In-Kind IRA Transfer?

Moving your investments to a new custodian without selling them first. It sounds like a technicality. It is the difference between staying invested and sitting in cash during the wrong week.

Penny Brief
Penny Brief
How Do You Read a 401(k) Statement?

Sep 17, 2026

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12 min read

How Do You Read a 401(k) Statement?

Most people look at one number and close the envelope. There are six numbers that matter, and two of them are not printed anywhere on the page.

Penny Brief
Penny Brief
What Is a Brokerage Window in a 401(k)?

Sep 17, 2026

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12 min read

What Is a Brokerage Window in a 401(k)?

A door inside your retirement plan that opens onto the entire market. Very few people use it, and the ones who should are usually not the ones who do.

Penny Brief
Penny Brief
What Is a Stable Value Fund in a 401(k)?

Sep 17, 2026

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12 min read

What Is a Stable Value Fund in a 401(k)?

The option in your plan that never goes down, pays more than a money market, and exists nowhere else in the investing world. Here is how it works and what it costs you.

Penny Brief
Penny Brief
What Is an In-Plan Roth Rollover?

Sep 17, 2026

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12 min read

What Is an In-Plan Roth Rollover?

A Roth conversion that happens entirely inside your 401(k), without the money ever leaving. It is the quiet engine behind the mega backdoor Roth, and most plans never explain it.

Penny Brief
Penny Brief
Can You Do a Backdoor Roth With an Existing IRA?

Sep 17, 2026

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12 min read

Can You Do a Backdoor Roth With an Existing IRA?

Technically yes. Usefully, often no, because of one rule that turns a clean maneuver into a surprise tax bill. Here is how to tell which situation you are in.

Penny Brief
Penny Brief
What Is a Roth Conversion Ladder?

Sep 17, 2026

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12 min read

What Is a Roth Conversion Ladder?

A legal way to get at retirement money years before 59 and a half, built out of a five year waiting rule that most people think of as an obstacle.

Penny Brief
Penny Brief
Do You Pay Taxes When You Sell Stocks in an IRA?

Sep 17, 2026

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12 min read

Do You Pay Taxes When You Sell Stocks in an IRA?

You can sell everything you own inside an IRA tomorrow morning and owe nothing. The tax has not gone away, it has just moved to a different door, and the difference matters.

Penny Brief
Penny Brief
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