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Dive into a collection of past posts and rediscover timeless content.
Roth IRA vs. Roth 401(k): What Changes in Retirement?

Sep 16, 2026

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11 min read

Roth IRA vs. Roth 401(k): What Changes in Retirement?

They look identical until the day you stop working. Then the ordering rules, the five-year clocks and your beneficiaries all start behaving differently, and the account that was winning during your career quietly becomes the weaker one.

Penny Brief
Penny Brief
What Happens If You Contribute Too Much to a 401(k)?

Sep 16, 2026

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16 min read

What Happens If You Contribute Too Much to a 401(k)?

Change jobs mid-year and two payroll systems will happily let you blow past one personal limit. Miss the April 15 correction deadline and the same money gets taxed twice, and extensions do not buy you a single extra day.

Penny Brief
Penny Brief
What Happens If You Accidentally Overcontribute to an IRA?

Sep 16, 2026

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13 min read

What Happens If You Accidentally Overcontribute to an IRA?

The penalty is not a one-time fine. It applies every single year the excess stays in the account, and nobody in the system is watching for it. The fix is easy inside your filing deadline and expensive after.

Penny Brief
Penny Brief
How Does a Backdoor Roth IRA Actually Work?

Sep 16, 2026

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14 min read

How Does a Backdoor Roth IRA Actually Work?

Two ordinary transactions in sequence, because contributions have an income limit and conversions do not. It is clean if your traditional IRAs are empty and expensive if they are not, and that has nothing to do with what you earn.

Penny Brief
Penny Brief
Can You Have Multiple 401(k) Accounts?

Sep 16, 2026

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14 min read

Can You Have Multiple 401(k) Accounts?

Yes, as many as you have had employers. But your employee contribution limit belongs to you, not to each plan, and no payroll system will enforce it across two jobs. That gap is where the expensive mistakes live.

Penny Brief
Penny Brief
Can You Have Multiple IRAs?

Sep 16, 2026

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14 min read

Can You Have Multiple IRAs?

Yes, as many as you like. No, that does not give you more contribution room. The IRS looks straight through your account structure, which means where your pre-tax money sits matters far more than how many statements you receive.

Penny Brief
Penny Brief
What Happens to a Roth IRA When You Retire?

Sep 16, 2026

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14 min read

What Happens to a Roth IRA When You Retire?

Mechanically, almost nothing changes. It becomes the only account nobody can force you to touch and the only withdrawal that never shows up in your income, which makes it the one most retirees wrongly spend first.

Penny Brief
Penny Brief
Can You Convert an IRA to a Roth IRA After 60?

Sep 16, 2026

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14 min read

Can You Convert an IRA to a Roth IRA After 60?

There is no age limit and no income limit on a Roth conversion. The years between retiring and 73 are usually the cheapest tax window of your life, and almost nobody notices it before it closes.

Penny Brief
Penny Brief
Traditional IRA vs. Roth IRA: Which Tax Rules Apply?

Sep 16, 2026

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14 min read

Traditional IRA vs. Roth IRA: Which Tax Rules Apply?

Same contribution limit, same investments, same account family. One word changes when you pay the tax, and that single difference decides your income, your Medicare premiums and whether the government can force withdrawals at 73.

Penny Brief
Penny Brief
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