Welcome back to another edition of "Rolling in Dough" Newsletter, where we serve up the simplest ways to save more, spend less, and build wealth with regular insights, behavioral science hacks, and tiny tips to do today. I hope to make your financial journey a little fun, simple, and totally doable, where ever you are on your wealth journey.

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BEFORE THE BALL DROPS (BBD) - MINI MONEY MOVE TO MAKE BEFORE THE NEW YEAR #5

 💸 Mini Money Move #5: Balancing Out Investment Wins & Losses

What to do:
Before Dec 31:

1. Open your investing app and look at everything you sold this year.
Most apps show this under “history,” “activity,” or “tax documents.”
You’ll usually see which sales you made money on and which ones lost money.

2. If you have profits:
Check whether you also have investments that are currently down (worth less than what you paid).

If you don’t want to hold those losing investments anymore, you can sell them before Dec 31.

Those losses can help cancel out some or all of the profits you made earlier, which can reduce what you owe at tax time.

This step is optional; only do it if it fits your plan. As always, you should consult a tax professional.

3. If you don’t have any profits:
You could skip this completely. There’s nothing to balance out.

4. If you’re unsure about anything you’re seeing:
Take a screenshot or make a note. Even that small bit of clarity will help you avoid surprises in tax season.

This check is ONLY for regular investing accounts, not retirement accounts.

Reason #1. You only owe money on the profit, and losses can help reduce that.

If you made money on something you sold earlier this year, selling something you’re down on before Dec 31 can help offset it.

Reason #2. You might have small wins you forgot about.

Even tiny profits from automatic sales or rebalancing count.
This check keeps you from getting surprised in April.

Reason #3. You’re not required to sell anything, this is just an option.

If you don’t feel comfortable selling a losing investment, you don’t have to.
It’s simply a tool you can use if it makes sense for you.

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🤔 Things to Consider

1. Don’t sell something you believe in long-term just to save money this year.

Only consider selling things you truly don’t want to hold anymore. Don’t let year-end pressure push you into decisions you wouldn’t make otherwise.

2. Watch out for “wash sale” rules.

If you sell something at a loss, you can’t buy the same investment back right away and still count the loss. (Your app will often warn you about this.)

3. This only applies to regular investing accounts, NOT retirement accounts.

Roth IRA, Traditional IRA, and 401(k) accounts are not part of this check.

4. Timing matters; “balancing out” only works if the sale happens before Dec 31.

After that date, it counts toward next year.

5. This is education, not personal tax or investment advice.

Everyone’s financial situation is different, and apps/accounts work differently.
You can use this as general information, not a directive, and talk to a tax pro if you’re unsure, or to a financial advisor.

👋  TO GO BITES: The Wrap Up

If you sold investments this year and made a profit, you can sometimes use losses from other investments to balance things out, and lower what you owe.

It’s one of the simplest year-end money moves of the wealthy, and it keeps tax season from feeling like a surprise attack.

NEED HELP / GUIDANCE ON WHAT TO DO FIRST OR NEXT?

If you have questions about the money moves you should be making next, here’s how I can help. You can also reply to any email.

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3 Tricks Billionaires Use to Help Protect Wealth Through Shaky Markets

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