January 19, 2026

Happy Monday, everyone ☀️
Good morning — here’s to a fresh week, a clear start, and a little momentum building early.

Let me throw out a quick question to get things moving: what if one of the most “responsible” money habits wasn’t always as helpful as it seems?
Reinvesting dividends sounds like a no-brainer… until the tax side quietly sneaks in.

Today’s post breaks down why automatically reinvesting dividends can increase your tax bill — and how being a bit more intentional can give you better control without giving up growth.

Because smart investing isn’t just about what you earn — it’s about what you keep.

— Ryan Rincon, Founder at The Wealth Wagon Inc.

— Theodore Roosevelt

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This is not about poor investing.
This is not about bad funds.
This is not about underperformance.

This is about mechanics — and how reinvestment changes tax outcomes even when nothing “new” happens.

Most people assume:

“If I don’t touch the money, I won’t owe tax.”

That assumption is wrong.

When a dividend is paid:

Whether you receive cash or immediately reinvest it doesn’t change that.

But it does change control.

When dividends auto-reinvest:

You created income without access to cash.

Reinvestment happens automatically.

You don’t choose:

The system decides for you.

Auto-reinvestment creates:

Selling becomes administratively painful.

That friction discourages better decisions later.

In high-income years:

You didn’t need more income.

You needed control over timing.

Because reinvestment feels disciplined.

But discipline without control is still expensive.