What is tax loss harvesting and why should I care?

The tax trick almost no one talks about

If you’re paying taxes on investment gains—but have positions that are down—there’s a silent strategy that could be saving you thousands.

It’s called tax loss harvesting (or tax-loss harvesting), and chances are, it’s already happening to you.

But here’s the problem: most investors have no idea when, how, or if it’s being done. And the consequences of not knowing? Overpaying taxes, underperforming portfolios, and missed opportunities.

Let’s fix that.

What is tax loss harvesting?

Tax loss harvesting is the process of selling investments at a loss to offset capital gains elsewhere in your portfolio. You can also use up to $3,000 of those losses to reduce ordinary income, with any unused losses carried forward to future years.

A quick example:

• You made $12,000 in profits from selling some winners

• You sold other positions at a $9,000 loss

• Now you’re only taxed on $3,000 of net gains

That’s tax loss harvesting in action. And in volatile years, it can mean the difference between a painful tax bill and a more optimized return.

Platforms like Fidelity tax loss harvesting services or robo-advisors often perform these actions automatically—but many investors never realize it’s happening.

So, is tax loss harvesting worth it?

If you’re in a taxable account, the answer is almost always yes—especially when tracked and coordinated properly across all your assets.

The hidden power behind direct indexing tax loss harvesting

One increasingly popular method is direct indexing tax loss harvesting. Instead of holding a single ETF, direct indexing platforms hold the underlying individual stocks. This creates more opportunities to harvest small, temporary losses on specific holdings—even if the overall index is up.

The result? More frequent tax savings opportunities, especially in choppy markets.

But whether your advisor uses direct indexing or traditional ETFs, you still need a way to see what’s happening and understand why.

It’s probably already happening — but you’d never know it

If you’re working with a financial advisor (or a robo platform), chances are tax loss harvesting is being done for you.

But here’s what’s interesting: almost no one tells you when it happens. You don’t get a notification. You don’t see the tax benefit. You don’t know what was sold or why.

It’s like getting dental work in your sleep—you hope it was helpful, but you can’t feel the results.

And when something this important is invisible, how can you trust it’s being done right?

According to a CNBC report, fewer than 25% of investors fully understand how tax loss harvesting works, let alone whether it’s active in their portfolios.

The missing conversation in most portfolios

Tax strategies shouldn’t be hidden behind quarterly reports or buried in year-end summaries. Especially not ones that could reduce your tax bill by thousands.

But here’s what the average investor gets:

• A 1099 form with numbers, not narratives

• Portfolio statements full of tickers and percentages

• No real-time explanation of what’s happening or why

And here’s what they really want:

• "What actions were taken in my account?"

• "What did that save me in taxes this year?"

• "Was this decision part of a plan—or just a reaction?"

The truth is, financial transparency shouldn’t stop at fees or performance. It should include tax moves too.

Let’s talk about the tax-loss harvesting 30-day rule

One reason tax loss harvesting feels murky? The IRS doesn’t let you sell something at a loss and immediately buy it back. That’s called the wash sale rule—or more specifically, the tax-loss harvesting 30-day rule—and it voids your ability to use the loss if not followed.

But good advisors know how to work around it:

• Sell ETF A at a loss

• Buy ETF B (very similar exposure, but technically different)

Now you’re still invested, but your loss still counts.

The IRS Tax Topic 409 lays out the details on how capital losses and wash sales work.

So why isn’t this being explained more clearly?

What if you could actually see what’s happening in your portfolio?

Imagine this:

You log in and see:

• A snapshot of your year-to-date tax savings

• A timeline of loss harvesting moves made on your behalf

• A breakdown of what was sold, what it was replaced with, and why

• Suggestions for follow-up questions to ask your advisor

That’s what investment monitoring should look like.

And now, it can.

How Truthifi helps you take back visibility

Truthifi is the first investment tracker built not just to show you what happened—but why.

Think of it like a layer of clarity over everything your advisor is doing. It doesn’t replace them—it makes them more transparent.

Here’s how Truthifi supports smarter tax strategy conversations:

Make invisible losses visible

Truthifi maps unrealized losses across your entire portfolio, so you can see potential harvest opportunities and confirm what’s been used.

Understand the strategy

See how much of your tax loss has been applied, what positions were involved, and whether any wash sale issues occurred.

Talk to your advisor—with better data

Use "Ask My Advisor" to raise questions about recent moves, clarify strategy, or check whether loss harvesting is in play at all.

Spot missed opportunities

Even great advisors can miss things. Truthifi helps you double-check, spot patterns, and suggest potential follow-ups.

In short? Truthifi helps you go from passive recipient to informed participant.

Other platforms fall short

Robo platforms like Betterment and Wealthfront offer automated harvesting—but only within accounts they control. And most won’t show you details unless you go looking.

Traditional platforms? You’re lucky if the year-end summary tells you anything helpful.

Truthifi is different. It pulls back the curtain on your entire portfolio—not just the parts one firm manages—and puts clarity in your hands.

If you want to know what’s really happening to your investments, this is where it starts.

Final thought: even your losses have value

Tax loss harvesting doesn’t fix a bad market. But it can turn pain into planning—and create real savings in the process.

The catch? You have to know it’s happening.

With Truthifi, you do.

Want to see what your portfolio is really doing?

Start monitoring your investments like a pro.

✅ Explore Truthifi’s features
✅ Try the Fee X-Ray to uncover hidden advisor fees
✅ Use the Score to track your portfolio health

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