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Quick note before we get into this one: there's an idea related to what I'm about to walk through, and I mention it at the end. Curious what you think, I'll ask once you get there.
A client of mine at Nike was about to sell $20,000 worth of company stock at a loss. On its own, that's a reasonable move. Capture the loss, offset some gains, move on with the year.
Then I looked at her calendar. Her next round of RSUs vests in September. Same company. Same stock.
The buy you didn't know you made
The wash sale rule disallows a loss if you buy the same or a substantially identical security within 30 days before or after you sell it. Most people picture that as a deliberate trade: selling something at a loss, then buying it back on purpose to reset the cost basis.
A scheduled RSU vest counts too. The IRS doesn't care that she didn't place an order or pick the date. Her employer handed her new shares of the same stock, and that's a buy. Land that inside the 30-day window and the loss on the shares she sold gets disallowed. The write-off she was counting on disappears.
She had good reasons to want the cash. She's getting married soon and selling her home, so freeing up $20,000 during a down year in the stock wasn't a bad trade-off. She's also not attached to holding a concentrated position in one company, and once the new RSUs vest, they get taxed as ordinary income like a bonus. There's little reason to hold onto those shares either.
If you're sitting on equity compensation and you're not sure how your vesting schedule lines up with anything else you're doing, you can grab 20 minutes on my calendar, and we'll go through your situation so you know exactly where you stand.
Where this gets caught
We caught this during a regular check-in, the kind we run on an ongoing basis, months away from tax season and nowhere near a year-end review. We look at what's moving in a client's accounts and what's scheduled to happen next.
Because we already knew her vest date was in September, we had room to work with. She can sell the $20,000 position now and take the loss, because September sits more than 30 days out. Wait until late August to make the same trade, and it turns into a wash sale. Same stock, same client, same intention, a completely different outcome, based only on timing.
What almost happened instead
If nobody had been looking at her equity calendar specifically, this plays out differently. She sells the stock and feels good about locking in a $20,000 loss right before a wedding and a home sale. Two months later, the RSUs vest on schedule like they always do. Now the loss is gone, she still owns a concentrated position in Nike stock, and nobody notices until a CPA runs the numbers the following April.
She'd already been reading up on this herself before we talked. Reddit threads, a few finance newsletters, the general advice about selling your losers before year-end that shows up everywhere this time of year. Plenty of it was reasonable. None of it mentioned the wash sale, or what a scheduled RSU vest does to a loss you're trying to capture.
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That's the gap with most financial media. It's built to inform you, not to check your situation against your calendar. If you're ever looking for a place to get unbiased, straightforward facts on what's happening in the markets, without digging through hot takes to find them, that's what I use 1440 for. One email every morning, no spin, no noise. Link's below if you want in.
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This is the part of financial planning that gets me excited. You can build a smart plan on your own. But plans have moving parts, and moving parts collide when nobody's watching the calendar.
Which brings me to the idea I mentioned at the top. Equity compensation keeps showing up in these check-ins, and I've been kicking around building something specifically for people navigating RSUs and ISOs. Before I do, I want to know how many of you this actually applies to. Reply to this email with "RSU" or "ISO," whichever one you're holding, and I'll factor it into what comes next.
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