Most people in tech don't decide to bet their entire financial life on one stock. It just happens. The RSUs vest, you pay the tax, you hold the rest, and you do it again next quarter. Nobody ever sat down and chose to put 60% of their net worth into a single company. Inertia chose it for them.

Here's the risk in plain terms. If a big chunk of your net worth is in your employer's stock, you're doubling down on a single bet. Your salary depends on that company. Your health insurance depends on it. Your ESPP, your bonus, your career trajectory — all the same company. And then a huge slice of your investable wealth sits on top of all of it.

A single company-specific event — a botched product launch, a regulatory problem, a leadership scandal, a layoff round — can hit your job and your portfolio at the same moment. That's not diversified risk. That's the same risk, stacked.

Now, here's the part about human behavior that always gets me. When a stock drops, people panic and sell at the bottom. But when a stock runs up — exactly the moment a rational person might trim — they hold on, convinced it's the next NVIDIA. The higher it goes, the more certain they become. Optimism and fear of missing out quietly push your concentration to dangerous levels right when you should be reducing it.

Think about a blackjack table. If you sat down, bet your initial stake, and watched it triple, your friends would be begging you to pocket some of those chips. Nobody would call you a coward for taking winnings off the table. But somehow when it's company stock, taking gains feels like a betrayal of the team.

It isn't. Selling a portion of your vested RSUs doesn't mean you've lost faith in your company. You still participate in the upside through the shares you keep — and through every future vest, which keeps refilling the position automatically. You're not exiting. You're rightsizing.

The cleanest way to do this is to remove the emotion entirely with a systematic plan. Instead of agonizing share by share, you decide in advance: a set percentage of every vest gets sold on a schedule, regardless of where the price is that week. That capital then goes to work somewhere useful — a down payment, a home renovation, your kid's future, or a genuinely diversified portfolio that isn't 100% correlated with the tech sector.

Consider how a couple I'll call Carlos and Mandy approached it. Married, north of $900K in combined income, with most of their wealth concentrated in stock from current and former employers. We talked through a phased diversification approach — evaluating selective sales, looking for tax-loss harvesting opportunities along the way, and weighing charitable gifting strategies like a donor-advised fund where it fit their tax picture. The goal wasn't to dump the stock. It was to dial the concentration down to a level that matched their actual goals and risk tolerance, and to do it tax-efficiently rather than all at once.

Everyone's situation and risk tolerance is different. For some people, a concentrated position is a deliberate, eyes-open bet they can afford to make. The problem is the people who never made the choice at all — who are concentrated purely because selling felt like a decision and holding felt like none.

Holding is also a decision. It's just an invisible one.

If you've got a vest coming up and you've been meaning to "deal with it eventually," eventually is a good time to build the system instead. If you want help designing a sell-down plan that fits your goals and minimizes the tax hit, book a complimentary consultation. No judgment — almost everyone in tech is more concentrated than they think.