10/01/2026
I don’t think I’ve ever heard a client tell me that they don’t pay enough in taxes.
It’s one of the most common pressure points that I hear from people. And yes, paying taxes can be painful. But oftentimes, I think people allow taxes to dictate every financial decision in their lives, and frankly, that can be even more expensive.
It’s a common concern I see often from people who’ve accumulated large amounts of company stock. The stock has appreciated and selling would create a large capital gain. Holding it just feels like the more comfortable choice because they don’t have to pay the taxes on it now.
Meanwhile, the value of that stock continues to fluctuate. It could keep appreciating, which just compounds the capital gains “problem” further, or it could decrease in value, at which point you may be kicking yourself for your decision to hold on to the stock when you could’ve sold it earlier at a higher price.
At some point, avoiding those capital gains taxes can mean accepting much more single-stock risk than you’d choose otherwise.
If you find yourself in a similar situation, ask yourself this question:
“If this money were sitting in cash today, would you use all of it to buy your employer’s stock?”
If the answer is no, the tax bill may just be the cost of moving some assets toward a portfolio that better reflects your actual goals and the level of risk you actually want to take in your investments.
This doesn’t mean you should log into your account and hit “sell all.” The sales may need to be spread across tax years, coordinated with charitable giving opportunities, paired with offsetting capital losses, or timed around other events that require liquidity.
Sometimes, paying taxes is evidence that an investment worked! “Making peace with the tax man”, as my dad told me once, gives you the freedom to reduce risk, create liquidity, and make decisions based on where you’re going rather than the tax bill you’re trying to avoid.
Are you planning for the lowest possible tax bill this year or a more resilient financial position over the next five years?