When is the Right Time?

It's summer in Texas. If you're outside for any length of time, you either want to be in a pool or you're planning your next trip to one. Otherwise the other option is to stay inside, which is rarely the better option.

Here's the thing about the pool, it's cold when you get in. Every time. You hesitate, you ease in, maybe someone pushes you in because they have no patience for your indecision. Usually though, when you get in it only takes a few minutes to get acclimated. Then, you pretty much don't want to get out.

I think about investing the same way.

Recently in a lot of my conversations I hear it constantly: "I'm just not sure when to get in." Sometimes looking at valuations, it feels like jumping into a cold, crowded pool. Everyone's already in. What if you jump and it's a mistake? Here is what overthinking actually costs, time in the water. Markets fluctuate. I'm not telling you to ignore that, but waiting for the "right" moment usually just means staying inside, missing the whole afternoon.

Missing the afternoon matters more than you think. Some of the best days in the market show up right when things feel the most uncertain, which means the people waiting on the sidelines for things to "calm down" often miss exactly the days they needed to be in the water for. Here's the other thing about a crowded pool, it's never crowded everywhere. There's always a quieter end, a spot by the steps, an open chair nobody's claimed yet. The whole pool isn't packed just because the part everyone's looking at is.

The pool's nice. Bring me another drink.