It’s all about the timing.
What people don’t realize is that the difference between something going positive or going negative may be a matter of minutes—or hours, or days. Timing is everything. As we approach April 2nd, the day after April Fool’s Day 2025, there’s a lot happening. That date marks the supposed start of new tariffs, and it lands in a time of year when taxes, market shifts, and financial decisions collide.
People are selling stocks, buying stocks, rolling their 401(k)s, and doing all kinds of things to avoid paying taxes. It creates waves in the stock market—sudden drops, spikes, and volatility. It’s a moment of action. For some, it’s time to buy. For others, it’s time to sell. And for many, it might be time to do both. Because again—it’s all about timing.
And fortune rewards the bold.
But here’s the deal. No one can truly predict the future. You can come close—you can look at patterns, experience, and probabilities—but you can’t predict it with certainty. What you have to do is kind of predict the future, and then be ready to adjust as you go. Watch the signs. Read the shifts. Make your move when the wind tells you it’s time.
That’s where another metaphor comes in—sailing.
The wind, like the stock market, doesn’t care about you. It’s an external force. You can’t control it. It will do what it’s going to do. But you can set your course. You can decide where you want to go, point your boat in that direction, and then—most importantly—you keep adjusting the sails. The wind changes constantly, and so must you. You kind of predict where it’s going, but you’re always fine-tuning. And sometimes, something happens—unexpectedly—and you have to change your plan entirely.
Same thing in real life. Same thing in investing.
In sailing, you look for the telltale signs—those little red and blue ribbons on your sails. They give you subtle but crucial signals about where the wind is coming from, whether you’re trimmed right, whether you’re off course. In the stock market, the telltale signs are different. You’re watching what other people are doing—reading the consensus. And here’s the twist:
The consensus is usually wrong.
If you’re going with the herd, chances are you’re already late. So you learn to do the opposite. When the average person—the latecomer, the retail investor, the scared seller—is buying, that’s often your signal to sell. And when they’re panicking, when they’ve just lost money and are afraid to touch the market—that’s often your cue to buy.
But again—it’s all about timing. You don’t just blindly go against the crowd. You wait. You observe. It’s like playing chicken. You’ve got to wait until the very last moment to act. Because you’re not really 100% sure until you start getting more than a few signs. You have to hold steady, even when it’s uncomfortable, until the wind really shifts.
And that’s where we are right now.
The market has gone down a few notches. It’s bounced a little. But I think there’s one more drop to come—a final slide. After that, it might just be the time to buy. But not yet. It’s not time to sell either. Even if it dips a bit more, the major shocks might already be behind us. My instinct, based on experience, says we’re close to a bottom. But there’s no telltale sign—not yet.
And I’d rather wait. I’d rather know than guess. When the regular folks are still talking about how bad things are, when the fear is still in the air but starting to fade—that’s the window. That’s when I’ll start buying. Not when people are calm. Not when they’re optimistic. But when they’re still licking their wounds—that’s when opportunity shows up.
Sailing. The stock market. Life.
They don’t sit still. They don’t wait for you. And they certainly don’t care what you want. But if you watch the signs, stay flexible, and move when the moment is right, you just might catch the wind perfectly.
It’s all about timing.
EPILOGUE
Some people say it’s best to stay all in the stock market all the time and not try to time it. And honestly, for most people—because we’re not great at timing—that’s probably good advice. But here’s the thing: most of the real gains in the market happen in just one or two key years out of every ten. If you can time the market, even just decently, you can avoid some of the big losses and ride the big waves up. The trick is not to get too greedy—because, as the old saying goes, “Hogs get fat, pigs get slaughtered.” It’s all about the timing. And if you time it well, maybe you get to spend more time sailing. That’s my goal.
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