November 18

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Don’t Invest at the Wrong Time

Family Update

My doctor finally convinced me to start tracking my glucose because I’m close to pre-diabetic territory. I’m using a device called a Libre. It sticks to your arm (without hurting at all) and shows how your blood sugar levels change throughout the day. Watching how much a single cookie spikes it is mind-blowing. I’ve gone mostly low-carb now, and I have noticed more energy and focus, and even lost a few pounds. You start to realize 95% of the grocery store is just a sugar trap disguised as dinner.

Meanwhile, the Great Lanai Expansion has begun. My orchids are completely smushed together, which, in the orchid world, is basically an invitation to a bacteria, fungus, and bug party. The rule of thumb is that every orchid pot should have enough space for a cat to squeeze between them. Right now, even Stinky stands no chance. 


Scene: Greg’s office. Jim and Nancy, both in their 60s, sit on a couch facing their financial advisor, Greg. Nancy’s arms are crossed while Jim nervously fiddles with his watch.

Greg: Alright, let’s recap. Last year, you didn’t invest because the market looked too uncertain. Now it’s up 26%, and you don’t want to invest because it’s too high.

Nancy: (nodding) Exactly. You’re not supposed to buy when it’s high.

Greg: Got it. So just so I’m clear, when the market’s low, it’s scary, and you won’t invest. When it’s high, it’s too expensive, and you won’t invest. Are there any scenarios where you’d actually put money in?

Jim: (pausing) Well... there’s got to be a sweet spot, right?

Greg: Ah, the mythical Goldilocks market. Not too hot, not too cold. You know when that happens?

Nancy: (leaning forward, hopeful) When?

Greg: Never. You’re chasing a unicorn.

Nancy: (defensive) Okay, but what if we invest now and the market tanks? We’d lose money.

Greg: Sure, that could happen. But what if it goes up another 26%? Or 10%? You’re stuck in this loop where the market’s always "wrong." If it’s not too risky, it’s too expensive.

Jim: (shrugging) Well, it’s hard to know the right time.

Greg: But here’s what actually happens: if it drops tomorrow, you’ll say, "We can’t invest yet—it might go lower." Then, when it starts climbing again, you’ll say, "We missed the bottom; now it’s too high."

Jim: (laughing) That does sound like us.

Greg: It’s not just you. Everyone talks themselves out of investing this way. But think about it. If every excuse keeps you out, you’ll never actually invest. You’ll sit on cash while inflation quietly eats your savings.

Nancy: So what’s the solution?

Greg: Get out of your own way. Invest gradually using a strategy called dollar-cost averaging. Spread your investing out over several months. While your cash waits, keep it in a money market account earning interest. Some months, you’ll buy high; others, you’ll buy low. Over time, it balances out.

Jim: (nodding) And if the market drops after we invest?

Greg: Then you’re buying more shares at a lower price.

Nancy: (smiling reluctantly) You make it sound so simple.

Greg: That’s because it is. You’re the ones making it complicated. If you keep waiting for the "perfect time," you’ll never invest, and five years from now, we’ll still be having this same conversation. Only then you’ll be complaining about missing even more growth.

Jim: (grinning) Alright, Greg. You win.

Greg: No, you win if you stick to the plan and stop trying to outsmart a system that doesn’t care about your feelings.

Be Blessed,

Greg (Dave) 

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