Easy Does It. Ride or Die. You’ve probably noticed I sign off with that a lot. Maybe you think it has nothing to do with investing — but it does. In fact, it’s the perfect way to explain one of the core principles of portfolio management: asset allocation.
That’s just a fancy way of saying how you divide your money between stocks and bonds. If you have a target date fund in your 401(k), you’re already using asset allocation — or at least the fund company is doing it for you. And that’s smart. It lets you ride the line between speed and control — or as I like to say, go rails on edge.
Let’s break it down:
Bonds = “Easy Does It.”
Bonds are loans you give to governments or companies. They’re slower, steadier, and generally more predictable than stocks. They won’t make you rich fast, but they help keep your portfolio grounded. Think of them as the green runs — smooth, measured, low risk.
Stocks = “Ride or Die.”
Stocks are ownership in companies — and just like ski runs, they come in all levels of risk. Big, established companies are your blue cruisers. Startups? Triple black diamonds. You could soar. You could crash. That’s the deal. High risk, high reward.
The Key is Balance
When I was in my early 20s, I sent Corbet’s Couloir. Would I do it today at 56? No chance. I don’t have the reflexes — or the desire to end up paralyzed. And it’s the same with investing. When you’re young, you can afford more risk. As you age, you shift to safer terrain. That’s why target date funds gradually reduce your stock exposure over time.
Speaking of Corbet’s — most Mainers don’t know this, but a kid from Maine who grew up skiing Sunday River won the Audience Award in 2024 at Kings and Queens of Corbet’s. I was chatting with a couple of young guys this past weekend, and one of them — who knew Tristan from high school. He was proud of his buddy, even though he doesn’t ski much anymore. And he should be. All of Maine should be.
These athletes are elite — best in the world. Watch what they do and you’ll get it.
Tristan didn’t win because he stuck the landing or as they say “putting down the landing” gear. He over rotated and ate it. Hit his head hard. But he went BIG. No safety net. No holding back. The crowd loved it.
And there’s a lesson there. Sometimes, creativity means going big — even if it means crashing. The crowd can tell when you’ve laid it all out there.
Rails on edge & Send it
But — and this is crucial — don’t send it with your retirement savings. This is where balance matters. A good portfolio blends “easy does it” with “ride or die.” More stocks when you’re young. More bonds as you get older. A target date fund handles this shift automatically. But once you retire, the game changes. You’re no longer just growing money — you need to start generating income.
That’s a whole other conversation — deeper water. We’ll dive into that another time.
