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If you’re trading your retirement portfolio, let me give it to you straight: the biggest threat isn’t missing out on a hot stock—it’s taking on more risk than you realize. At this stage, it’s not about maximizing return. It’s about preserving the engine that keeps your income running. That’s why every strategy I use, and teach, starts with one principle: define your risk first.

There are options strategies that give you the best shot at staying in the game without blowing up your retirement. You want tools that allow you to participate in the upside while protecting the downside.

The good news is, there are smart, structured ways to do that…

Let’s start with the big umbrella: defined risk strategies. That means you know exactly how much you can lose before you ever put the trade on. We’re talking about long calls and puts, verticals, credit and debit spreads, calendars, butterflies, iron condors—you name it. These are strategies where the risk is baked in from the start. If you’re managing your own money in retirement, this isn’t optional. It’s mandatory.

One of my favorites, especially for equity investors, is the married put. It’s straightforward: you buy a stock, then you buy a long-dated put as insurance. That’s it. It gives you unlimited upside if the stock runs, but you’ve capped your downside. You can also sell short-dated calls against it to help pay for the put, but that’s not required. Think of the married put as a seatbelt; it doesn’t stop the car from going fast, but it’ll save your life in a crash.

Now, some folks like collars, which add a short call on top of the married put. You own the stock, buy a put, and sell a call—usually with the same expiration. That creates a band: limited upside, limited downside. Personally, I don’t love collars. They’re restrictive. You end up capping your gains too early, and in retirement, you need growth when you can get it. I’d rather protect the downside and leave the top open. That’s what the married put gives you.

Let me walk you through a real-world hedge we covered in a streaming session using Apple stock. Here’s the setup: I sell a short-dated call (22 days out, delta around 30) and buy a longer-dated put (57 days out, delta around 36). The math matters. That short call pays me $2.85 and decays at 13¢ a day. The put costs $7.00 and decays at 8¢ a day. So I’ve got a net positive time decay, which means the hedge starts to pay for itself.

Bottom line: these strategies aren’t about hitting home runs. They’re about staying in the game. In retirement, risk isn’t just uncomfortable, it’s existential. You can’t afford to go backwards in a big way. Use options like the tools they are. Define your risk, control your outcomes, and protect the portfolio you’ve spent a lifetime building. That’s how you trade smart in retirement.

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