The Win-Win-Win Trading Strategy

Boosting Your Retirement Dividend Portfolio with Options

Building a robust retirement portfolio takes patience, discipline, and a willingness to evolve. Over the years, I’ve shifted from simply collecting dividends to adopting a more active approach that not only enhances my yield, but gives me more control over my long-term holdings. I call it the Win-Win-Win Strategy.

Here’s how it works

Step 1: Let the Dividends Flow

It starts with receiving dividends from my portfolio. This is the foundation. A stream of passive income that rewards me for holding high-quality, income-generating assets. But instead of automatically reinvesting those dividends through a Dividend Reinvestment Plan (DRIP), I put them to better use.

Step 2: Sell Cash-Secured Puts Instead of DRIP

Rather than using the dividends to buy more shares immediately at market price, I sell cash-secured put options on stocks I want to accumulate. This allows me deploy my capital more strategically by:

• Setting my own price for acquiring the shares (the strike price),
• Gettong paid an options premium upfront

If the put options expire out-of-the-money (OTM), I keep the premium and repeat the cycle. This becomes an income booster, adding an additional income stream to boost the yield of my portfolio.