Winner, winner, steak dinner!

Investing isn’t just about numbers—it’s about psychology. Over the years, I’ve come to believe that successful investing isn’t about picking the “best” single strategy, but having a mix of them. My approach balances income, growth, and hedging, giving me flexibility and resilience no matter what the market does.

Today, I want to focus on one part of that strategy: income investing. And yes, we’re going to talk about steak.

The Psychology of Investing

Ask most people what makes a good investor, and they’ll start quoting numbers: returns, compounding rates, expense ratios. But in reality? Investing is as much about psychology as it is about math.

Seeing results—even small ones—keeps you going. It reinforces your belief that your plan is working. On the flip side, when you don’t see results, even a smart strategy can start to feel pointless. That’s when people quit.

This is especially true for long-term investing. Waiting years to see big growth is hard. So how do we stay motivated?

Why Income Investing Matters

That’s where income investing comes in.

I’m talking about dividends from stocks. Regular payments from REITs. Steady interest from bonds. These are the cash flows that show up whether the market is up or down. They’re tangible. And they help you stay on track.

You don’t need to chase high-yield garbage or overcomplicate things. Even modest yields, compounded over time, can build something meaningful. But the real key is to feel that progress.

My Hot Stock Story

Before I focused on income, I chased what a lot of investors chase: the next big thing.

Years ago, I put money into a hot biotech penny stock. I just knew it was going to explode. I imagined doubling, tripling my investment—maybe retiring early. But instead of skyrocketing, it went straight to zero.

That loss stuck with me—not just because of the money, but because it revealed something important: I’m not great at picking stocks. Most people aren’t. And even when we get it right, it’s often more luck than skill.

That experience pushed me to rethink my strategy. I didn’t want to wait years hoping for a win. I wanted real income, now—something I could see and use. That’s when I started focusing on the income portion of my portfolio: dividends, bonds, REITs. Real money, showing up consistently.

Over time, this became a core part of how I invest—because it works.

Income Investing

That loss taught me a valuable lesson: consistency beats hype. Since then, I’ve shifted my focus to building a base of income-generating assets—things that pay me no matter what the market is doing.

These include:

Dividends from reliable companies

Bonds, which provide steady interest payments

REITs, offering exposure to real estate with regular payouts

I generally allocate 30% to 40% of my portfolio to income-generating assets. It’s not everything—but it’s enough to give me psychological stability and cash flow I can actually use.

It’s also the part of my portfolio that helped me stay invested through volatile years. Because even when prices dip, the income keeps coming.

Buy Yourself a Steak Dinner

Here’s a rule I live by: When you earn enough income from your investments to buy a steak dinner—go buy it.

Seriously. Don’t reinvest it. Don’t save it. Spend it.

That dinner is proof that your money is working. It’s your reward. It’s a psychological win that reinforces the habit and keeps you in the game. You’ll remember that meal more than you’ll remember a 2.7% yield.

If you’re just getting started, make that your first goal: Earn enough investment income to cover one steak dinner a month.