The Calm Investor Wins

I used to watch a lot of shows about investing. Sometimes I’d get tips from the TV broadcasts and act on them. I’d call my broker, or later, when technology made it possible, enter a buy or sell order, and be jacked all day waiting for the result.

It was basically gambling. The brain rush was true, but rarely in my state of awareness.

What was more damaging than the losses, which were rarely offset by the occasional win, was the mental preoccupation with the whole exercise.

You’d be sitting with someone having a chat, or worse, with your family, but your brain would be somewhere else, thinking about that stock, call, or put option. The time investment and emotional stress far outweighed even the most incredible gain. I had bet that the market would drop in 1987, and I remember proudly displaying the check from my brokerage on the profit from that bet, for $5,700. I neglected to report that it barely offset the number of put options that had expired prior to the event, as I had been predicting a market drop for over a year. As someone once said, being right at the wrong time is being wrong. I guess I hadn’t learned that yet. Don’t think the $5,700 was enough to cover my put expiration losses.

Things changed when I started investing in real estate as my primary way to support my family. Unlike stocks or options, you can’t sell real estate quickly. It also required a lot of work to buy, doing the right analysis when you find a property and convincing a bank to loan you the money. It also generated instant cash flow, which I desperately needed while holding on to that silver. Real estate is a long-term hold, so investing in it taught me patience and the importance of waiting.

That then translated into my purchase of public equities. What I learned, mostly by accident, is that the more stress-free an investment is, the more successful it can be. In future newsletters, I will dig deeper into some of the most relaxing investments you can make. For now, let’s ask Hank to give us the breakdown on how we can all develop Stress Free Investing Principles. 

Stress-Free Investing

Stress-free investing starts with securing your survival. When you have at least six months of living expenses in cash or short-term government notes, money stress immediately drops. This reserve protects you from layoffs, business slowdowns, or unexpected emergencies.

The next part is automation. The more decisions you eliminate, the calmer you become. Automatic transfers every payday allow your investing life to run quietly in the background. You never debate whether you should save—it happens automatically.

Simplicity is another core pillar. Complexity creates confusion, and confusion creates stress. Choose one investment lane—broad ETFs, a handful of companies you truly understand, or long-term real estate—and stay in it. Fewer moving parts lead to better decisions.

Knowing the value before you buy removes uncertainty. Stress-free investors do not predict the future. They decide what an investment is worth, then wait patiently until the price drops far below that value. This eliminates guessing and emotional reactions.

Finally, review once a year and ignore daily price movements. Wealth is built slowly, through compounding, not through constant activity. When your system does the heavy lifting, you can remain calm, patient, and confident—exactly what creates long-term success.

This information is for Educational Purposes only. Do not make changes without speaking with your financial advisor. I am not a financial advisor.

One place for your money, parenting, and life decisions, powered by Ask Hank™, my cloned brain in an app. Simple answers. Ask your first question.