Stephen Dybwad

Stephen J. Dybwad | Highly Individualized Financial Guidance

Play Like A High Roller

Several years ago, I traveled to Las Vegas to attend a training seminar for my business. While walking through the casino to get to the conference room, I watched people at various gambling games. I had to wonder how much money was being lost while trying to win big, and then it hit me. This is precisely what people do with their retirement accounts in the stock market.

At that time, the stock market was at an all-time high, and with it being the 4th longest bull run in history, I saw many people who wanted to stay in the market to "win big." 

In many ways, the stock market is like Las Vegas, which is why I advise my clients who want to stay in the market to play as the high rollers do in Vegas. Only gamble what you can afford to lose, and quit while you're up.  

How do you know how much you can afford to lose? This is where planning comes into play. Take all your monthly expenses; not only what you need to live, but what you need to thrive – vacations, eating out, hobbies. After all, retirement is meant to be enjoyed, and you can't enjoy it if all you are doing is barely making the bills. But you also need to factor in inflation and rising healthcare costs. I take those numbers and subtract out the income you receive from Social Security and pensions (if you're receiving one), and then that gap is what we need to plan on to be there forever. That is the money you cannot afford to lose, the money you cannot put on "25 red" or gamble on a "4 of a kind".  

Then we talk about quitting while you're up. I advise my clients who want to still play in the market that the money they are willing to gamble on still needs to be played with wisdom. For example, if you are ready to risk $100,000.00, I advise my clients that every time you're 10 – 15% up, take the winnings off the table and invest it in something safe.  

With this approach to market risk, you can protect yourself from losing all your winnings when the market goes down, and you can walk out of the "casino" with only losing the money you felt was ok to fail.


Many people have learned about the power of using the Safe Money approach to reduce volatility. Our Safe Money Guide is in its 20th edition and is available for free.  

It is an Instant Download.  Here is a link to download our guide: 

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Stephen Dybwad picture

Stephen Dybwad

Stephen J. Dybwad | Highly Individualized Financial Guidance

Cincinnati, OH, Louisville, KY, Indianapolis and Madison, IN,

(800) 959-3526

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