We had dinner with an old friend last night.

We talked about regret.

Our dinner guest is quite successful. He has a wonderful family, successful kids and runs a profitable business that seems to want to grow all on its own.

“What’s to regret?” we thought about asking.

We didn’t need to, though. We already knew the answer.

We’ve been doing this a long time – so long that we can name the tune just by hearing the first note.

Life is good, so many folks tell us… but it could have been better.

Money Trouble

Our pal lives a comfortable life. He doesn’t need to worry about a tow truck hauling his car to the bank in the middle of the night. He doesn’t lie awake at night worrying where the next mortgage payment will come from.

But he is human.

He has regrets.

For him, it’s money. He’s made some investing mistakes.

As a businessman, he’s an independent guy. He doesn’t like to sit around and let the markets determine his fate. He moves in quickly and gets out just as quickly.

But with the gift of time on his side, he looks back and sees his comfortable life could have been a whole lot more comfortable.

His 26-foot boat could have been a 46-foot boat.

Sticking his chin into his palm, he quietly asked us what we’d do.

It’s a question we hear a lot. It’s quite natural… especially these days.

The markets are making folks rich.

The S&P 500 is up 20% this year. It’s up 50% over the last five years and up by more than 270% since those infamous lows in March of 2009.

There have been a lot of ups and downs during this, the greatest of bull markets. There have been plenty of rational reasons for folks to sell or to stay out of the markets. But none of them had the endurance to pull stocks down for long.

It’s what leads to the two greatest investment regrets – selling too early and not buying when the buying is good.

The Solution to Your Money Troubles

That’s certainly the case with our friend.

He was in the markets and doing well. But he got spooked… another victim of the headlines.

Most of his money is on the sidelines.

Worse yet, he used some of his cash to buy depreciating assets, like new cars. That’s money he’s never going to get back.

“Look,” we told him. “We’re as old school as anybody, but it’s 2019. You’ve got to take advantage of the tools available to you.”

With that, we told him of the latest advances in investing technology – mathematical systems that can track the market’s moves and act as quite accurate gauges of overall sentiment.

Used correctly, they are the perfect tool to overcome investment regret.

It’s been said many times, many ways… Emotional investing is bad.

It’s the chief ingredient in the recipe for mediocrity.

Our hearts tell us when to buy and when to sell. It’s bad news for a system that’s all about numbers.

Math Always Wins

Times have changed. This isn’t the old days when we opened the newspaper and checked how our stocks closed yesterday.

These days, the action is in real time. And it’s not driven by humans. The markets are driven by machines.

Something like 90% of all trades each day are initiated by a computer.

That’s good. It means we, too, can use computers to turn a buck into two… or three.

But most folks aren’t doing it. They’re not taking advantage of the latest tools available to them.

They’re still scanning the headlines, looking at yesterday’s action and trying to make a judgment about tomorrow.

It leads to regret.

The smart way – what we told our friend at dinner last night – is to use the latest technology to make your trades.

It’s easy. Almost any online brokerage account can do it.

Set up your price limits. Tell the computer when to buy (lots of folks use relative strength as a main indicator), and tell it when to sell (again, relative strength or trailing stops will get the job done here).

Lots of folks spend lots of time debating which system(s) to use. It matters. But what matters more is that you’re using a system and sticking to it.

It will ensure that you avoid those two oh-so-common regrets above.

A smart system will get you into stocks when they’re cheap and will keep you holding them even when your heart wants to run.

Better yet… a good system could get you into that 46-foot boat.