Are You Gambling or Investing? Here’s How to Tell

Gambling and investing are two very different things, but people sometimes get them mixed up. One’s good for a cheap thrill (if you’re lucky), but the other is designed to reliably build your wealth over time and eventually allow you to retire.

Stacks of white dice showing a single dot surround one red die with a six on it.
(Image credit: Getty Images)

Investing in the stock market over many decades offers most people an incredible opportunity to build wealth.

Does that surprise you? If so, you’re not alone. Over the course of my career as a financial planner, I’ve found that many people look at the stock market with skepticism, anxiety or even fear.

To these people, investing money in the stock market doesn’t look any different than walking into a casino and putting your life savings down on black at the roulette wheel. It doesn’t seem like a reliable way to grow assets.

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Instead, it looks like gambling.

I can understand why people feel this way — especially if most of what you know about the stock market comes from mainstream media headlines and talking heads on CNBC. It always feels like things are slightly out of control, and while you may hear about a big winner, there sure are a lot of losers, too.

Here’s the thing: You can gamble when you invest. But that doesn’t mean all investments are speculative bets that rely on luck to help you make money.

In fact, at my firm we specifically advise against making speculative investments. When we help investment clients, we design a thoughtful strategy designed to help portfolios earn a reasonable return over time while avoiding excessive risks.

Unfortunately, this kind of investing doesn’t make headlines. It’s boring — as it should be! No drama is a good thing when you’re investing for the long term.

Instead, it’s speculative betting that grabs people’s attention and can make all investing feel like gambling. We need only look at the latest market madness to see how it plays out.

The Latest Gambling Saga: GameStop’s Rise and Inevitable Fall

At the end of 2020 and throughout January 2021, a group of individual investors banded together in an online forum to pump up the price of a beaten-down stock: GameStop.

GameStop, a company arguably in trouble and certainly the target of short sellers (or those who bet against the future increase of value of a company’s shares), traded at about $18 per share before the madness began.

As the users of the subreddit who started the rally, Wall Street Bets, piled into GameStop, the share price rose to a high of $483 in January — a gain of over 2,500% in a three-week span.

As of late February, GameStop traded around $43 per share.

People should be afraid to lose all of their money if this was representative of strategic investing. But it’s not. The GameStop saga was a raw display of pure speculation. People gambled on the stock. And just like in a casino, a lucky few won big. Most everyone else went home with lighter pockets and losses.

Other Ways to Speculate in the Financial Markets

This is just one example, of course. Speculating happens in all kinds of ways when it comes to the financial markets.

In financial terms, you’re speculating, or gambling, when you engage in any business transaction that risks a substantial loss in pursuit of the chance to rake in a large gain.

Buying meme stocks like GameStop certainly fits the bill, and so does taking huge amounts of your income or net worth to dump into a single position.

Gambling is often easily influenced by herd mentality. It’s driven by emotion. There’s no analysis or fundamental reason why you’re choosing this stock or that asset. That’s what makes it speculative.

Are You Gambling or Investing, and How Do You Know?

If the GameStop rally was a classic case of speculation that is not representative of wise investing, it’s fair to ask what true investing actually looks like.

There are many strategies that can work, but they all rely on systematic, rules-based systems that remove emotion and guesswork. To give you a sense of what this can look like, here are a few of the ways I personally invest:

Contributing to a Retirement Plan

Contributing to retirement plans, such as a 401(k), 403(b) or some kind of IRA (traditional, Roth, SIMPLE or SEP), is a good way to invest strategically. I invest in my company 401(k) through Vestwell as a way to build assets for my eventual retirement.

I use dollar cost averaging to contribute money to the account. That means I contribute the same amount, at the same time each month, and I don’t deviate from that, regardless of what the market is doing at the time.

I’m not concerned about day-to-day or even month-to-month market movements. I’m focused on the long term, and the data shows the market gains value over time. “Over time” might not even mean years — it’s more likely to mean decades!

The dollars I contribute to the account are invested into a set of low-cost, globally diversified ETFs that mirror my risk tolerance and goals. This is long-term money that I plan on not touching for another 29 years.

Using Other Investment Accounts

A retirement account is a great place to start investing. But once you contribute the maximum allowable dollars each year, you don’t have to stop there.

You can also use a brokerage account — but not for stock picking. We advise clients to use the same low-cost, index fund approach that I described for my retirement account.

Building a Business

As a business owner, I am trying to grow the value of my company. While this avenue to investing isn’t for everyone, it is an option you may want to consider.

To grow the value of my firm, I need to invest in people, technology, marketing and so on. I need to do this consistently over time, just like I consistently contribute to other investment accounts over time.

Therefore, I consistently reinvest a share of the business’ profits back into the company itself. As the sole owner of the company with no shareholders or other partners, I could just as easily pull out the profits and take the cash now to improve my current lifestyle.

But that’s not investing, and it doesn’t do anything to help me grow wealth for the future, which is the true goal and purpose of a sound investment strategy.

You should be fearful of speculating or gambling, because doing so forces you to take outsized risks. You base your hopes of return on chance, rather than reasonable expectations.

Investing, on the other hand, is a disciplined, calculated and tested approach built on facts. It’s a reliable way to build your assets and grow your wealth over time.


This article was written by and presents the views of our contributing adviser, not the Kiplinger editorial staff. You can check adviser records with the SEC or with FINRA.

Paul V. Sydlansky, CFP
Founder, Lake Road Advisors, LLC

Paul Sydlansky, founder of Lake Road Advisors LLC, has worked in the financial services industry for over 20 years. Prior to founding Lake Road Advisors, Paul worked as relationship manager for a Registered Investment Adviser. Previously, Paul worked at Morgan Stanley in New York City for 13 years. Paul is a CERTIFIED FINANCIAL PLANNER™ and a member of the National Association of Personal Financial Advisors (NAPFA) and the XY Planning Network (XYPN). In 2018 he was named to Investopedia's Top 100 Financial Advisors list.