The Pros and Cons of Gambling for a Living

Gambling for a living might sound like a great deal. After all, who wouldn’t want to play games of chance for a living?

The problem is that it’s impossible to make a living playing most gambling games. And when you get good enough at a gambling activity to earn a living at it, the game often loses its “fun factor.”

That being said, some people do gamble for a living and enjoy that lifestyle. If you think professional gambling might be something you’d like to do, this post offers some insights into the pros and cons of gambling for a living.

Gambling is the ultimate independent contractor position. This means that you don’t get paid vacation, medical benefits, or anything else you’d consider a normal benefit from having a job somewhere. Even your retirement fund is entirely your responsibility.

This isn’t the end of the world, though. Like other independent contractors, if you budget well enough, you can take as many days off each year as you like.

If you’re not sitting at the poker table, so to speak, you’re not earning. But if you know anything about being a schoolteacher, you’ll recognize a similar principle.

Teachers get summers off, and they still draw a paycheck. This doesn’t mean they’re getting paid for the 2 months they’re off in the summer, though. It just means that the administration is parceling out the money for a 10-month work year over the course of 12 months.

You’ll need to do something similar if you want to take paid days off as a professional gambler.

As far as health benefits go, you can buy your own health insurance now through Obamacare. Some might argue that Obamacare is more expensive than insurance through a company, but part of that is because some companies subsidize some of the cost of your health insurance.

As far as retirement goes, you could theoretically register a corporation and set up a 401k for yourself. But you also have the ability to set up a Roth IRA (Individual Retirement Account). Both of these options have tax benefits, but it’s up to you to determine which is more appropriate for your situation.

The hassle of putting together your own benefits package is one of the biggest drawbacks of being a professional gambler.

Obviously, if you don’t get along with authority figures, gambling might be better for you than working for some suit in an office somewhere. You do still deal with some authority figures—casino personnel—but it’s not like they have much control over you. They can’t fire you—although they can ban you from the casino if you’re counting cards.

A friend of mine once told me, “It sounds like you have problems with authority figures?”

“You have no idea,” I replied.

I’ve been an independent contractor and owned my own companies for years now. I don’t miss having a boss, I can promise you that.

I had a good friend who played professional poker online during the poker boom. He told me that he earned 6 figures a month, 5 months out of 6.

But 1 month out of 6, he saw a loss for the month.

Not everyone has the wherewithal to handle swings in their income like that. That’ll just plain rattle some folks.

No matter what kind of gambling you do for a living, you’re going to deal with short-term variance. In layman’s terms, even when you’re getting the best of it, you’ll have streaks of bad luck.

Being able to continue to gamble with an edge in the face of that streak of bad luck requires a certain temperament that many people don’t have. It also requires a large bankroll, because without a bankroll, you’re out of action.

And if you’re out of the action, you can’t earn a living gambling.

Okay, so this might be the biggest draw. If you enjoy playing poker or blackjack, or if you enjoy betting on sports, you’re basically getting to do what you love and get paid for it. That’s a hard pro to ignore.

The problem is that it’s not enough to just enjoy the game you’re playing. You have to be good enough at it to make a profit on a consistent basis. And some people learn that playing a game to such high standards isn’t as much fun as playing for recreation.

Remember, there’s nothing wrong with being a recreational gambler. It’s your money, and as long as you’re taking good care of the rest of your financial commitments, losing a little money betting on football, playing poker, or playing blackjack is just fine.

In fact, it’s probably important that you don’t overestimate your skill level. You’ll find plenty of blog posts describing how easy it is to count cards. But the number of people who can make a living at it is smaller than you might think.

Gambling professionally requires a certain kind of temperament that most people just don’t have.

Some people won’t approve of the way you make your living. Your wife might want you to do something more traditional to support the family. Your parents might be disappointed that you’re not putting that degree (that they paid for) to use.

If you want to succeed as a professional gambler, you need to be able to withstand this kind of social pressure. It’s not easy.

I quit my job over 10 years ago to run my own business. My wife was terribly distraught. I made a fortune, though, and it was the right decision for me. It was just so far outside her comfort zone that she couldn’t handle it.

Some people won’t understand your dream. That’s okay. Follow it anyway if it’s that important to you.

When you work as an employee of a company, you have little control over your destiny. Your day-to-day activities are usually decided for you by management. Your compensation package, including how much your salary increases year-over-year, is also determined by management. If you want to take a day off, you must comply with corporate policies and ask for approval/permission.

This doesn’t lend itself to a sense of agency on the part of the employee. Sure, some companies allow their employees more latitude to decide what to do and when. And some companies pay you salary plus commission, or even commission only, which puts your income back in your influence. Some managers might be really flexible with your time off, too.

But these are the exceptions, not the rules. Even if you get to adjust your own priorities, you still have a job description that was written by someone else. The company decides your commission percent, and they can (and often do) change it any time they want to.

And even if you do your job well, that doesn’t mean the company succeeds. If management is incompetent, you might lose your job just because the company goes out of business.

None of this compares with the amount of control you have as a professional gambler. You decide when you want to gamble and what you choose to bet on. How well you do determines your income. And if you want a day off, you just don’t place any bets that day.

That’s what I mean by “agency”—it’s the ability to choose your destiny in a real sense. The only limits to your agency are those imposed by your bankroll and skill level.

Not everyone needs or wants this sense of agency. Some people prefer to have someone else making the decisions. They might think it’s a fair trade to get a benefits package and a reasonable sense of job security.

You’re not necessarily going to deal with the criminal element as a professional gambler, but you’re more likely to deal with shady characters as a professional gambler than if you were in some other profession.

Think about it—if you’re betting with the neighborhood bookie you met through your buddy at the local bar, you’re dealing with someone who’s a career criminal. Sure, it’s a victimless crime, but bookmaking over the phone violates federal law. Some people think that’s a big deal.

The people who open and operate underground poker cardrooms are sometimes the nicest people in the world, too. But they’re not usually the upper crust of respected citizens, either.

I like dealing with shady characters, but only up to a point. I don’t like drug dealers, for example, especially the ones who deal in harder drugs. But not everyone you meet as a professional gambler is that unsavory.

In some circles, being a professional gambler will earn you a lot of respect. This is the opposite of one of the earlier cons, which suggested that there’s a social stigma attached to gambling for a living.

The difference is the people who have disdain for gambling versus the people who have respect for it.

Some people are religious or have other moral objections to gambling. Some just have a Puritan work ethic and think you should earn your money via the sweat of your brow.

But some people admire and respect professional gamblers. They think it’s exciting or romantic. Or maybe they just realize how much self-discipline and skill is required to succeed as an advantage player.

You’ll need to decide for yourself which group of people you prefer admiring you.

No matter what kind of gambling you’re going to engage in to make a living, you’ll need a bankroll—probably a big one.

If you’ve done the research and study to know how to beat gambling, you’ll know that in the short run, anything can happen. You can make all the right decisions and still go broke. The only way to prevent that is to have so much money in your bankroll that you’re confident that you won’t go broke before seeing the long-term mathematical expectation start to look like reality.

Poker players go broke. Blackjack players go broke. Sports bettors go broke.

But they only go broke for 1 of 2 reasons:

1. Their bankroll wasn’t big enough, and short-term variance did them in
2. They thought they had an advantage when they didn’t

If you want to make $20/hour counting cards at blackjack, your best bet of not going broke is having a bankroll of $20,000.

Being a gambler is like owning your own business. You need capital to keep that business running. One of my earliest mentors was David Litman, founder of Hotels.com. He told me that the #1 reason businesses fail is because they’re undercapitalized and have cash-flow problems. He impressed on me the need for a business to be profitable as soon as possible.

Let your career as a gambler be advised by his wise words.

Let’s face it. Being a professional gambler isn’t for everyone. It has its perks, but it also has some serious drawbacks. A lot of your decision about whether professional gambling is an appropriate career for you should be based on your own temperament.

What pros and cons on the list above matter more to you than others?

If you’re seriously considering a career as a pro gambler, I suggest using the Ben Franklin close on yourself. Make your own list of pros and cons on a sheet of paper. Cross out the pros that outweigh the cons. Sometimes a pro might matter so much that it will outweigh 2 or 3 cons, so keep that in mind on your personal list.

And don’t fret. Even if gambling professionally doesn’t work out, you can always return to the rat race if that’s what you want.