My father always advised me against four things in life: prostitution, drugs, crime, and gambling. Whether he meant “do not enlist the services of one” or “do not become one” in reference to prostitution, I’ve never clarified. But in either case, I’ve managed to stay away from this and two of the other things. But bless me father, for I have sinned on the fourth.

Gambling could be defined in one of three ways:

    • betting on an uncertain outcome;
    • taking a risk in the hope of gaining a benefit; or,
    • engaging in reckless behavior.
  • Under any one of these definitions, I gamble every day. I gamble in the morning, afternoon, evening, and night. Heck, I am gambling right now by writing this article, since it will yield me some direct and indirect benefits.In fact, most human beings — some of you readers included — are guilty of committing the sin of gambling.Suffice it to say, this is not the gambling that my father had warned me against. The gambling he had in mind was probably the high-stakes, high-risk type where one could lose his money, shirt and wife with one toss of the dice. Thankfully, I have avoided that form of gambling. The problem is that I partake in other types, all of which involve either betting on an uncertain outcome, taking risks in the hope of gaining some benefit, or engaging in reckless behavior.

    Why do I, and human beings in general, gamble?

    Not for the money

    Well, first let’s consider the notion that most gamblers do not gamble for the money. They do so for the thrill. It’s no coincidence that people with fairly mundane professions tend to take a liking to gambling — it provides a much-needed source of excitement to their daily lives.But stale professionals are not alone. Many of those with exciting lifestyles — actors, athletes, artists, and models — have all admitted to gambling at one point or another in their career.

    Ben Affleck gambles at casinos, and he does not need the money. Hockey player Jeremy Roenick admitted to gambling on other sports; he does not need the money either. Michael Jordan got into trouble for gambling, and he could have bought a casino if he wanted to. It is fair to argue, then, that all these men were driven by something other than material benefit.

    To some extent, the fact that these men gambled in the first place is surprising. After all, it is not like their gigs were mundane. Roenick and Jordan were athletes at the top of their game. Affleck had a golden touch with most of what he did (think back, pre- Gigli ). So why would they need the added escapism? Perhaps the addictive side of gambling transcends lifestyle changes.

    How to beat the house…

    Shortsighted risks

    As with anything else in life, some gamblers are successful while others are not. Those who are not might persist in the myopic belief that their next wager will prove to be a winner. Unfortunately, this way of thinking often only serves to bury them deeper in the hole.Those who are successful tend to view gambling as any other challenge. If they can beat one system, they think they can beat any system.

    I would never be interested in entering a casino and gambling money. The only entity that really wins is the house. Walk up to any table at a casino and focus on the players — all the players. While individuals might win here or there, it is the house that wins more often, and wins big.

    In life, anytime the odds are stacked so unfairly, you should walk away.

Playing the market

Some would argue that the stock market is a form of gambling. Not really. There is an inherent risk in investing, but while the house wins more often than not, the fact of the matter is that individuals stand a very decent chance of coming out ahead. The problem is, when an investor does come out ahead, often he suffers from hubris and fails to cash in his gains and walk away.

Yes, in the strictest sense of the word, any investor is a gambler. But an investor is a gambler who, provided he has some liquidity, can hedge himself to an extent. You can buy most securities at 100 and sell at 99.9 if you wish. Try doing the same with any other asset.

The market is a peculiar beast in that you can be far out of the money, but if you have the patience and nerves of steel to ride your losses sufficiently, they can turn to gains before you know it. This was the lesson learned by trader John Meriwether at Salomon Brothers. The trader became legendary when his Long-Term Capital Management fund almost took down the financial system circa 1997. At the time, Meriwether’s track record and confidence allowed him to borrow $4 for every $1 of capital he managed. Some reports pegged this ratio at a much more dizzying ration of $25 of debt to $1 of capital. In either case, Meriwether was not only taking risks, but was taking such gargantuan risks that a misplaced chip would wipe out his entire fund and the funds of his lenders. You might know the saying, “If you will owe any money, owe a bundle!” This is exactly what Meriwether did.

Gambling with your career

This being a career column, it is important to note that many young professionals gamble their careers. Sooner or later, we come to realize that career fulfillment is only one piece of the total picture. People want more, and this means that they are often willing to trade in their stable paycheck and hefty title for a new environment, more free time or anything else they fancy. Some might even gamble away their careers because they need a bigger or different challenge.

Risking your own future…

When should you gamble?

When should you gamble? It depends. Frankly, I find it acceptable to gamble on oneself so long as ego and vanity are not the driving forces in your decision. Gambling means getting serious, focusing and executing the task at hand. Even then, there will be externalities that might force you to reconsider your bets. Moreover, gambling on yourself doesn’t always pan out like the market: it might be impossible to remain patient and “ride your losses.” On the flip side, if you have no one to answer to, you might have all the time in the world to wait for things to go your way.

No bet comes without considerable risk and uncertainty. So long as you can minimize the uncertainty and hedge your bet, gambling is necessary to succeed in life. Without risk, after all, there can be no reward.

Whether you are gambling on sports, the market, your health, or career, you should only roll the dice if you are willing to lose everything. If you are under the myopic belief that you can beat any system, you might just find yourself in a predicament.

E-mail of the week:
Editor’s note: This reader’s e-mail has not been edited and is presented as is.

I am a 32-year-old young professional with a wide array of experience. I have saved up enough funds and am thinking about launching a new consultancy. What kind of advice can you give me?

Age is a bad metric here. Experience and contacts are the key. After all, no matter how many contacts you have, you will run out of them sooner than you expect.

What kind of consulting do you have in mind? Consulting for a firm will help you land clients and gain immediate credibility, whereas consulting via a new firm means that you will have to do a lot of selling to win clients. This means that you might go months without a client, and thus without revenue. If you are a superb salesman with a stellar contact list of people who would realistically pay for your services, then go for it. But do so with the assumption that you might go for a full year without a single penny coming in.

If going for long periods without income will not hurt you too much — both financially and emotionally — then dive in. Otherwise, stick to your work for some time longer, lay down the foundation properly and, once you meet these guidelines, take the plunge.

Ash Karbasfrooshan is also the author of Course To Success, available at His new book, The Confessions of Alexander The Great: 33 Lessons in Greatness, is available at