Home > Personal Development > Freerolls: The Better Part of Aggressiveness

Freerolls: The Better Part of Aggressiveness

A lot of people might not know what I’m talking about when I say “freeroll.” A freeroll is a gambling term. It means you make a bet with a potential payoff, but no potential loss. Let’s say in a game of no-limit hold ’em you and your opponent both hold AK on the river on an uncoordinated board. The freeroll bet would be to push all in. If he calls, you split the pot. But if he folds, you win the whole pot. All upside, no downside–assuming your read is correct, of course.

I believe that there are many freeroll situations in our lives, and to the extent that a person is aggressive, he takes advantage of these situations.

If you’ve ever called to cancel your cable service, there’s a good chance they’ve offered you a discount to keep your business. That tells me there might be a freeroll opportunity there. If I called my cable company, cell phone company, and all my other service providers tomorrow and asked for a discount, what would happen? It’s not like they would raise my rates. They might try to get something from me, like signing a longer contract, in exchange for the discount. Or they might just give me what I asked for. Out of all the plausible scenarios that could occur, the only things I’m losing are some time, and maybe a little bit of awkwardness.

I really think there’s a lesson here, and I hope it’s not lost in my particularly clumsy writing this evening. I could sit down and write a list of dozens of things that I want right now: a case for my new iPad, for baseball season to be here, some more good MMA training partners, and so on. I’d be willing to bet that a lot of things on that list are just a request away. There are a ton of undiscovered freerolls in my life that I have the opportunity to act upon if I am just willing to take the initiative to do so.

One anecdote and two practical exercises:

Several years ago, I took a job in sales in order to develop some skills I would need as an entrepreneur starting a business. Some of the guys I worked with had a game they would play: they would go into a restaurant and see which one of them could get the most free stuff. There was usually some flirting and “assuming the sale,” as it’s called, but the key was just having the guts at some point in the conversation to ask for something free. You probably wouldn’t believe how many free drinks, appetizers, desserts, happy meal toys, and phone numbers we all got every time we went out.

So if, like me, you think you could benefit from being more aggressive, I would first encourage you to start looking for freeroll situations in your life. Pull out a legal pad and start brainstorming. You’ll come up with a lot. If you have cable and a cell phone, I’ve already given you two ideas. And once you actually start acting on these and making simple requests, you’ll start noticing a lot more opportunities.

If fear of rejection is keeping you from rolling the dice, take the Rejection Challenge. The challenge is that you have to be rejected at least once every day for 30 days. There is even a set of playing cards you can buy with ideas for rejection opportunities (ask a stranger for a bite of their food at a restaurant, et cetera). You might be surprised to discover that there’s a certain gratifying exhilaration to taking these risks.

One minor caveat: I’m not saying that this should be how act all the time from now on. We all have material things we want, but if you start asking your friends and family for money every time you talk to them, they’ll stop taking your calls. In other words, there are valid reasons for not asking for things; fear, timidity, and passivity are not among them.

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Categories: Personal Development
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