Disproportionate Risks: Ask for What You Want

Note: This article is based on a blog post by Chris Guillebeau, in which he discusses asymmetric risk.

I'll talk about some of these risks. For example, a travel article might offer "expert advice" on how to get better deals at airports, but inevitably the advice would also mention how to "dress properly and order nicely."

However, genuine travel experts are never pleased with such suggestions. They might even write their own articles to argue against this particular piece of advice.

I agree with those experts because tips for getting better offers are useless. I took a trip from Copenhagen to Chicago a few years ago.

I don't believe I dressed any better or worse than I normally do, but I dared the portal administrator with a bold request. I had already taken two business class flights across the Atlantic and another one across the Pacific from Hawaii to Japan at that point. All those times, I enjoyed the extra features, and I really liked this encounter.

It's hard to be content with flying in second class after becoming used to first class travel on lengthy flights.

I asked the portal administrator to make sure my name was on the list of extra features as I approached her with a smile on my face. I deceived her, as there was no reason for me to be on that list. However, she said she would check it out, and I thanked her before returning to the waiting area.

I doubted it would work, but five minutes before boarding, another employee called me back to the counter and gave me a new ticket. I was upgraded to business class, which amazed me when I saw it.

For the next ten hours, I had a great time on that flight. After a substantial cheese plate and chocolate cake, I dozed off in the flat seat. Although I've taken many flights since then, I can still clearly recall this one in particular.

Now, whenever I read silly travel tips about asking for extra features, I remember that experience. However, this advice is very stupid, and most of the time it won't work.

If you don't ask, you get nothing

Disproportionate risk is the right kind of risk, when the potential reward far outweighs the potential loss.

Start taking more of these risks if you want to improve your quality of life. You can do that right now. The simplest disproportionate risk you can take today is to live your life and ask for everything you want after recognizing these opportunities. So, think about it for a moment. It is possible to ask for something and not get it, but you also might get it.

If I didn't receive my flight upgrade that morning in Copenhagen, it wouldn't be a problem. Even though I might feel a little rejected or even embarrassed, there won't be any real damage, and I'll still be able to travel to Chicago.

So if you don't ask, you will never get anything.

Take risks of positive value every day

Life provides an opportunity to take these “Disproportionate positive risks” every day. Disproportionate risks can be either positive or negative. Negative risk is when you wager $10 to win $1, while positive risk is when you wager $1 to win $9. Risks are not perfect at all.

For example, even though it has been mathematically demonstrated that the lottery is a bad investment, it still carries a traditional disproportionate risk (at least when purchasing tickets with small amounts of money, you don't care about losing). The majority of people purchase lottery tickets as a chance to dream, not as an investment strategy. Whoever wins will receive a reward that far outweighs what they anticipate losing.

So what if you ask for everything you really want?

For example:

1. Ask for a promotion (or raise, bonus, etc.)
2. Ask for something free.
3. Ask your boss to give you a paid leave today.
4. Ask your boss to let you work on a different project that interests you, even if it is not your responsibility.
5. Talk to your crush.
6. Talk to strangers (at least when they also want to talk to you.)
7. When you attend an event where you can ask questions, be the first to ask (prepare a good question in advance).
8. Contact with a famous person who has influenced you.

In all of these situations, it's good to be prepared for a negative response. Actually, if you start asking for everything you want, and you don't experience any negative response at all, you need to think about whether you're really asking enough.

In conclusion

Identifying and taking disproportionate risks is an assured way to live a more purposeful life. The easiest way to practice it is to start asking for what you really want. Ask for something of value and you might actually get it.