Always Ask for What You Want: A Lesson in Asymmetrical Risk

TLDR: An asymmetrical risk is one where the potential reward greatly outweighs the potential loss. Identify and take more of these risks.

Every so often, a news article that offers “expert advice” on getting upgraded at the airport makes the rounds. Inevitably, the advice includes something about how you should “dress well and ask nicely.”

Real travel experts always roll their eyes at such advice. These days, almost all upgrades are handled through computer systems based on elite status, travel disruptions, and other automated factors.

The travel experts then write their own articles explaining why the advice is dumb, and the process repeats a few months later.

I’m with the real travel experts: the advice on asking for upgrades is just clickbait. Yet I can’t help but remember a time many years ago—way back in 2007, I think—when I was traveling from Copenhagen to Chicago.

I don’t think I was dressed any better or worse than I usually am, but I did approach the gate agent with a cheeky request.

At that point I had flown transatlantic Business Class two times, and another time across the pacific from Hawaii to Japan. Each of those times, I’d been upgraded at the last minute, and I loved the experience.

Once you fly in the front on a long-haul trip, it’s hard to schlep to the back with the rest of Peasant Class.

I walked up to the SAS gate agent with a smile and my request: “Hi there! I just wanted to make sure my name was on the upgrade list.”

I was bluffing—there wouldn’t be any reason for me to be on such a list back then. But she said she’d check, and I thanked her before walking back to the seating area.

I figured nothing would happen, but five minutes before boarding, another agent paged me to return to the counter. That agent swapped my boarding pass for a new one, and I looked at it in wonder. Business Class!!

For the next ten hours, I enjoyed unlimited refills of champagne, a large cheese plate followed by chocolate cake, and a lie-flat seat where I could sleep off my food coma. I’ve been on well over a thousand flights since then, but I still remember that day very well.

Now, whenever I read the lame travel advice on asking for upgrades, I always remember that experience. Yeah, the advice is dumb … and most of the time, following it won’t pay off. Except, of course, when it will.

If You Don’t Ask, You’ll Never Receive

The right kind of risks are asymmetrical, which means that the potential reward far outweighs the potential loss.

If you’re looking for a way to level-up your life, start taking more of these risks. You can do so right now, today, by identifying disproportionate opportunities in your life.

The easiest asymmetrical risk you can take is to simply go through life asking for what you want.

Just think about it: if you ask for what you want and don’t get it, oh well. That happens. Meanwhile, creating the possible outcome of not getting it also creates a possible outcome of getting what you really want.

That morning at the airport in Copenhagen, if I didn’t get the upgrade, no big deal. I might feel a little rejected, maybe slightly embarrassed, but no real harm would be done. I’d still be able to continue on my journey to Chicago, just with less free cheese and wine.

If you don’t ask, you’ll never receive. It’s a winner-take-all scenario.

Take Positive-Value Risks Every Day

Life offers the chance for these “positive asymmetrical risks” every day.*

*Asymmetrical risks can be both positive and negative. A positive risk is betting $1 to win $9. A negative risk is like betting $10 to win $1. Not as ideal!

Take the lottery, for example. Even though the Powerball lottery is mathematically proven to not be a good investment, it’s a classic asymmetrical risk (at least when you’re buying tickets with small amounts of money that you don’t care about losing).

Most people don’t buy lottery tickets as an investment strategy but rather as a chance to dream. Someone has to win the big prize, right? Whoever it ends up being, that person’s reward far, far exceeds their expected loss.

So what if you went through life asking for whatever you really wanted?

  • Ask for the upgrade (or the raise, the promotion, etc.)
  • Ask for something for free
  • Ask your boss if you can skip work today
  • Ask your boss if you can work on a different project that you’re excited about, even though it’s outside your defined responsibilities
  • Talk to the person you have a crush on
  • Talk to strangers (at least when they want to talk back)
  • When you attend an event where questions are welcomed, be the first to raise your hand (have a good question prepared in advance)
  • Reach out to a famous person who’s influenced you (when in doubt, try the Gmail trick and write to them at

In all these situations, it helps to be prepared for a negative response. (“The answer is no? Okay, that’s fine.”)

In fact, if you start asking for what you want, and you never encounter a negative response, you should consider whether you’re really asking enough.

Identifying and taking asymmetrical risks is a sure-fire way to live more intentionally. The easiest way to practice is to start asking for what you really want. Just be careful what you ask for—you might get it!


P.S. I originally started thinking about asymmetrical risks in the context of investing. As I mentioned last week, the world of decentralized finance (or DeFi) offers opportunities to earn returns that far exceed what banks are paying. This is just one example of a real-world asymmetrical risk.

Images: 1, 2, 3

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