The Toughest Travel Question I’ve Ever Been Asked to Answer

At first I thought the toughest questions came from Erich in my request for requests post.

1. Write a post in praise of Tyler Cowen (or another non-points inspiration who made you see things differently)
2. Give a Hansonian take on why Travel is not about vacation
3. How has your hobby modified your job or vice versa?
4. Write a post about how you think a smart but not involved person sees the points game (status chasing all the way down? Coupon clipping dressed in beach vacation dreams?)
5. Write a post on what the credit card game looks like 3 years from now. Don’t post it, but send it to a third party for a scheduled release 3 years hence
6. What are your best travel tips for introverts?
7. Invent a cynical twin, what are the thoughts that leak out of his mind?

Turns out those weren’t even close to toughest.

About a week and a half ago I spoke about travel at Chris Guillebeau’s World Domination Summit.

It was one of the most difficult talks I’ve given because it was scheduled for less than 3 hours after the Asiana crash in San Francisco. All of a sudden the kinds of things I was going to be talking about seemed so utterly mundane. How to save a few dollars on airfare? How to get your rental car for less? At some level, on that day, who cares?

Very few people in the audience were aware of the Asiana crash at the time, they had been holed away in talks and events. People generally put their phones down, they weren’t getting news alerts.

But I felt like it was important to lead off my talk with the news of the crash, acknowledging how so much of what I was planning to talk about seemed small, and then spending a few minutes talking about why I travel, what I get out of it, how saving money or having greater comfort when I travel made it possible and likely that I would travel more, and that the time I spent flying Asiana, the time in South Korea, rather than feeling small because of the subject matter it actually made me feel more connected to the tragedy. There are plenty of terrible things that happen in the world, each and every day, yet this one really affected me.

I was talking about how I approach travel, and the people working for travel companies, and I was asked one of the most difficult, challenging questions I’ve ever gotten from an audience.

I talked about hang up, call back as a strategy to get what you want — to be nice, to ask, to ask someone else if necessary. I talked about simply being nice and connecting with the person at the front desk as a strategy to get hotel upgrades (elite status is just an entry card, there’s still employee discretion, they have their excuse now you want them to use it).

An African American woman, I’m guessing in her early 30’s, asked me “these sounds like great techniques, can you talk about how well they work if you aren’t a white male?”

Wow. Such a great question. And what could I possibly have to add?

I paused. I looked at the ground. And I answered,

I’m pausing because I’m taking your question really seriously. I am not going to pretend that I can speak to the experience of someone that’s not white, that’s female. So all that I can offer you is to think about the conversations I’ve had with people that are familiar with these same basic principles. And none of them have ever told me that they don’t work for them, or that they work differently. But I’d be interested in hearing from folks about their experiences, too.

There’s no question that I’m a moderately successful professional that’s getting close to pushing middle age.

And my experiences may not be typical (although I hope they’re still useful, and I would guess they are useful to folks who are situated similarly).

When I was in my early 20s I was a frequent flyer, I earned elite status, and I was frequently flying up front. This was certainly true for me once I was two and a half years out of college.

There are frequently discussions amongst frequent flyers about the flying experience for someone who is you, many people relate that they don’t get the same level of service and they get lots of assumptions that they don’t belong in the forward cabin.

I never experienced that — When I was barely 24 and flying up front I always felt perfectly at home, and I was never made to feel like less of a customer or someone that didn’t belong. It’s possible my experience is typical, or not, or just that I was oblivious to the social cues that others would have picked up on.

But the techniques I began learning then worked for me, and continued to work. Although of course I have no experience as a female, or as visibly a minority, to say that my experiences would transfer — but I also don’t have reason to believe or expect that they won’t.

For that reason I’d be really interested in hearing about your experiences — what you’ve experienced, or what you’ve witnessed — at the broadest level, are frequent flyer tips and tricks race or gender specific?


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About Gary Leff

Gary Leff is one of the foremost experts in the field of miles, points, and frequent business travel - a topic he has covered since 2002. Co-founder of frequent flyer community InsideFlyer.com, emcee of the Freddie Awards, and named one of the "World's Top Travel Experts" by Conde' Nast Traveler (2010-Present) Gary has been a guest on most major news media, profiled in several top print publications, and published broadly on the topic of consumer loyalty. More About Gary »

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