#40KFaraway: Stretching the boundaries of possibility


“It’s amazing to me what seems reasonable when we don’t understand what’s possible.”

On the eve of the launch of our 40K to Far Away challenge, I found myself most excited about the vast possibility that lay before us (and writing this post that I’m just now publishing from a plane). Over the next week or two, Greg, Stephen and I are competing to see who can get the farthest away on 40,000 points and $400. But if you think the purpose  is just to see who can spend the most time hopping around the world in a plane, I think you’re missing the point(s). 

a collage of people in a car

On Monday this week, I had a travel day flying from Houston back to Albany, NY. I set the music on my phone to shuffle and I found that I had a couple of Now Boarding podcasts mixed in. I listened to one with Zachary Abel of Monkey Miles. At one point, Zachary was talking about a trip he took to India years ago with a friend using his miles and points. Not being as savvy then as he is today, they had traveled in economy class. Host Ed Pizzarello shortly afterwards remarked that he had never flown coach to India. My first thought was, “Really? I have!”. But then Ed said the words quoted at the top of this post and I instantly understood where he was coming from:

“It’s amazing to me what seems reasonable when we don’t understand what’s possible.”  -Ed Pizzarello. 

In an instant, I understood where Ed was coming from. I paused the podcast immediately to write it down because it rang so true to me.

I mostly grew up what I would call comfortably middle class. I had everything I needed and most of what I wanted. Life was good. However, one thing we didn’t do though was fly. Travel by airplane was unreasonably expensive, a concept that seemed reasonable enough to me throughout my youth. By the time I was 20, I had flown three times in my life. The first was a trip to Puerto Rico with my grandmother when I was 7 or 8. The second was when I was 16 and had been chosen to attend an all-expenses-paid leadership conference and the third was when I was a finalist for a university scholarship and the school flew me and my parents to campus for an interview.

And so, in my mid-20’s, when my now-wife asked if I would consider moving to South America with her for a little while, I was very much intrigued but also way out of my element with no frame of reference for what that would look like. We had a blast living on four bucks and hour for the better part of a year and living as cheaply as we were working. That sparked years of travel for us, always on a shoestring budget. Of course we flew coach to India — and also to Hong Kong and Honduras and Peru and San Antonio and Seattle and Lithuania and Thailand and so many other places, too. In fact, you won’t believe this and I don’t blame you, but one time we flew to Europe and were offered an upgrade at the check-in counter. The agent asked if we would like to upgrade to business class for $99 each. In my mind, I was like, “These tickets cost us $200. I’m not paying 50% more! The front end of the plane gets there the same time as the back end!”. As we walked past the flat-bed seats that I’m sure I didn’t know were flat bed seats at the time (since I’m sure I didn’t know that kind of thing existed), I thought “well those look pretty nice actually”, but that was it. I went to my seat and traveled to Europe and we had the time of our lives galavanting around with no clue about hotel points or airline miles or elite status or first or business class. We just traveled for the love of seeing places. Refusing that upgrade seemed totally reasonable to me at the time as did spending as little as humanly possible on a place to sleep since we “weren’t traveling to Rome to see a hotel”.

a woman lying on a bed
Yup, this seemed reasonable to us when we didn’t know about points.

Of course, I eventually discovered miles and points. And when I did, it didn’t even cross my mind to use them on business or first class travel: I just had it in mind to travel as far and often and I could. It was at a conference where I heard Ben from One Mile at a Time speak that my perspective was challenged: he asked the crowd by a show of hands how many people primarily used their miles to fly in first and business class. Nearly every hand in the room went up. It was such an overwhelming majority that I didn’t feel defensive about my position but rather had to question whether I was missing something.

And when we finally flew in a premium cabin for the first time — Etihad first class from Cairo to Tokyo — I realized that I absolutely had been missing something. Arriving places rested and full meant that we could hit the ground running on Day 1 rather than spend it adjusting to a new time zone. Staying in a nice hotel meant that we had a great shower and comfortable bed to recover from a day of running from site to site. Some of the best food and wine I’d tasted began coming from airlplanes. And the journey became not the destination for me but rather something as much fun as the destination. Vacation suddenly began eight hours earlier — at the airport instead of at the arrival point.

a man and woman sitting in a chair
Our first time flying in a premium cabin. What a surprise it was!

But now, today, I’m embarking on a journey that brings me back to those early years of travel with my wife where we’d stay in a $3-per-night hammock on the beach on Colombia getting eaten alive by sand flies. And it’s kind of exciting. 

a group of people sitting at a table with a building in the background
I couldn’t possibly tell you how filthy this place we stayed at in Agra was nor do I want to remember. But when we didn’t know we could pick up easy points to stay at the Holiday Inn, it seemed reasonable to spend five bucks each to have this rooftop view.

Even more importantly, to me, this 40K to Far Away trip demonstrates possibility in a way that I think is both entertaining for the experienced and eye-opening for those who are new to miles and points. Years ago, my wife and I were in a AAA office and overheard a family planning a trip to Disney World, being quoted something like $800 each for economy class airfare from upstate New York to Orlando, with the husband taking an audible sigh at the price before tilting his head to the side in that way that says, “What can ya do? It is what it is.” Paying eight hundred bucks for that kind of flight sounded ludicrous to us then and probably does to you now if you’re a reader of this blog — but it’s amazing what seems acceptable when we don’t understand what is possible.

And so, through this challenge, what I hope is that we provide some surprises in terms of what is possible (and indeed I think we already have to some extent, even for the highly experienced out there who were not aware of the Turkish sweet spot to Hawaii or how to leverage the excursionist perk). I don’t expect that any readers will try to replicate my specific trip (though from what Stephen has said, maybe you will want to replicate his). I know that traveling like I do over the next few days is not reasonable if you’re collecting enough miles and points to do better — indeed, if you know what is possible, you will find my trip totally unreasonable. But my sincere hope is that someone reading this will see it and say, “Wow! If that guy took less than the points being offered by this welcome bonus and did all that, I can figure out how to take this trip to Paris or Polynesia or Puerto Vallarta or Patagonia or see some new place I didn’t previously know existed just because it is possible. If one or two people do that after reading about the crazy shenanigans that this week brings, I’ll consider it a huge win. 

What’s the point of this post? Honestly, it’s just to share my excitement. I sat up late last night somewhat planning, somewhat nervous, somewhat overwhelmed at what still needs to be done, but mostly just darn excited to see how it goes and to finally find out what Stephen and Greg have up their sleeves. I’m certain that Greg is going to stretch things beyond where I’d imagine and I’m actively excited to see how he surprises us. My mind is blown at how long Stephen Pepper is going to be traveling: I definitely wouldn’t have thought that possible. I certainly don’t expect this week to be the most comfortable and I imagine that one of us is going to run into a snag somewhere, but I hope that no matter how our trips work out, this drive to test the boundaries inspires someone else to think outside the box in your own way — and I look forward to hearing all about it.

On that note, the seat belt sign just turned off, reminding me that it is possible to actually stretch my legs, so it definitely doesn’t seem reasonable to stay in this cramped economy seat for a minute longer right now. Check back for updates from me later…

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