This post is a result of a lot of different things that have been rattling around in my head the last few months and some interesting conversations I had with some of you as a result of this post. 

There’s some takes that may be classified as hot in this post, and I don’t expect even the people I know with philosophies aligned the most to mine to agree with me 100%. To quote one of those people I’m thinking of, we may not all be simpatico on these things, and that’s ok. 

Intro

A few weeks ago when I got home from a trip to Europe, some friends that I had only known for a little while asked where we’d been and how it was. When they said that sounded like the trip of a lifetime, I just kind of shrugged and said it was ok. When I saw the look on their faces when I said that, I felt like a complete jackass. 

At first it was easy to rationalize that feeling away by looking at the facts. My P2 and I travel primarily for wildlife, and this trip was a scrambled replacement after flights to Tanzania and Kenya via Doha were cancelled. While the highland “coos” on a day hike near Edinburgh were cute, it wasn’t a 1:1 replacement for the safaris and diving we had planned.

But back when P2 and I first flew business class (and had multiple more planned thanks to my initial forays into MS), I told myself that I never wanted to become jaded to how good it felt to turn left on the plane (and more importantly, how good it felt to arrive somewhere much farther than Europe fully rested). 

It did kind of feel like I was jaded to it on that trip, and it wasn’t just because there are no leopards in Scotland or manta rays in Poland. 

I thought back to some of the things I did on that trip and cringed a bit – bringing 3 burners (rookie numbers to some of you), getting pissed off because I forgot to check my Tailscale exit node was all good before I left, getting way more pissed over some (admittedly consequential) shutdowns that happened to me while I was there. 

I made money thanks to shenanigans on the trip, but it was hard to ignore that the inability to stop the hustle made it harder to just enjoy the moment. And I’ve started wondering how much that same neverending pursuit of more has affected the relationships we’ve built with each other.

Points vs. Cashback Pt 2: Electric Boogaloo

Points vs. cashback is a good old classic genre of Big Blog posts because you’re guaranteed to be able to have a minimum of 2 affiliate links in the post. 

I won’t spend much time on rehashing the basics of the discussion (especially since I already did that) because we all know you can buy and sell virtually every award program out there and therefore points do work as cashback.

One thing I’ve always found interesting about individual earning and burning strategy is how your gateway to MS affects your preferences. 

If you come from some of the MS adjacent worlds like gambling or cooking/botting, it makes sense that you’d be 100% all in on maximum cash since that’s what you get as the fruit of your labor (plus a dwindling amount of free cruises, but I can’t mention that method since it’s trademarked, after all.)

But the vast majority of us came from churning, and whether you found churning via an interest in travel or personal finance, you were exposed to points earning as generally being used for travel, with anything else being a bad use. 

That prevailing sentiment is both correct and incorrect – using flexible currencies for gift cards and statement credits is suboptimal (unless the axe is falling, of course). 

But if you’re reading this, you’d likely need to be FIREd to have a chance of ever using all your points on travel. And I know plenty of people that are FIREd and would still never be able to use them.   

So you end up falling down the wacky rabbit hole that is the secondary market for points and miles. You make a lot, and you get exposed to other types of points that are also transferable, but are seldom used in that way. So you earn and earn and earn, and you start cashing out more and more. 

There’s something intoxicating about earning money for clicking a button a handful of times, especially when it pays out at least marginally more than what an AAdvantage opinion survey pays. 

And for me at least, it felt like it stopped being about travel completely, because it had. It had become something else entirely, something I was arranging my entire calendar around.

As long as I had the back pocket convertible currencies for SQ, QR, BR, or any other airline that would take me far and far away to see the animals I wanted to see and eat the food I wanted to eat, I didn’t need to think about travel. 

So I stopped thinking about the fun quirky aspects of the hobby like Companion Pass. And you probably did too. And can you blame us? As Meek Mill so wisely said, there’s levels to this shit, and when you’re operating at the level many of us have been able to over the last 5 or so years, it’s easy to get jaded to the little things that used to be so exciting. 

Moving on

One person reached out about last week’s post and asked if it was really about Companion Pass, or a greater look at the hobby as a whole. Looking back, I think the latter was probably true. I haven’t flown Southwest in 8 years, so losing the theoretical ability to earn something I’d never use wasn’t important. 

Furthermore, I completely zoned out on the fact that there are still some fun things out there that functioned in a similar way. Jetblue 25 for 25, Turkish 1 million mile challenge, Etihad new routes challenge. I just don’t have the time for them in the same way I had time to spend $6,000 over 3 months back in 2016, and that’s on me. 

But in thinking about the commoditization of the hobby that I was whining about last week, I imagine that things like this will become few and far between and more and more a gimmick for UGC on social media than a widely applicable achievement to target. 

In the end, this current environment feels like a natural consequence of the sheer amount of money involved in turning churning (and by a bit of an extension, MS) into a marketing machine for the big banks and the cottage industry that sprung up to support it. 

It’s odd to think that not all that long ago, this hobby was confined to mileage running sickos on Flyertalk. Now I see TPG credit card ads on the luggage bins at LGA right before going up the post-security escalator with a 30-foot tall banner advertising the CSP. 

Hell, even at a micro level and what we’re doing – imagine if there was no 35% rebate on name mismatches, or if a certain serial entrepreneur had never graduated from selling controversial reactionary t-shirts to gift cards. 

I’m not saying that either of those two examples are bad things, because that would be very hypocritical of me to do. 

But it’s an interesting thought exercise to think about what we’d all be arguing about if couch earning and cashout hadn’t scaled to a level that even 365 days a year of PTO isn’t enough. 

And maybe we wouldn’t even have much to argue about. After all, the interpersonal dynamics of our weird little hobby would be a lot different if all we were after was a reservation at the Park Hyatt Kyoto. 

It’s one thing to share helpful information with a friend and fellow hobbyist about how to book something aspirational, but attainable. When there’s potentially life changing money on the line, things get quite a bit murkier.

Enjoy the money you’re making, and try not to let it consume all of your thinking even though that’s really, really hard. It’s something I struggle with, and I’m trying to do better at it.  

We’re all lucky to be here, and stopping to reflect on the things you’ve been able to do because of MS isn’t the worst idea in the world. 

And while you’re doing that, maybe think about the friendships you’ve made along the way.

Kea leboha!