Oh no. I’m becoming one of those people

Last year, I traveled about 25% of the days. This year, I have more individual trips but fewer miles and days away from home because of a strategic change in how I travel. (More quick trips, less stringing together 2-3 trips into a really long trip.)

Between now and June 1st I have 10 trips away from home. It’s a lot. Not the most of people that I know, but a lot for me.

Slowly, almost annoyingly so, I’ve started to grow affinity for certain brands as I travel:

  • This year I’m flying Southwest domestically exclusively. I like their style of travel, it works for me. Their fare structure makes sense to me. I like the open seating because it means the boarding time is far shorter than those with assigned seating. And, more important than anything, I like that Southwest employees like serving customers more than they are chained to a policy.
  • As much as possible, I’m renting cars from Enterprise. Despite some bumps in the road, so to speak, I’ve had a lot of great experiences with Enterprise. I’m loyal to them for two reasons. 1. I use their neighborhood locations a fair amount since we only have one car. Any time we need a second car, I just rent one. (Way cheaper than owning a second car!) 2. Back when I first got started I was under 25 years old and they were the only ones who would rent to me.

Read into it what you want. But neither of those brands are the traditional BIG BOYS of the travel industry. Southwest has steadily grown over 40 years of profitability to become the largest domestic carrier in the U.S.. And Enterprise has similarly grown, usually profitable, in a space where the BIG BOYS don’t play fair.

Also, in both cases, these companies haven’t traditionally catered to business travelers very well. Only recently have they started to add perks for their most loyal people. They don’t offer lounges. They don’t offer better classes of service. But they do offer little perks along the way that are appreciated and useful.


I have to admit that I’m chasing status with both of these companies.

  • Southwest A-List: Sometime this spring I’ll graduate to Southwest’s first tier, A-List. I am gunning for this for three specific perks. 1. I want to get through security as fast as possible. (I paid for TSA Pre-Check, this helps a ton.) And if I’m checking a bag it means I don’t have to wait in line at the counter. Those save me tons of time. 2. In most cases, that’ll put me in the first 15 people to board the plane and I won’t have to checkin ahead of time to do that… it’s automatic. That means I’ll consistently get to sit in the front of the plane. (A change for me, up until this year I’ve always happily sat in the back.) 3. It means I will earn more free tickets, faster. And who doesn’t love a free flight?
  • Enterprise Platinum: Far fewer perks here. My current status allows me to pretty much get what I’m going to get from Enterprise, I can bypass the lines at the counter and get to rent cars a little cheaper. But getting the highest level with Enterprise will mean I more regularly get the car I want for the lowest possible rate. (I always want a Prius or a Fiat 500. I know, weird.) And of course I’ll earn more loyalty points and get more free rentals.

The Dork Part

The long story, short is that frequent travelers do this stuff for simple reasons.

  • Convenience. You know what to expect. 
  • Speed. I can show up to the airport later and get out to my destination sooner.
  • Price. Being loyal means I save money. 
  • Perks. If you’re going to be on the road 20%-30% of a year, a little perk is meaningful. I know that sounds dumb… but it is meaningful.

So here’s the dork part. I’m chasing this silly Southwest perk. And to get there I need a combination of flights or points earned by my travel spending at Southwest partners.

This week, since I have a total of 5 hotel nights this week and my Airbnb deal fell through… I decided I’d stay at 5 different hotels to earn a total of 3,000 points towards the 25,000 points I need. Each “qualifying stay” is worth 600 points. So if I’d stayed in one hotel for 3 nights in New Orleans it would have been 600 points. But if I stayed in 3 different hotels, that’s 1,800 points. Money-wise, it was all the same and didn’t matter. I literally just did it for the points.

Yes. I have become that person who changes hotels 3 nights in a row in the same community just to earn mileage points. 

I. am. that. person.

And I have to live with myself.

But at least I’m living with myself with some perks at the airport. 

And if you want to be a travel dork with me. Let’s connect on Tripit.






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