I fly often for work.  Some months I’m home for a single-digit number of days spread out throughout the entire month.  So like any seasoned traveler, I look for the best companies to remain loyal to and in return I receive status and upgrades from them.  It’s a win-win.  

I changed over to Southwest Airlines last year.  I had high-ranking status with another airline and Southwest offered to match that status provided I kept up that level of travel with them.  Deal.  

For the past year I’ve enjoyed A-List status with Southwest.  While not their top-tier, it’s been great and exactly what I needed.  The biggest thing was not having to worry about purchasing Early Bird options for each of my flights when I book them to ensure I have descent boarding position.  I’ve never had a problem paying for Early Bird (Lord knows I’m not going to have my thumb having the check-in button on the Southwest app 23 hours and 59 minutes before my flight check opens 24 hours before the flight time…).  But the status has changed my behavior over a year’s time to not having to worry about it.

In late December last year I had to book flights for January 4 the following year.  I called Southwest to ask if my status would carry over to next year - I honestly didn’t know.  I was told yes.  Cool.  Flight booked.  No Early Bird needed.  Awesome boarding position.  Who da man?  I da man.

Fast forward to end of May this year.  I was on Southwest.com reviewing one of my many upcoming flights for all the trips I had booked already.  And I notice (1) my A-List status isn’t showing anymore and (2) the site was prompting me for Early Bird purchases on all my flights now - it never did that before.  

So I called Southwest Customer Care and I was informed that my status was a promotional offer and it expired in May this year.  Now I’m scrambling online to buy Early Bird for all my upcoming booked flights to ensure I’m not sitting in the back row, middle seat.  Yeah, no one wants that.  

Ok, so now we’ve got a poor user experience right here.

1. I was told my status would remain in 2016 when I called last December.  
2. Southwest and every other airline (and hotel) reward program keeps that status for a given customer throughout the entire calendar year and it renews the following year if that customer earned it that current year.  So there’s a cultural precedent that’s set and historical behavior that I’m referencing given my years of travel and consistency of this model across many different companies and many different verticals.
3. There was no communication from Southwest to me that my status was expiring or ended.  So had I not called, I would never have known what happened.  

What Southwest could have done to make it better was to send me an email notifying me that my A-List status was ending in May and an explanation as to why it was ending (i.e. my promotional offer was over).  And since Southwest has access to not just my account status, but all my flight data, why not send that a month before my status ends and give me the time to buy Early Bird for my upcoming flights that are scheduled for after my status ends?  Like I said, I don’t mind paying for it, it’s just that I’ve been trained for the past year I don’t have to and then BAM! - bye Felicia.  The email could have been something like this:

Would I have been upset that my status was over?  At first, of course!  But I’m a mature adult and would have gotten over it quickly.  I didn’t earn it in 2015, so I can’t expect Southwest to just give it to me for free.  But if they had been proactive about notifying me that it was ending and giving me the chance to buy Early Bird sooner, then that would have been a much better experience.

Are there different ways you would rather be notified about something like this?

I travel a lot for work. And rather than deal with the learning curves of different alarm clocks in every hotel room and then re-familiarizing myself with my own when I get home (not to mention my own impromptu personal getaways), I use my phone as my alarm. It’s always with me. It’s consistent. 

Unfortunately, I have an iPhone. 

With all the innovation and UX design that goes into Apple mobile products, I’m surprised this one basic feature is so…basic. 

I can’t turn off the vibration nor can I set an ascending volume for a given tone or song. And trying to snooze after being jolted awake from a deep sleep by the rumbling of my phone on the nightstand next to my bed is like trying to get the Writer’s Cramp piece from Operation out without touching the sides. It’s damn near impossible. 

I know there are their plenty apps out there that address this, but iOS doesn’t let them function on the lock screen like you would expect. And half the hotels out there didn’t put enough forethought into accessible plugs next to the bed, so leaving the screen on and unlocked all night just isn’t an option. 

In a world where sleep is so important (especially for those of us starting to get up there in years), why do you think Apple – in its “leading innovation” role – still hasn’t figured this one out yet?

It’s no secret Uber changed the game for getting around. I can’t remember the last time I actually called a cab. Not hailed a cab, but called one. 

I’ve been using Uber for over a year now. And recently I started using Lyft as well. Both apps sit side-by-side on my phone. I tend to use Uber first since I’ve had them the longest. But if Uber has surge pricing, I immediately flip over to Lyft and see what their rates are. 

Why? Because there’s no reason for me to have loyalty to either of them. They both provide the exact same service and quality (at least for the use-your-own-car experience).  For me, it’s all about cost savings. 

These companies need a loyalty program. Something that entices me to stay with one over the other, even if it’s slightly more expensive every now and then. If I could earn free rides every month or so, I’d certainly stick with one brand. 

What percentage of surge pricing would be your cutoff for loyalty to a ride service brand?