I haven’t paid for a Southwest flight, yet I’ve flown tens of thousands of miles with them.

All my travel has been free. Or at least very close to it. The points took me maybe an hour to earn (via a credit card) and cost $99 for the initial annual fee. The voluntary deboard (VDB) vouchers I’ve earned ($392 and $456) were earned on flights that I paid for with points and another voucher.

Free has its costs

But I’ve paid for it in other ways. More than half of my itineraries with Southwest have required connecting in some random midwest or Texan city, when plenty of other airlines fly the route direct. Not that Texas and Missouri aren’t great. It’s just that when you add in connections, a route that normally takes three hours and fifty five minutes becomes six hours and twenty-one minutes. A transcon that takes six hours and thirty minutes becomes ten hours and twenty minutes. That last one’s extreme, but they always end up taking over eight and a half hours.

My pre-and post VDB itineraries

My pre-and post VDB itineraries

I’m not losing anything in terms of opportunity cost, since I’m usually just working from the plane or airport. But the extra few hours take their toll. By the time I’m on my second connection, I’m tired, and I wish more than anything that I were home already.

Yet I keep doing it

Despite not having pre-check at my second most frequented airport, and despite these obscenely long travel days, I keep flying Southwest.

I do it so I can use my other airline miles for international flights.

I do it because the placeholder flights I book before I’ve firmed up my travel plans (Southwest offers free cancellation on all flights) often end up being the cheapest.

I do it because I have a short-term memory.

Above, all I do it because it’s free. When I fly Southwest, I lose nothing on paper. I don’t see the ‘lost’ hours. I don’t see the tiredness. My mental accounting ends at the transaction in which I purchase the ticket.

Going forward

Because the Southwest vouchers expire within a year, and I don’t travel to destinations within a thousand miles of San Francisco frequently to burn through the Southwest voucher on only short flights, I’ll have to either a) throw in a transcon or b) change my travel habits to use it up. For the former, I would probably limit myself to an eastbound transcon because the flight is shorter to begin with, and the latter would mean that I would search for mistake fares or award flights originating in destinations to which Southwest flies and use the voucher for a positioning flight.

And when I’ve exhausted the voucher? Well, hopefully I’ll have pocketed another one by then (the current one I’m on was earned on the last flight I had booked with the previous voucher), but if not, then I’ll start to draw down my points balance. In that case, I’ll need to define some system of handicapping similar the Hipmunk or Google Flights ‘best’ sort order, which ranks flights in terms of a combination of cost AND comfort. Maybe that means I penalize 10% for every extra hour of flying time versus a direct flight and 20% for each connection. Seems arbitrary enough that it could work…

The point is, math can only get me so far. Math will always tell me the cheapest flight is best, no matter how insane the routing or how crappy the airline. It can’t quantify my comfort.

Maybe I need to change the equation.