Point Being: Travel Hacking Takeaways

Come on in, the water’s fine!

Come on in, the water’s fine!

Summer vacation expenses got you thinking about dipping a toe in travel hacking? As this neophyte is finding out, the rewards can come surprisingly quickly. Here are a few takeaways from my experiences since taking the plunge last month.

A Big Splash Right Out Of the Gate    

“We're impressed with how many points you've earned,” hailed the congratulatory email, notifying me of 40,000 bonus points posted to my Southwest Airlines Rapid Rewards account. I was impressed, too, by the fact that this happened in the promised time frame without intervention.

It seems travel rewards accounting has come a long way, baby. That’s true on the promotion side as well, with multiple helpful messages explaining how to further boost my points total. Opportunities go well beyond the obvious “get on an airplane,” but is it possible to keep up the initial torrid pace? That could be a big ask, given the criteria I’ve set:

  • Minimal time commitment
  • No increase in spending 
  • Decent bang for the buck
  • No impact to financial well-being – The really big points come from credit card churning; for me, it’s not worth the risks or the tracking headaches.

The Next Wave

Depending on your criteria, your mileage may vary. Given mine, I concentrated my efforts on accumulating points incrementally. My experiments met with promising, if mixed, results. 

  • Making hotel and car reservations with Southwest travel partners, the obvious cross-sell, was as easy as the doggy paddle and netted several thousand points. 
  • You can also earn points by responding to e-Rewards® consumer surveys.  Alas, offers of $9.50 in e-Rewards® currency (whatever that is) to complete a 40 (!) minute survey represented too much complexity and too little bang for the buck.
  • On the other hand, shopping with Southwest’s retail partners has great potential.  If you’re going to buy a baby shower gift, vacuum, printer ink, and cat litter from Target anyway, why not get points and discounts by buying them via Southwest’s portal? If your timing’s right, you might also be eligible for a big chunk of bonus points, e.g. 900 for that $300 Target order during Back to School bonus time.

Beware the Undertow

Rewards partner shopping is not for the faint of heart or math-shy. Are prices competitive? Which of the 850 (!) vendors to use? What if one offers 4 points per $1 vs. another’s 1 or 2? If shopping at Target, do you use your 5% off REDcard or your Southwest VISA?

Then there’s the math involved if you’re aiming for a certain spending level to qualify for bonus points and avoid shipping costs. This can lead to temptation to buy more than you need, or keep unwanted items since returning them may void your bonus.         

Buying from multiple stores further ups the complexity and time to place the order.  And it might induce procrastination. That’s OK when buying a vacuum; cat litter, not so much.

Clearly, this kind of shopping can be tricky, but it gets easier with practice.  And these small tweaks to my normal buying patterns have already increased my total to a whopping 53,958 points, with 3,500+ pending. So I’d have to say my experiments in points-gathering are going swimmingly.        

Sink or Swim?

But let's not forget the real reason for doing this: to save actual dollars. By that measure, I’m doing a little better than treading water, having saved a couple hundred bucks through Southwest deals. That’s what happens when you’re a newbie with bad timing and a minimalist approach. 

  • I started too late for the big bonus to make my next flight free. 
  • I shifted spending away from my longtime Marriott Rewards card, ruining my chance for free hotel nights. (Cue Homer Simpson.)
  • Others with greater expertise, time, or patience might dig deeper to explore options such as converting miles to hotel nights.   

As for me, I’m going to chalk it up to experience and look to the future. There, on the horizon, it’s not hard to make out the cumulative effects of even minimalist travel hacking. In the meantime, if anybody knows how to get a rental car for less than a king’s ransom, please share in a comment below.