When Travel Gets in the Way of “Travel Hacking” & How This Week Turned Out to Be a TERRIBLE Time To Travel!

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Travel Hacking & Travel
My current view.

Travel Hacking & Travel

As a small business owner with two active and busy businesses, it’s hard to take any amount of time off. Thankfully my passion for travel and my ability to earn a lot of miles/points overrules the time issue. I simply make sure that I travel, even if it means I will have to do some work along the way.

For me working while traveling is fine and something that I am used to, but I hate it when the travel takes me away from opportunity. As much as I like to book trips at the very last minute (like my recent Asia trip), it isn’t possible most of the time. That means I have to look at a calendar, book some flights, reserve hotels and travel somewhere.

But what if the week you choose to travel is a terrible one from the “travel hacking” perspective? That is exactly what happened to me this week. A couple of months ago Alaska Airlines had $200 roundtrip tickets from the West Coast to Hawaii. With a companion cert I needed to use, I managed to book tickets and we were committed.

Then of course this week happened. Among the deals going on are:

and so many more gift card deals…….

Of course someone smarter than me could have looked at the calendar and predicted an onslaught of gift card deals before Mother’s Day, but that didn’t happen in my case. So here I am traveling and missing out on all of these deals. But it’s ok. It truly is.

This Is Why We Do It

The MtM team is probably tired of seeing me send the crying emoji every time an awesome new deal surfaces. Part of the reason this blog exists is because I have a thirst for deals and genuinely get excited when awesome promotions come to light. I am equally pained when I miss out. It isn’t the best character trait, but it’s me. And I suspect I am not alone.

Thankfully Miles to Memories is a travel blog too. It is after all the travel that drove me to both create this blog and drives me to earn miles/points so I can continue to have amazing travel experiences. I never try to lose that perspective, because I am able to travel to amazing places and do amazing things. Deals come and go, but the travel memories really do last a lifetime. It sounds corny but I do believe it.

Do I Regret It?

Whenever I am traveling and doing what I absolutely love to do, it is impossible to have regrets. Sure, it would have been better if I had booked this trip for next week, but let’s consider that a lesson learned. Over the years I have never regretted traveling even when things have gone poorly and I certainly won’t regret taking this trip where I can spend time with my wife and daughter while enjoying these amazing views.

Has travel ever gotten in the way of a great deal? Do you regret taking the trip? Let me know your thoughts in the comments!


  1. At the end of the day, travel is a much more enriching experience. These deals have a pretty consistent cycle. Also, just up your volume on traditional MS and you’ll easily make up for it.

    To be honest, I gave up gift card selling a few months ago and am so much happier. The constant checking for deals and FOMO when i was on vacation was too much. I’ll just do traditional MS when I’m in town and be content.

    • I hear you on the FOMO feeling on gift card reselling. Some times it gets exhausting and when you are in the middle of it you never ask yourself if this is really worth it lol.

  2. I’m waking up at 4 am tomorrow to drive 5 hours back down to Denver to spend all day Saturday and Sunday hitting all the king soopers for this gift card deal. Tried to explain that to my colleagues and they couldn’t figure out why I was driving 1000 extra miles to”buy gift cards…don’t worry about it”

  3. I’ve found that sometimes there is a merchant or service opportunity available where I am traveling that I didn’t have back home! Like some of those AMEX offers?

    Thanks for always watching out for us, Shawn!

  4. It’s just a fact of life; you’re going to miss some travel deals when you travel. Not much you can do about it. I do try to keep up with the blogs and such on the road but, obviously, I still miss some deals.


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