MMMT: Do You Ever Miss the Simplicity of Ignorance?

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The Stressful Side of the Travel Hacking Hobby

Monday Morning Miles Talk is a regular series that has some smaller, more quirky ideas to kick off the work week.  These are essentially random ideas that I wanted to share with you.  Here are the 4 most recent topics.

If you would like to read even more articles in the series you can click HERE.

The Stressful Side of the Travel Hacking Hobby

The Stressful Side of the “Travel Hacking Hobby”

I have been going deep these past few weeks, talking about preparing for tragedy and removing money fights from your relationship.  This week is more of the same, I want to talk about the stressful side of the travel hacking hobby.  Do you ever miss the days of one credit card and one bank account?

The trips and travel are great but we usually only show the glamorous side of “The Hobby” and very little about the spreadsheets, tracking, and running around to catch the deals etc.

Romanticizing Simplicity

I sometimes find myself longing for the days of putting everything on one credit card and paying for said credit card from our one bank account.  No binders of credit cards, no keeping track of 30 log ins, no reading various application rules.  Those were the days, right?

I realize this is a romanticized version of the past.  Kind of like all of those things you hated doing as a kid but now remember fondly.  Or thinking about how fun life was before you had kids but you know you would never trade them in to go back.  Well almost never :)!

I find myself thinking about this during times of stress.  When there is a week of endless deals, like this past week, I find myself regretting doing them because other things get left behind.  But as soon as it is over I regret not doing more.  Probably since easy deals continue to dry up.  It is almost a compulsion, an addiction.  The high from the latest deal is never quite as good as you hoped it would be but when it is over you are longing for the next one.

I guess I am at the point where I need to find perspective and start to do a better job prioritizing deals.  I am not at the point where I earn a ton more miles than I need for my current travels like Shawn does but I do have a little bit of a cushion that I don’t have to hit every deal.  Having said that banking rules and regulations are getting tougher, and earning avenues are drying, up which means I have to do more work for the same amount of gain.

The Stressful Side of the Travel Hacking Hobby

My Place of Compromise

I was already planning on trimming down my credit card portfolio to help out my wife if anything tragic should happen to me or our family. If that ever happened simplicity would become much more valuable.

Doing this should also make approvals easier since my overall credit will drop.  This will also drop me below limits set forth by issuing banks like American Express’ 5 credit card limit or Bank of America’s 4 credit card limit.  Both of this things should hopefully improve my successful application rates.

I also need to learn to say thanks but no thanks to certain marginal deals.  This will be tough but I will need to work on it.


I may be alone in this feeling. It does wash over me from time to time like a warm summer sun coming out from the clouds lasting only a brief moment.  But most of the time I truly enjoy all of the quirky things we do in the name of travel and points.  The key is finding that level place that balances this hobby, my family time, and my other obligations.

There are so many things I would have never been able to do without this hobby. I used to take 2 trips per year when I was paying my way.  Now I average at least a trip somewhere every month.  That is pretty insane…especially when you consider my income dropped by 90% or more at one point when I chose to be a stay at home dad.

The Instagram worthy pics are the fun part but don’t forget the hard work that goes into it to get there.  Heck sometimes even that part is fun, but sometimes it is exhausting.  Don’t forget to takea little time away from “the hobby” to gain perspective!

Mark Ostermann
Mark Ostermann is a father, husband and miles/points fanatic. He left the corporate world after starting a family in order to be a stay at home dad. Mark is constantly looking at ways to save money and stay within budget while also taking awesome vacations with his family. When he isn't caring for his family or taking a weekend trip, Mark is working towards his goal of visiting every Major League Baseball ballpark.

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  1. I like developing a long-term repeatable & sustainable system that I can tweak & augment when new opportunities arise & rules change.

    For me right now that is (mostly besides sign-up bonus spend): 3x everything CFU + 5x CF (quarterly categories) + 5x CIC. I rest easier because there is generally little extra margin to be earned over 4.5 & 7.5 URs respectively, from organic spend.

    Chasing every available opportunity is exhausting & can create a barrier to better offers that can come along. Between my husband & myself, for instance, I leave at least one 5/24 spot open at all times for Chase offers.

    I have found a 1-yr Points Plan, both for accumulating & redeeming, helps with the anxiety on both. I am still subject to the occasional AMEX/Hyatt/Wyndham card wild hare offer but for the most part have targeted spend for specific goals.

    • Good points Pam. I am focusing more on cash these days which probably leads to more issues since cash is cash. I always can use more cash haha


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