Know Thyself – Why I am Scared To Travel Hack

My passport is sitting in a drawer in my home office, cold, alone, and unused for almost a year. I have not been outside the confines of these United States since I spent New Year 2017 defining my tan lines in Havana. It’s not that I haven’t been anywhere since then. I’ve flown home to New York several times, jetted to L.A. to be the flower girl in my friend’s wedding, gave myself a spring break in D.C. to hang out at the Blacksonian for two days (Go there. Now!), and even took a few business trips below the Mason Dixon. But international travel, I have had none.
first world problems 2

I save $150/month in a vacation sink fund in the hopes of building up enough money to go abroad once a year. When I found out I was going to be laid off, visions of Bali’s beaches danced in my head as I contemplated renting my condo and getting out of the country for a while. Alas, domestic travel has depleted my sink fund so stateside I must stay.
i know what you're going to say

Yes, I know that there is a solution to this “problem,” and it is called travel hacking. Everybody. Is. Doing. It. I too could open new rewards credit cards for the points bonuses and spend pennies on the dollar to travel to my heart’s content. I have excellent credit so getting approved n’est pas de probleme. So why haven’t I done it yet? I want to. Believe me I do. We all know how I get at the prospect of  getting something for next to nothing.
I also love earning points. I’m that friend who’s always saying, “Let’s just put it on my card and y’all can Venmo me your share.” Still, when it comes to opening multiple credit cards and having to spend thousands of dollars in a few months…
I'm so scared

We’re Off To a Bad Start

It all started with a t-shirt in the beginning weeks of my freshman year of college. I can’t even remember why I wanted the flimsy screen print on a basic Hanes undershirt. Maybe I was avoiding laundry, which would be a probable explanation.

lazy condition.gif
All it cost me was my name, address, and social security number on an application, thousands of dollars in interest, and a decades long battle with spending money before I get it.

Although my first American Express card sat unused in a drawer for months, eventually it became the devil on my shoulder, telling me that I could afford that orange hoodie with the three quarter length sleeves, the gray skirt with the thigh high slit, and the platform wedges too, even though my only income came from a $7.00/hour work study job at which I clocked five hours a week.

What started at 18 years old with a single account ended with a charged off Amex balance and four maxed out store cards by the time I was 22.
you better get your life.gif

Still Not Doing It Right

With the fear of bankruptcy forever embedded in my soul, I dug myself out of collections and paid off all but one of my store cards. I knew my credit was improving when I started getting offers from Discover and Master Card. The Limited (RIP) even raised my limit all the way up to $1000. It was at this point that I felt confident enough to apply for a Capital One Visa. Because I had once been an authorized user on my mother’s account, the good folks at Capital One granted me a platinum card with a $200 limit.
don't spend it all in one place

I spent the next two years acquiring higher limits and a few new cards. However, unlike my college days I now used credit “responsibly,” which really meant that I no longer missed payments and didn’t max anything out. Sure, I carried balances at 19% interest, but the monthly payments weren’t a problem. I owned a house, had a couple thousand dollars in savings, and paid my bills on time, so you couldn’t tell me I wasn’t a money management beast.
you can't tell me nothing

Turning Point

In late 2005 my outlook on debt was forever influenced after a church sermon based on Dave Ramsey’s principles in Financial Peace. Up until that point it had never occurred to me that I did not have to have debt. When an idea resonates with me I can go from zero to sixty in no time, and so it was with this one. While paying off my mortgage and student loan seemed insurmountable, clearing the few thousand dollars off my credit cards seemed totally doable. I canceled my gym membership, cut back my cable package, and cut up my Visa Platinum and Macy’s cards in front of the entire congregation. Within five months the debt was gone and I started a cash only existence…For a little while at least.

Back and Forth

Since then I have cycled in and out of using credit. After a weeks’ long shopping binge in early 2006 culminated in opening another store card, I was convinced that credit cards weren’t nothing but the devil trying to knock me off my path.
not today satan

I once again vowed to leave the plastic alone, and I did so for years…until around 2009 when rewards cards started coming in vogue. That Capital One card that I’d cut to pieces may have been dead, but the account attached to it was very much alive. The allure of rewards got the best of me and one day I called Capital One and converted my card to a Quicksilver. Free flights here I come!
not so fast

It took a month of buying crap I did not need or want just to accumulate points, for it to register that at a 1.5% earn rate it would take $20,000 of spending just to get a $300 flight. I quickly realized that I was on a journey to nowhere and gave up the quest, but not before pushing my balance close to $2000.

With a windfall from the sale of my house in January 2010 I freed myself of credit card debt (all of my debt actually) and pledged to stay that way.
forever cardi b
I did not care about rewards points. Credit cards were not for me. Even in grad school when traveling to Fiji, Telluride, Ghana, Ethiopia, Paris, Scotland, Sweden, Israel, and more I refused to break the glass on my still open (albeit once again dormant) Capital One account. If I could not afford it with savings and Stafford loans then it just wasn’t happening.
more responsible than most people

Groundhog’s Day

Coming to the end of my savings after graduating from business school and before landing a job drove me to once again call Capital One for a new card. After more than a decade of false starts had I finally mastered the rewards card?of course not

While everyone says, “Just use the card for your everyday spending and then pay it off at the end of the month,” I couldn’t quite follow that advice. I used my debit card for everyday spending and the credit card for stuff I couldn’t afford right away and then carried a balance month to month. It wasn’t a large balance, but it generated enough interest to wipe out the $5-$10/month I’d earn in rewards.

It got worse in the weeks leading up to starting my first six-figure salary job and closing on my condo. That living room ain’t gonna furnish itself so obviously it needs Restoration Hardware everywhere!
making it rain

I took my card to the brink of its limit, but paid it off the same billing cycle with my signing bonus. The combination of a zero balance, three figures worth of points, and a fatter paycheck swelled my confidence that I could finally play the credit card rewards game and win. I put every dime of spending on my Quicksilver card and paid the bill off in full at the end of the week. Seeing the points rack up as my balance stayed non existent had me feeling myself.

Well ego tripping only works for poetry, and it wasn’t long before my “everyday spending” started to include more home decor than my paychecks could cover in a month. Pretty soon the bonus checks I’d planned to use to knock out a large portion of my student loan were diverted to covering my five figure credit card bill, until even that wasn’t enough to keep me from once again carrying a balance.

For the fifty-leventh time I stopped using credit while I spent the better part of a year paying the debt. The points balance that had made me giddy months before just looked like a poor life decision as I paid ten times the rate in interest than I’d earned in rewards.

Bling Bling

No sooner had I freed myself from Capital One than the mother of all rewards cards come to my attention, thanks to a GroupMe chat with my sorority sisters.sapphire_reserve_card

And to this card, I thee wed. It wasn’t the $300 travel credit or the 3% earn rate on the very liberally defined travel and dining categories. Nor was it the complimentary TSA pre-check or the Priority Pass membership. I was all about the 100,000 point sign up bonus and 1.5x redemption on Ultimate Rewards travel. Finally, a rewards card that could feasibly get me the one thing I’d always wanted: free travel; and all I had to do was spend $4000 in three months.

I got it done in six weeks and promptly used my points to get me to Cuba for New Year’s Eve. I’d love to say that after my trip I curbed my expenditures and settled into a more reasonable spending pattern.

Every month as my balance climbed higher I played tag with my purchases to keep the bill paid in full at the end of the billing cycle. What does that mean? Let’s say in December my credit card bill was $1500. Before the bill is due in January I’d simply charge another big ticket item that I do have the funds to cover immediately, pay it off before the previous bill’s due date and promise myself I’ll tighten my belt enough to cover December’s purchases in February, which would inevitable get pushed to March, then April, and so on.

Borrowing money on borrowed time has an expiration date and it was only a matter of time before I was raiding my savings to continue to make payments in full. I even took the interest hit for a couple of months when I couldn’t bear to touch my “emergency fund” one more time.


In October 2017 a miracle occurred. I paid off the monthly balance on both my Quicksilver and Sapphire Reserve with just the cash I’d earned that month. A month later the miraculous happened again. And just yesterday I sent a payment to Chase to clear my purchases for the week. Is it supernatural intervention? Nope. It’s just a budget. There’s nothing quite like getting laid off for making one stick.

What everyone forgets to mention when they say, “Just be sure to pay your bill in full every month,” is that you need to know how much you’re going to spend before swiping your card. It turns out that it’s actually very easy to manage credit when you’ve planned where the money is going ahead of time.
who knew

Decisions Decisions

Although it looks like I’ve at long last reined in my spending, I am not rushing to fill out another credit card application. Sticking to a budget is still a recent habit for me. I’m worried that just like exercising and eating right, it’s a struggle getting on the wagon but super easy to fall off at the slightest jolt.

Spending on a deadline was a trigger for overspending with my Sapphire Reserve. Even when using a card for everyday purchases, the earn rates aren’t enough to amass significant rewards without spending tens of thousands of dollars, so the bonuses are where the real value is. I worry that the pressure to hit a target will have me once again deluding myself that I cannot get there on the strength of what I buy everyday.

I developed an aversion to paying credit card interest long before I actually stopped paying it, so I am not naive enough to think that knowing better automatically equates to doing better. Even though I have technically come out ahead with my Chase Sapphire earnings, I still lost because I spent way more than I ever would have if I was operating on an all cash basis. With no steady source of income for the foreseeable future I cannot afford to charge impulse purchases and figure it out later.

Really this is a matter of trust. Do I trust myself to choose a card that provides the rewards I need in a way that aligns with my budget? Do I believe that I will continue to stick to my budget? Do I have the patience to use the entire promotional period to earn those bonus points? I’d like to think that I do, but my track record when it comes to credit cards is less than stellar. Yeah, it’s been a long time since my days of missed payments and collection agencies, but that doesn’t mean I’ve been winning in the years following those follies.

I would love to be like the bloggers I see who are traveling the world in first class accommodations for less than the cost of a roundtrip flight between O’Hare and LaGuardia. I am so tempted to cancel my Sapphire Reserve and fire off an application for the Preferred and the 50,000 points that come with it, but something always holds me back. They say that the definition of insanity is doing the same thing over and over again and expecting a different result.
you know I'm not crazy

Am I alone? Is anyone else hesitant to jump on the travel hacking train? Is there hope for a recovering directionless spender? Hit the comments and share your thoughts.

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28 thoughts on “Know Thyself – Why I am Scared To Travel Hack

  1. Interesting read! I haven’t gone through what you have, but don’t really do much travel hacking. We get 2-3 credit cards a year, but mostly used the points to get the money back.


    1. I use the cash back rewards on my Capital One account to get people gifts. For Chase the redemption value is much higher when the points are used for travel. I’m trying to bank enough for an awesome first class trans Atlantic (or Pacific) flight. It just took me way too long to figure out that a budget has to guide all the points earning I do.

      Thank you so much for stopping by and leaving a comment. Looking forward to keeping up with your countdown.


  2. Great blog post!! I hate credit cards! I remember you telling me last year about all the points and benefits you got from your card, and I listened but didn’t say much. I just can not be a regular user of credit cards. Since I paid off my credit card debt and student loans whle living in Germany, the only debt I’ve really carried is my mortgage and car payments. I will use a credit card for major purchases or home repairs, but pay them off aggressively. I love a good deal and getting what seems like something for nothing, but it just sounds like a trap to me!


    1. Hey girl! Thanks for commenting. So good to see your name pop up.
      I’m not 100% anti credit card for everyday purchases. The rewards purchased Christmas this year. I just think people oversimplify things with the whole, “just don’t spend more than what you can pay off.” That doesn’t simply happen just because. When I operated on just cash my boundary was what was in my bank account. It took way too long to click that if I was going to try to game the credit card companies then I’d have to set up boundaries again (i.e. a budget). I ned to get that part down before I try to bonus points my way to traveling the world.

      Please do come by again!


  3. You are smart to be afraid! This story reminds me of dieting. You can say you’re going on a diet, but if you’re keeping Ben & Jerry’s and chips and crap in house…well good freakin luck! I can see the temptation of spending the amounts you need to get the free travel. I think you should just say No to all that and look for cheap last minute deals that come up with the airlines. You’ll be better off in the long run! Now I gottta go find some holiday cookies..ha!


    1. Girl, that Ben & Jerry’s Half Baked ain’t nothing but the delicious devil! I definitely think that the points and rewards can be useful, but not enough ink is spilled on the planning piece of it. It literally did not click that an in use budget was step 1 for all of this. I think some people take it for granted that money management doesn’t just happen for everyone.


  4. It is helpful to only sign up for a new card when you have a plan on how to complete the spend. Don’t take on a bonus requiring $4000 in spend without some big necessary expenses coming up. It has become easy for my family with college tuition. It sounds like the incentive to hit minimum spend levels has been a challenge for you, so take it slow.


    1. I never had a plan, but necessary expenses (usually related to Silver Betty or healthcare) always come up anyways and put a big dent in those spending minimums without me using the need to meet the minimum as an excuse to buy $700 boots. But I do love those boots sooo….

      Thanks for stopping by and leaving a comment. I hope you come through again.


  5. This is the critical thing. Unless you are going to master manufactured spend (and be ok with the nominal costs associated), you really have to be disciplined and buy only things you 1) can afford; 2) would have purchased in cash anyway; and 3) are substantial enough to put you over the spend thresholds for the card in question.
    If you can do these three things, travel hack! I have been hacking for over 5 years and I have made my fair share of mistakes (accounting/overspending) and not been disciplined at times. If you aren’t careful, your “free” vacations won’t be so free anymore. My advice would be to start with and limit yourself to a card with a small ask and discrete bonus (like the IHG or the Hyatt) and build from there.


    1. You so get me. Thank you so much for stopping by and commenting. I hope you come back.

      I would move down to the Sapphire Preferred if I could think of $3000 in expenses I will definitely have over a three month period. In the absence of that I’m sticking with the Sapphire Reserve I have now and being happy with what I earn. I’ll definitely keep in mind the IHG and Hyatt cards.


  6. I feel you … but I don’t feel you.

    I 100% agree with the pain of avoiding overspending when you have the CC. I’m dangerously close from a 1-2 month hiatus just to get my mind right.

    But when it comes to the bonuses, there are a lot of options to get there without risking it all.

    One big one is paying your rent or mortgage with the CC. I don’t do this regularly, because the fees don’t make it worth it. But for a sign-on bonus, you can pay the $10 transaction fee. This is a way to drop a few thousand, but it’s not new spending on random junk.

    I also used to pay my student loans with a CC. It was only one of them that allowed this without fee and had a $1,000 a month limit … but damned if I didn’t put $1,000 a month instead of paying it all off at once.

    Last thing, there is a trick called manufactured spend. It’s gotten harder and the loophole have been cut out, but you can still “pre-buy” things with the credit card (CC) that you need. Amazon gift certificates in my house are as good as cash. You used to be able to get $500 gift cards or load a pre-paid visa to increase your spend without actually spending the money.

    So … I feel you … but I did take that trip to Bali and Bali is bomb as sh*. I can help you out on the finer details if your still thinking about it.

    – Damien


    1. See, I’ve tried to pay things like my property taxes, mortgage, HOA fees, or student loans with my card, but I can’t get over the mental hurdle of transaction fees. They hurt my feelings.

      And of course you’ve been to Bali. Of course.


  7. This is interesting. I had never thought of it this way before. I get the bonus and stop spending on the card. I don’t spend anything I don’t need for the month.

    I guess this is why the credit card companies allow for travel hacking websites, because some people might be tempted into carrying a balance. Have you tried limiting your credit on a card? Say your budget is $1000 a month, then just use one card and lower the credit limit on it to 1,000 so that you don’t go over for the month. Don’t use any of your other credit cards.

    If you’re opening an account for a bonus, then just use that $1,000 limit on the other card for the month.


    1. Hey Olivia! Thank you for commenting. Lower my credit limit actually hurts my credit score because it raises my credit utilization.
      I do like the suggestion of setting a limit per month for how much can get spent on a card. I guess I do that now because I’m following a budget. Since September my spending has become much more mindful as I’m directing my money toward what I value most. Suddenly my credit card bill isn’t filled with hundreds of dollars of Grubhub. Go figure!


    1. Thanks for the words of confidence. I’m sure I’ll try it one of these days, but I want to feel like my spending is a well oiled, frugal machine before I get into.

      Now would be a great time to do it since my expenses now include money spent running a business. I could put all of my business expenses on a new card and hit my spending limit lickety split.


  8. I’d like to have a travel rewards card, but I’m just starting out actively living a cash-only lifestyle in order to pay down (AND OFF!) my current debt. They SOUND good, and are tempting, but I just don’t travel enough and don’t want to add to my already stress-inducing debt. Maybe some day I can return to the credit card game, but until then it’s pay down time. Wonderful read!

    Liked by 1 person

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