Rewards Gone Wrong: Recovering from Financial Mishaps

Rewards Gone Wrong - picture of empty wallet

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I know, I know.  All of you credit card rewards naysayers think it’s hilarious that my nearly free vacation cost me almost $1,500 due to my flights being cancelled by Snowpocalypse. (You can read about my financial mishaps hereI’m sure you’re laughing your cracks offWell, laugh all you want, fools.  Meanwhile, I’m laughing all the way to the bank.  Well, kind’ve.  I am doing my best to recoup some of the extra dough I lost by being stranded in Jamaica for an additional two days.  Here’s how:

  • I filed a travel insurance claim with Chase– Because I paid the $96 for our trip to Jamaica with my Chase Ink Bold card, I was able to take advantage of the free travel insurance that they offer.  I waited a few days for the claim forms but it looks like I will be reimbursed for the two days at the hotel plus any meals we paid for during those two days.  Since the two extra days at the hotel cost us $520 and we spent around $30 on meals at the airport, we’re expecting a refund of around $550.  All we have to do is submit our receipts for the hotel and proof that our flights were cancelled due to inclement weather.  Winning!
  • I got an extension on two writing jobs- Two of my writing jobs were due Friday and I thought that I was going to lose out on them altogether.  However, I was able to get an extension on two and completed them on Monday.  Woot!
  • Greg picked up some overtime- As soon as we got home, Greg went back to work.  Fortunately, he was able to get some overtime almost immediately.  It’s not quite enough to make up for his lost wages, but it all counts, right?  Hopefully he will get some additional overtime over the next few weeks and be able to make up for all of the income that he lost.  Either that, or he’s getting a part-time job.  Muaaahahahhhahhhhhhhhhhhhhhh! (Kidding)
  • My website is makin’ it rain- February is turning out to be one of the most profitable months for my website in terms of affiliate income and Google adsense income.  I’m also expecting to get a few large payments in the next few months that will hopefully make up for any shortfalls.  I like that.  Thanks to Erin at Broke Millennial for interviewing me about credit card rewards at Daily Finance and sending all of those people my way to sign up for said credit card rewards. XOXOXO
  • We’re on a no-spending spree- I’m not going grocery shopping (except for bread and milk) until the 1st rolls around and our new grocery budget starts over.  I don’t care if we have to eat canned corn for dinner.  I’m not going to go.  (Ok, maybe I’ll go…but I’ll just get the basics.  And maybe some Ramen.)  We technically do have $184 left in our grocery budget for the month of February but I would rather save it if at all possible.

The truth is, there are all kinds of way to recover from financial mishaps.  Sometimes it takes tightening our budget.  Other times it might mean selling our stuff, taking paid surveys, or picking up overtime at work.  But there are ways to recover from financial mishaps quickly and easily.  So, even though my vacation didn’t turn out to be as “free” as I initially planned, it was still awesome and I have no regrets.  Plus, I was stranded in Jamaica, remember?   It’s not quite the same thing as sleeping on the floor at the airport in Mexico City.  (I did that once)

How do you recover from financial mishaps?  What are your favorite ways to raise extra funds?

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  1. Nice going! It’s gonna be tight for us with me getting my wisdom teeth pulled out and T being laid off, but I have some freelance work going and we’ll just see what happens.

    1. Ugghhhh….how much does it cost to have wisdom teeth taken out?

  2. Wow, Holly!!! I am loving this!! So many people would’ve said, “Oh well, what’s done is done, and we’re fine financially” You guys chose to step it up big time and make up the shortfall, even though you don’t “need” to. This is the difference between “good” and “best”. Great job. 🙂

  3. Yes, but your “free” vacation was still more free than someone who PAID to go to Jamaica and was then out an additional $1500… just saying…

    Also it is good to hear some real world proof that Chase’s travel insurance is as good as they say it is!

    1. So true, Brian!

      I will write about the process once it’s over. All they ask for is proof from the airline that our flights were cancelled due to weather and all of our receipts. Since our hotel was all-inclusive, we don’t have a bunch of separate receipts for meals…which helps. Hopefully they will pay out. I don’t see how they can’t.

  4. I really enjoyed Erin’s article on credit card rewards and I’m glad it sent people your way! I recover from financial mishaps by, well, panicking haha. Okay not necessarily panicking but I do get laser-focused on analyzing our finances and figuring out a way to recover, much in the same way it looks like you will recover from the weather-induced spending.

    1. We actually didn’t get stranded at the airport thankfully, just at the resort.

  5. Very cool Holly, especially on the travel insurance and the affiliate income – definitely got to like the latter of those two. 🙂 Thankfully we’ve not run into anything major lately (knocking on wood) but when we do run in to something where we need more cash it usually just means picking up some extra writing jobs on the side.

    1. Yep! Totally. I like having the option to find more work- one of the things I love about being self-employed!

  6. That’s great that you’ll get reimbursed by insurance! Love that you’re keeping a positive outlook on the whole thing.

    1. Hard to be angry about anyone about the weather. Plus, I DID NOT want to fly if it was unsafe.

  7. That’s pretty awesome, Holly. Talk about a silver lining.

    The way you guys use credit card rewards to fund these mega-awesome vacations is just super awesome. It’s not a surprise to me at all that your affiliate income is following suit.

    1. Hopefully it will stay high, although I need some more strategies.

  8. Great point about tightening the budget. Sometimes life just happens and you need to make some adjustments for the short-term. They aren’t all welcomed or pleasant, but the better able you are to adapt and change things up, the better off you will be in the long run. After all, I’m sure this isn’t going to be the first time life throws a curveball your way.

  9. Looks like you will be able to recoup the costs in no time. I don’t know why some people are always such haters.

  10. I love when the website makes it rain! Nice work on the recovery Holly. I usually just work harder and get the money back. I am doing that right now with an unexpected carpet expense.

    1. Hell yeah, Grayson! I hope you like your new carpet =)

  11. I LOVE this Holly! I love that you had a financial set back and you didn’t sit there and cry like a baby, but you put your big girl panties on and went about making up for the setback. It is a great lesson for everyone when they have financial setbacks. Good for you!

    1. Thanks, I’m trying to stay positive over here.

  12. I wouldn’t have thought that the credit card offered insurance for such incidents. Good to know for the future just in case something like that happens to me.

    1. Yep, Chase Ink Bolg does. I think the Plus card does too.

  13. Just goes to show, a little effort is worth a whole lot more than a lot of moping and complaining. That travel insurance perk is pretty sweet!

    1. Yeah, I know. I would never pay for it but love it when its FREEEEEEEEEEEEEEEEE

  14. This post made me laugh, a lot!

    It’s nice when things end up lining up. I’m really anti-travel insurance, but honestly, maybe I shouldn’t be considering it should be reimbursing you about a 1/3 or your losses.

    1. Well, it was free since I used my Chase Ink Bold card. I’ve never paid for travel insurance before!

  15. That is awesome that the travel insurance will be refunding you, I need to make sure I have that next time! Good job on making it rain as well 🙂

  16. You are extremely lucky for being able to recover around a third of your losses through insurance. Who would’ve though $100 worth of insurance would end up paying you $550? And kudos for the website profits this month. Many famous rick people say it’s important to diversify your income streams and I think you’ve shown us why.

    1. Actually, the insurance was free because I used the Chase Ink Bold card to pay for my flights.

  17. Love this, Holly! So many people would just grumble about the extra cost and do nothing but grumble. You and Greg did everything you can to recoup the lost money and sounds like you’ll at least make a good dent in it. We had to spend an extra couple days in Turks and Caicos once because Taylor got an ear infection and couldn’t fly. We were miserable. So, so miserable. LOL! Okay, there was some mild panic because both Chris and I were supposed to back at work and I had an event that I was supposed to attend … but we managed to survive somehow. 🙂

  18. Get it, woman! Your resourcefulness is awesome. I really enjoyed reading about your trip, too!

  19. Nicely done! Trip insurance is something a lot of people don’t know they have. AAA reimbursed us over $500 when my truck broke down on last summer’s big road trip. I wasn’t even aware of it until a friend told me to look into it. Glad you’re more than making up for your $ loss!


    We got a few signups as well, and some new readers. That’s was a pretty awesome article Erin put together.

    Glad you are recovering that money, because vacation mishaps suck 🙁

    So where are you two off to next? London, right?

    1. We’re actually going to Florida in April…but I’m not counting it 100% since I plan to work all week. It’s more of a vacation for Greg and the kids.

  21. It’s awesome you were able to file a claim with Chase and get reimbursed! Sounds like the rest of February will be going well for you. I try to cut back however possible when I have an unexpected expense that doesn’t quite justify the use of my emergency fund. Otherwise, overtime is a nice option to have.

    1. Yeah, definitely. The overtime he gets is really random, but I like it when it comes along.

  22. Love that my DF article might have sent you some sweet, sweet cash! Nice that you had the travel insurance. I never end up purchasing those, but seems like they do pay off from time-to-time especially traveling during the winter! Sounds like your mostly free trip will still have been totally worth it and quite cheap.

    1. I’ve never bought travel insurance either. The insurance we’re filing a claim with is just the free travel insurance that the Chase Ink Bold card offers if you use it to buy flights.

  23. Good for you Holly (and Greg!) insurance can be such a life saver!

  24. We also got jacked by the Snowpocalypse. Looking back, I wish we’d been “trapped” in Cancun. Instead I flew us back to Philly because I was scared we’d never get a domestic flight back home. The trip from Philly to NY in the middle of a blizzard was miserable. As was trying to fly my grandparents back to snowcity (err Maine). 4 cancelled flights in 5 days ugg. Thank god for travel insurance that will hopefully cover some of our expenses. Glad everything seems like it will work out on your end too!

    1. Thanks. It looks like we’ll be covered but we’ll see!

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