The Best Bad Money Decisions We Ever Made

if you’ve been reading here for a while, you may already know that, unlike a lot of folks in the pf blogging community, we are not naturally frugal. we came to this lifestyle of aggressive saving for retirement by thinking hard about what we value (time, freedom) and what it would require to have what we value all the time (some big changes in our spending and saving, as well as a clear plan of attack). we’re 100 percent on board with the minimal spending and maximal saving required to be able to retire early at the end of 2017.

but these are habits that did not come naturally to us, and as proof, today we’re sharing the story of some very, very bad money decisions we made once upon a time. some very bad money decisions that we couldn’t be happier about.

confession time: though you probably would never guess this by meeting us, we’re total romantics. which, it turns out, is a great thing, because we wouldn’t be together today if we weren’t. our beginnings as a couple were highly impractical, and only die-hard romantics would have been willing to stick it out.

(cue the rom com music…) about a decade ago, when we were in our mid-twenties, we were living on opposite coasts from each other, in expensive big cities. (picture us each living very cosmopolitan lives, but often staring out the window forlornly, knowing we were missing something… okay, not really.) we were working for the companies we still work for today, and just happened to have a client in common. during an event for that client in another city, we met. not to be overly dramatic about it, but it was love at first sight. (we didn’t think that was a real thing, either. but now we know.) after the event, we grabbed a casual dinner, had a smashing time, and then each went back home to our separate lives, now carrying this little spark within us.

a year passed with little contact. we probably each wondered if the spark was one-sided. or if it would be weird to flirt with someone who lived 3000 miles away. or if we’d get a “who are you again?” reaction if one of us reached out. and so neither of us made a move.

we have friendster to thank for breaking the ice and kicking off an extended email flirtation. (friendster now seems to be some kind of gaming thing, but used to be an early facebook, before it got supplanted by myspace. we know we’re dating ourselves. gen x, woot!) then we moved up to extended phone conversations. and quickly we realized that we both felt something that seemed real, and needed to figure out if it was real. that meant only one thing: we had to arrange a visit.

this is where the string of bad financial decisions begin. one of us was in pretty good financial shape at this point, but certainly didn’t have huge savings or anything. the other had a student loan, a car loan and credit card debt, but didn’t hesitate for a second to book a cross-country flight.

that first visit was pretty spectacular, and we both knew that this was the real deal. only problem: that whole living on opposite coasts thing. and we were both practical enough that no one suggested one of us moving that early on.

what followed were months of flights back and forth, and often to weekend meet-ups in locations where neither of us lived, requiring hotels and more restaurant meals. we were both in that place in life where we were getting our first taste of career success and wanted to impress each other — so the weekends tended toward the more extravagant: tickets to pricy shows, meals at the trendiest restaurants. when we met in cities where we didn’t live, let’s just say we weren’t staying at the motel 6.

we easily spent thousands on this cross-country spending spree. we aren’t sure how many thousands, as we weren’t keeping track back then, but it’s not a small number. we saw each other, on average, every three weeks for almost a year. assuming we got incredible airfare deals, which we’re sure we didn’t, that’s at least $5000 just on plane tickets. not counting meals, taxis, hotels, entertainment and all the rest. we wouldn’t be at all surprised if the total was approaching $15,000 or even $20,000.

just under a year after the cross-country travel started, we officially become a west coast couple. and a little while after that, we got a handle on where we each were financially, got serious about paying off debt, and got on the path that’s led us to where we are today. along the way, we got married, moved to a smaller town, and committed ourselves to saving for early retirement, which means living so very differently from our extravagant beginnings.

but we’ve never once looked back and regretted having blown all that money. we think of that time in our lives as the best bad money decision we’ve ever made.

our relationship, not to be too schmoopy about it, is everything to us. we’re best friends, we laugh together constantly, we support each other, and even though we both work from home and have plenty of time together every day, we can’t wait to retire early so that we have more time together. and every single day we feel lucky that we’re both so committed to the same life vision and financial goals. we couldn’t do what we’re doing without that shared vision of where we’re headed.

in other words: worth it. every penny. we’d blow every dollar again in a heartbeat if that’s what it took to find each other.

because some things are more important than money, love chief among them. and sometimes it’s important to invest in your future, which can mean relationships and not just job or home, even if relationships can’t be tallied up the way your other assets can be. to us, the money we spent on our long-distance year is some of the best money we’ve ever spent, even those dollars that just went on the credit card and raised our debt. and those memories are some of our favorites, whether because of the cool places we visited or the amazing meals we splurged on, or just because we had time together.

our relationship is our most valuable asset, and while some might call that “priceless,” let’s pick a number and say it’s worth $500 billion, plus the dividends it pays each and every day. it’s our best bad investment ever.

have you ever made a spectacularly bad financial decision that you are happy about? or had to shell out a lot for love? think we’re romantic fools, and we should have saved that money and found partners closer by? ;-) tell us what you think in the comments!

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36 thoughts on “The Best Bad Money Decisions We Ever Made

  1. Ah, I love this post so much! I often think back on my partner and I’s coming together, and although it was not super extravagant, I spent quite a bit more money than I would have if I were just kicking it single. I agree – I don’t regret it one bit.

    I also often think back to my college days. I spent tons of money on partying, attending cultural events, traveling, and just plain having fun. I wouldn’t take it back if I could. In those formative years I got to do a lot of soul searching and I wouldn’t even be close to the same person today if it hadn’t gone down like it did. Back then my goal wasn’t to retire early, be less wasteful, or spend smart. My goals were to have fun, form strong friendships, and to have crazy experiences that would shift my perspectives forever. So I would say at that point in my life my spending was fully aligned with my goals. Now, my goals have changed, and my spending patterns have shifted alongside. To me keeping all aspects of my life in line with my goals/ purpose is more important than “saving money.”

  2. Wonderful post. I just wrote a very similar one myself, though not of a romantic nature. Like you, I do believe that some of the bad decisions of our past turn out to benefit us greatly in the future. I bet all those weekend trips were quite a lot of fun. Experiencing new cities, nice hotels, amazing restaurants; not only did that bring you two closer together, but you kinda got all that out of your system now, so when you do begin traveling again, you know what you’re not missing. You’ve stayed in those hotels before. While nice, you realize they aren’t necessary to have fun and be happy with one another.

    And you two definitely picked the “correct” coast to live on. :)

    1. Agree with you on the coasts. :-) and you nailed it on the travel stuff — been there, done that on the fancy stuff. If someone else is paying, we’ll never turn down a nice hotel, but we’re just as happy camping in the dirt. πŸ˜‰

  3. I’m in a long distance relationship myself… not 3,000 miles, but around not close either. Definitely understand where you’re coming from. Glad you guys were able to make it work out!

  4. I’m married to a big romantic, and I wouldn’t have it any other way. I think that he would spend every penny on me, if he thought it would make me happy. As it is, he will invest every penny for love.

    Unfortunately for him, I am not a romantic. I can’t even come up with one gift idea per year, much less one for birthday, Christmas, anniversary and Father’s Day. He gets love notes on these events, and not because I believe that my love is priceless or that my prose is outstanding.

  5. Love this post! What an awesome and romantic story you guys have! While our courtship wasn’t quite as extravagant as cross country trips, it did involve expensive dinners out, tickets to expensive sports events and concerts, and lots of flowers. And while we may be keeping things a little more frugal now, I don’t think a single dime of that was wasted.

    1. Haha — Maybe if the spending had seemed deliberate at the time, we’d call it an investment. But in truth we just blew a lot of money and we’re just thankful it all worked out! πŸ˜‰

  6. On paper, my now-husband was a nightmare. He has health problems that made it hard for him to keep a job. (He’s now on disability.) Meanwhile, he had $20,000 in defaulted student loans. And I was on disability myself. Oh, and his ADD made him spend incredibly impulsively.

    Our getting together wasn’t a good idea… technically. But we’ve been together for 9 years, married for 7. I was able to get a job I can do from home, so we paid off the student loans, the $12,000ish of various medical expenses he accrued along the way, own a house and even have savings. Sorta. There’s a $25,000 oral surgery bill next year that we’re socking away for.

    But then we’ll be pretty much in the black.

  7. What a lovely story, it’s wonderful to learn the personal side of your relationship! :) I think it also goes to show that it doesn’t matter when or how you create financial goals, but once they are aligned the rest will follow. I always look back to my time spent in college and not recognizing the repercussions of the money I spent then that could have been saved to pay off my student loans after graduation. But those four years of building my education, holding internships, joint clubs, volunteering, and building relationships/connections I will never, ever regret!

    1. That’s great that you have that perspective! We sometimes wonder if people who are frugal for life miss out on some experiences. Having a few years to make some mistakes isn’t a bad thing, and gives you confidence in your decisions later.

  8. My favorite post to date. I was hoping you would say that you didn’t regret spending that money, because my mind immediately went to “well you may have never met each other…”

    So cool how you can look back on that and think what a great experience it was, as well as learn from it in a positive way. Let’s face it – we all want to retire early and we all talk about ways to save money, be more frugal, etc. The fact of the matter is, we don’t know what will happen today or tomorrow, or a week from now or a year from now. All we can do is live in the moment and do the best with what we have. It’s great to plan for the future, but it’s also incredibly important to live in the present and not forget the past.

    Thank you for sharing your experience!

    1. Thanks for that! We absolutely don’t regret a thing about spending that money. Like you said, the future ain’t guaranteed, and we think making memories is the best use of money, especially when it’s to form or strengthen relationships that stick with you. 😊

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