Throughout my 20s and 30s, I spent with reckless abandon. Never beyond my means, but never with an eye on setting anything aside. If I made it, I spent it, almost always in the service of good times. Often, this included stumbling in and out of bars, at home and afar, as was common of the listless Gen X twentysomethings during their coming-of-age period. Since I moved far away from home right after college and wanted to maintain close relationships with all my college buddies, I did a lot of drinking from “afar,” traveling back to the Heartland and the Coasts, or wherever else they landed. I also did a lot of destination traveling during those decades, meeting up for football and basketball games, concerts, or rendezvouses to destination cities like New Orleans. In some ways, I wish I’d kept a running tab on everything I spent in the name of fun and overindulgence for that first 20 years after college, but I think it might make me cringe now. I don’t think I’d trade a lot of those experiences back for money, but lord knows I did waste a lot of it on marginal-at-best experiences for my bar crawling escapades. Travel to see friends and take in new cities and novel experiences is one thing, stumbling around town in the hopes of getting some action and pissing away your paycheck is another story. There was a lot of that for me. Fortunately, I grew out of it. It certainly took longer than it probably should’ve, but here I am, firmly middle-aged and intentional about my imbibing and spending habits. Mostly.

A few years ago, I made up my mind that I wanted to buy a piece of property out west to spend my vacations and opportunities to work from “home.” Initially, I envisioned a big chunk of wooded land, maybe 20-25 acres, with a nice little cabin, off the grid and away from the hustle-bustle of anywhere and anything. That became almost immediately unrealistic, at least now, especially when I’m still paying a mortgage on my primary home. So, by necessity, it evolved to a little cottage in a cool mountain town, just big enough to hang my hat, as they say. Though, that ain’t exactly cheap either, but it’s cheaper. We’ll see if it becomes a reality. Stay tuned.

I hope to leave behind this mode of travel very soon. I’ve logged enough miles for a lifetime. (Image comes courtesy of Pixabay and was retrieved from here.)

So, I started setting aside money to do this, with a goal of making this purchase before I hit the half-century mark. Since I’m not exactly interested in dead farmland in northeastern South Dakota, but some idyllic mountain hamlet in the Rockies, the current market and interest rates are making it even more challenging. But save I have. As I’m a few years out from when I hope to make this purchase, I haven’t really looked at anything specifically or in-depth, just enough to gauge what the market holds and will bear; you know, to get a range of what’s realistic. Recently, I started punching numbers into a mortgage calculator and was disenchanted to see how much my monthly payment would be based on what I expected to have for a down payment and my hopes for lower lending rates in a few years than what I can get now (side note, my mortgage on my house now is 2.25%; if only I could be that lucky on the next purchase…).

So, reality check: I’m probably not going to be able to buy what I want, when I want it. But that doesn’t mean I’m not going to still try. The thing is, for me to even get close, I’m going to have to tighten my purse strings, something that I haven’t been exactly great at over the course of my life, even if I’ve gotten better over the last few years. I told myself I won’t take any social trips by plane starting in 2025 until I’ve made the big purchase. This will certainly help, as flights are often ridiculously expensive, and typically when you fly somewhere, you also need lodging, and you spend a little more liberally (or maybe that’s just me). We’ll see how I do on it. I told my best friend this and he immediately doubted my ability to hold myself accountable in this way…

But it’s not 2025 yet, and I’ve got one last social trip by plane on the books, one I wavered on a lot (which in the end caused me to spend more money because the price went up during that period of hesitancy). It’s a trip back to my undergraduate alma mater to see a bunch of friends from college for homecoming, most of whom I haven’t seen in 2-3 years, some in five or more. Usually, I see most of them in the Chicago-area where they all largely ended up, and that city lost its luster for me years ago, plus, it’s usually just one night, or really, a handful of hours, that I get to actually hang out with them. This trip will get me close to a day and a half, and in a nostalgic context. Since I haven’t been back there for a football/dude’s weekend since 2016, it could be a long time again until I’m able to return, especially if I hold myself to my new policy.

But it was a more aggravating decision than I’ve let on so far. I was literally trying to determine the economic trade-off and ROI of what would very likely turn into a debaucherous weekend of drunkenness, one that might not live up to the hype, and certainly one that I wouldn’t remember a lot about, and probably struggle to recover from. But in the end, I said “F___ it” and bought the ticket. I hope it’s as good as it can be, but I’m going to do my best not to set myself up to be let down.

And my doubting best friend might be correct in his assertion, I may not be able to fight the urge to travel by plane in the next few years. Just last night a friend in Florida and I were texting about going to see a DJ we both like next time he comes to NYC – in early 2025. Today, another friend told me he’s going to NOLA in March (2025) to party – my favorite city, and one that will always have my heart. I’ve got terrible impulse control. My dad used to tell me to count to ten before I said anything, because I always said stupid stuff. I think that applies to some of my social escapades, too. Here’s to hoping I can be a little more mature and have a little more self-control soon. I don’t think any bookie in Las Vegas would place a bet on my ability to do that, though…

You may be wondering what I’m going to do once I’ve bought this second home, assuming it ever becomes a reality, as I’ll be paying two mortgages, at least for a couple years, and thus won’t have any discretionary income to travel even if I wanted to. Well, my plan moving forward is that if any of my friends want to see me, they need to come visit me in either the Mid-Atlantic (which, admittedly, isn’t exactly a marquee destination), or at my mountain home out west, wherever it ends up being. Since I’ve traveled to see them so many times in so many places over the decades, it’s only fair that they pick up the slack now. Otherwise, that’s the end of the line for getting together, I guess. I don’t mean to be so curt or crude about it, but there comes a time for everything, as Neil Young famously sang. And the time for me is to set down another set of roots out west.

Marco Esquandoles
Social Butterfly