The 3 Best Things I’ve Ever Spent Money On

I’m all about saving money, but I also think money’s meant to be spent. My money philosophy is simple: as long as you’re meeting your financial goals, then you can do whatever you want with the rest. Even if it’s something “frivolous” like a $300 dinner.

So, I’m not afraid to spend money. But how do you spend it wisely, and on the stuff that really matters to you? Now that we’re into a new year, I’m in a reflective mood. I thought it would be a fun exercise to look back and think about the spending that stands out to me the most. Specifically, what are the best things I’ve ever bought with my money? Here are my top three:

1. Pre-Marital Therapy

Cost: $190 ($19 per session)
What I really bought: Investing in my marriage

I’ve always been hyperaware when it comes to relationships. So much so that I refused to move in with any boyfriends unless I thought the relationship was going to last. I didn’t care if it was cheaper to split the rent, or that I lugged around my weekend bag to and fro for years, like a bag lady. My worst nightmare was “sliding” into marriage, because of inertia.

I mean, you’ve seen how long it takes me to decide on buying a measly T-shirt.

Since marriage affects you your entire life (in theory), there’s no way I wasn’t going to take it seriously. After a handful of long-term relationships, my husband was the only one I moved in with. And that was after we talked a lot about money. I wouldn’t move in unless I was sure we could get on the same page in terms of financial goals.

Then, four months after I moved in with my husband (then boyfriend), and after two years of dating, I suggested we go to couples therapy.

Dating. Couples therapy. Yes, those two can mix, despite tweets like this:

We didn’t have any of the drama that Selena and Justin have, and there were no doubts we’d get married someday. So why go to therapy if you’re not married and you don’t have any real issues?

Because the best time to fix a problem is before the problem starts.

And I could see a massive problem coming down the road. It was ME.

Specifically, my non-existent communication skills. I didn’t know how to express my needs in a healthy way. When hurt or angry, my only communication strategy was The Silent Treatment. I saw my mom using that tactic growing up, and my past boyfriends put up with it, so I had no incentive to change. Just like money skills, communication skills are learned, too. This resulted in my husband and me failing hard at having productive conversations about touchy topics. We’d work through it a day or two later, but I could see how the stonewalling was hurting my husband each time. And for the first time, I cared enough to want to change.

To further complicate things, my husband had a divorce and a child under his belt. I had neither of those. There were some, um, feelings to unpack.

Poor communications skills plus lots of feelings swirling around in my head was a disaster waiting to happen. So for two and a half months, we paid $19 per session to talk through whatever unresolved feelings we had with a third party. It’s an incredibly privileged position to be in: 1) To have extra money to take preventative measures, and 2) To have decent insurance to cover 80% of the costs. While we’ve been married for less than a year, I can’t say the sessions will make our marriage last forever, but that’s actually not the point. It’s about practicing how to show up and do the work. The sessions showed me exactly what I needed to know: that IF a problem comes up, we’re willing to work through it together.

2. Taking Mom on Vacation

Cost: $3,600
What I really bought: Quality time with family

Hands down, the most rewarding money I’ve ever spent is anything for my mom. It’s not because I’m a big softie, either. She never asks me for anything because she’s independent as hell (where do you think I get it from???).

The first “material” thing I bought for my mom was an iPhone for a few hundred dollars. Every time she Facetimes me to show me what she’s cooking, or to say hi to one of our cats, I feel a surge of happiness. She not only gets a boost of confidence for knowing how to FaceTime, but FaceTime is the second-best thing to visiting in person.

But my favorite spending has been on family vacations.

A few years ago, I’d read a blog post called “The Tail End” on the blog Wait But Why. The premise of the post is that you only have a limited number of days with your loved ones. So if both my mom and I live for another 30 years, and I visit her once a year, I potentially have only 30 more opportunities to hang out with my mom. Ever. If that.

I thought about all those times I could have visited, but didn’t. Some other time, I’d told myself. But maybe there won’t be some other time. The time is now.

And what made me particularly sad was how my mom had never been on a vacation before. So for the past couple years, I’ve made a conscious effort to take both my mom and my uncle (who practically raised me) places to expand their horizons. The first trip was to New York City, the next was Las Vegas and the nearby national parks, and this year we went to Hawaii. I still remember how exhausted I was, driving us from Vegas to Arizona. But every now and then I’d look in the rearview mirror and see my mom, holding her camera out the window, marveling at the southwestern landscapes she’d never seen before.

Or this year in Hawaii, I woke up at 2 AM, noticing the light in the living room was still on. My mom was on the phone, and had been for hours, bragging to her friends about her trip.

Those are the moments that are worth every cent. (I’m not the only one who thinks that. Funny enough, a few weeks ago I was listening to a Tim Ferriss podcast where he talked about getting inspired by the same exact post I linked above and organizing family trips. So yeah, let’s go on the record here, that Tim Ferriss totally copied me.)

3. Solo Travel

Cost: $5,000 (three trips)
What I really bought: Self-confidence, adventure

I’ll make a bold statement: I think everyone should travel alone at least once in their lives.

There seems to be a trend now where people like to bag on how much traveling alone sucks. Maybe it’s because the trend right before that was about how traveling alone was the fool-proof way to “find yourself.” I blame those books Wild and Eat, Pray, Love.

Traveling alone can be really hard and lonely. When you’re by yourself, the logistics and problems are all on you. But while I love traveling with my best friend, there’s one thing I’ve only been able get when I travel by myself: random adventure.

Case in point: me, so many times.

When I say “adventure,” I don’t mean going bungee jumping in New Zealand. I’m talking about the adventures that don’t cost much money at all. I’m pretty sure the only way I got into a famous club was by rolling up to the door by myself. Or those happy accidents that would have never happened to me otherwise. Like missing my flight and staying out all night with someone I just met at the airport. And the people I would have never met if I was with a friend. Like the bookstore worker I chatted with and who then showed me all her favorite local spots. You ALWAYS meet people when you’re by yourself. It’s how it works.

Besides adventure, solo travel reminds me what I’m made of, when things are scary or hard. Imagine landing in Vietnam, not speaking the language, no transfer booked to the hotel, and 10 cab drivers are circling around you like sharks. What do you do?

And lastly, traveling alone is about not making excuses. I’ve traveled alone because I wanted to go somewhere and either my friends had no money, no vacation time, or just plain didn’t want to go. So was I going to let that stop me, just because I had no one to travel with? Life’s too short to wait around for other people. And your significant other doesn’t have to stop you, either. I went to Japan without my husband (then boyfriend), and that was a good sign for me — that we don’t have to do everything together to have a healthy relationship.

Final Thoughts

So for me, the common themes are relationships and memories. I’ll never put a budget on those items, because what I get for my money is worth much, much more.

I’m curious, what are the best things you’ve ever bought? From material goods, experiences or relationships, I want to know!

The Luxe Strategist is a New Yorker saving half of her income. She chronicles her money-saving strategies on her blog.

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