My Top 3 Best and Worst Money Choices

Let's start with this: I don’t really have regrets with how I’ve used my money. Yes, I definitely consider some of how I’ve spent money to be a mistake, but I’m an optimist. More than that: I’m a lifelong student. I’ve learned from these mistakes.

They are, in every sense of the word, mistakes. It’s important I share them because no one is perfect, but everyone can come around to accept that their money mistakes led them to a place of better understanding.

That’s why I’m looking forward to sharing these money wins and money mistakes with you–however vulnerable it makes me.

Best Move #1: Chose to go to college for free instead of where I wanted to go (at first).

College was a wonderful rollercoaster of four years. I worked hard to get my degree, but I got a degree in a field which–though versatile–is not specifically known for being high-paying. I was able to gain formative experiences that not only made me who I am, but got me my first several full-time jobs.

But, it was a difficult decision to make. I was a kid and all I wanted to do was go somewhere where I could start over and be myself. At the time, that meant moving to a big city and going to an expensive private school. However, now that I’m years down the line with equally amazing experiences under my belt–with no debt. I can go back to get my graduate degree (which is the plan). I can make all my decisions without being saddled by student loans. That is a big, big win.

The main lesson is: college is what you make of it. I appreciated where I went even though it wasn’t my first choice, and I made the most of it. It’s a decision I appreciate in hindsight, and if I could go back and tell the younger me that was devastated by the decision that it will all work out in the end.

Worst Move #1: Chose a grad program with a possibly a low ROI

Let’s be fair: I never finished this degree so technically it was a waste of 100% of the money.

I love the field I was working in at the time. I made a decision to get a degree in that field. That was before I started to be really bad at the coursework (because I lacked discipline–and the free time to actually do the work), and I was also setting myself up not necessarily to make more money in my field, but to do even more work in my field (it was a degree in higher eduction).

I wouldn’t call this misguided, because I loved the job, but I did notice that there were some pretty serious blind spots to how I moved forward. I was naive, and I ended up wasting a lot of money.

The lesson I learned: I don’t think I was ready at the time for remote coursework. I should have learned that from going through COVID and having a genuinely rough time. However, I overestimated my ability to do a job and be a student when I hardly had any discipline. You live, you learn, and sometimes you pay what I call, “life tuition.”

The other lesson I made was: don’t give up! I could have also stuck to the curriculum and been done by now, and I would have a different life.

Best Move #2: Invested in living with a partner

This one is one where I lucked out because, if you ask me, it is not a smart idea to live with someone before you are married or engaged. However, in this case, this was a good money decision because I’m actually saving money–because I’m investing my time and inspiration into a relationship I believe in.

When he wanted to move into a large farmhouse, having no experience living on a farm, I offered an alternative:

Not doing that.

Instead, we are both investing our time and money into a nice, liveable condo while we both pursue our careers. I’ve never lived with anyone, before, and while it is a challenge, it is a challenge that makes us both happy–while also saving us both money on bills, travel costs, and all the other things that make a relationship pricey.

Now: I’m NOT paying any bill that isn’t in my name. So, technically, I’m saving a lot of money. However, the effort that I’m putting in to making the home nice is paying off in ways that increase both of our mental heath and we are starting off on a road to more happiness.

Worst Move #2: Gave money to help a friend pay their debt

Okay, they were more than a friend. He was my crush. But they shouldn’t have even been a friend in the first place. I was young and when someone I really cared about explained that they needed a large sum of money to pay the bills, I decided the best way to help them get to like me

The lesson I learned: there’s no amount of money you can lend someone to get them to like you if they don’t already like you.

Best Move #3: Traveled because I was chasing something

I had always wanted to go to Prague. Prague is where my family on my Dad’s side is from and I had always been curious about it. I promised myself that I would go. So, even though I ran the risk of over-spending, I went to Prague anyway.

It was amazing. I made friends, saw some incredible things, and generally felt like I had accessed a part of my spirit I didn’t know that I had. I would do it again in a heartbeat. Plans are already underway!

The lesson: sometimes, you need to follow-through on your promises to yourself. They're promises that you're making for a reason.

Worst Move #3: Traveled because I was running away from something

I thought I wanted to go to London. When I got there, I realized that I didn’t have the mental foundation to be living in another country–I could barely live with myself!

THAT was an expensive mistake.

I was running away from a bad breakup, and trying to leave the stress of college behind. That’s not how you deal with problems, though, and while there were many good moments during that ENTIRE SEMESTER, I was walking around with a rain cloud over my head (and not just because I was in the UK!)

London is also, frankly, an expensive town. If I wanted to travel to chase something, I could have gone somewhere much, much cheaper.

The lesson: you can travel to make your life even better, but traveling itself isn’t the antidote to your problems.

I offer all of these examples as an authentic way to see how someone who is generally successful with money still makes stupid decisions. These were setbacks, but even setbacks can make a positive difference in how you go about approaching your money.

Let this also be a lesson that not everyone has the same money experience! If someone made the opposite decisions as me but had the opposite impact, I wouldn’t be surprised at all. Life is ups and downs, setbacks and steps forward.