My Worst Financial Decisions—Ever

Sharing some financial mistakes from the past few years

Thanks for checking out Ten Dollar Latte! I’m not a financial advisor, just a 27-year-old trying to afford life in NYC. I write about how I spend my money while enjoying a $10 latte.

Back in February, I shared my best purchases from last year. Now, I’m going to share my worst financial decisions—ever.

Thinking about things I’ve purchased and regretted makes me feel wasteful, careless, and honestly just bad. And I’ve wasted a lot of money on things I didn’t need—or even really want: drinks out that I didn’t need, produce that ended up going bad sitting in the fridge, and clothes I didn’t end up wearing. I’ve said “I’ll return that,” and forgotten to return it.

I don’t want to dwell on those, so instead, I’m going to share my worst financial decisions ever—not physical things I’ve bought, but what I’ve done with my money. 

1. Not contributing money to my 401K for a year and half during a previous job.

   There was a small window of time when interest rates were low, and I thought I might be able to afford to buy an apartment. I was honestly delusional for thinking that—and I wasn’t ready for the responsibilities of homeownership regardless—but I decided to save up my money in a high yield savings account for a down payment rather than contributing to my employer’s 401K. I didn’t get an employer match, so I figured I wasn’t missing out on much. But honestly, I wish I had put a small percentage of my paycheck in that account over time to grow. I never bought that apartment, and I have no plans to buy one anytime soon.

   Also, the job I got after that one didn’t offer a 401K at all. So, I ended up not contributing to a 401K for almost three years. Luckily, now my part-time job has a great 401K match program, and even though I can’t afford to contribute a lot to it right now, I am contributing!

2. Single stock & crypto investing

   I have lost hundreds of dollars on single stock and crypto investing. Back when it became a craze in 2020, I treated it like a game and invested a little bit of money here and a little bit of money there, which eventually added up to a lot of money. Sure, I made money back on some (I’m looking at you, Dogecoin!), but it was an overall loss, and made me realize that single stock investing and day trading is all a game, not a real long-term investment strategy. Now, any money not going into retirement or savings goes to mutual funds or the S&P 500.

3. Not negotiating my salary

   I worked a co-op (semester-long internship) during my junior spring semester of college. I got an offer for a summer co-op and took that at the same rate as my spring co-op—$20/hour. Often, at large companies, you can’t negotiate internship salaries, so I didn’t negotiate. Later in the summer, I learned that many students made more than that on return co-op programs—I definitely could have negotiated, and I hadn’t even bothered to ask. I’ve negotiated at every job since then.

The good thing is that I learned from all of these mistakes. Maybe you’ll be even luckier and get to learn from my mistakes, without having to make them yourself!

When I revisit this post in five years, I bet I’ll realize that I’m making three more money mistakes right now that I’m not even aware of yet. And maybe then I’ll be able to share a similar post. But for now, I’m just doing my best.

Thanks for reading! I post weekly on Thursdays (previously Mondays) about living in NYC, personal finance, and growing my small business. I also post a monthly reset on the 1st of each month sharing everything I spent money on the previous month and goals for the next month. My small business is called Sidetracks—it’s a collection of party card games I designed. Grab a game to make your next happy hour unforgettable.