Dec. 30, 2022

My Biggest Money Mistakes – Part 1: Quitting My High School Job

We all make mistakes with money at some point or another. Most are small, and our finances can struggle to survive death by a thousand cuts. Today I’ll start sharing my biggest money mistakes.

Quitting My High School Job

In High School I worked for a local pharmacy. Most of my time was spent cleaning up around the shop and delivering medication to customers. It was a pretty easy job that I started my Junior year.

Every day after school, I went downtown to the pharmacy. I made sure the products on the shelves were orderly and pushed out to the front, vacuumed, took out the garbage, went on drink runs, took the boss’s car to get detailed and near the end of the day ran out to deliver a few prescriptions.

Quitting my high school job
This is what I drove around delivering Rx’s in, a rusty 1991 Toyota. How it got stuck in this snowbank is a post for another day.

I can’t recall how much I made, but it definitely covered the cost of gas, dates and whatever else a high schooler would need to buy. Maybe I was making $8 an hour and working 3-4 hours a day. I may have made around $150 a week, or $7,500 a year.

Counting the Cost

Upon graduating High School, I decided to quit my job. I just wanted to have a fun summer hanging out with friends before heading to college that fall. The problem is that most of my friends had part time jobs and other things to do besides hang out with me all day.

I spent 3 months hanging with friends when they were off work, riding my dirtbike and nothing else really notable.

quitting my high school job
I willingly left a pile of cash behind for no good reason.

Looking back, I would have much rather had an extra $2,000 from working part time. There would have still been plenty of time to be social. Instead I lounged around a lot, and hung out with a lot of people that wouldn’t even a part of my life in the next year. Having a job would have given me some structure and broken up the monotony of a forgettable summer.

Using this calculator, I can see that if I had put an extra $2,000 into the S&P500 ETF (SPY), it would be worth $7610. That’s almost a 400% return!


Sure, losing $8k isn’t a huge deal in the big scheme of things, but it’s enough to live for 3 months and save me a couple months of work. I can easily think of how an extra $8k would help me now (we’re currently replacing the windows in our condo).

Did you make any money mistakes in High School?