The Start of My Lifelong Side Hustle Obsession

iPod Mini

The Side Hustle of a 13-Year-Old

My first side hustle started when I was 13 years old. Of course at that age, I didn’t know what a side hustle was. All I knew was that ‘getting a job’ was out of the question, no one would hire a 13-year-old kid.

iPod Mini - My First Side Hustle GoalThe prize:

An iPod mini. For any of you that remember, this was a BIG deal. Up until this time, I could only listen to my favorite CDs one at a time, or sit and listen to the radio. An iPod changed all of that, and of course, I wanted one.

This, however, lead to a problem. I didn’t have any money to buy one. I didn’t just have $300 laying around.

The Job:

I vividly remember my parents telling me that my number one priority was school. “School is your job” was something that I was commonly told as a result of my complaints about homework or not want to get up in the morning. Enter the side hustle…

Within a mile of the house I grew up in was a golf course. Not a public golf course, but a private golf course. At the time I didn’t realize it, but this was the thing that set my first side hustle on the right track. On Saturday and Sunday mornings I would get up between 4-5am, hope on my bike (remember I’m only 13!), and head to the golf course. From there I would hang out in the “Caddy Shack” (feel free to insert your favorite movie quote here). From there my job was to wait. If I got lucky, one of the club members wouldn’t want to rent a cart that day and need someone to carry their bag.


The Pay:

Now gets into why I consider this my first side hustle. Simply put, being a caddy didn’t pay anything. The only way I got paid, was by tips from the members, however, there were times when you would carry someone’s bag around all 18 holes and you would walk away with nothing.

This is where the “hustle” had to come in. I figured that if the member I was carrying the bag for like me, or got a laugh at my expense, maybe they would pay me more. I would start the day off by introducing myself and trying to find something that they liked. From there the hustle became simple. I became their biggest fan on the golf course, the one they never knew they not only wanted but needed. Clapping on a good shot, giving tips about what I had seen other golfers do, and simply being there with the bag whenever they needed it.


The result:

After almost 3 months and over 20 rounds. I finally completed my goal and had saved enough to buy an iPod. I don’t know if working so hard for something made me appreciate it more? Maybe it did, maybe it didn’t. I used that thing for years. I actually found it a few months ago. It still works. This led to a great afternoon of throwback hits, some of which I had completely forgotten about.


What are you doing this for? Shouldn’t you be out there enjoying summer?

What most people didn’t realize is that I was enjoying my summer. Every day I was out on that course got me closer to my goal, most of all that was my motivation. Really that hasn’t changed. Whatever my goal helps me focus my efforts. Whether it is a long-term goal (retiring early) or a short-term goal (traveling?) knowing what your goal is before you start your side hustle helps me be super focused. It reminds me why I am doing something. Even if there’s a day I wake up and think “do I really want to do X?”, I remember that every day is one day closer to my goal.


What was your first side hustle? Did it work out the way you were hoping? What did you learn from it?

Let me know in the comments!



  1. Baby Boomer Super Saver

    Nice to know your determination at such a young age really paid off. How long were you a caddy? I recently found out there are college scholarships for caddies and there’s not as much competition for these scholarships as some other scholarships.

    1. Post

      I was a caddy for two summers then off and on for a third. I had no idea you could get college scholarships for being one! That’s really cool.

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