My Wildest Side Hustle Yet

It wasn’t that I was trying to make a fashionable entrance to the side hustle party, but I arrived late nonetheless.

Some people side hustle their way through college and nowadays, probably even high school, but I was a late bloomer.

During the majority of my twenties, I spent most of my time outside of work either at school or doing homework. I spent 7 years in night school while working full-time during the day.

That didn’t leave an abundance of time to focus on side hustling, especially when coupled with having a beautiful, amazing girlfriend with whom I wanted to spend every waking moment (that investment of time definitely paid off handsomely though).

Growing up, and even during college, I did random things to make extra money. I never sold plasma or visited the sperm bank or anything like that, but I did things like mowing lawns, recycling cans and bottles (a key component in paying off a 5 year car loan in under 2), house sitting, etc. You know, run-of-the-mill type stuff, but nothing major. It wasn’t until I finished school that I really turned my attention to making extra money through side hustling.

After reading ESI Money’s post about how a side hustle can help you reach financial independence in 10 years, I decided that if I wanted to have a legit shot at ever reaching financial independence or retiring before my future grandchildren do, I needed to get more serious about side hustling.

Now, my eyes are attuned to ways of making extra money. I don’t really have a lot of criteria for a side hustle other than it needing to be ethical, legal and not something that will take time away from my family (i.e., something I can do online after my little humans have peacefully drifted off to dreamland).

And So It Begins . . .

Last summer, I had been reading and commenting on a new personal finance blog when the blogger announced a contest.

He regularly ran various types of random giveaways on his blog and on social media, but I never really paid much attention to them because I’m just not that lucky. But this one was different. It bucked the trend of probability and random chance and was something I could control.

The top three commenters (in terms of absolute number of total comments on the blog) would win the option of choosing an iPhone X or $1,000 cold hard cash. I knew within about half a second which option I would be choosing. Care to venture a guess?

The decision was easy for me, but was made even easier since I had just upgraded my (non-iPhone) cell phone the month before. Fun fact — it was my first smartphone . . . at age 30.

I liked the idea that I had control of how much I could comment and decided I was in. I quickly began referring to the contest to my wife as my “$1,000 side hustle.”

My Master Plan

The rules of the contest allowed for commenting on any old posts, as well as on any new posts which were published during the two-month contest period. Replying to other comments also counted as well.

At the time the contest started, there were about 3 month’s worth of older posts which had been published on the site. I figured if I went back and commented on each of those posts and asked open-ended questions to get the blogger to reply to me so I could respond back to him, plus comment on the new posts, I would have a good shot at being one of the top three. Little did I know . . .

Comments, Comments and More Comments

I was reading the articles, which I actually enjoyed, and leaving well-written, thoughtful comments on each post, trying to add value with each comment. Everything was going well until the blogger posted a scoreboard in the margin of the site showing the comment count for the top ten commenters. Immediately after the scoreboard was posted, pandemonium ensued.

I was in the top ten when the comment counts were posted and at first, I was happy to be able to see where I stood amongst the competition. However, I quickly realized I was naive in my assessment.

Comment counts began to shoot up like a Tesla rocket launch, quickly jumping at times by more than 100 comments over night. Sadly, as the quantity of comments increased, the quality of comments sorely diminished.

Frustrated as all get-out, at this point, I was committed. I had considered cutting my losses and tapping out, but I decided I had “invested” too much time to wave the white flag and walk away. So, I doubled down.

Coffee, Comments and Competition

The competition became fierce. What I thought was going to be a pretty easy win quickly turned into late-night comment fests. As soon as my kids went to bed, I would fire up the laptop, sit down to a cup of cold brewed coffee and get to work. Most nights I would comment until at least 1:00 a.m. Some nights, the commenting would continue on until 3:00 a.m. or later, especially when I could see that my competitors were online and commenting as evidenced by their comment counts steadily increasing.

This nonsense continued on night after night for a few weeks. I would get super frustrated with all the time I was spending on the contest and want to quit, but if I couldn’t walk away 3 weeks prior, how the heck could I now? If only I would have remembered back to learning about sunk costs in business school, maybe I would have realized that walking away probably would have made the most sense.

Nonetheless, I continued on. I forged ahead. I dug down deep to find the strength to carry on. Okay, so that was a little dramatic, but I did manage to muster up the wherewithal to stick with it.

Winner, Winner, Chicken Dinner

After all the blood, sweat and tears, hour after hour, comment after comment, my efforts finally paid off. I managed to come in second with a total of . . . wait for it . . . 2,919 comments. Yeah, like I said, nonsense. Definitely not my proudest moment, but I was $1,000 richer, nonetheless.

What I thought would be a cakewalk little side hustle turned into countless hours, little sleep and lots of frustration.

Was it worth it? It depends. The extra $1,000 was nice to have and was put to good use by applying the whole amount toward debt payoff.

At the same time, I shudder to think of the hourly rate that $1,000 broke down into. This post could likely be called My Ten Cent an Hour Side Hustle.

In addition to winning the money, I also became pretty good friends with another commenter (and fellow winner) and we still keep in contact with each other.

It was definitely a wild ride, but in the end, I guess it all worked out. Maybe though, in the future, I will stick to mowing lawns.

Do you have a side hustle? What is the wildest side hustle you have ever done?