The Side Hustle Income Challenge

A few weeks ago at FinCon I met some amazing people like Jason at The Butler Journal. We met while waiting for lunch at the food truck on Thursday and sat in the shade with Alex Whitehouse.

We talked about each others business and they both gave me some great advice on what to do tax wise for my business as it continues to grow.

When I got back home, went through notes, business cards, and keeping up with the new friends I had made I came across Jasons’ Side Hustle Income Challengeand of course I had to participate.

The competition starts on October 3rd and ends on November 4th giving us 5 weeks to hustle our way to a thousand.

According to the “rules” you can pick any side hustle, have as many as you like, and only side hustle income counts. So for me the only income that doesn’t count is my normal 9 to 5… which at this point is probably my smallest take home income anyway.

My Plan to WIN

If you have been following me, or just look at my income reports, you see that my income already exceeds $1,000. So I want to increase it to $3,000 during the contest.

So here is how I intend on doing it.

Go Heavy On Amazon

Amazon is by far my highest side income maxing out so far at $1,717.70. If I make that again I will be happy, if I make more I’ll be happier.

I want that to grow, I want to get cash together  to get out of debt, and to have capital for Amazons busiest time of the year.

This is my first Holiday season selling on Amazon. Some say they make 50 to 70 percent of their annual income during November and December. To do that I need capital, so this competition can assist with an influx of capital.

Increase My “Blog Income”

Looking at my current side hustle income “Blog Income” is by far the lowest, only making me $50.

To change this I will add a resource page. The majority of the links on the page will not make me income and will only be there to help others. However, some of the links will be affiliates.

Also due to FinCon I have added some ads to the site. I spoke with many there and a company Media.Net that works with site owners, making sure that the ads match the owners beliefs.

So far it has been pretty easy putting up ads, and I look forward to seeing the success of it in the future.

Rideshare Driving

I’ve shied away from this lately for a number of reasons. First, my car already has a LOT of miles (over 150,000). Second, it feels more like work than any of my other side hustles. It’s very time intensive and keeps me away from doing other things like writing.

But, it’s easy money.

I don’t have to think about how I’m going to find a new client, or will people really like what I say or even read it. Instead I just wait for a passenger who is usually more than happy to just get in the car, not talk, and go to their destination.

I need to do more of this, not only for the competition, not only for the money, but because I write about it and want to be up to date on how the current situation of rideshare.

Find Freelance Clients

A main goal of this site, and of going to FinCon, is to find clients to write for. This site already produced my very first client and I can’t thank her enough for the opportunity she gave me.

Since Hayley stopped writing on DiseaseCalledDebt, however, I haven’t found a new client. Partially because it’s not easy, and partially because it is absolutely terrifying to put myself out there.

I did go to the freelancing networking event at the conference and a few things may come from that, only time will tell.


To be completely honest, I don’t think I’ll win this competition. Not because I won’t make money, I know I will. But, because I’m up against some pretty talented people who have been doing this longer than I have. I really look forward to the challenge.

I am curious if I already started though, see I count my income as when it is deposited into my bank account not when I actually make the sale. So on October 3rd I received a payment from Amazon of over $1,000, does that mean I was at $1,000 on day one of the competition? I really don’t know I don’t think I’ll count that but we’ll see.

I’m not sure if I’ll recap this in its own post or not, but I will for sure bring it up in Octobers Income report so come back then to see how I did.

If you want to join in the fun, please do, head over to Jasons’ site and leave a comment. I’m sure he would welcome more participants. If he doesn’t I’m sorry but you can leave a comment here and we’ll have our own side, side hustle competition.

Image courtesy of renjith krishnan at

*Part of Financially Savvy Saturdays on brokeGIRLrich. *< and The John and Jane Doe Guide to Money & Investing. *


13 thoughts on “The Side Hustle Income Challenge”

  1. Tyler, a side hustle challenge sounds like a great way to up your game. As for gaining freelance clients, I believe every freelance writer there is will tell you that “imposter syndrome”, or feeling terrified of putting yourself out there, is part of the deal. Don’t let that stop you and you’ll do fine.

    1. This! But you are a great writer, so try not to stress!!! Also, I think this hustle is awesome. Healthy competition can be a good thing. Just remember that even if you don’t”win,” you’re still going to propel yourself forward, and that’s a win in and of itself.

      1. Yes, as long as I aim high, even if I don’t make it I’ll still get closer than I am now. Thanks for the compliment, I’m far from great but I’m getting better.

    2. Definitely agree! And of course if you never put yourself out there, you will never know your true potential. I think the key is to start small and grow from there while always keeping your eye on the big prize. Good luck on the challenge!

    3. Thanks Gary, I’m not going to let it stop me. I have big plans and hope that they are fulfilled. I’m going to work hard and get over my own “impostor syndrome”.

  2. Sounds good. I do think that maybe you should count your Amazon accruals for the challenge rather than your deposits. While it’s a bit more of a pain, it does show any increases in activity. (Isn’t the lag time on deposits at least a week, and possibly 3?)

    And, I hope you give the challenge its own wrap up post. It will be interesting to see how you used it as motivation.

    1. Maybe I will do a post at the end Emily. Not sure how I’ll track it, if I keep track of the sales that doesn’t really show how much money I’m making. And yes sometimes it takes 2 or more weeks to get paid after an item sells, it can be very frustrating especially since it may have been purchased 2 weeks before it arrived at amazon to sell.

  3. I agree with Femm – even if you don’t win, participating in the challenge should help you earn more money. I participate in a Fitbit challenge with my sister and she wins almost every week. Last night, feeling discouraged after losing the up-teenth week in a row I told my husband I should just quit. He advised against it saying I need to understand I will most likely never win competing against someone who works part-time and walks in her job when I sit at a desk all day. But working the Fitbit and participating has motivated me to move more, so I should keep at it.

    Discouraging to see you make the least amount of money from blogging. Something else I know is true, but keep at it anyway.

    1. So true, I just want to do my best, better than I have been doing anyway. If I reach my personal goal I’ll be happy, if I win the contest I’ll be even happier.

      The blog income will come, I haven’t really been trying to make money from blogging but I will be from now on so hopefully the numbers will show my effort.

    1. Thanks Jason, I’m going to do my best, I’ve already got to work on amazon, and building up the traffic to this site. Amazon is my best bet to getting there, and if I can find a few freelance jobs that will probably put me over the top.

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