I Suck at the Side Hustle and Need Your Help


I’ll keep at it and see if there is something I can find out there, but it’s been 6 months of not having much luck. I’m totally fortunate in that I’m not looking for a primary source of income before they come and shut my lights off, but at the same time it’s killing me as a highly-motivated person to think about the hours I’m wasting that I could be using to dig out that much faster.


Obviously there are two pretty straightforward ways to get out of debt:

  1. Pay off your debt.
  2.  Make more money so that you can pay off your debt faster.

In other words, your debt is what it is. It ain’t going away, and so if you’ve got a lot of it like I do, it’s really just a matter of trimming what you can where you can to focus every possible cent onto paying that debt down.

As step #2 also calls out, bringing in extra income helps, as long as you maintain your focus and use that extra income to get out of debt that much quicker. If your boat is filling with water, you can scoop it out much faster with a bucket than with a spoon.

My problem is not the focus part. We are so insanely committed to paying off our debt that I could probably require life-saving brain surgery and still have a tough time deciding if it was worth it over putting that money towards one of our higher interest accounts.

No my problem is getting that extra income. That side hustle. I’m just not good at making that kind of thing happen… or maybe deep down I just don’t want to be good at it.

I work a lot already, so please don’t think that I’m a lazy person. I hold a 40-60 hour a week job for a software company, and I’ve been working for this same company for almost 20 years now. Along with this, I have taught at local universities, and have a semi-regular freelance job as an illustrator for a company I’ve been fortunate enough to work with for the better part of 15 years.

What I do know however is that I’ve still got some extra time. Think like 2-3 hours every night after my wife and kids go to bed, and an extra 10-15 hours on the weekends. I stay up that late anyway, but usually it’s consumed with dumb things like playing videogames or noodling on a guitar.

Monetizing on that 2-3 hours is what’s eluding me right now, and it’s driving me nuts!

My wheelhouse in terms of skills (I guess I could have just said “skillset”) is primarily centered around art and writing. You know… creative junk. What I’m not sure how to do is parlay those skills into a little extra scratch to use to pay my bills.

Let me run down a few things I’ve tried and/or explored. Get your mind out of the gutter. I’m talking in terms of finances. Here we go:

  1. I’ve poked around on Fiverr. Just signed up yesterday, so we’ll see how this goes. I’ve been a part of a few other similar sites, and the results haven’t made me fall over with excitement…
  2.  I searched the standard job websites for part time and freelance work. It’s rare to find one that fits my “2-3 hours per night plus weekends” timeframe, and even less likely to get an offer. I’ll keep applying though. I’m not giving up!
  3.  I’ve tried UpWork, but man… that is a confusing mess of a site. I’m not sure if I’m doing something wrong or if I just suck, but I have received zero replies. I wouldn’t mind knowing that it’s because I stink at what I do. The killer for me is that I can’t tell either way.
  4.  I’ve considered getting a part-time job at a big box store of some kind. I guess if I worked part time at Walmart at least I could say my job has “art” in the title. To be honest, I haven’t looked into this one too much, as I don’t think I can dedicate enough time to the commute and hours to make the pay worth it. I need something I can do from home.
  5.  Uber and Lyft are unfortunately not good options for me. For now (until we can get them paid off) I drive a Dodge Challenger that seats 2 mildly uncomfortably and 5 WILDY uncomfortably. On top of this it gets around three-tenths of a mile to the gallon. My wife drives a big truck, so that’s not a good option either.

I’ll keep at it and see if there is something I can find out there, but it’s been 6 months of not having much consistent luck. I’m totally fortunate in that I’m not looking for a primary source of income before they come and shut my lights off, but at the same time it’s killing me as a highly-motivated person to think about the hours I’m wasting that I could be using to dig out that much faster.

There is a scene from Seinfeld where George and Jerry are going through the things that George is good at as he looks for his next job. If you’ve seen the episode I’m referring to, then you know just how I feel. If you haven’t seen that episode then I feel like you’ve already stopped reading this paragraph and moved on to the next one, so at this point I’m only still talking to the folks that did see the episode. Since it’s just us Seinfeld watchers now, I feel like I can be myself with all of you. Seinfeld was a great show right? I still watch it often, but I was never a big fan of Jerry himself though. That show was all about the supporting cast.

I’ve spent a good portion of the posts on this blog offering up advice or sharing tips. Now I look to all of you for guidance. Do you have suggestions for a good side hustle? It doesn’t have to be art/writing/creative related. I’m open to all suggestions. Please don’t pepper me with lame get-rich-quick gimmicks either. I’m looking for legitimate work suggestions where you put in honest work, and you get an honest return.

And no… I will not send photos of myself in a bunny costume. Fool me once…


Quick Update: In less than 24 hours I have received 3 messages on Fiverr, all with phishing links that wanted me to click for “great opportunities.” Things are going well so far…


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11 thoughts on “I Suck at the Side Hustle and Need Your Help

  1. Have you tried network marketing? I know there are a lot of negative connotations regarding MLM, but a lot of companies are legitimate. It helped me during the times I am unemployed. I still do that on the side. The thing about network marketing is you get what you worked for. If you work minimally, you earn minimal. It’s also a business in itself. It has a lot of rejections too, so it can be disheartening. But the rewards are beneficial, and highly substantial. It doesn’t have to be the product I endorse. Look for a company you believe in. You can definitely do this on the side.

    Liked by 1 person

    • Really appreciate you reading the blog and the feedback! I have some experience with MLM, as does my wife. In fact, we have just enough experience to know that we suck at it! 😉 We’ve done it with a few products, but we just don’t have the wiring that make us good salespeople. I might have to look into it again though, as it’s been 4-5 years since we last tried.

      Liked by 1 person

      • you could also try teaching online. it’s kind of my permanent job at the moment, but i set my own schedule. 🙂

        Liked by 1 person

      • If you have facebook, there are several groups about online ESL teaching. Most of the sites prefer native speakers and some even prefer those that have teaching certificates and experience.

        You can join thosw groups. They will also help you with the hiring and training process.


  2. What about dog walking/sitting? Housecleaning? Or do you have stuff you can sell on Craigslist or eBay? Do you have space on your property to rent out? You lost a lot of weight, I think I read. Is there anything there that you could teach other people? You might need to work harder on something like selling articles/content, or becoming a trainer or something, but if you enjoy that it could be cool.

    Liked by 1 person

    • All fantastic suggestions. I’ve at least done one of them, in that we have sold a TON of items online. If it isn’t bolted down in our house or required to cook, clean or refrigerate, we’ve probably already sold it. I think my kids are starting to get nervous that they might be next!

      Someone else suggested weight loss coach. That’s a really good idea.

      Thank you!


  3. What about renting a room out in your house? Easy to make at least $500+/month with no extra effort on your part. The kids can double up. Or make the real sacrifice of renting out the master bedroom/bathroom and make another $1k each month to put towards your debt!

    Liked by 1 person

  4. I’m having a similar experience with Fiverr for VO work, but I have found some success with UI/UX testing. each test only pays around $10 and they’re first-come, first-serve. it won’t be a total solution, though I’m managing to get around 1 test per day. $300 extra a month isn’t nothing. Good luck, man!

    Liked by 1 person

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