You Need A Side Hustle and 15 Terrible Ideas

Note: This post grew pretty lengthy, so I broke it up into three pages:

8 Reasons Why You Need a Side Hustle
The Problem With Side Hustle Lists
15 Terrible Side Hustle Ideas

Navigation is also at the bottom of each page.

The Problem With Side Hustle Lists

It is incredibly easy to come up with huge lists of side hustle ideas. Literally, anyone can do it (and you’re about to see this in action…). If you ever want to write a stupid-easy blog post, just do a post called “1000+ Side Hustle Ideas” and watch it go viral.

Don’t believe me? Observe…

Right now I’m sitting at my desk. Idea #1: Assemble desks in new office buildings. Idea #2: Take down desks in old office buildings. Idea #3: Repurpose/restore old desks and sell on Craigslist. Idea #4: Design kitschy desks for spendthrift hipsters. Idea #5: Find the one person in the world who will pay for a picture of you sitting nude on a desk, and sell a “Nude on Desk” photo to that person.

Boom! Five ideas in less than thirty seconds! None of which you will ever consider doing. That is about par for the course when it comes to big lists of side hustle ideas. Basically, if I throw enough darts, eventually a reader might say, “Hey, I could do that!

I could write ideas all day. And in fact, a lot of people have…

Among these lists were the following ideas (yes, these were actually on those lists), that could be classified as:

  • Jobs (Join the Military? Work Overtime? Start a Vending Machine Company?)
  • Gambling (Online Sports Betting)
  • Investing (Use Lending Club or Prosper)
  • Oft-mentioned but universally impossible to obtain (Is anyone really hiring personal shoppers?)
  • Hilarious (Sharpen knives? Be a Gun Tutor?)
  • Horrifyingly inefficient (If I hear about one more pay-per-survey site I swear I’m gonna hire that gun tutor.)
  • Degrading (Shower Cleaner? Rent-a-Friend? Phone Sex Operator? Professional Cuddler?)
  • Scumbaggery (Club Promoter)
  • Illegal (Sell Weed? Thanks Elite Daily)
  • Not for the faint of heart (Participate in medical trials?)
  • Highly targeted (Become a Doula? Dial-a-Santa? Bueller?)

There’s a reason a sane person can (and usually will) look at a list of hundreds of side hustles and take no items for action. To a given person, a certain side hustle will just make them grab nuts and shrug, whilst they head back to his or her normal employment. You know why? For a side hustle to be worth doing, it must be:

A) something you enjoy doing anyway, thus not feeling like work; or,
B) something you can do better than the average person, thus making it more lucrative than it normally would be.
(Preferably, your reason is ‘A.’)

If I peddle a list of 200 odd jobs, nearly all of them will sound terrible to a given person. Each job will require a certain person with a certain level of interest to take notice and take action. That is why articles titled “50 Great Side Hustle Ideas” are total misnomers, since those ideas probably suck to just about everyone.

This is why my list on the next page is called “15 Terrible Side Hustle Ideas.” Because, to a certain person, most of them will be terrible, but hopefully one of them will strike a chord. If none do, then head over to one of those lists I link to right above, and maybe you’ll find better luck (Spoiler Alert: You Won’t).

So, proceed to the next page for my list of side hustle ideas that I feel I can actually speak about with competence…


    • Scott,
      Come back! I never get feedback like this and I love it! I removed that second ad that was up top and decided to place it elsewhere. I’d hate to think somebody thought Retire29 was covered in ads. I hope it’s a little better now.


  1. Could you tell me a bit about how you treat your seeking alpha income for tax purposes? Do you put all the revenue into a sep ira (I don’t know if this is possible. Maybe after incorporating?) or do you take the money in cash and pay loads of taxes (federal, state, fica, …)?



    • Hi Darren,
      I just started writing this year, so I haven’t filed taxes yet. But, I plan on writing off several costs to offset about half of that income (depreciation on laptop, portion of internet cost), then with the remainder, I’ll recognize it as ordinary income and I expect I’ll be owing 15.3% (2.9 Medicare and 12.4 SS) on that income, plus income taxes.

      However, this sounds like a good post I should make. I’ll do one early next year when I file discussing how it all shakes out.

      Thanks for commenting!


  2. Good post. I’ve found that my side hustle has turned into some pretty big cash, but not the way I intended.

    I retired early (at 50) after selling my software biz. To keep my yearly draw to 4%, I figured I needed a little side hustle income to allow me to play heartily in retirement.

    So I started a blog and started developing mobile apps. My mobile apps are bringing in some monthly cash but based on the amount of time I put into them, it’s like minimum wage.

    However, I put lots of time into driving traffic to my blog and building my Twitter following (now over 21,500 followers – twitter handle is @2hourappreneur).

    I posted a blog post about how I built my following and a friend I worked with years ago asked if I could help him do it for his blog for $50 an hour. Cool, work a couple hours a day and bring in some decent side hustle money. That has worked out great.

    Two weeks ago, I was called by another friend I worked with in the past and he wants to me to help his new company develop a software solution. I told him I could only oversee and advise it, work 2-3 hours a day max. Rate: $200 an hour. Now that’s some good side hustle cash and I should be starting that engagement in November.

    It’s funny how a little blog turned into this type of cash and allows me to work a couple of hours a day and play the rest of the time.
    Steve Miller recently posted…Don’t Worry Be HappyMy Profile

  3. Great read, always looking for extra ways to make cash around the office. I just wanted to share something I’ve been doing recently. I run an office and have noticed that unused toner was piling up in storage. Looked into returning but that was no good. Tried out the site and was impressed. They had quick service and that payout was nice.

  4. Hi terrific website! Dooes running a blog like this require a large amount off
    work? I’ve virtually no understanding of computer programming but I had been hoping to
    start my own blog in the near future.Anyhow, should you
    have any ideas or tips for neew blog owners please share.
    I understand this is off subject however I simply wanted to ask.
    Cheers! recently posted…marketersmedia.comMy Profile

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