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.

15 Terrible Side Hustle Ideas

1. Take Surveys For Money

If you’re in the business of trading large amount of your time for mystifyingly insignificant amounts of money, then I have some sites to recommend to you: CashCrate, SwagBucks, InboxDollars, iPoll…oh, here’s a list of 30 of these God-forsaken companies. Let me tell you the lifecycle of a person who goes down this road (and I have…several times).

    1. Through whatever means, you find yourself at a paid survey site.
    2. You look at testimonials of people who are “Really making a killing” for “answering a question or two” while they “relax on the couch and watch TV” and “Score big cash and gift cards to retailers like Amazon and Starbucks.”
    3. Convinced, you sign up.
    4. You wait for targeted survey offers.
    5. You get an offer.
    6. You are asked to answer some questions to see if you “qualify” for the offer.
    7. You proceed to spend thirty minutes answering every possible question about your demographics, tastes, and opinions.
    8. You are declined the offer.
    9. You throw your laptop at your children.
    10. You get a second offer. You fill out the pre-offer questions for a half an hour. You are approved. You spend an hour watching videos, making comments, timing out of the questionnaire and having to do it all over again, and finally finishing up. You are awarded 10 credits. Redeemable for a $5 gift card once you amass 500 credits.

Exaggeration? I think not. The best case is that you spend a half-hour a night in a state of semi-conscious dread answering belabored questions for the opportunity to score a couple credits. After a month or two or grinding and missing out on every new release on Netflix, you reach the threshold where you can redeem your credits for a $5 Gift Card to Target, which is just enough to replace the bottle of Advil that was depleted during the two months of brutal survey taking.

2. Blogging

I feel like everyone should have a blog, even if you take money out of the equation.

The problem with blogging as a source of side income is that there’s usually a lot of “blogging,” but not a lot of “income.” Income starts coming in after you’ve sunk a good thousand hours or so into it, and then it’s rather paltry compared to the level of effort. However, if you stick with it long enough, blogging can be quite lucrative. A good rule of thumb is that you can expect $2-6 in advertising income per thousand page views (the more niche your site, the higher the number). Obviously, ad revenue is just the beginning. Affiliate earnings, sponsored ads and posts, product sales, and the list goes on, allow for much higher earnings. This post by AuthorityHacker details how 23 Top Bloggers make huge income online—very informative. The name of the game is good content, build a reader base, then you start working on monetizing that base. Blogging is a great way to side hustle if you have a long runway ahead of your without much need for the income right away.

If you do decide to start a blog, I might recommend hosting through BlueHost (shameless affiliate link). Hosting comes with a free domain, top notch customer service, and customization ability. I wouldn’t go elsewhere if I was starting over.

3. Mow Lawns

I see myself doing this one day. Hop onto VistaPrint and create a nice postcard size flyer, complete with my All-American face and competitive flat rate of $25 per yard. I’ll set myself apart by accepting payment through all the latest payment apps. I’ll use a push mower, the no gas kind, so that I don’t violate any HOA rules when I show up at 10 pm to knock out a job. Money in the mailbox? That’s good with me.

4. Freelance Writing

In my deepest, darkest moments, I’ve typed into Google “Bronies meetup locations and after-party safe words.” Thankfully, several hundred destitute, slave-wage content mill freelancers gave me all the information I needed to know on the subject. Here are 110 sites that will literally pay you just to put on paper the jumbled nonsense that courses through your cranium. Whether it’s 10-cents-per-word of $100-per-article, freelance writing about a subject you somewhat enjoy researching and talking about can be an enjoyable and easy way to make some decent coin.

I pretend to write for SeekingAlpha. After five articles, I have 269 followers and I’ve made a little over $409. Each article takes me about three hours to put together, which means I’m making a decent hourly wage (~$27/hour). Like blogging, as you build a reader base on SA, each article tends to get a bit more lucrative ($35-flat-fee per article + 1-cent per desktop page view). I have a loose goal of getting a big pile of followers over the next few years, so when I write during retirement, each article have a high floor for page views.

If you have a niche that you enjoy writing it, there is a site willing to pay for it.

5. Deliver Pizza

I can’t speak to this one personally, but I do have a bunch of friends who have done this. If you happen to enjoy driving and you’re not this guy, then delivering pizzas seems like a rather mindless way to make some hustle income. Since you’re generally hustling for tips, my advice is to set yourself apart by, you know, wearing a collared shirt and saying hello. If you want to really juice your tips, have a sack of doggie treats for houses with dogs, or maybe some balloons for houses with kids. Otherwise, just be courteous, and watch your tips skyrocket.

6. Sell Your Stuff

This has to be the single best side hustle that has ever existed. I’ve sold well over $1,000 worth of stuff in the past two months on Amazon and Craigslist. I gave up nothing in the process, gained a fair amount of money and, most importantly, decluttered my mind and my space. The beauty of selling your stuff is that there seems to be a never-ending supply of it. I’ve never opened a drawer or closet and said, “Dang, I wish I hadn’t sold _____.” This little hustle probably deserves its own post. But, for now, this post from The Minimalists will do just fine.

7. Credit Card Hacking

Okay, I spoke too soon on #6 being the best side hustle. Lucky #7 is most definitely the tops. Credit card hacking is using credit card bonuses and rewards to gain absurd amounts of travel, miles, hotel points, and cash back. I only wish we’d started sooner. In February of this year, we signed up for a 50k bonus on two Southwest Visa’s from Chase–it’s only grown from there. In eight short months, we’ve flown to Minnesota, Miami, and Orlando for free. We’ve stayed in Nashville, Baltimore, and Miami hotels for free. Next month, we’re heading down to Atlanta for Thanksgiving, on Amtrak, also free. And maybe the best part, we have tons of free travel just waiting for us. We have around 15 hotel nights and over $1,300 in airfare just sitting there, waiting for a vacation. And we’re adding more to that pile faster than we can use it. All told, we’ve “made” about $600 per month in travel rewards just for doing the spending we otherwise would be doing. In all this time, our credit scores have only increased.

Other than gas, the occasional Uber, and a couple rental cars, we really won’t have any travel expenses for the foreseeable future.

If you want to get started, head over to The Points Guy, he’ll set you straight.

8. Be an E-Juror

It sounds sexy. You sign up, and shortly thereafter, big name law firms will call upon you with hefty check in hand, asking, “Do you think he’s guilty?”

Well, the wife has been signed up for about six months now, and no calls. Crazy, huh? I would’ve figured these “no barriers to entry” side hustles would be gold mines.

9. Book Re-seller

Yah, I did this. I was convinced I had it figured out, too. I would go on eBay, where gross mispricings can be had easily, and buy some college textbooks. Then, I’d turn around and head over to Amazon and sell those books for a sweet profit. I’d read enough of Flipping A Dollar’s blog to know that people have done this. Well, I didn’t have so much luck. I bought four books. One came as the international edition—which Amazon wouldn’t let me list. Another I had on Amazon for over a month waiting for it to sell, as the price plummeted. The other two were sold for a decent profit (like $15 each). After shipping, though, it was just too much movement for too little margin.

10. Sell Your Photos

In a moment of insanity, I actually thought I could do this, which should tell you a little something about how saturated the supply of this market has become. There are a pile of sites that will hold onto your photos and pay you a royalty every time somebody licenses the image. However, in the several forums I’ve checked out about this, it seems like a very meager living. There is typically a lot of formatting, tagging, labeling, and guidelines surrounding each image, and that process can be tedious. The recommendation seems to be to build your own image library and host it privately, benefitting from owning the whole domain. However, if you happen to have a bounty of high quality images that aren’t selfies, then maybe this is a path for you.

11. Sell Your Crafts

Etsy has just about cornered the market on knick knacks and paddywhacks. If you make something original, like a wooden bracelet for yuppies or one of these worst items ever on Etsy, then sell your craft on your Etsy storefront.

12. Football Game Food Delivery

Can you believe I actually did this? I was hoodwinked into doing food-to-seat delivery at FedEx Field for the Redskins games back in 2007. It was sold to me as a do-nothing gig where you can “watch the game” and “get sweet tips” just for hand carrying chicken fingers to the luxury suites. Man, what a load of bull. First off, there’s no “watching the game.” Basically from moment one, it is drilled into you that there is no game watching to be had. I became paranoid, like I would turn away from the field at every opportunity. I wouldn’t even look at the screens in the concourse. Then, as you can imagine, the type of person who is not moving from their seat isn’t the type of person to order only chicken fingers. And tips? Yes, there were no tips.

But hey, if this sounds like your kinda deal, just Google “(Stadium) + concession jobs” sometime in mid-summer, and a bounty of really awesome football spectators awaits you.

13. Write an eBook

A natural extension of blogging in many cases, the advent of Amazon publishing has turned even the most lowly bloggers into modern-day Jane Austens. I’m actually not too mad at this idea. I could see myself putting Retire29 in eBook form, sweet and condensed for 99-cents per download. Jason at Dividend Mantra did something like this, and he seems to be doing pretty well with it.

14. Offer Professional Services on Fiverr

I’ve used Fiverr several times for things like logo design, some CSS help, or general wordpress issues. If you’re keen on making $4 for a job with a buyer that acts like he’s paying you $100, then Fiverr is the game for you. Otherwise, you might want to take a look at why Fiverr sucks for side hustling, and some alternatives.

15. Drive with Uber/Lyft

The most contentious topic on the internet has to be “How Much Does an Uber Driver Make?” The answer varies significantly, as would be expected. If you drive during bar hours in urban centers, you can make some serious coin (Over $30/hr). Sam at Financial Samurai has done a stint with Uber and he made about $22/hour after you back out expenses. Not bad at all, especially given that he drove at some of the least lucrative times of day.

That Is It!

I hope you enjoyed my list. I would guess most things on this list you’ve already seen, and that’s cool. I just hope my perspective might make your decision a bit more informed. Side hustles are no doubt a great way to make some money that flows straight to your bottom line, but don’t lose sight of the big goal. You’re not in the business of trading your life for money, so when you side hustle, try to make it be something you can do better than most others, or something you otherwise really enjoy doing. That’s the sweet spot.

Thanks for reading Retire29!



    • 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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