Top 3 under the table jobs that PAY A LOT in 2021

There will be times in your life when under the table jobs might look attractive and I want to help you keep yourself efficient when you find yourself there.

I always fight to help you keep pushing your pay rate and efficiency up through the roof but if you are on hard times it can get hard to keep that trend up. Even so, you might be forced into that bad money situation.

I get it. Everyone needs a little extra cash in their pocket, especially if there may be a looming financial crisis. And sometimes stimulus packages do a number on the economy too. So I won’t judge if you’re thinking about some jobs that pay under the table. You can even use it as an opportunity for starting a business from home.

The topic of under the table jobs has been popping up all around me.

  • Readers are messaging me with questions about it.
  • AND the contractors for my rentals have been telling me that they’ll only do jobs that pay under the table.

So. Frustrating. 

So today you’ll learn:

Let me get this straight.

I don’t advocate for any tax avoidance.

It’s both illegal and unpatriotic. However, bankruptcy is bad too and legally there are ways that under the table jobs can be legal (mainly hobbies that don’t intend to produce a profit) so my conscience is clear to write about it. 

I pay my babysitter in cash. I don’t know what she does with it. \_(^_^)_/

Plus if you make a significant amount, make it your new job and report it at the end of the year.

What jobs are getting cut, right from the get go:

  • Illegal activities because those are obviously not ok
  • Serving. While servers might clear a lot of tips on a good night, I doubt a financial crisis are great for tipping culture…also COVID makes eating out hard.

Know what else I’m not putting up with?


If you’re the type of person who always says “well, I can’t do X because of Y, blah-blah-blah” you’re on the wrong blog. Get out of here and go read some dumb news or something. 

My recommendation is to keep a “how can I make this work” attitude while you’re reading this. But first… 

The IRS and what they think about under the table jobs

The IRS knows that regular people exchange cash for goods. Case in point, selling your used junk.

Congratulations, you made money. But it’s usually not a profit compared to what you bought it for, so it’s a net loss, thus not taxed.

Or if you had to buy tools to do a job, you don’t really profit. Who really knows if you bought those tools for yourself or your cash gig, right? 

I’m just being mean now. (Image source) 

When the IRS gets really in your face is when someone issues you a 1099MISC for your service. That means they gave you the payout form and the IRS the same form. If you don’t report it, I’m pretty sure the IRS will notice and attack you.

Grandma down the street won’t give you a 1099 MISC for cutting her lawn. Umbrella corp that you do engineering design for, will.

So what makes jobs that pay under the table great?

Easy. 1 – Repeat work. 

Ideally, you don’t want to waste your time hunting work. If you’ve spent an hour looking for a 2-hour gig, you’ve just cut your hourly pay rate down by a third.  

2 – It actually pays cash, and it’s not recorded online somewhere. Something like Upwork would be bad because they log everything and report it to the IRS. 

(So if you read my tri-millionaire article, and your main takeaway was that YOU should be a VA for some fancy shmancy blogger, you’re out of luck. You’ll have an extra hurdle to cross – but it’s all below.) 

Top 3 under the table jobs: 

1 – Handiwork for a landlord: 

This is something I know well. I have rentals, they need fixing and most contractors get paid more by NOT working right now. So as a landlord it is HARD to get things fixed these days.

And you can charge a lot for repairs too!

Roofing a house costs over $6,000. I don’t know how much of that is material but even if it’s half and it takes 20 hours, – you’re still making $150/hr!

You can charge quite a bit for fixing up a toilet too!

The best part though?

Find a property manager with multiple houses in the area and be their go-to guy. Trust me, they have an endless amount of jobs to follow up on. 

No hunting, no endless calls, Just a slew of toilets to smash through. 

(Bonus, if it’s your landlord, you might be able to use this to negotiate rent!)

Consider yourself an artist. (Image source)

2 – Freelancing for small online businesses and websites

If you want to keep it strictly in the “under the table jobs” category, I don’t recommend anything through hour tracking platforms like UpWork. But there are a lot of online job boards for website owners who are likely to just pay you with PayPal if you ask.

I’m very into these right now because I was just hunting for a VA and there were piles of job boards I could have used. is a decent one if you’re good at writing, marketing, or anything else in the website space. And the rates seem pretty good for that work.

I checked on writers rates while I was in there, and good ones charge around $0.10/word. I type at 70 words per minute so I suppose I could make $420/hr! Why do I have a blog when I could just sell these articles?! (And I’d just need 2400 hrs of articles to reach my millionaire status!) Yay?

3 – Jobs to do with kids, pets, or houses (i.e. tutoring):

Kids and houses aren’t going anywhere anytime soon, and the era of Covid has made people who help us with those things very important.

We’re talking tutoring, cleaning and handiwork. 

But cleaning has a low pay-rate, and handiwork isn’t so repeatable. 

Dog-walking or pet-sitting, could be a fun and repeatable way to make some extra cash too. Throwing a ball to a dog seems like more fun than vacuuming anyway.

But I recommend tutoring because everyone has skills they can teach, you can charge a lot, you can teach young kids or even older college kids depending on your skills. There’s an endless slew of kids too. If you have:

  • Some serious skills to teach
  • You are just an awesome tutor
  • If you live in an expensive area – you can make up to $100/hr!
Send this flyer around your neighborhood and you’ll be alright (Image source) 

How to find jobs that pay under the table?

So this is the part that is no fun and results in no actual money. Job hunting. Blech!

Worst of all, cash jobs are notoriously short-term and also not easy to find.

So you have to go old school. Job boards, networking, and paper. 

1 – Job boards are online and the application process is often slow and annoying. But you can hire a virtual assistant to do the applications for you for $5/hr! (#myVAdidntmakemewritethis) 

Craigslist especially has under the table jobs, plus you get to learn a lot about human psychology when you wander Craigslist.

2 – Networking and cold-calling is a time-tested way to get work. Just reach out to someone you know or don’t know and ask “hey, would you happen to be looking for someone who needs what I do? Do you know someone who does?”

Really I just recommend this for ‘awesome customers.’ Mainly, this would be a great way to reach out to property managers for handiwork, but it would work for other types of services as well – including freelancing. Get creative here!

3 – Paper delivery and flyers may seem like a waste of time and money, but people use it because it works. We hired our cleaner after someone dropped off a flyer at our door. It would work for something like a tutor or dog-walker too.

Is walking around with flyers fun? Probably only for the first 100 houses, and unfortunately there’s no VA for that.

BUT there are cheap delivery companies or even better – paper delivery kids.

I’m sure your paper route running neighbor would take an extra $20 to drop off an extra sheet of paper. (Hey, they need under the table jobs too!)

This is the test. If your paper-route kid finds this funny, don’t hire them. (Image source)

TL;DR – Under the table jobs

  • Jobs that pay under the table aren’t entirely unethical. (Except for the ones that are – don’t do those!) 
  • A mark of a good under the table job is one that’s REPEATABLE so you don’t have to waste hours job-hunting
  • My recommendations: A handyman for a landlord; A freelancing gig; A tutor
  • Find these jobs through old-fashioned time-tested methods. Job boards, networking, and sending out flyers. 

So what do you think? Ever taken on an under the table job? What was it and how did you find it? Leave me a comment, I’m actually super curious if I missed something good. 

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