Tips for Setting Up a Stress-Free Side Hustle

Here’s how to make that second job work for you without going crazy.

15 Tips for a Successful and Stress-Free Side Hustle

Welcome to the gig economy, folks: A place where there are countless side hustles that can help make ends meet or fatten your savings.

New side hustles pop up every day, ranging from new writing gigs to the latest ridesharing program promising you’ll make $30 an hour. But you need to take a few things into account before tackling the side-hustle world.

Here are a few tips that’ll help make your side hustle successful.

Do What You Love

One of the keys to a successful side hustle is making it something you love. Doing extra work isn’t fun, but if you’re doing something you love to do anyways, it helps. Even if it’s something you’re not necessarily good at, you can learn on the fly or take a few classes before signing up.

If you like computers, learn to program or to fix them; if you love being on camera, learn to film and edit your own videos, and so on.

Remember the old saying, “If you do what you love, you never work a day in your life”? Well, that’s sort of hogwash — a job is a job, regardless of your love for it. But if you love it, that job remains tolerable at its worst moments.

Crunch Those Numbers

A big part of having a side hustle is the extra money that comes rolling in. It seems like free money, right? Well, it’s time to put your accounting visor on, pull out that adding machine and start organizing your cash.

No, you don’t need to get a degree in accounting to make it all work, but having some cheap accounting software, like Quickbooks, will help you organize it all without driving you crazy.

Make a Plan

No one gets into a side hustle just because they want to — well, almost no one. They generally get into it out of a need: They want to pay off a credit card, crush their student loans, pay off their car, etc.

Once that goal is complete, what are your plans? Are you going to just keep aimlessly working that side hustle? Will you just stop? Will you keep working it and use the extra cash to pad your retirement savings? You need to make this plan ahead of time and stick to it.

If you decide to keep working that side hustle, you need to...

Stash It

If you decide to keep the side hustle going after hitting your goal, the last thing you want to do is adjust your lifestyle to meet your newfound liquid capital.

I adjusted my lifestyle, and my expenses eventually ballooned to the point that my side hustle became a financial survival tool. If I didn't work those several hours a night after my full-time gig, we would go bankrupt. This led to three years of no sleep and constant stressing over money and time.

Instead of doing as I did, start stashing that extra cash into a retirement account. Use your side-hustle money to retire early instead of paying for that new car or a big house.

Yes, Income Tax Still Exists

You don’t want to know how many times I’ve heard a side hustler say, “Oh no, I don’t have the cash to pay my income tax!” Remember, even though no taxes come out of your side hustle paycheck, you still need to pay income tax every year.

Here’s how to handle this new responsibility. Open a new interest-bearing savings account and immediately transfer 30 percent of your side-hustle pay into there. Every quarter, send whatever money is in that account to the IRS as a quarterly payment for estimated income tax.

Yes, 30 percent sounds like a lot, but as a self-employed person, you now have the joy of paying self-employment tax, which is about 15 percent of your taxable income. Add to that your standard income tax, and you’ll likely be around 30 percent. Of course, you can take the guesswork out of it and just use IRS form 1040ES to figure out how much you should send in and when to mail it.

Scheduling Matters

Whether you’re an Uber driver, building IKEA furniture with TaskRabbit or writing articles, you need to set up a schedule. Find out when you work best or what hours are the most profitable and work those hours.

Let everyone who matters in your life know this schedule so you can avoid productivity-killing interruptions.

The beautiful thing about a side hustle is that you generally don’t need to be regimented with the hours. If something comes up that you have to tend to, don’t put it off just for your side hustle; take care of it and catch up on the side hustle later.

Watch Out for Burnout

This is massive because there is no way you can be productive if your brain’s fried. Keep a close eye on your sleeping and eating habits, and if you see them changing dramatically, you may have too much on your plate.

At my peak, I was finishing my side hustle at 11:00 p.m. and waking up by 4:30 a.m. to get ready for my full-time gig. This was not a sustainable schedule, and it takes a long time to recover.

Be cognizant of your body and its health and, for goodness sake, stop saying “it won’t happen to me.” Yes it will, I promise.

Don’t Let It Bleed

Your side hustle can be a good way to make a little on the side, but “on the side” is the key here. Don’t let your side hustle get so out of control that it starts bleeding into your daily full-time gig.

If you find yourself checking emails, responding to requests or accepting tasks while you’re on the clock, you’ve already let the side gig get the best of you.

Yes, you will get caught double-dipping one way or another, so just stop. Would you rather lose that side hustle that gives you a few extra bucks or lose the full-time gig that provides insurance, an 401(k) and a steady paycheck? Time to turn the side hustle down a few notches and focus on the full-time gig.

Read the Fine Print

When you have a skill that you learned from your full-time employer, it can be tempting to take that skill and market it on the side. Slow your roll for a second. You need to make sure you’re boss and your boss’ boss are cool with this.

First, check to see whether you’re subject to a "no compete" in your employment contract. If so, read that from top to bottom to determine if your side hustle will be considered a competitor. If that all checks out, chat with your boss about the side hustle and get her OK on it — preferably in writing.

Also, even if your boss does rubber stamp it with her approval, don’t go around talking about it on the job. The more people you tell, the more problems you make for yourself.

The Tools for Success

An exciting side hustle can turn into a draining struggle without the right tools in place. Make sure when you sign up for that new side gig that you find out what tools the company will provide you and what tools you’ll need to succeed.

If you need specific software that the company will not provide, bite the bullet and buy it. Sure, this will hurt up front, but that software will pay for itself quickly.

On that note, make sure your hardware is ready too. If you’re jumping into the Uber ring, you may want to fix your broken air conditioning. If you’re doing handy work with TaskRabbit, those dollar-store tools likely won't cut it. If you’re a graphic designer, you may want to upgrade to a computer that can handle the task.

Hit Those Deadlines

This article was due on Friday, and I am writing it on Wednesday. You see what I did there?

Hitting your deadlines is key to maintaining happy clients, whether you’re a driver or a writer. Happy clients mean more work, and more work means more money. Plus, if you consistently hit your deadlines sans excuses, the one time a legit excuse does pop up, you’ll likely get the benefit of the doubt.

A key part of hitting deadlines is not waiting until the last possible second to finish a job. If my computer dies today, I have a good 48-hour buffer to shift to my backup computer, regain access to my systems and finish banging on these keys. Waiting until the last second is just asking for trouble.

Don’t Be a Know it All

If you happen to fall into a side hustle that’s right up your alley, perfect! You have a leg up on most others coming into that same gig. But don’t let that knowledge make you think you already know everything.

There will be nuances about the company and the processes that you need to figure out, and taking advice from others in the company is a great way to accelerate this process.

If you remain stubborn in your "I-got-this" mentality, then you risk falling behind the crowd. So, ask questions, take advice to heart and treat criticism as one of the many avenues to improvement.

Take a Break

Jumping straight from your 9-to-5 gig into your side hustle seems like a great idea, right? Not so fast. Sure, you may think it’s best to just blast through it all in one 12-plus-hour shift, but sometimes your brain needs a reboot.

If you find yourself dragging after your full-time gig, go veg out on the couch and take in a movie before diving into the side gig, if that’s possible. That little bit of relaxation could be just what you need to get recharged and ready to roll again.

Don’t Chase Dollar Signs

You made your plan and have your money figured out. Now don’t go chasing those extra dollar signs thinking, “Oh, just one more side hustle won’t hurt.”

Stick to your plan, and make what you need to make — no more, no less.

It can be tough to turn down cash, but my best advice for avoiding the temptation of more money is to stop looking. Get you core side hustles in place and let the rest pass you by without you noticing.

If It Seems Too Good to Be True, It Probably Is

And finally, much like those shady used-car ads with the fake key attached to them and the scratch-off circles that always seem to be winners, there are lots of side-hustle scams and half-truths out there.

Don’t be lured in by a job ad that says you can “make money doing practically nothing!” Generally, those do not exist. If you do find one that pays you for practically nothing, we’re talking pennies. Plus, these gigs typically live in a very dark-grey part of the internet.

Just find legitimate clients that pay you decent money for the skills you can provide. Trying to take a shortcut can lead you down a scary path.