6 Steps to Turning Your Skills into a Lucrative Side Hustle


Even if you’ve managed to find a full-time job you truly enjoy, it’s tempting to imagine another life you could live.

When I was freelancing full-time, I heard it from friends with traditional jobs more often than I could count. “I wish I could work for myself like you do.” I wasn’t about to deny the joys of self-employment, but don’t be naive enough to think there aren’t any downsides to working for yourself, too.

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I was only able to make the decision to pursue my freelance work full-time, after several years of maintaining a steady side hustle of freelance work, alongside my traditional full-time job.

After striking out and working strictly freelance for several years, I’ve returned to the world of 9-5 employment, while still picking up occasional side work. It’s a routine I feel comfortable in, and it definitely has its benefits, especially if your goal is to eventually be gainfully self-employed again one day soon.

Though the perks of full-time employment can be plentiful (a salary, health insurance, unlimited coffee and the occasional dozen break room doughnuts), the lure of self-employment is always there. The independence, freedom, and ability to make your own hours each week, is all very appealing.

According to a recent release from the Bureau of Labor Statistics, about a third of all workers in the US now consider themselves freelance, and that number is only expected to grow.

While the self-employed lifestyle seems delightful, for many of us the idea of breaking out and venturing into the world of freelancing full-time, is too intimidating. It’s impractical and risky, but that doesn’t mean you can’t pursue your passions on the side.

Some people pick-up freelance work on the side for purely financial reasons. Rent is high these days, and most people I know wouldn’t say no to a few extra bucks each month. Your full-time job might pay you enough to afford rent, bills, and food every month while putting some money aside for savings.

Adding some freelance work as a regular side hustle, can act as a financial supplement, so you can do some traveling, eat out at your favorite restaurants, and make the occasional frivolous purchase. Freelance income can act as an excellent money “buffer,” when your full-time income isn’t quite enough to leave you feeling as fancy-free as you’d like to be.

6 Steps to Starting a Profitable Side Hustle

For some, it’s the need for more creative outlets. Maybe your full-time gig, while financially gainful, isn’t artistically rewarding enough. Picking up a side hustle that engages your interests more frequently might just be the creative release you need. Though I find my own full-time work very creatively rewarding, my freelance gigs present very different opportunities. For a busy-brain like myself, maintaining multiple projects at once is a must.

Juggling freelance work and a full-time job is complicated. You end up working more than full-time—constantly looking for balance and searching for more hours in the day. It’s difficult to manage your full-time commitments with your freelance projects and responsibilities, let alone find time for a social life.



But the true entrepreneurial spirit knows you should never equate “difficult” with “impossible.” While it’s no doubt challenging, picking up some independent work on the side while still working full-time can be a fantastic option.

Here are some of my personal tips and tricks for earning a lucrative income with a freelance side hustle, without losing your mind (or your job, for that matter).

1. Decide Which Skills You Want to Monetize.

For many of us, the question of, “what do you do?” is becoming more and more complicated.

Most creative-types find themselves straddling several different worlds at once. When someone asks me what I do, I sometimes just randomly pick one of the many things I do, rather than rattling off the endless (and mostly mundane) list of things I do for work on any given day.

How to Start a Side Hustle That Makes Money

While working in multiple fields at once can certainly help keep life interesting, it can present a challenge when attempting to pick up some freelance work. I suggest you start the process by picking one skill you’d like to monetize first.

For example, if you’re a photographer, writer, and dancer, consider focusing on looking only for extra photography projects for a while. There will always be time to look for work within your other fields in the future, but it helps to just dip your toes into one world at a time, while you’re still figuring out how to balance your side hustle with your main gig.

When deciding which of your skills you’d like to go with, think about it in simple terms of supply and demand.

Some skills are inherently more lucrative than others. If you’re looking to pick up some extra coding work on the side, for example, there are serious financial gains to be had. Just check out James Knight, who left a lucrative job coding at Google to make twice as much freelancing!

In other worlds, especially worlds where you might not have as much experience or as many connections, there could be less money to be made, at least in the short term.

Just because something won’t make you a lot of money doesn’t mean it isn’t lucrative, though, and it doesn’t mean it won’t make you a lot of money one day. Check out Ryan Robinson’s list of over one hundred profitable side business ideas and see if one sparks your interests and aligns with your skills.

2. Ask Around and Do Your Research.

Chances are, you know someone who works in the same field you’re interested in working in. If you’re trying to get your foot in the door as a freelance photographer, for example, it’s worth reaching out to your friend who works as a freelance photographer already.

Consider reaching out with a simple, “Hey! I’m thinking about picking up some freelance photography work and would love your advice on getting started. Could I buy you a coffee some time and pick your brain?”

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If you don’t know anyone working in the field you’re interested in, the Internet is your friend. The World Wide Web is full of forums with folks who have asked the same questions as you.  If you’ve got questions about freelancing, CreativeLive actually has tons of resources for creative professionals like yourself! Download our free eBook, The Freelancer’s Roadmap today.

Reach out to people online, whether it be through a forum, blog, Twitter, Instagram, Facebook, or other. Listen to their advice.

3. Be Sure Not to Risk Your Full-Time Job. 

If your full-time job consists of doing work that’s similar to the work you’d like to do on the side (for example, if you’re a full-time magazine editor looking to pick up some freelancing writing gigs), it’s worth rereading your employee contract or quickly checking with your supervisor.

Many creative jobs these days come with pretty strict non-compete clauses. While you’ll be making some decent additional income soon, it’s not worth risking your full-time salary quite yet. Better safe than sorry!

Why You Should Start a Side Hustle

I’ve found that supervisors generally appreciate this transparency from employees. Don’t be too intimidated or scared to just simply mention to your supervisor or boss, “Hey, I’ve been thinking of picking up some extra freelance work on the side. Of course, it won’t interfere with my work here. I just wanted to check and make sure there isn’t any issue with that in my employment contract.”

On that note, do be careful not to dedicate time or energy to your freelance projects while on the clock at your full-time gig. It’s disrespectful to your current employer, to work on unrelated projects on their dime.

Being upfront and honest about the fact that you’re working on other projects outside of your work hours, can be an awesome way to preemptively make sure your supervisor never suspects you’re working on your side hustle during work hours.

4. Be Selective With Your Projects and Your Time. 

Because you have a full-time job, you don’t need to rely on your freelance paychecks as much as someone whose freelancing full-time. (That’s not to say you should work for free, or for less than you think you deserve.) But, freelancing on the side means you can work on projects that might be more fulfilling creatively than financially.

If you’re a writer, this is a great opportunity to pick up some work with an independent magazine that might have a modest budget, but whose work you really respect.

That said, because you have a full-time job, your time is very precious. If you’re looking into a few side jobs, make sure it’s work you enjoy doing, or at the very least, won’t hate doing. If you’re planning to come home from your all-day work, just to dive into your freelance work, you really don’t want it to drain you. On top of that, you’re going to need a good morning routine that sets you up for success.

Seek out work and projects that fuel you. Finding work you enjoy will make you more productive and creative during both your full-time work hours and off the clock, as well.

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5. Form Good Relationships with Managers & Supervisors.

In the same way you should be honest with supervisors at your full-time job, be up-front with any editors, managers, or supervisors that oversee your freelance work.

There’s a way to clue these managers into your lifestyle without oversharing or annoying them. They’re humans too. We all have busy weeks and we all have unexpected things come up. Forming a good, honest work relationship with your freelance managers will help everything run much more smoothly.

Start a Side Hustle and Find Meaningful Work

I highly suggest creating a spirit of complete honesty with the folks for whom you freelance.

For example, I once made a short but honest joke with an editor about how I was hurting a bit for cash that month. Because the editor and I had formed a trusting relationship, she responded by telling me she actually needed some writers to pick up some of the higher paying assigned gigs and would like to offer them to me. She knew because of my full-time work commitments, I didn’t always have time to pick up more serious, higher paying work, but she was glad to offer it to me, if I could find the time.

Don’t just start telling your bosses about how broke you are all of the time (seriously, don’t do that), but maintaining an honest, yet professional, relationship with supervisors can seriously pay off when you least expect it. It’s also helpful in case, down the road, you need to use these managers for job references.

6. Set a Schedule and Stick to It.

The most challenging aspect of picking up freelance work alongside a full-time job, is time management. In my personal experience, this is the most challenging part of my life, in general. Picking up a time-consuming side hustle means, you’ll need to be very strict and professional with the way you handle your time management.

Put serious thought into forming a schedule each week, and then live by it firmly. This requires a lot of discipline on your part.

I like to give myself strict hours. For example, I work from 9AM to 5PM at my full-time job on Monday-Friday. My schedule changes slightly from week to week, depending on workload and travel, but for the most part, I stick to a predictable schedule. I try not to work more than 60 total hours each week, between my full-time and freelance gigs.

That means I can only dedicate twenty hours a week to freelance work. I try and divide my time up evenly to accomplish everything, without sacrificing my social life or enough time to sleep.

For me (and for most freelancers), this means I dedicate a lot of weekend hours to work. So, on a standard weekday I work from 9-5 and then from about 6-8. Most Saturdays I work on freelance projects from around 9-4 and I work a couple hours on Sundays as well. That’s the schedule I stick to almost every week. Knowing my “hours” in advance helps me make plans with friends and schedule my life out.

If you don’t create a schedule and stick to it, you’re setting yourself up for failure. Divide your week up by hours, and don’t neglect things like sleep, social life, and self-care.

Decide how much time you can reasonably dedicate to freelance projects, and then pick up assignments from there.

Whether you’re just starting a freelance career, or looking to grow your existing business, download our free eBook, The Freelancer’s Roadmap and accelerate your business.

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Rachel Perkins FOLLOW >

Rachel Perkins is a writer, editor, event planner, photographer, social media-er and all around creative-ish person. @rachie_claire