Freelance while working

For a long, long time people have sidetracked from their primary jobs to do a little something extra. Whether for financial reasons, exploring a hobby, or personal fulfillment, it’s not out of the ordinary to feel the itch to branch out on your own a bit.

Thanks to more digitized communication, having a side hustle has become a lot more attainable. It’s also made it so that tapping into a secondary source of income isn’t confined to just having a store on Etsy (though that’s cool, too). Nowadays, you can take almost any talent—especially one that translates across digital properties—and use it to your advantage by becoming a freelancer.

Though freelancing may sound attractive (we mean, who doesn’t dream of ditching the 9-to-5 grind), we understand—and recommend—the need to dip your toe into the water before diving in headfirst.

Keep in mind that being a freelancer requires a certain kind of personality—one that is driven, organized, and realistic. But we know that has y-o-u written all over it, so let us share insider tips on how to get rolling.

Free Download: Do’s and Don’ts of Freelancing

Why Freelancing?

A study found that one-third of companies were using freelancers in 2016, and that 55 percent of those expected to use more in 2017.

It’s likely that prediction rang true—and then some—considering that more and more people are choosing to freelance. According to Forbes, “A study commissioned by Upwork and Freelancers Union pegs their number at 57 million and predicts [freelancers] will make up a majority of the U.S. workforce by 2027.”

This comes as no surprise; hiring a freelancer to perform specific tasks or pitch in on projects is appealing to companies for a number of reasons.

For one, employers don’t have as many overhead costs—very few, actually—when using a freelancer. They don’t have to pay for the worker’s benefits (health coverage, paid time off, sick days, maternity leave), set annual salary or bonuses, workspace (if working remotely), parking, etc. Though they may still be on the hook for specific software or services, they also aren’t ponying up for a desktop, laptop, or work phone.

All of these things are expenses that freelancers take responsibility for once they essentially become a small business owner.

Freelance while working

Aside from just the financials, using a freelancer means that a manager can really hone in on a specialized skillset since they don’t need a more well-rounded employee to fill 40-plus hours a week.

Though when you break it down hourly, they may find themselves paying a premium rate, the time it takes to complete the task or project—or the higher level of work itself—will probably make it worth it.

It also gives the employer the freedom to choose to have a freelancer dive in when the workload gets heavy, but they don’t have to worry about paying out when budgets are tight or assignments are light. (This obviously is dependent on the contract you have with the employer; i.e. if you are on retainer or not.)

Even if a company is in need of a whole team (like a creative one, perhaps) to carry out a project, assembling a mishmash of experts may end up being more economical than hiring a full-service agency—after all, firms have their own overhead to worry about. Though this process may be more tedious and require more coordinating, over time companies tend to build out a healthy Rolodex of freelancers to call upon.

Assess Your Abilities

Though it’s likely that the thought of freelancing came to you because you realized you could outsource some of your skills, you may also be feeling that you want to start freelancing, but don’t quite know where to set your focus.

We are more than sure that you have talents across the board, but it is smart to really zoom in on one or two specialties. For example, if you are a marketing professional, dial in to the programs and situations you understand best. Is it graphic design? Website development? Writing? Project management? Email marketing?

Choose the area where you have experience and work on both amplifying your skillset and learning how to articulate it in order to make yourself appealing to a potential employer.

Choose the area where you have experience and work on both amplifying your skillset and learning how to articulate it in order to make yourself appealing to a potential employer. Share on X

Remember, we can’t be everything to everyone, and if you are supplementing a full-time job with a freelance role, you won’t have the time or energy to exert yourself in multiple directions anyway.

Make Sure You Have the Time


Freelance while working

Because you are a dedicated time tracker (right?!) then you should already know if you have the capacity to take on additional projects. Though you should never be doing freelance work during regular work hours, you’ll have the opportunity to see where you’re spending your time outside the office thanks to Timing automatically tracking all time spent on your Mac.

Plus, once you start to pick up assignments, diligent time tracking will be one of the essential elements of balancing work with more work. Plus, like any good freelancer, having a detailed and organized overview of all your time will help you to bill freelance clients appropriately and even back you up in a situation where an employer accuses you of freelancing on the clock.

Value Yourself

We’re going to bet that before you have a meaningful conversation with a hiring manager for a freelance gig, chances are they are going to ask about your rate. After all, successful companies have to keep their bottom line in mind.

So, how do you even go about quantifying what you do into a numerical value?

If you’re just starting out, you probably feel the pressure to be on the company’s lower end of possibilities when it comes to cost. And while it’s understandable to want to the chance to show your chops, there is a fine line between getting your foot in the door and putting yourself into undervalued purgatory.

Our advice? Don’t fall over yourself for any opportunity, but rather think critically about the worth of your work and choose projects accordingly.

Decide if you prefer hourly, project-based, or monthly retainer work. If you were a career freelancer, you’d likely be leaning toward the retainer option (after all, one of the biggest downsides to freelancing is unreliable income).

However, if you are adding on top of a full-time job, you may feel that having a “trial period” of sorts with an agreed-upon hourly rate is best. This way you get paid for the work you put in and there aren’t really any other strings attached.

Figuring out your hourly rate may be a bit tricky, but a good starting point is to take your annual salary, add on any guaranteed bonuses and the estimated cost of benefits, and then divide that number by 52 weeks and then again by 40 hours a week. This will give you an idea of your hourly rate in your full-time position, but keep in mind that freelancers are carrying around some of that extra weight when it comes to expenses (devices, WiFi, etc.). In addition, it helps to compare your desired hourly rates with the rates listed on freelance jobs sites such as Jooble.

Also, as with nearly every question we come across in our lives, it’s helpful do a little online research. You’ll probably find some websites or message boards that can give you a sense of what people like you are charging for similar services in your market.

Be Honest

Your parents have likely been telling you to “just be honest” since you were a kid, and we’re here to tell you that they were right.

Once you’ve decided the kind of freelance work you’d like to pursue, your desired rate, and done some digging into prospects (by the way, we recommend connecting with former managers and coworkers first to put out some soft feels about freelance needs at their current companies), then it’s time to tackle the issue with your employer.

We get that this can feel like an awkward conversation. After all, what boss wants to hear that you’d like to spend your time doing work for someone else? However, as we discussed in the beginning, this kind of situation has become the norm.

When broaching the subject with a higher-up, it’s important to stress the following:

  • You are happy with your current position (if that is indeed true) and are just looking for additional creative outlets or income.
  • Any freelance work will in no way impact your dedication to your job (reassure them that you will only use hours outside the office to complete projects, and stick to it).
  • The freelance work you are planning to take on will actually improve your job performance as it will help you develop additional skills and experience (and be sure to be specific about these).
  • You will confirm along the way that freelance clients/projects do not provide a conflict of interest with your job or the company.
  •  You’ve come to ask permission because you respect your boss and company, and would never do anything to jeopardize their trust.

Honestly, what manager could shut a great argument like that down?

Free Download: Do’s and Don’ts of Freelancing

The Bottom Line

Chances are you have everything you need in front of you to go off and start to do some freelancing, just as long as you have the passion and drive behind it.

By being honest with yourself about your goals and what you have to offer, being upfront with your employer about your plans, and taking advantage of helpful tools (like Timing!) to help keep you informed and organized, you’ll be on the fast track to earning some serious bonus cash.

In the end, what do you have to lose by trying?