To Freelance or Not to Freelance? That is the Question.

Julie Cortes shrugging

It’s one of the biggest questions I get.

So, let’s dive into whether or not freelancing is right for you.

First Off, Know You Are Not Alone

Freelancing is an animal in and of itself. This single fastest growing segment of the U.S. workforce is taking the country by storm.

We used to say that, by the year 2027, more than 50% of the United States working population would be freelancing … in some capacity, whether that was full-time or part-time.

And that didn’t just include those who’ve traditionally freelanced, such as folks in the advertising / marketing industry. (Think graphic designers, writers, photographers, etc.) This number also included hair stylists, insurance salespeople, Uber and DoorDash drivers, and more. Ya’ know, “gig workers.”

But then, the pandemic hit. And people were forced to work from home.

This gave many people a firsthand glimpse into what that looked like …

No commute. Ability to wear comfy clothes. And a flexible schedule that really worked with their lifestyle.

Office workers suddenly understood why working from home was so great!

And, once the world started opening back up, many decided they didn’t want to give up those benefits.

All that to say, while the freelance workforce (AKA, the “gig economy”) was already on this steady incline—because of the pandemic—the numbers are now skyrocketing.

So, if you were ever wanting to test out the freelance lifestyle, now’s as good a time as ever.

The Pros and Cons of Freelancing

As with any job, there are pros and cons to freelancing.

First, the pros:

  • Freedom! Obviously, this is #1. You get to work on what you want, with whom you want, when you want, where you want, how you want … while wearing what you want.

  • You are Your Own Boss. No question about it. That means you get to make the rules. Contracts, additional fees, policies, and procedures … they’re all up to you! And, it’s pretty dang awesome.

  • Set Your Own Schedule. Not a morning person? Gotta take the kids to school or go to a doctor’s appointment in the middle of the day? Don’t want to work 8-hour days? No problem!

  • Choice of Clients / Projects. Got a target audience in mind? A niche industry or medium? Perfect! This also means you don’t have to work with people you don’t like. It’s hella empowering.

  • Unlimited Earning Potential. No salary caps here! You can make just as much—if not more—than you would at a similar full-time job. And a raise every year? Yes, please! #BestBossEver

In my personal, humble opinion, the pros far outweigh the cons.

Yet, of course, there are still cons, such as:

  • No Guaranteed Paycheck. Call it what you will: feast or famine, episodic income, rollercoaster paychecks … there’s no real stability in how often or how much you’ll get paid.

  • No Health Insurance / Benefits. It must be some kind of cruel joke, right? But alas, at least here in the United States, self-employed folks don’t get health insurance. Or a 401k for retirement savings.

  • The Isolation Factor. No boss, supervisor, or coworker to bounce ideas off of … no watercooler or breakroom chat … unless you co-work … if you can afford that when first starting out.

  • Must Be Self-Disciplined. Mindset and motivation play a huge role in determining one’s freelance success. You gotta ensure you show up for work every day, and work like you mean it.

  • You Have to Wear All the Hats. You’re the CEO, CFO, CMO, COO … and any other “O” you can think of. You are the salesperson, administrative assistant, marketer, accountant, and more.

As a freelancer …

You’ll be doing more than just your craft. And some people don’t inherently recognize that.

Is Freelancing Right for You?

And now, to the question of the hour … Is the freelance life right for you?

There are many quizzes and coaches out there who will ask you a variety of questions such as if you:

  • enjoy doing a variety of tasks or prefer to focus on your core talent / skill

  • are organized or disorganized

  • mind sales and self-promotion

  • have (or can get) a dedicated workspace

  • are easily distracted or can easily focus

  • can self-motivate or if you struggle with motivation

And those are all very good questions.

(Honestly, the motivation thing doesn’t bother me so much. Because, like I said before, it CAN be taught. It CAN be acquired. How do I know? Because I’m a prime example. Having gone from lack of motivation to all sorts of motivation—simply by changing up my mindset—I can tell you firsthand that it’s completely and totally possible. It’s teachable and attainable. And, not gonna lie, it’s a total game-changer.)

But, overall, in my opinion, these are the two biggest things to consider—especially if you’re just starting out:

  1. Do you have a financial safety net? Do you have a partner / spouse who has a steady paycheck and would be willing to support you as you build your business? Do you have savings you could dip into? Would you be open to taking a full- or part-time job while you build up your clientele?

  2. Can you get health insurance? Again, this could be through a spouse with a full-time job if you can get on their plan. Or, (if in the U.S.), is Obamacare a feasible option? I don’t recommend going without health insurance at all. See if you can at least get a major medical plan.*

If you answered yes to both the questions above, then I think it’s worth looking into. If not, consider if you can get your situation to change.

For those of you who currently have a full-time job and are considering making the jump to freelancing, ensure you build up at least six months’ worth of income before leaping to give you that safety net. Also, start freelancing NOW on the side (if your employer allows) to build up your client roster.

If you’re someone who’s recently lost their job unexpectedly—which, unfortunately, seems to be the norm these days, don’t despair. There ARE ways to navigate the freelance waters early on (such as taking a part-time job, onsite gigs, etc.) to make things work.  

So, at the end of the day, the question remains: Should you freelance? Or should you not?

That’s a very personal question. And really, only you will be able to answer it.  

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Need help in determining your path to freelancing freedom? Let’s chat and see how I can help you with your journey.

*Consult with an insurance provider / broker to determine the best course of action for you and your particular situation.

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Mindset Matters: How to Master it as a Freelancer