An ancient Greek philosopher once said:  Know thyself. Whether she or he was talking to a timid gladiator or someone who just binged on gyros, we’ll never know. But what we do know is that this sage Greek aphorism still holds true thousands of years later. And it’s probably never more applicable than when it comes to deciding whether an exciting new freelance writing career is for you.

There are many — I repeat many — things you should know about yourself if you’re going to ditch full-time work to seek out an increasingly more popular freelance writing career, full-time. Perhaps you’re a talented scribe who works in-house (copywriter, editor or blogger), and the lifestyle has been seductively eyeing you from afar because of workplace politics and endless back-to-back meetings. Or perhaps you’ve been thrust into it, after a layoff forced you into the freelance economy — aka the “free” world with more “free” time, “free”-dom and some not-so-“free” bills to pay. Or perhaps you’re just a novice looking to change careers.

Regardless of the scenario, establishing an independent freelance writing career is a very real option these days. It’s no longer a hobby or a side hustle, or a stigmatized euphemism for “unemployed.” If you’re going to take this potentially rewarding plunge into bold new waters, here are seven things you should know about yourself before diving head first, so that it doesn’t feel like a brick wall when you get there.



1. Know if you’re the kind of person that’s disciplined enough to work from home… at off hours… and on weekends…

Question: What career choice allows you to work three hours in the A.M., catch a matinee, a power yoga class and then finish it off with a surreal sunset from the Santa Monica Boardwalk? Answer: Freelance!

Moving freely through the world during the “work week” (when others are on conference calls with the East Coast) has long been a HUGE plus and is probably the main driver of people who choose to make freelance writing their full-time “business.” That’s the biggest blessing: dictating your hours and enjoying the flexibility to do what you want on days that are slow, or once you’ve wrapped up an assignment.

But it can also be a curse. If you don’t have the discipline to set aside real time to do — and pursue new freelance work — then you might find yourself living the life of a retired person long before you can actually afford it. Let’s be honest, some sit down to work for the day, click on one push notification and end up in a six-hour social media rabbit hole sponsored by Facebook, Twitter and Instagram. To be a smart freelance business person, you must feel confident and comfortable in a routine that involves working from home — and productively — to stay on course. The only way you’ll make enough to pay rent is if you spend the right amount of time over-delivering for happy clients who become repeat customers while pursuing new ones (just in case those “happy ones” have to bring work in-house to save money).

Diving Into Freelance Writing Career

Commit yourself to working hard for the clients you have (even if it’s at unconventional hours), and you’ll experience the perks that come with being a freelance word whiz — the kind that doesn’t have to punch a clock.

2. Know if you’re the kind of person that can sell well (i.e., yourself, ideas, concepts)…

Let’s face it, we all work in sales to a degree. Trying to land a date via Tinder? Sell yourself. Need to recruit a buddy to go on vacation with you? Sell the destination. Want to land a promotion? Sell your wins to your bosses to show how effective and profitable you’ve been for the company.

Opting for the freelance writing life? Prepare to sell yourself, your talents, your business, like never before… not only to get jobs from new clients by expressing your unique value to them and your razor-sharp thinking, but by sending new ideas out the door for article pitches, copywriting projects and new possibilities that can help push a client’s business forward in new and impactful ways. Find your unique angles, and then pounce. Because unless you have a couple of whale clients that keep coming back to you, you’ll need to get out there pitching yourself, your capabilities and your undeniable talent and value in order to keep the lights on.

If you want, you can start this “sales” process by establishing a CV Portfolio right here on the ClearVoice site to showcase your work, talents and quick elevator pitch for all prospective employers/clients to take in.

Get that down, and the clients will come.

3. Know if you’re the kind of person who already has money and/or doesn’t need a whole lot of it…

Maybe you fell into money when Aunt Mildred died. Or married a so-called “breadwinner.” Or had a successful go on NBC’s ‘The Wall‘. Whatever the windfall is, first congrats… and second, know that having a savings account isn’t a terrible idea when you first enter the full-time freelance game. It takes the sting off having to land x number of jobs every week and gives you time to establish new clients and be choosy about who you take on. This, of course, may not be an option if you’re in dire straits. But it’s certainly worth mentioning here since, for all the wins you’ll gain by being a freelancer, freelancing can be susceptible to several factors outside your control, such as the following:

Three Factors That Inevitably Affect Your Freelancing Writing Career

4. Know if you’re the kind of person who enjoys working with different clients…

Some people need the reliable, steady paycheck that comes with a full-time job not just for bill-paying, but for peace of mind. And that’s fine. But if you’re the kind of person who gets bored easily and views going to the same place everyday as a monotonous humdrum you’d rather not add to an already predictable life, know that an independent freelance career offers a variety that could easily spice up your work life in the form of new contacts, challenges and, most notably, the fun reality of writing about different products, with new collaborators, in exciting places.

Over the years, freelance has taken me everywhere from Las Vegas for CES to the Los Angeles Lakers’ locker room to a luncheon at the Playboy Mansion. Just last month, it took me to the La Brea Bakery to sit down with the guy who let the world into the most awkward teen diary entries ever written.

Variety keep things interesting. And if you’re the kind of person who has the ability (and financial flexibility) to move project-to-project, client-to-client, without knowing exactly what the day, month or year could bring, then freelancing could be for you.

5. Know if you’re the kind of person that doesn’t need to be around other people…

In the age of cell phones, social media, telecommuting and working remotely, it can be easy to forget how to actually converse with a human being. And that’s okay. For some. But you should know how you function working alone for most of the day without human interaction before you decide to freelance full-time. Being isolated in a room, with maybe just a cat and Amazon Alexa can be a recipe for doubt and potential feelings of loneliness. BUT, it can also be a welcomed change from cubicle life, open floor plans and that super-chatty co-worker who’s this close to becoming the next contributor to the #MeToo movement.

Early in my career, in my 20’s, I found the isolation of being alone in a room, for eight hours a day, a bit alienating. And since I wasn’t ready to be a shut-in right out of college, I freelanced for half the week and got a part-time job the other half as a concierge at one of L.A.’s top hotel destinations — the most social kind of job you could ask for. That worked for me back then, but I had to spend a good amount of time with myself — alone — before I realized that this was what worked for me.

Diving Into Freelance Writing Career

Know what works for you and you’ll be a lot happier when the inevitable fluctuations of freelancing full-time kicks a little dirt in your face now and then. It happens.

6. Know if you’re the kind of person that likes to take guilt-free vacations…

It seems the average vacation time at a full-time job these days is two to three weeks a year. Two to three. The year has 52 of them, so the idea that you only get this little time for yourself, your partner, spouse or family isn’t, well, that much.

Now, if you’re a full-time freelancer, you have every right to book that two-month Euro trip you’ve been eyeing once you clear your schedule. You deserve to be off the grid/clock from time to time. You only get one life. It replenishes the creative well, adds experiences to draw from and can keep your writing fresh. And, given there’s a disturbing trend that shows millennials — especially millennial women — don’t use their allotted vacation time out of fear and guilt that they’re putting too much of a burden on other employees, you should know that when you’re freelancing full-time, you are your own boss.

So, if you need time off, simply ask yourself this question: Can I go away for two months at some point this year? Answer: Yes. Book vacation.


7. Know if you’re the kind of person that likes to work smart, not hard (…okay, you’ll work hard too)…

One of the best things about being a freelancer is the flexible hours, as previously stated. But, unless you figure out how to work smart, for instance, by knowing when you’re the most productive, you could find yourself working longer and harder than a more traditional (yet increasingly non-existent) 9-to-5 job.


Why’s that, you ask? One of the most compelling reasons an agency or client will use a freelancer is because they’ll handle the in-house jobs that are either too time-consuming to handle internally or the ones that nobody wants. Which is fine, ’cause work is work. In that realm, you are a vital cog in the wheel of productivity as a specialist. But know this: Sometimes turnaround times aren’t ideal.

So, make sure you understand the nature of what could be coming your way and what you can handle as a freelance “gun for hire.” Be aware that you hold a degree of power when it comes to negotiating jobs and turnaround times that work for you, and adjust accordingly. You want to help people in a crunch and get paid for it, not crunch all the things that matter in your life. Be professional, true to who you are, and understand the limits of what you can do.

If you do those three things, you’ll win many fans… And fans like to hire, and re-hire, people. And that’s your goal, isn’t it? To be as successful as possible in your new freelance writing career? Now, go get ’em!

If the above sounds good and you’re ready to take the next step, check out the CV Portfolios section of the ClearVoice site and put your best writing samples forward for all to see. Once you have everything in one place, it’ll make it easier for prospective employers to experience your talents, specialty areas and ultimately, hire you. Good luck!