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15 Questions to Ask Yourself Before Freelancing Full-Time

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Taking a leap of faith into the freelance world can feel more like hurtling off a cliff into the great unknown. I know because I did it a year ago. In the time since, I’ve discovered many things, ranging from which neighborhood cafes have shoddy WiFi to the best way to follow up on a check that’s MIA.

[Related: 3 Signs You’re Ready to Turn Your Side-Hustle into a Full-Time Job]

Even through the minor annoyances, though, almost every day I have some blissed-out moment where I can’t believe how much control I have over my life. Freelancing is thrilling because there’s no pre-existing career path for me to follow—it’s up to me to chart my own. Sound intriguing? While I’m certainly not a freelance know-it-all, I’ve learned enough ins and outs over the past year to compile a list of questions that will help you determine whether the freelance lifestyle is right for you.

1. Do you have six months’ to a year’s worth of living expenses saved up?

Don’t get me wrong, you don’t actually have to answer yes to this before becoming a freelancer. It’s not like I would have when I set out on my own a year ago. An early-20s magazine assistant with a penchant for Seamless-ing tacos and a long-distance boyfriend to visit, my savings were laughable. Would it have been smart of me to build a financial buffer before I took that leap? Absolutely, and I’d recommend it to anyone considering freelancing. But I scored a few steady gigs, which saved me from financial worries (until tax time came about, which I’ll get to later).

[Related: How to Start Saving for Major Milestones While in Your 20s]

2. Do you have a solid professional network?

Without a doubt, I wouldn’t have been able to land on my feet in freelancing without the people I met in college, during my internship at Glamour, my job at SELF magazine, and a few informational interviews along the way. Almost every freelance job I’ve gotten has been via someone I know in that capacity, or someone they know and have connected me with.

3. Can you advocate for yourself?

Do you know how cringe-worthy it can feel to follow up, yet again, on an invoice you submitted three months ago? It’s like a group of miniature elves are using your insides as a bounce house, aka pure, stomach-churning discomfort. You’ll still have to do it confidently, with poise, and without burning bridges.

[Related: How to Get Paid as a Freelancer (When Your Money is *Way* Overdue)]

4. Are you an introvert?

As in, does being alone for most of the day bring you inner peace, or does just the thought make your soul crumple up into a horrified, neglected ball? Either way, you can still make it work. I’m a huge introvert, so working alone all day soothes me. If you’re an extrovert, co-working spaces are cropping up everywhere so you can still have human interaction while getting it all done.

5. How will you get your office gossip?

I don’t mean the mean-spirited type, more the buzzings of the day’s happenings or industry news. Every time I hear about something big in the magazine world, I imagine what it would be like to be back at the SELF office, talking about it with colleagues. I still Gchat about it all with the ex-coworkers I’d be talking to in person, but it’s not the same.

6. Are you prepared to deal with skepticism?

Some people will think you goof off all day, others will question when you’re going to get a “real job.” If you’re able to brush them off and continue doing what you love, your life as a freelancer will be that much easier.

7. Do you have freelance friends?

You’ll need someone who understands your specific brand of professional frustration and who can toast to you when you snag something major. Even better if you can find one who works for or has done work with the same companies you have!

8. Is your inbox an unsalvageable mess?

It’s a major clue that speaks to how organized you are. Staying on top of my inbox sometimes feels like the digital version of Sisyphus rolling that boulder up a hill, but it’s key for making freelance life work.

9. How will you maintain old office friendships?

I made some of my closest friends on the job. Whereas before, we could go grab a coffee when we wanted to catch up, now we have to make an actual concerted effort to hang out. It’s a tough adjustment, but it’s doable if you really love your office BFFs.

10. Do you have an office space at home?

If not, can you make one? When I was living in New York City, my office was my bed, the couch in my stamp-sized living room, or a coffee shop that presented the drawback of having to spend money to be there all day. Now that I’m in DC and have much more space, I’ve created the office nook of my dreams. It’s automatically made me feel more like an actual adult with a job.

11. Are you scared of taxes?

Speaking of things that make me feel like an adult, let me level with you. Sometimes I’m tempted to move to a cave on an inaccessible cliffside, hunt my own food, and live by the glow of a Zahra-lit fire just so I can avoid filing taxes as a freelancer every quarter. They’re overwhelming, but that’s what accountants are for. Get one if you can!

12. Do you like PB&J?

Or ramen, and not the trendy $14 a bowl type? Or whatever cheap food you can subsist on when you have a ton of theoretical money in the bank, but all your actual, can-use-this-to-buy-food money is being held up in an accounting center somewhere?

13. Can you self-motivate?

As a freelancer, you are your own boss. You’re in control of ticking off every item on your to-do list, whether you feel like it or not. To make it a little easier on yourself, try doing these genius freelancer-approved tips before bed.

14. Are you into having a steady stream of work?

Some days I spend 18 hours in front of the computer. Others, my work’s wrapped up at 3:00 p.m. and I’m free to do what I want for the afternoon. Unpredictability is the name of a freelancer’s game, so you’ll have to adjust if you’re really into living an orderly life.

15. Do you believe in yourself?

I know, it feels cheesy to ask yourself this. But you need to embrace that cheese like it’s a big block of mouthwatering brie, because if you don’t answer yes, you might not be ready for a freelance career just yet. Freelancing is all about selling yourself: proving to this editor that you can tackle that huge investigative piece, pushing yourself to take on a big client that scares you in a good way, and cheering yourself on like you’re in a SoulCycle class when things get rough. If you can do that, it might be time to put in your notice—your new life as a freelancer is waiting for you.

Photo: AleksanderNakic / Getty Images

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