5 Questions to Ask Yourself Before Quitting Your Job to Freelance

Freelancing might sound like the perfect introvert job, but there are five questions you should ask yourself first.

“Don’t you get bored and lonely and watch Netflix all the time?” My extroverted friend asked me with a quizzical look.

“Nope, nope, and nope,” I replied.

I quit my full-time corporate job over two years ago, much to the shock of my family. I had a shiny job as deputy editor of a magazine and content manager of a leading women’s website. I actually loved the work itself. As an introvert, I loved telling people’s stories and playing with words for a living. It was a dream gig.

But, in reality, I hated going into the office every day. My manager was a massive extrovert, and even her presence made me tense. I’d be mind-deep in writing and constantly interrupted. Meetings were unpleasant and distracted me from my work, and I loathed the requirement of constant small talk.

Oh, and let’s not forget team brainstorming days. Just hearing the word “brainstorm” was enough to make this introvert shake in her slippers.

Managing People Was Not This Introvert’s Thing

Before I quit, I was promoted to Acting Head of Communications when my boss went on maternity leave. Suddenly, I found myself managing a team, which I was horrible at. I’d eschew conflict at all costs. One time, I found myself running a strategy day, which was one of the worst work days of my life. I was so nervous that I got no sleep the night before. Grossly unprepared, I stammered and sweaty-palmed my way through seven hours.

Turns out, I’m not a “strategy” person. I like making puns and writing poems. How on earth did I end up here? I wondered.

Like many introverts do, I made the huge mistake of thinking there was something desperately, horribly wrong with me. I felt awkward around colleagues and terrible at leading others. Once, in a one-on-one with the CEO, I cried because I felt the pressure was too much, then felt foolish and ashamed. I’d seen other people step up as head of a department with ease, so why couldn’t I?

I wish I’d taken the time to be kinder to myself. I was a shy subeditor and writer who’d had no management training; I’d been thrown into a foreign world. And, as an introvert, I felt like a square peg in a round hole.

Freelancing Meant I Could Do My Own Thing

Don’t get me wrong; there were upsides. I made some close friends there, and it was a relief when my boss came back from maternity leave.

But, as a bundle-of-contradictions introvert, I suddenly hated that I was being told what to do again. I didn’t want to be the boss, but I also didn’t want to have a boss. I wanted to do my own thing.

That’s when I discovered the answer: freelancing.

So, without any other job to go to, I resigned. And, after ten years in a soul-crushing office environment, I’ve started living the life I’ve always wanted as an introvert and a freelance writer.

I’m two years in, and so far, things are great. Surprisingly, my productivity levels have soared. Sure, sometimes I go to the gym at 10 a.m. just because I can. But now that I’m not being interrupted or having to go to pointless meetings, I can keep my head down and actually get shit done. I can be creative, on my own terms. If I miss company, I’ll meet a friend for coffee or call my boyfriend, or take my laptop to a buzzing cafe.

Now, I’m always in control of my environment — which does wonders for this introvert’s energy levels and happiness.

5 Questions to Ask Yourself Before Quitting Your Job

Are you an introvert who’s thinking about quitting your job to be your own boss? Here are five questions you should ask yourself before you do:

1. Are you willing to sell yourself?

It can be hard for introverts to promote themselves; we hate the spotlight and introducing ourselves to strangers, and we’re allergic to anything that feels like bragging. But if you’re running your own show, you have to get used to putting your name out there, networking, and telling everyone how awesome you are (let’s face it, you are!). If you don’t, you just won’t get clients, and your business won’t survive.

Does self-promotion make you nervous? That’s okay. Thanks to the internet, you no longer have to attend big events or shake hands with stranger after stranger. There are introverted ways to grow your business contacts; here’s how to network without actually attending networking events.

2. Can you get organized?

Clutter is my middle name (actually, it’s Kathleen, but I should probably change it to that or McSloppy). I’m hopeless at being organized, but as a freelancer, it’s absolutely necessary for me to keep track of invoices, stick to deadlines, and set timelines. I had to learn to stretch myself and develop some skills and habits that don’t come naturally to me. It took effort, but nothing will motivate you faster than the awkward situation of losing a client’s piece the night before deadline. That will only happen once before you come up with a system that works for you.

Adding to the chaos, for most freelancers, their kitchen table becomes their office (at least at first); that can throw a wrench in even the most organized introvert’s plans. You’ll save your sanity if you learn to set boundaries and separate your personal life from work life, and if you have small kids at home, you’ll have to work even harder at this. Here are some tips for introverts to survive working from home, which are especially applicable to parents.

3. Can you be flexible?

When someone calls you with a last-minute project, you might just have to pull an all-nighter if you need the cash, or be willing to work weekends if your projects are piling up. For routine-loving introverts, this may sound, let’s just say, not ideal. However, the good news is, once you’re established, you can call the shots — but you’ll probably have to do some unglamorous things early on to get your business off the ground. In those initial stages, it may be a lot of not-fun work. Can you grind through it?

4. Do you have a cash buffer?

This is a no-brainer, but you shouldn’t leap from the security of a full-time job unless you’re out of debt and can survive without steady income for at least a couple of months. If you can’t, start a side hustle first, then quit your day job when the numbers make sense. Introvert or extrovert, there’s nothing worse than desperately trying to rustle up clients with the threat of unpaid bills looming over you.

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5. Are you okay with uncertainty?

Freelancing, like any entrepreneurial adventure, comes with a side of instability. Some weeks you’ll be crazy busy; other weeks you might be frustrated and idle. People might not always pay you on time, and the lack of a regular paycheck can be stressful. Nobody likes uncertainty, but for introverts, who thrive knowing what’s up ahead, it can be even more nerve-wracking. Yet if you become your own boss, you’ll have to get comfortable with some level of risk and uncertainty. But, over time, things do even out, and you find that something brilliant (like your next paying client) is always around the corner.

Freelancing isn’t right for everyone, and there are plenty of great jobs for introverts. But for this introvert, it was definitely the right move.

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Written By

Lucy once worked for Cosmopolitan, where she worked on sealed sections and wrote about lip gloss. She’s now a happier, full-time freelance copywriter, feature writer and subeditor with a penchant for puns. Follow her on Twitter or email her at [email protected]