‘I Want to Quit My Job and Freelance’ — How to Know It’s Time

'I want to quit my job and freelance. Is it time?. Makealivingwriting.comI hear this a lot, from aspiring freelance writers: “I want to quit my job. I’ve always wanted to earn a living from my writing. But…I’m scared.”

Indeed. We all are. How do you know when it’s your moment to quit working for the Man and make the leap into freelance writing?

After a decade coaching writers in making this transition, I’ve discovered there are common ‘tells’ that show writers the time has come to head for the door and launch their freelance career.

If you’ve been wondering how you’ll know it’s time to act on your urge to quit, take a look at my list of common traits of writers who have reached their freelance moment:

Are you sleeping?

Whenever I’m at the tipping point of making a major change in my life, I tend to develop massive insomnia. I can fall asleep, but then I wake up in the middle of the night and lie there for hours, fretting about my fears, the direction of my life, the future.

If you’re unable to catch a good night’s sleep, and instead find yourself writing poems in your head or coming up with blog-post titles or just worrying about work stuff, you’ve hit a point of diminishing returns in employee work.

Because when you’ve hit the level of stress where you don’t sleep, you make mistakes at work. Which leads me to…

Shaky ground

Though you hear that a full-time job is supposed to bring stability to your life, I find that’s not always the case. Wannabe writers often confess to me that they’re in trouble at work. Their performance reviews are poor.

It’s hard to do your best work when you loathe every moment you’re warming that chair or standing at that counter. Soon, you may be demoted, transferred, or fired. Life is about to get harder at the day job.

This is exactly what happened at my last staff writing job, by the way. The editor staff turned over and I got a new boss. First, my work-from-home privileges were revoked, and I had to come into the office five days a week. Next, my workload got worse. Finally, I was fired.

If this sounds like your situation, read the writing on the wall. You might want to start freelancing on the side and building your business up. You might as well jump, before you get pushed. Failure at work isn’t a guarantee you’ll be a great freelancer — but if you are failing at it, you have little to lose by trying another path. I’ve seen many fired writers land on their feet in freelancing (including me).

Shakier ground

The flip side of the job-uncertainty coin is that thing where you see signs your employer is floundering. Paychecks start to come late, for instance. Or a round of layoffs has spared you — so far — but doubled your workload.

Or this: I recently talked to one longtime daily paper staffer who confided that she’s already required to take two 1-week unpaid furloughs a year.

“Can you believe that?” she said. Yes, I can, I told her.

I also believe that a year from now, maybe less, this paper will no longer exist. Furloughs are a sign of impeding death, merger, or cutbacks. I asked her what plans she was making to escape the paper’s death spiral? She looked at me with doe eyes of confusion. It hadn’t occurred to her to do anything except hang on and pray, until the paper closes its doors.

“I want to quit my job…but…the security has been great,” she tells me. And I’m thinking: What security? You’re riding the Titanic down into the icy deep here. Time to jump ship!

If your company sends smoke signals that they’re in big trouble, don’t ignore them. It’s a great time to ask yourself if you want to scramble for another day job. Or if maybe, it’s time to start executing on your freelance plans.

You’re down

Do your friends often ask you if something’s wrong? Are they dropping off muffins or asking you out for drinks, in hopes of cheering you up?

If you’re mired in depression and can’t seem to find the positive in your life anymore, it’s usually a sign that a major change is due.

Every sunrise, every child’s laughter, is cause for rejoicing. So if you find you rarely smile any more and can’t appreciate what you’ve got going for you — like, you’re still above ground — you may need to quit and freelance.

It’ll either be that, or you end up curled up in a ball on the couch, sobbing, eating Fritos Scoops, and watching Survivor all day, waiting for your eviction notice to get tacked on the door.

Questioning the status quo

Most of us were raised to believe security and success lies in a traditional career path, where you’re an employee. Perhaps you’ve now noticed that life isn’t working out as promised.

Corporations are not loyal to employees. Decisions to transfer you, pass you over for a raise, or demote you seem random, rather than based in your performance.

Once you begin to doubt the line you’ve been fed about secure employment — and realize there may be more security in running your own diverse freelance business — you’re well on your way out the door.

You become unable to get up and play the farce any more, once you get a little experience with the dead-end reality of being a corporate drone.

Your job quits you…again

I run across quite a few writers who have been fired from a string of jobs. Working for a boss just isn’t something they do well, for a variety of reasons. Short temper. Inability to respect authority. Unwillingness to set an alarm clock for 6:30 a.m. Whatever.

But instead of doing what their heart tells them is their calling, writers often desperately grab onto another unfulfilling day job. At some point, you’ve got to admit that finding a ‘day job’ isn’t bringing that hoped-for stability. You might have better luck building a freelance business, where you captain your fate and can steer your own ship.

The biggest fear

We all have fears. The question is, what do you fear most? You will instinctively act to protect yourself from your biggest fear.

So how do you know when to quit your job? You’re looking for the point where quitting stops being your biggest fear.

When your fears of financial insecurity are less than your fears of being trapped forever doing meaningless work you hate — that is the moment you quit your job.

That’s when “I want to quit my job” becomes “I’m quitting my job.” And you lay out a timeline, give notice, buy a business name, and make it happen. Or maybe you start quietly freelancing on the side, looking to put your portfolio together so you can make the leap.

The tipping point

One day, you wake up smiling in the morning, and finally know your truth: You cannot go to that job anymore, or any other one. You are done being a cog in someone else’s wheel.

You are ready to face the financial bumps that come with becoming a business owner. You’ve ignited your drive to be in charge of your destiny.

Because after all, what’s the worst that can happen? It doesn’t work, and eventually, you take another job. Big whoop! In the meanwhile, you’ll have the satisfaction of knowing you went for your dreams.

You are a writer, and need to use your gift to earn your living. No matter what. It can’t be a hobby or pastime for you anymore.

It’s time to start.

Are you ready to make the leap to freelancing? Let’s discuss on Facebook or LinkedIn (have we connected on there? If you have ‘writer’ in your description and a photo, send me an invite).

"I want to quit my job" - Bust your fears and earn more as a writer

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