The Specific Times I Wished I Didn't Quit My Corporate Job, and What I Did About It

The Specific Times I Wished I Didn't Quit My Corporate Job, and What I Did About It

(This story has also been published on Entrepreneur. I share it here solely to expand its reach.)

In early October of 2016, in an out-of-character burst of confidence, I quit my corporate job. I threw my safe, cushy corporate life out the window in favor of a volatile career as a freelance writer. And I've loved every damn second of it.

But, like any human, I've had doubts and fears along the way. Some so severe they've left me poking around on LinkedIn for job openings in the middle of the night.

Instead of mull over the specific times I've regretted quitting my job, I figured I’d share them with you.

October 10th at 8:08 a.m.

It was the first Monday after quitting my job. For a brief moment, I felt like my whole world was falling apart.

"Could I really do this? Aren't I breaking some sort of law? It's 8:09 a.m., and I'm still in my pajamas..."

Then I remembered that I got to write that day, all day. And everything calibrated.

October 24th at 3:47 p.m.

My freelance writing coach had invited me to join the Real Freelancers Slack channel. Immediately, I saw the activity, success, and income happening for all these other freelance writers.

"Allie, you'll never be as good as these folks..."

Then I remembered that I'd only been freelancing full-time for 14 days and that I needed to give myself a damn break.

November 12th at 11:10 p.m.

My routine, late-night quests for inspiration had turned into massive intimidation after reading a few too many websites, portfolios, "big break" stories, and testimonials of other freelance writers.

"Holy shit, this will never happen for me. I'm chugging along with just a few clients, and I haven't even determined a niché yet.

Then I shut off my computer, rolled over, and went to sleep. (A full night's sleep can cure any moment of crazed insecurity, no matter how silly.)

January 15, 10:30 a.m.

The contract with my first remotely consistent client ended, and I was completely unsure of where my next paycheck of that size was coming from. 

"This is it. My career is done. Mom, Dad, I'm moving back in. Yes, Dad, I get that you told me freelancing full-time was a mistake..."

Then, in another out-of-character burst of confidence, I picked myself up and began again. I cold emailed, searched for jobs, polished my website, and grew my self-published portfolio. And I remembered why I loved what I was doing. 

January 25 at 2:32 p.m.

I had met with my wealth manager to start allocating the funds in my Roth IRA. He's a family friend who knew my story, but he still took the time to question me about what freelance writers actually do and how much I really expected to make in 2017.

(I'm not even going to explain the doubts and insecurities that swelled at that moment.) 

Then I remembered that I was sitting in a wealth manager's office at 22 years' old attempting to provide for my retirement and my children's well-being. It shouldn't matter what I do for a effing living.

February 22 at 5:45 a.m.

In a bout of night sweats and anxiety, I had realized that my decision to freelance full-time had hindered, if not obliterated, my love for writing.

"I've got to get published. Two measly recommends on Medium is nonsense, Allie. Work harder. You're not a good writer, and you'll never be able to live on this salary..."

Yeah, anxiety can have a life (and sharp tongue) of its own.

The next day, I did some digging on my favorite writers. Jeff Goins's A Writer's Manifesto helped remind me to stay centered with the reasons behind my major career move. I routinely return to this when freaking out.

When I started this journey, I didn't expect it to be simple. But, I also didn't anticipate that so many different and silly things would make me question my confidence and passion. As certain as I felt about myself and my skill, they sure took a beating every time a wave of anxiety, pressure, or intimidation hit.

Freelancing full-time is scary, and the salve for that fear can look different every time it arises. In my experience, the best way to face that fear is to:

  • Acknowledge it — Fear is here.

  • Feel it — Alright, Fear, what do you have to say?

  • Calm it — Fear, you're being silly!

  • and, Knock it out — Fear, GTFO.

The reality is that fear is going to get you nowhere (except maybe mentally huddled in a corner, shivering, with your nails bitten down to stubs). If you can't pull yourself out, lean on a close friend, a funny movie, or even a good night's sleep to help you feel centered again.

It's OK to acknowledge that you're feeling uncertain or scared. Face it, then turn around and run in the direction of your passions. That's what I've done by turning my fear into the kickass blog post.

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