What it’s really like to quit your day job and freelance write


By Amanda Cleary Eastep

I spent the first-month anniversary of my full-time freelance writing business on top of a mountain.


OK, it’s not Mount Everest. But the symbolism in the act of driving down the winding Blue Ridge Parkway, seeing the seasons change before our eyes in the veins of a trillion leaves, and climbing a slippery slope to the summit is almost too obvious. (But I love obvious. I have to think less.)


I had cleared my project list for five days (thank you, freelancing) to explore a few towns my husband and I envision moving to in the future…or at least until God shakes us and yells, “Wake up! You have a physics test today that you didn’t study for. What? You were dreaming of a view of the mountains? Foolish mortal! You’re late for the bus!” Until then, we keep pursuing ideas and possibilities, goaded by nudges and why-the-hell-nots and the promise of milder winters (jeez, that makes me sound old).

Since I quit my day job on Sept. 30 and launched full force into freelance writing after three years of working hard toward that goal, supportive friends and curious onlookers have asked me “how things are going.” 

I imagine the underlying sentiment may be, “Do you need us to donate a block of cheese and some hardtack to get you through the winter?” But, also, it may be, “Do you mind if I watch how this works out for you before I take a leap, too?” 

First, I’ll clarify something. I’m not making a living writing stuff like this blog post. (Please refrain from answering, “Duh.”)

Let go of visions of a writer sitting at a fancy desk (although my husband found this one on Craigslist for $50, and it is lovely!) and pounding out best sellers as she contemplates the universe and a view of the mountains.


Freelancing writing looks more like:

  • profiles, internal newsletters, and web stories for colleges
  • blog posts on innovative trends in the insurance industry
  • copy that translates highly technical engineering jargon into regular people lingo

Romantic, huh?

The transition has been interesting. Here’s an insider’s view…

Week 1: I am not on vacation. I have to remind my daughters of this but also myself, because being home all day just feels weird. I have no problem being disciplined; I’ve had to be to get to this point, but the day is completely unstructured unless I build a framework with to-do lists, scheduled meetings, and calendar deadline alerts.

Week 2: Create a schedule (what?!). As free as “lancing” may be, I wake up early, dress smartly in jeans and a sweatshirt, and start writing by 7:30. I find this is kind of like homeschool without children; I can often accomplish so much by noon that it feels wrong. However, I have to remind myself that the time it takes to organize files, communicate with potential clients,  and create estimates and invoices is NON-billable.

Week 3: Buy a desk from an elderly woman who is selling all her possessions and moving in with her daughter…and then leave it in the garage for three weeks in case you decide to paint it. Continue to use couch as main workspace.

Week 4: Get organized, update your website portfolio, plan for new client acquisition. This last one is huge, because as busy as one month may be, you may suddenly find yourself wondering when the next project will be assigned and if it’s time to start rationing the cheese and hardtack.

4 a.m. on random days: You did it!!! You DID this! You did this to yourself. What are you doing? What in God’s name did you do?

Week 5: Take a vacation to North Carolina. Tell yourself you deserve it for the 10 years of dreaming, the three years of working in the wee moonlighting hours to make this happen, and just in case you have to find another desk job next month.

Ongoing: Fight the urge to type “job” in quotation marks or pronounce it as if in italics: “Why, yes, I quit my day JOB [i.e. legitimate career] to pursue a new ‘job’ as a freelance writer,” she said almost apologetically.

So, as of October 1, 2015, this is my career. This is what many writers dream of doing. And this leap has been a big part of my Year of Living Courageously.

As a way of recording the early stages of this journey, I note a WIT (What I’m Thinking), beside the task list I write in my fancy legal pad. 

These notes range from “Good pace, keep going” to “Breathe.” They keep me centered, or what I like to call, “keeping my WITS about me.” 🙂

Today, I’m sharing this WIT even though I didn’t write it. It’s a gift from my friend and former co-worker Jackie, and this plaque was one of the first things I set on my new desk.

(front row) Rocks I took from the top of the mountain
(front row) Rocks I took from the top of the mountain

“I am not afraid. I was born for this.” Really, this bold saying is not even about freelancing or leaping or climbing small mountains.

It’s about doing what you’re gifted to do–whether that happens at your day job or in the wee hours, whether you do it for the CEO of a big company or a few faithful blog readers, whether you do it for a paycheck or for no reward at all except the joy it brings you…


4 thoughts on “What it’s really like to quit your day job and freelance write

  1. We think you’ll do just fine.Your leap of faith shows how much you believe in yourself, and how much others should believe in you too. Look forward to watching your progress!


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