How to Know When It's Time to Quit to Freelance Fulltime

6 signs it's time to quit your job to freelance fulltime.

How many of them do you have, and how to quit even if you have none of them.


Many of my ebook ideas come from visitors to, my freelance writing website. This one is no different. Following is how this ebook came to fruition.

I like to tell readers why I write a particular title, so they can gain further insight and relate better to the material.

How the Idea for This Ebook Came About

One spring Sunday morning, I was sitting at my computer doing some research for a blog post. I don’t usually send out newsletters on Sundays but as I was conducting my research, the idea for an article came to me. I ran with it, and sent out the following newsletter, which can be found online at

Sunday Musings

I've been a freelance writer since 1993. I've been out of the "traditional workforce" for so long that I don't even know what the current styles are in workplace fashion these days.

When I used to work full-time, I lived for Fridays and hated Sundays because it meant the dawn of another work week.

I enjoyed some of the jobs I had and made some great friends I still have to this day. FYI, for me, this was the best part about working in corporate America.

What I've hated about most of my jobs is that they ran my life. Let me explain.

Smart, Efficient Workers Suffer the Most on FT Jobs

I tend to be a pretty quick learner and a hard worker. I excelled on almost every job I had. So when I'd finish a project before deadline, for example, I'd wonder, why do I have to come to the office?

I finished the project, the other one is not going to hit my desk for another two weeks, so why can't I just take that time off and do what I want?

Face Time: The Bane of My Existence as a FT Employee

But no, you gotta show "face time" at the office. Many times when I worked for the legal publishing firm in New York for example, I'd be sitting at my desk with literally NOTHING to do for a week or two at a time. But, BECAUSE I was a full-time employee, if I didn't show up, I didn't get paid. And this is why I knew that working for someone else was never going to work for me.

Hating Sundays: Ditching the Cubicle Life

And this is why I hated Sundays. I wanted to go to Florida with my boyfriend for the weekend, or visit my girlfriend in Charleston for a few days, or just chill out at home and watch Law & Order reruns until my eyeballs fell out.

This is why I could never go back to working full-time. While I put in many more hours as a freelancer than I ever did as a FT employee, I get to decide the where and when's of my life.

I don't ask someone when I want to go on vacation (I can't imagine waiting to get permission to go on 2, 3 or 4 weeks of vacation a year -- when you think about it, it's almost cruel);

I don't worry about using up all my sick days and not getting paid;

I don't stress if I don't feel like starting to work until noon (I'm not a morning person at all).

When's the Best Time to Start a Freelance Writing Career?

If any of this has resonated with you and you're serious about starting a freelance writing career, NOW is always the best time. Why?

Because NOW is always the best time to start living the life you want -- plain and simple.

That very same afternoon, I received the following email from a subscriber. She wrote:


I so resonate with this article! My business is in the start-up phase, which will entail doing lots of article marketing, and it's my goal to leave cubicle nation in a few years.

Would it be reasonable for you to write an article about the steps it takes to prepare to leave cubicle nation, and how to know when you're ready to go solo full-time? (emphasis added)

One concern I have is getting adequate health insurance. I'm 40-years-old, unmarried and have no children. Could you shed some light on this? Thanks so much.


After receiving K’s email, I thought, “What a great idea for an ebook.”

As I’d been through this myself (years ago), the Table of Contents formed itself in my head almost immediately.

As an aside, all of my ebooks on freelance writing, internet marketing and general small business issues are written from first-hand experience. You can find the entire library on (click on “Shop” from the navigation bar that’s on every page).

Following is the Complete Table of Contents




PREFACE: Page 12

Vacillating between a Job and Freelancing: My Story: Page 12

My Professional History: A Brief Overview: Page 12

Why I Took a Full-time Job Even Though I Had a Thriving Freelance Writing Career: Page 12

Downsized Out of a Job: “Full-time Entrepreneurship Forever” Ushered In: Page 13

Hard Work and Perseverance Pays Off: Page 13

PART I: 6 Signs It’s Time to Leave Your Job and Embrace Freelancing Fulltime: Page 14

Sign #1 It's Time to Leave Your Job to Freelance Fulltime: Page 14

Leaving a Job She Truly Hated – Even When She Was the Main Breadwinner of Her Family: Page 15

Are You So Unhappy that You’re Physically Manifesting Symptoms? Page 15

Sign #2 It’s Time to Leave Your Job to Freelance Fulltime: Page 16

No Way Out: Page 16

Sign #3 It’s Time to Leave Your Job to Freelance Fulltime: Page 17

Signs Your Freelance Job IS Your Primary Job but You Just Haven’t Recognized It Yet: Page 18

Embarrassing / Frustrating Situations Caused by Being a Busy Freelancer: Page 18

Sign #4 It’s Time to Leave Your Job to Freelance Fulltime: Page 19

Why You Shouldn’t Count a Client as a “Steady Client” Until They’ve Been with You for at Least Six Months: Page 19

3 Ways to Land Steady Freelance Writing Clients So You Can Leave Your Job That Much Sooner: Page 20

Freelance Writers: Why Your Skill is Worth Thousands of Dollars & How to Capitalize On It: Page 20

Freelance Writers: Tips for Packaging Services to Make Clients Want to "Buy Now": Page 20

How to Effectively Offer Discounts to Gain Steady Clients: Page 22

Sign #5 It’s Time to Leave Your Job to Freelance Fulltime: Page 23

Your Freelance Office: What You Need to be Fully Operational: Page 23

Why I Recommend Twitter for Freelance Writers As Opposed to Facebook (and Other Social Media Sites): Page 24

Why You Shouldn’t Spend a Lot of Time on Social Media Initially: Page 25

Why I Advise Freelancers Not to Ever “Officially” Register Their Freelance Writing Business: Page 25

Sign #6 It’s Time to Leave Your Job to Freelance Fulltime: Page 29

Money’s Tight, Bills Are Due, What I Did: How I Got Through Lean Times as a Freelance Writer: Page 29

About Freelance Writing Rates and How I Set Mine: Page 31

How to Determine How Much Money You’ll Need When You First Start to Freelance Fulltime: 5 Steps: Page 31

What are “Emotional Savings” & Why They’re Important to Making the Leap to Freelancing Fulltime: Page 34

Why Growing Up Poor Can be One of Your Greatest Assets as a Full-time Freelance Writer: Page 35

PART II: How to Make the Leap without a Stash of Cash: Page 36

Get Set Up: Page 36

How to Start a Freelance Writing Career in One Day for $0: Page 36

3 Steps to Take to Start Your Freelance Writing Career -- TODAY: Page 36

PART III: What to Do Before You Quit Your FT Job -- 5 Things Page 40

The Freelance Health Insurance Conundrum: Several Ways to Get It: Page 41

What is COBRA? Page 41

Other Ways to Get Health Insurance When You Freelance Fulltime: Page 41

2 Freelance Organizations To Consult to Find Less Expensive Health Insurance: Page 42

Get More Information on Health Insurance for Freelancers: Page 43

Why You Need Life Insurance – Even if You’re Single with No Children: Page 43

Disability Insurance: Page 43

11 Questions to Ask (and Get Answers To) before You Purchase Disability Insurance: Page 44

PART IV: What to Do After You Quit Your Job: The First Week & Beyond -- 5 Things Page 45

3 Reasons to Track Your Earnings: Page 47

Why Tracking Your Income is Important to Achieving Success as a Full-time Freelancer: Page 48

PART V: The 4 Keys to Achieving Success as a Full-time Freelancer: Page 49

Conclusion: My Brain Dump Is Complete: Page 52


Interact With Me via Social Media about the Info You Read Here: Page 52


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