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How to Actually Quit Your Job to Freelance

Freelancing often starts as a side hustle.

And if we’re lucky (and ambitious, and hardworking and about a million other things…), we can transition from a 9-to-5 job to a full-time freelance career when the time is right.

But few people actually talk about how to make the transition as smooth as possible. So Krystal is here today to share how she left work behind smoothly – without burning any bridges.

I would love to tell you that once you decide to become a full-time freelancer, you can just yell “See ya!” at your boss, dramatically throw papers in the air and run out the door.

Unfortunately, that is not how the transition to full-time freelancing works.

It’s a hard decision, and there is a lot to consider before you leave. Today, I want to share the six steps I took to tell my boss, “I quit.”

A Little About Me

I’m in my third year as a high school history teacher. I’ve actually had a great teaching career. I excel at my job, and I love my students. However, I’ve been plagued with what I have dubbed my “quarter-life crisis.”

My job is stressful.

I constantly feel like I am too young to have so much responsibility. I have to do things I find morally questionable (read: standardized testing). I’ve never had the freedom to just do whatever I want.

I have always been a writer.

From poetry to fiction to published academic papers, I love writing. I just always thought it was a hobby. When I took Gina’s course, I realized this was my answer.

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I could have the freedom to do what I wanted. I could travel, because I can work anywhere I have an internet connection. I can volunteer more and lobby for education reform. I can work in bed when my autoimmune disease kicks me down.

The Decision to Quit

I knew about three months into teaching that I would not teach forever.

This past December, I took Gina’s course, built my website and started pitching. It was hard. I didn’t get paid for anything till March. I cycled through horrible depression and excitement.

Becoming a writer while teaching full-time is the hardest thing I have ever done.”

1. Take the First Step

The first step sounds easy: decide to quit.

But this was possibly the most difficult step for me. I worried writing professionally was a pipe dream. I worried people would think I was a failure. I worried about giving up my stable income.

I finally had to say, “After this school year, I will not return to the classroom.” And then I closed my eyes and jumped.

How to Quit Your Job When You're Ready to Freelance2. Talk to Your Support System

If you have a significant other, the conversations you have with this person about freelancing will be incessant and uncomfortable. My fiance and I had to really flesh out our finances, his career goals and how my work-from-home job would change the dynamic of our relationship.

My poor mother endured a play-by-play of every lesson of the e-course, every pitch I sent, every new tidbit I learned.

I had to be honest with my friends that I was going to likely be a bad friend for a few months. I needed my free time to write, but they understood.


Your support system needs to understand that you have a plan, and you aren’t jumping in blind.”

3. Set Realistic Financial Goals

Once you decide to quit your job to freelance, you need to set financial goals before you pick a “last day.”

These financial goals should not rely solely on your writing career. It’s highly possible you will not make enough to support yourself and your family until you go full-time.

How much money do you need to live? How many months of savings should you have?

For my fiance and me, we decided that since we can easily live on his salary, we would just save up about three months of rent by the time I received my last paycheck. Your financial cushion may be different.

After you set your realistic goals, work toward them. That may mean your business can wait on those fancy business cards. It may mean you say goodbye to cable.

4. Tell Your Boss and Your Coworkers

For some people, this may be an easy step. For me, this was difficult.

My social studies department is full of people I am honored to call my friends. My principal is my role model and mentor.

The first person I told is the teacher who also happens to be one of my closest friends.

Our relationship extends far outside of work. After my first successful guest post on a major site, I told the administrator over my department, who is also a close friend. I told my department chair and planning buddy over lunch.

My boss had once asked me to give her plenty of notice if I ever decided to leave.

She wants to find an adequate replacement for me. So, the first Monday of February, I walked into her office full of fear. She was so supportive of me! Now that the cat was out of the bag, I felt so much lighter.

Prioritize who you need to tell first.

Make sure whoever you tell won’t tell your boss before you do. Make sure the people you care most about hear the news from your mouth and not through the grapevine.

5. Maintain a Good Relationship With Work

Don’t stop caring!

I’m still teaching my heart out. I still fret about testing scores, because I want my kids to do well. I’m still developing new, awesome lessons.

If you stop caring and start slacking too much, you’re just hurting yourself.”

You may need letters of reference from your supervisors one day. You may decide to return to the workplace sometime in the future.

You may also be losing potential clients. Many of my coworkers either run their own side hustle or have a family member who owns a business. These are potential clients for your freelance business! They know you and trust you. Keep it that way!

6. Know Your Limits

When I gave up all of my social life to focus on writing and pitching, I nearly ruined my writing and teaching career.

I was miserable. I was exhausted.

Once I had my main paying job, my fiance told me to slow down. He suggested I not take on any new jobs for a while.

I told my client that I could not take on additional workload until after my standardized test in May. Then I decided to put (most) of my pitching and my personal blog on hold until after my last day.

I am now making a point to still live my life and have fun.”

I’m constantly readjusting my priorities, but I’m a lot happier. I’m not working as far ahead as I would like, but that will come. Soon, I’ll have all the time in the world.

So, don’t cancel your girls’ weekend.

Don’t feel guilty if you didn’t do any writing this Saturday.

It’s okay if you didn’t pitch anyone this week.

Know your limits, because once you reach your last day of work, you will have the time to build your career the way you want.

Don’t Give Up

It’s really possible! Once you decide to quit and you do it right, you will be well on your way to the life you always wanted.

Ready to Kickstart YOUR
Freelance Writing Biz?
Grab two of our most popular workSheets and get started TODAY!

Have you decided to take the leap from a full-time job to a freelancing career? What preparations did you make to help you?

krystal craiker writerKrystal Craiker is a freelance writer-for-hire with a background in anthropology and education. She has been writing in various genres since the time she could construct sentences and now focuses on blogging and B2C writing. Krystal lives in Texas with her fiance, two dogs, and eight pet rats. Check out her writing portfolio and website, and follow her on Twitter @kcraikerwriter!

Gina Horkey

Gina Horkey


Gina Horkey is a married, millennial mama from Minnesota. Additionally, she’s the founder of Horkey HandBook and loves helping others find or become a kickass virtual assistant. Gina’s background includes making a living as a professional writer, an online business marketing consultant and a decade of experience in the financial services industry.

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