Quit Your Job to Freelance? A Teacher’s 5 Sink-or-Swim Moves

Evan Jensen

Quit Your Job to Freelance? Here's the Plan. Makealivingwriting.com.If you’ve been thinking about ways to quit your job and freelance full time, you’re not alone.

There’s a lot of unknowns right now. Wouldn’t it be nice to have a little more control over your income, your schedule, and your life?

When you’re a freelancer, you’re not at the mercy of a global pandemic, a hard-to-work-with manager, or the day-to-day drudgery of work you hate.

You make the rules. You’re the boss. Your schedule, your workload, and your income depends on you.

If you’re thinking about this, chances are pretty good you’ve got questions:

Do you have what it takes? Can you get freelance writing clients? Will you be able to pay your bills and do meaningful work?

The answer: Yes, you can. I quit my job as a mid-career teacher to be a freelancer. But instead of taking the side-hustle-for-years route, I decided to go with the sink-or-swim approach.

Ready to quit your job to be a freelance writer? Here’s what you need to know:

A former teacher’s sink-or-swim plan for freelance writing

Cevia Yellin: Quit Your Job

Cevia Yellin

A few years ago I had a shocking revelation: Freelance writing is a real career path. And I wanted it…bad.

And then I read this post by Carol Tice: The 3 Types of People Who Fail At Freelance Writing, and my heart sank.

Crap. I knew just from the title this post was about ME.

Here’s the short version: You’re going to fail at freelance writing if you lack self-discipline, you’re emotionally fragile, and you’re not fluent.

Does the voice inside your head sound anything like this? Darn, this is going to be hard. I’m not just one of these types of people…I’m all three.

That’s exactly what I thought seven months after I quit my job as a university English language instructor.

Are you ready to quit your job?

It’s not an easy decision at all, in a lot of cases. There’s the steady paycheck, regular work hours, and familiar colleagues. And if you’ve been pursuing one specific career path for years, it can be even harder.

But if full-time freelancing is in your future, there’s bound to be a tipping point.

Here’s how it happened to me:

Even though I was a capable and competent teacher, and accomplished in my field, after 14 years, it was clearly over.

My work environment was toxic and my doctor had repeatedly encouraged me to leave. I was at high risk for a serious hereditary disease and could not afford the toll it was taking on my health.

So, I had to make this work. I needed an income. My health insurance premiums were due. And I needed a flexible schedule so I could attend to my health and get back East to visit my father who was terminally ill.

So even though I didn’t fit the bill of a successful freelance writer, I had to make it work.

If you’ve reached that tipping point one way or another, here’s what you need to know to make this work:

1. Set process goals

Setting goals is the first step in gaining the discipline a lot of newbie freelance writer’s lack. Self-discipline is crucial to your success as a freelancer. Make a list of short and/or long-term process goals (things you can actually do and control).

  • What needs to get done today, this week, this month?
  • What do you want (or need) to achieve in the next six months or year?
  • Over the course of the next two to five years?
  • How many hours a day, week, month, can you realistically commit to working on your goals?

2. Establish a routine

If you’re used to working a traditional “day job,” the lack of a routine can really throw you off kilter when you jump into freelance writing. It can mess with your head, even your sense of identity.

Note: I was a self-confessed work-a-holic in my former career. Put in very long hours. And here, trying to make a go of freelancing, I was floundering like a fish out of water.

If you’re going for the sink-or-swim approach to freelancing, you’ve got to be prepared for the learning curve, and the fact that you won’t have a boss telling you what to do. If you don’t plan for this, you’ll be spinning your wheels wasting time, when you could be making money as a freelancer.

Believe me, I know what it’s like. I vacillated between spending hours and hours immersed in reading about freelancing to avoiding it all together.  And I was also working side jobs, making ends meet (barely) teaching yoga and cooking, cleaning, gardening, tutoring…you name it!

The remedy to this problem…routine

After you set freelance writing goals, create a routine and a plan for how you will spend your time:

Decide what you can and can’t do during those hours and stick to it. Those hours are for working on your freelance business – researching, writing, marketing, editing, marketing, and more marketing.

You’re in control of your schedule now. But you can’t spend all day every day on doctor’s appointments, cleaning, doing the laundry, scrubbing the bathroom floor, or having coffee with your neighbor. 

Your work hours are for freelance writing and marketing (whip cracking!). Got it?

3. Find a conducive workspace

Where do you FEEL productive? Is there a dedicated space in your home where you can work uninterrupted? A spare room, corner, living room, or office?

Something that helped me a lot initially was working outside of the house. Coffee shop. Library. The local community college. My favorite bagel shop. Or maybe you could find a co-working space like The Riverter, a favorite for Carol Tice.

Find a place to work that fosters creativity and productivity. If you don’t, it can mess with your mojo big time.

  • If you can afford it, consider renting office space. I earned more from freelance writing the month I signed my lease than I had in any single month prior, breaking $3,000 for the first time. I even met a new client in the communal kitchen! This fellow tenant, a holistic doctor, needed help with his blog. Bonus…he also hired me as a speech writing/public-speaking consultant. Double win!

4. Strengthen your emotional side

Do you take rejection personally? Are you devastated when your queries go unanswered or worse, are outright rejected? Are you emotionally fragile and sensitive?

That basically describes me when I quit my job to be a full-time freelance writer. And it’s why the first two years were really hard.

If you’re nodding your head, rest assured you can strengthen your emotional side. Here’s how:

  • Learn that getting freelance writing clients is largely a “numbers game.” This will help take the sting out of rejection.
  • Know that the “odds” can help you detach a bit from feeling personally rejected. Is it hard for you to recover when you don’t win the lottery? See, not so hard to handle your pitch being denied after all!
  • And if you can’t seem to get past those feelings of total failure, it may be a sign of a deeper distress or trauma that needs the attention of a counselor or therapist.

If you’re an introvert or highly sensitive (I’m both), you can learn not to take the losses in freelance writing personally. Be a bit detached from the work. Do your best and move on. 

5. Learn the language of freelance writing

My take on fluency, as a newbie in this biz, has more to do with the language of freelancing, than English language fluency. (If you’re an ESL writer trying to freelance for U.S. clients, read this.)

What’s your freelance writing fluency?

Like any profession, freelance writing has its own unique vocabulary. And just like learning a new language or traveling to a foreign country, it takes time to understand the lingo, to get the lay of the land, to figure out how things are done. 

It’s very similar to the stage in second language acquisition called the silent period – when people new to a language are absorbing it, but not yet producing it. Emerging from this stage can take as long as a few months up to a year or more.

My advice to speed up the process

Read this blog. I read countless posts, listened to podcasts, and consumed materials in the Freelance Writers Den. And I wrote down key words and phrases to study. Little by little, I started to incorporate those things into my pitches and conversations with prospects and clients.

Pretty soon, I was charging $250 per article vs. $60 for the same kind of work I was doing months earlier when I wasn’t as fluent.

Jump into freelance writing…you can do this

You might be feeling like a freelance writing failure – stalled by fear-inspired procrastination, lost in the details, or like you’ve landed in a place where you don’t speak the language. Maybe even all three. But, if you really want this – you can make it happen!

Ready to quit your job to freelance full time? Let’s discuss in the comments below.

Cevia Yellin is a freelance writer in the Freelance Writer’s Den 2X Income Accelerator. She believes in going after your wildest dreams, even when the odds are against you.

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  1. Todd Davis

    I’m ready, my pocket book is not though.

    • Carol Tice

      It’s interesting you think of it that way, Todd — many of us who are longtime freelance writers didn’t get to save up and make a planned leap into freelancing, as we were laid off or (in my case) fired. Into the pool! It’s amazing how motivating it can be when you don’t have a financial net.

      I’d expect we’ll see droves of additional people in this boat in the coming year.

  2. Jeff L.

    When it comes to the self-discipline which anybody will need to write freelance, I am skeptical that someone could **inherently** or genetically lack self-discipline. I believe that one can train oneself to become disciplined. If one truly resolves, or vows, to train oneself, that person can find a way to achieve discipline, I am sure.

    I can imagine, for example, that one could begin training to achieve self-discipline by starting with small steps or, say, by working over short sessions, each session a little longer than the previous one. And then one might gradually increase the length of active sessions. After one has learned to sustain activity over short times and over longer and longer times, eventually one would be able to keep active automatically and to stay active, for as long as desired or needed.

    And one would then be a disciplined writer or a disciplined student or a disciplined reader or a disciplined something. One would no longer lack self-discipline.

    • Cevia

      I agree that while we may have tendencies towards a certain behavior, with discipline and the right mindset, we have the capacity to move beyond them. Nice point, Jeff.

  3. Jim McCarthy

    Great tips, Cevia!
    I think you covered all the bases very nicely. And, you’re living proof that they work, too.
    Thanks 🙂

  4. Lori

    Great article. I always love your posts. Looking forward to more. 🙂

  5. Precious Marho

    I totally agree.

    Lacking clear goals and having an unstructured routine is damaging to a newbie freelancer. I should know.

    Nice post, Cevia!

    • Cevia

      I hear you, Marho. The good news is that we can move beyond those initial habits. Keep at it!

  6. Chiemeka

    This article have helped me to an extent. I am grateful. Thanks.

  7. Jared James

    I think quitting the job upfront its not the perfect option, running both things parallel first its kinda way I like…

    • Cevia

      I agree, Jared. It’s definitely not for everyone. Freelancing as a side gig while holding onto a day job is more feasible for a lot of people. Just wasn’t possible in my case and others like me.

  8. Cevia

    Thanks Jim! I appreciate the feedback.

  9. Ana

    Thank you for this post. I have yet not started with freelance writing. I have realized that discipline and how to tackle anxiety its crucial to not only getting started but achieving long term goals. Like right now I was procrastinating because in my mind I was thinking I could not start writing yet but keep researching and reading… However, practice makes the master and if I don’t start writing there is no way I can improve. Again, thank you for this article Cevia!

    • Cevia

      You’re welcome, Ana! Just remember that you’re not alone. So many of us are held back for the same reasons. But, you’re right! Practice makes perfect, or at least…better! So get writing.

  10. Sharon Waters

    Cevia, thanks for this post. I quit my stable job to work full time on a presidential campaign, which ended shortly after I started. Now I am pursuing freelance writing/editing as my career. I had an intermediary step but can relate to your post. Establishing a routine, which involves setting goals, is my challenge but your post has helpful advice.

  11. Simeon

    According to me, running your freelance writing career as a side hustle is a great first step. During this period you can learn the basic specifics, build the routine and self-discipline. Of course, this is not always the case. Maybe the learning process could be much faster if you are pushed by external circumstances to quit your jor and start freelancing 🙂


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