A Quick Guide to Knowing When to Quit Your Job to Start Freelance Writing
By: Anna Meyer
Tags: Careers, Freelancing, Freelance Writing, Entrepreneurship, Career Advice

A Quick Guide to Knowing When to Quit Your Job to Start Freelance Writing Anna Meyer Sep 22, 2020·4 min read

Photo by Maxwell Ridgeway on Unsplash

It’s a common question asked among newbie writers:

“Am I ready to quit my current job to freelance full-time?”

It’s a simple yes-or-no question. But unfortunately, like many elements of freelancing, only you are capable of knowing the right answer to that question.

I can’t tell you whether or not you’re in the best place to quit. I don’t know your job situation, your income, your savings, your monthly spendings, your needs at home, or your goals as a freelancer.

But I can offer a few suggestions. You probably won’t ever be 100-percent ready, but even the smallest clues can help you make a wise decision.

Here are a few things to consider:

1. Be confident

In the early stages, you will be tested on why you’re doing all this.

Often.

Finding a support system is vital to your success, but knowing what to say when people ask you questions is equally important.

“What have you been up to lately?” “It must be wonderful to be at home all the time.” “So you’re a blogger?”

How do you plan to answer these?

Gather up your mental courage and hold your chin up high. The success you’re working toward (and the remaining tips in this post) depends on it.

2. Have a specific plan

I didn’t do so well on this one. I had general ideas, but I didn’t back them up with action or consistency.

Obviously, you’ll be writing. But during what times of the day? How many days of the week? Are you going to reduce your hours to part-time as a way of easing out of your current job, or are you going to quit cold-turkey? What will your daily routine look like? Are you going to respond to emails first thing in the morning or wait until the afternoon?

Don’t just have a plan. Be specific.

3. Have a backup plan

Nobody likes having these conversations, but you’ll be minimizing the risk by addressing the ugly now. What would qualify as the worst-case scenario for you?

Running out of money is a common concern.

What are you going to do if this happens to you?

Think long and hard about your backup plan — the more specific, the better. You’ll be saving yourself loads of time, stress, and pressure later on.

4. Give yourself time

Nowadays, I can get a post on Medium written and proofread lickety-split compared to when I first started. (My first post took over two weeks. I’m not kidding.)

The learning curve is real when you’re starting as a freelance writer. And I grossly underestimated how long it would take to find my groove.

I also wanted to live up to all the hype of freelancing: flexible scheduling, working a few hours a day, things like that. Having these as goals to work toward isn’t wrong, but I became blind to the time I would spend

building my website

setting up social media profiles

the pitching process

creating samples

finding a morning routine that works for me

And more. A lot more.

Being slow is not a bad thing. But being unrealistic with your speed as a beginner will hurt you (and your business) in the long run.

5. Take calculated risks

A calculated risk generally means “a risk taken after careful evaluation of the probable outcome.”

Risk-taking is an inevitable part of freelancing, especially in the beginning. But that doesn’t mean you have to “wing it” every time. In many cases, you can study your options and evaluate your outcomes in advance.

If you’re thinking about purchasing an online course, what do you do? You might look at payment options (if available), read some reviews, or wait a while to prevent impulse-buying. These are all excellent ways of increasing your chances of making a worthwhile investment.

Risks are scary, but they don’t always have to be if you do your homework.

6. Be prepared to change

This was the biggest surprise for me to deal with after I quit. It also showed up in very subtle ways:

Handling rejection

How I felt when my work was rewritten to the point where it didn’t sound like me anymore

Sticking to a schedule

Taking a weekend off without feeling guilty

Balancing work life and home life…at home

For me, being a freelance writer hasn’t been easy. But I’ve grown as a business owner and as a person. I’ve learned to trust my gut, even if it means I’m going against what others suggest. I’ve learned to take ownership of my mistakes. I’ve improved in speaking up rather than shying away when I notice an opportunity for improvement.

But more than anything, I feel a real sense of purpose and meaning, not just within my career, but in my life. Despite all the drawbacks and twists in the road, it feels pretty effing fantastic.

Photo by Brooke Cagle on Unsplash

Wrap-up

As stated before, only you can answer the question posed in the intro: “Am I ready to quit my current job to freelance full-time?”

But if you have a confident response to these tips, you’re well on your way to saying “yes.”

With planning and sincere commitment backed by consistent action, you can make quitting your current job the best part of your career.