One of the best parts of being a freelance writer is how many different writing career paths are available to you.

But this leads to a problem a lot of new writers face:

Which writing career path should you choose?

Is there only one path that’s going to work?

Quite simply, no.

Every writer needs to decide on the best writing career path for them. And the ideal path will look different for everyone.

On this page, we’ll look at how to choose a writing career path that suits your individual needs, wants, and goals, and transition from where you are now…

To creating the freedom-filled writing life you deserve!

Why Transition to a Paid Freelance Writing Career?

In our guide on how you can make money as a writer, we explain why freelance writing is such a massive opportunity.

And one of the first things you need to know is that you don’t have to be an award-winning, credentialed, or even experienced writer to make this a lucrative career.

Companies have an ongoing need for the many layers of written materials that drive their businesses, from web pages, to emails, to sales letters.

And those same companies desperately need informed writers to put those pieces together.

After working as a freelance copywriter for over 14 years, I know for a fact that freelance writers are in high demand and typically get paid very well for their services (picture part-time writing work that earns you upwards of $80,000 or more…).

But… there are LOADS more reasons to transition into a freelance writing career other than the income potential. Below, I share the key reasons why I chose to ditch my day job and become a professional writer.

1. Paid Freelance Writing Can Provide the Lifestyle YOU Want

Personally, I wanted a career where I didn’t have to deal with the stress and energy-draining demands that I had in my previous profession.

Something where I was completely in charge of my schedule and how I spent my time…

Where I didn’t have to ask permission from the boss to take a long lunch or leave early for an appointment…

And where I could choose the work I did based on what interested me… and give myself a raise whenever I needed.

If you’ve ever had a job where you feel stuck or overworked, I bet you can relate.

For many freelance writers, the flexibility that a writing career provides is the number one reason they choose this career path. The ability to put their lives first and work second is priceless.

And that’s certainly true for me!

That’s because these days, I work from my home office, where I regularly watch the sun rise over mountains I can see from my window.

And I’ve gotten to be there to watch my kids grow up, from cheering at soccer games and applauding at recitals to patching up bumps and scrapes and having special “date lunches” each month.  

This is the life that fits into my dreams…

But I know other freelance writers who work from their private boats, live as digital nomads while traveling the world, or permanently move to an exotic location.

It doesn’t matter what your version of the writer’s life looks like. The point is, with some effort and focus, you can make it happen by choosing a freelance writing career path.

2. As a Paid Freelance Writer, You Can Decide Your Work Hours

Another benefit to being a freelance writer is the freedom to work as much as you want, and no more.

You can choose to take on as many writing projects and clients as you’d like. But you never have to accept more work than you’re prepared for, and you never have to do more than you feel like doing.

If you want to work part-time, or only work occasionally, that’s fine. It’s pretty easy to find the few clients and projects you’ll need to meet your goals.

But if you aspire to work full-time and make a higher income, that’s also very doable as a freelance writer.

And that’s largely because the demand right now is huge…

In fact, for many copywriters, including myself, one of the biggest moments in our careers is the first day we have to turn down work because we already have too much!

Nearly every copywriter will hit this day sooner or later in their career.

When I first started out, I didn’t believe I’d ever have an upper limit. But eventually I got to the point where I had all the work I wanted to handle!

And because I knew my priorities and how I wanted to spend my time, I happily turned down any contracts that would have over-extended my work hours. Being able to determine my own hours is one of the greatest benefits of being a freelance writer.

3. For Paid Freelance Writers, the Barriers to Entry Are Super Low

You almost couldn’t ask for an easier industry to get started in than freelance writing.

Want to know how I got started? I took one course.

Yes, that’s it. One course.

I signed up for The Accelerated Program for Six-Figure Copywriting by AWAI in 2007. It only took me a couple months to finish the course, but I didn’t even wait to finish before I quit my program management job and launched my freelance business.

No going back to college or university.

No more student loans.

And definitely no need to scrape by and live on instant noodles for years on end as I retrained!

As my freelance career has progressed, of course I’ve taken additional courses and continued to improve my writing skills. But all I needed to get my copywriting career rolling was one course.

And my story is not unique. Most freelance writers working today got a similar start, by taking just a course or two and putting themselves out there. You can’t ask for a lower barrier to entry than that.

What Most People Get Wrong About Changing Their Career

If you’ve ever considered changing your career, you’ve likely come up with a long list of reasons why you can’t do it.

My list looked something like this:

  • I didn’t want to lose more time and money by going back to school to retrain
  • I was afraid of failing at a new career or business
  • I wanted the security that I thought came with a good profession
  • I was afraid of being judged by my friends and family if I made a change
  • I didn’t want to have to “go backwards” financially

If you have a list similar to this, don’t let it stop you.

That’s why Barefoot Writer is here – to help you gain the skills and knowledge necessary to overcome these concerns and make your own transition into a freelance writing career path.

How to Create Your Career Transition Pathway

As I mentioned earlier, a freelance writing career looks different for nearly every writer. That’s one of the reasons freelance writing is such an awesome profession – it’s totally customizable to your needs.

But the fact it’s so adaptable can also be a stumbling block for some of us. With so many options, you might find yourself wondering where you should start…

Fortunately, transitioning from where you are now into a freelance career can be fairly straight-forward, as long as you follow a few basic steps.

Step 1 to Your Career Transition: Determine What Your Goals Are

Before you can effectively decide which type of freelance career path you want to take, you need to have a clear picture of exactly where you want to be once you’ve achieved it.

Clearly visualizing your future has also been shown to improve the chances of achieving your goals. For example, one study found that job seekers who had received training that involved visualizing themselves accomplishing their goals were 45 percent more effective at finding work than those who had not used visualization.

So, it pays to take some time to develop an in-depth image of what you want your life to look like after you transition into a freelance writing career.

Try answering these questions to help sharpen the picture of your future as a writer.

1. What’s My “Big Why” for Getting into Paid Writing?

Why do you want to be a paid writer?

For the freedom? To follow your passion? To have more control over your life?

It’s easy to throw around the idea of becoming a writer. But for many, it remains only an idea that they never take serious action on.

The best way to get motivated and move into action is to dig deep for the reason why you want to write and allow this to fuel your journey to well-paid writing.

2. What Do I Want My Paid Writing Life to Look Like?

Don’t limit yourself on this one. Let your mind wander and imagine every detail of your ideal life.

Will you write part-time? Full-time? Just in the summer?

Where will you write? At home? On a beach? In another country?

And what other parts of your life are top priorities? Things like your favorite hobbies, your kids, or community involvement?

I’ve already talked about how great the flexibility is when you’re a freelance writer. You can prioritize the way you work from day to day. Although, keep in mind this comes with its own responsibilities.

This is why it really helps to get clear on what your priorities are and what you want your writer’s life to look like before you get started.

3. How Much Money Do I Want to Earn Through Paid Writing?

It helps to determine your income goals up front, so you don’t need to take on more or less work than you need.

Are you hoping to replace your full-time income and walk away from your day job?

Do you just need an extra $10K for a big purchase this year?

Or are you trying to build up a bigger nest egg?

Maybe you’re just hoping to raise your standard of living, with an extra dinner out each week, or a newer car…

Whatever your income goal, it’s helpful to consider the ideal number of hours you’d like to commit to work each week, and how much free time you want for hobbies and other types of enjoyment.

This will give you an idea of how much you’ll need to make on a monthly basis to meet your income goals.

Step 2 to Your Career Transition: Decide Which Freelance Writing Career Path Best Fits Your Goals

Now that you’ve figured out your personal goals, let’s take a closer look at the different freelance writing career paths you can take.

Path #1: Transition from a Full-Time Job to Freelance Writing

If you want to leave your current job, you can go about it in a multitude of ways.

We’ve had Barefoot Writers back out of their day jobs by secretly building up their writing careers in the off-hours. Then they quietly give notice and walk away, fists in the air.

Krista Jones
Krista Jones

We’ve had other writers tell their employers up front that they want to transition to full-time writing.

For Krista Jones, telling her boss about her writing dreams made it possible to cut down to fewer and fewer hours each week at her day job until she was officially ready for her transition.

Wendy Ripmeester
Wendy Ripmeester

Wendy Ripmeester did something similar and ended up getting an entirely new position through her existing employer — including doing the writing work she loved, but still in a salaried position.

You know your situation best, so it’s up to you to determine who you tell when you decide to transition out of a full-time job, and how you’re going to do it.

Path #2: Become a Part-Time Paid Freelance Writer

Regardless of your reason for wanting to write part-time, few paid and work-at-home opportunities fit the bill as well as Barefoot Writing.

Because you can follow your own schedule, only take on work that you want, and do your writing from anywhere, it’s one of the most versatile money-making ventures out there.

Part-time writing is great for those who want to keep their day jobs, for those who spend the bulk of their time caring for kids or elderly relatives, and for those who have other interests that occupy their time.

Path #3: You Could Supplement Retirement with Paid Freelance Writing

Most retirees have plenty of spunk in their step and a ton of energy left to share with the world. Many would love to have extra money coming in, but they want to have fun doing it — not to mention do it on their own time, on their own terms.

Enter freelance writing…

We’ve seen loads of successful retirees supplement their pensions through writing, and many have an arsenal of professional experience and wisdom to leverage as they move forward.

Path #4: Become a Seasonal or “Occasional” Freelance Writer

What do you do if you like the idea of writing and earning extra money, but you enjoy your current job and don’t want to leave it? Great news! You don’t have to leave your current job or career to become a freelance writer.

Many of our Barefoot Writer members are teachers, or work in the educational field and have summers off, so they do most of their writing in the summer.

Some are contractors and do writing between job assignments.

Others just like to work a little and then take a break for several months. Or they work here and there while they travel the world.

Freelance writing is something you can do in addition to whatever you’re already doing. You don’t have to go “all in” with freelance work – you can easily fit it in around your other passions in life.

Step 3 to Your Career Transition: Make an Exit Plan

Once you’ve determined the freelance writing career path you want to pursue – it’s time to start planning for your transition.

1. Map Out Your Action Steps

Determine what steps you’ll need to take to get from where you are now to where you want to be.

Some of those steps might be things like:

  • Get training and develop the skills you’ll need for your new career
  • Decide if you’re going to leave your current job completely, or continue to work at it part-time.
  • Determine the practical steps needed to transition out of, or reduce your hours in, your current career.
  • Write out your goals and share them with people in your life who will support and encourage you.

2. Set a Realistic Time Frame

It’s also important to make a schedule for your career change to help keep you on track.

First off, when do you want the transition to be complete?

Set a date now for when you want to be fully transitioned out of your current career into the one you want.

Based on that, start going backwards and see when each of your action steps needs to be finished.

Give yourself a realistic time block to complete each one, with a clear deadline.

And make sure you share your plan with as many people as possible. It can be tempting to change our plans if no one else is involved. But if others are holding us accountable, we’re more likely to keep our word and take action.

Step 4 to Your Career Transition: Build Your Support System

We all get stuck and need help at times, and knowing people you can reach out to for support along the way can make all the difference.

Whenever I’ve hit a roadblock in my writing career, fellow writers in the Barefoot Writer community have been there to help me find the resources I need to move forward, share their experiences, or simply provide some encouragement.

I’ve been able to go much faster and farther in my freelance writing career than I could have gone alone.

I know I couldn’t have gotten through my career transition without the benefit of a good support system from the start, and that’s what the Barefoot Writer world was for me.

That’s why it’s definitely where I suggest you should start as you plan your freelance writing career path.

For more suggestions on mapping out your career transition, AWAI has an excellent free webinar called Creating Your Own Personal Roadmap to a Well-Paid Writing Career that you can access on their website, or watch here:

When Will You Be Ready to Call Yourself A “Real Writer”?

One of the questions we’re asked most often here at Barefoot Writer is: “How will I know when I’m ready?”

And the truth is… there’s no hard and fast answer.

Some people think it happens when you get your website launched… yet there are working, six-figure writers with no web presence.

Some people think it happens when you land your first client… but we have several Barefoot Writers who earn money through their own money-making websites and never do client work.

And then some people think it’s official when you get your first paycheck. That’s absolutely cause for celebration, but you don’t magically become a “real writer” once you cash it.

It’s not like graduating college, where you’re handed a degree that signals to business firms that you’re minted for hire.

Nor is it like licensing programs, where you log a few hundred hours of competent work to earn a title.

Honestly, it’s a lot easier than all that.

You see, Barefoot Writing is a lot more like a journey than a race with a finish line.

As soon as you make the commitment to be a paid writer and learn persuasive skills, and you set your goal statement and lay out your career transition pathway… you’re a writer!

A new writer, but a writer nonetheless.

Because making up your mind to do this, and then following through… quite honestly, that’s the hardest part.

The rest of it will come in time.

Real writers constantly learn, improve, test, try, fail, succeed, and wake up to do it all over again the next day.

Six-figure writers will tell you they’re still learning as they go…

Seven-figure writers will tell you they don’t know everything yet…

And even the multimillionaire writers associated with our Barefoot Writer Club regularly share stories about where they recently messed up and what they learned.

That said…

If you’re keen to have at least a few benchmarks to hold yourself to, we recommend the following:

  1. Set up a professional LinkedIn profile.
  2. Set up your own professional writer’s website. Here’s how you can do it in four days.
  3. Take The AWAI Method for Becoming a Skilled, In-Demand Copywriter to learn all the copywriting fundamentals you’ll need to know to write any kind of project – from sales copywriting to informative content writing.
  4. Attend an event for paid writers like you — because standing among your own and building a support network face-to-face will help you feel both validated and accepted. We recommend AWAI’s FastTrack to Copywriting Success Bootcamp and Job Fair — it’s the premier event for persuasive writers, and marketers are there every year looking to hire new writers for paying projects.

Regardless of when you call yourself a writer out loud and proud, whether you’re still biding your time or have had the title proudly displayed on your desk for years…

Keep doing the little things that ensure you’ll be a great writer: Write every day, learn something new every day, and connect with someone in the writing world every day.

Six Things You Should NOT Do While Transitioning to a Freelance Writing Career

Freelance writing is the answer to a lot of challenges different people face.

As we’ve discussed, you can make, or replace, a very good income with a freelance writing career. Or you make some extra money writing in your spare time to fill in the gaps.

The flexible schedule can allow you to create real work-life balance and regain control over your life and how you spend your time.

All these benefits of a freelance writing career path can solve a lot of problems for a lot of people.

And it has solved those problems — permanently — for hundreds of our members. Click here to read a few Barefoot Writer success stories.

But over the years, as we’ve seen our success numbers grow, we’ve also seen a few people try and then not succeed in their writing goals.

So, to make your career transition to successful freelance writing as quick and easy as possible, here are a few lessons on what not to do when you’re first starting out.

1. Don’t Think You’ll Be an Overnight Success

Barefoot Writing is not a quick-fix, check-these-boxes-and-you’re-in kind of thing.

You need to learn about persuasive writing techniques, and then you need to do the work — albeit fun, interesting, well-paid work — to hone your craft and connect with people willing to pay you.

Now, you absolutely can start making a lot of money in a very short time — we’ve seen it done repeatedly.

But that takes us to the next item on our list of what not to do…

2. Don’t Expect Your Journey to Look Like Anyone Else’s

The truly fantastic thing about Barefoot Writing is that you create your own career path. You work as much or as little as you want, on the projects you choose, in the niche you enjoy.

Which means you write your own success story.

You also get to go at your own pace and work around whatever constraints you’re dealing with. That means some writers may achieve their goals faster than you… and others will be slower.

Just like anything in life, don’t compare yourself with others. Focus on your Big Why — your reason for pursuing paid writing — and go at the pace that’s right for you. That’s how you’ll cultivate income-earning, long-term success.

3. Don’t Put Yourself in a Desperate Situation

Yes, you can make great money as a Barefoot Writer, and yes, you can do it relatively quickly.

But if you’re in a situation where you need to make rent by next Tuesday and you’re brand new to writing, you’re going to be disappointed.

That’s not to say you can’t earn great money in a short amount of time. Once you have contacts and you’ve established yourself in your field as a trustworthy, credible writer, it becomes easier to find new clients or get repeat work with existing clients fairly quickly.

So yes, you can get to that point. It just takes a little time.

4. Don’t Think You Can Skip Doing the Work

Most Barefoot Writers have a natural love of writing. Often, they excelled in high school English. But what you learned in high school English is not what you need to know as a professional writer.

In fact, the writing we do is very different from what’s taught in school. So, it’s important to sit down and take in all the tried-and-true lessons we share with our Barefoot Writer members so you can hit the ground running.

5. Don’t Think You Have to Be a Natural Writer

Even though most of our members have a history of doing well at writing, that’s not the case for all of them. Plenty of our writers never dreamed of writing for a living. Some of them used to consider themselves downright bad at writing – like Barefoot Writer Sean McCool, who flunked high school English and yet today makes $200K+ as a paid writer!

It’s because the persuasive writing techniques we use as professionals can all be learned (and they’re very different from what you learned in grade school). So your history as a writer — or lack thereof — doesn’t matter a bit. You can learn everything you need to know.

When you join the Barefoot Writer Club, we walk you through the fundamentals of where to start and what to know about paid writing to get you up to speed.

6. Don’t Let Fears, Mistakes, or Lack of Knowledge Keep You from Your Paid Writing Goals

Look, we all get cold feet at some point when we take on a new challenge. And we all make mistakes as we go forward in new ventures.

That’s going to happen to you at some point — we’ve all been there! But don’t sweat it. The best things in life are worth working toward, and if it means you have to get up and try again a few different times, you’ll be armed with new lessons-learned every time you put yourself back in the ring.

Also, it’s common in this business to feel like you just don’t know enough. Like I mentioned before, even our most successful, six-figure, big-name experts say there’s still plenty they need to learn!

The best way to deal with that is, once you start studying persuasive writing, to remind yourself that you know more than your client. And that should be enough to get you going. Any questions that come up along the way, you can find an answer for by reaching out to fellow Barefoot Writer members.

Thanks to our members-only Facebook page, you’ll have quick and easy access to veteran writers and up-and-comers, and the level of generosity on that page is enormous.

Remember, everyone has been in your shoes and knows what it’s like to start at the beginning. And as a Barefoot Writer Club member, you get 24/7 access to our private Facebook group, meaning you can ask questions, reach out for support, or connect with other writers whenever you need.

What Are You Waiting For? Go For It!

Here’s what all of this means:

Freelance writing can bring you the freedom-filled lifestyle you’ve always dreamed of.

And it can happen faster and more easily than you could ever imagine. Not overnight — because it involves learning and focus — but you could be making extra money, double your income, or earn more than you ever thought possible in just a few months to a few years.

Just start taking the steps I’ve outlined in this article and you’ll be well on your way to transitioning into your ideal version of the writer’s life. Learn more here about how to become a Barefoot Writer.