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 many 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 needs, and transition from where you are now to creating the writing life you want.

Why Transition to a Paid Freelance Writing Career?

Ever feel like your dreams are bigger than what your income currently allows?

Or are you just bored with your job, looking for something more fulfilling, and aching for more freedom?

Paid freelance writing through the Barefoot Writer Club can satisfy those needs.

Yet one of the biggest questions on most would-be writers’ minds is “How do I get from where I am now to where I want to be?”

It’s different from wondering about how to get started as a paid freelance writer.

And it’s separate from just getting paid for your writing.

Really, it’s a lot like moving to a new house in the same town…

You’ll still have the same connections and friends…

But you’re ready to upgrade your neighborhood.

You’ve done your homework, so you know the new neighborhood is right for you. (From the new writer’s standpoint, this means you’ve read up on how to get started as a writer, you’re interested in a few of the different writing jobs for beginners, and you know what it takes to get paid and you have confidence you really can make money as a writer.)

Still, even when you know where you want to move, you’ve got to pick out the right house, redirect services, and let everyone know your new address.

Here’s what that looks like when your “move” is over to the neighborhood of paid freelance writer…

How to create your career transition pathway

If there’s one concept we really want to hammer home, it’s that the Barefoot Writing dream looks different for everyone:

  • Maybe you’re just looking to pocket some extra spending money. You could use it to fund a few extra vacations or upgrade your flight and hotel. You plan to write on the weekends every now and then.
  • Maybe you’re looking to bump up your income just enough to send your kids to private school or to college without debt. You’re committed to writing in your spare time — perhaps an hour in the evenings and a little on the weekend.
  • Maybe you want to purchase a new car or a boat or an RV this year, but you’d rather not take out a huge loan to do it.
  • Maybe you work part-time hours at a job you love, and you’d like extra income to fill in the gaps.
  • Maybe you have a full-time job you love, but you have summers off, or you do contract work and you want a way to fill your time — and wallet — when you’re not working.
  • Maybe you can’t wait to leave your day job, and you want to leave it far, far behind and replace it with your writing income.
  • Maybe you’re already retired and enjoying your golden years, but you want something fun to do to keep yourself busy and bump up your cash flow.
  • Maybe you can’t work in a traditional workplace because you have small children at home, or you’re a caretaker, or you have a disability, and you want something to do with your extra time that also helps pay the bills.
  • Maybe you want to travel the world, but you need a way to pay your expenses as you trot around the globe.

In all the situations above, paid writing is the answer.

But as far as what your actual writing career path looks like… it’s up to you. Start by asking yourself three questions:

  1. What’s my Big Why for getting into paid writing?

Why do you want to be a paid writer? For the freedom? For fun? To follow your passion? To have more control over your life?

  1. What do I want my paid writing life to look like?

Will you write part-time? full-time? just in the summer?

  1. How much money do I want to earn through paid writing?

Are you hoping to replace your full-time income and walk away from your day job? Do you just need an extra $10K this year? Are you trying to build up a nest egg?

Answering these three questions helps you figure out how writing fits into your life goals.

And that’s what helps you map out your career transition pathway. Because the first step is to clarify where you’re going and the role you want writing to play.

Then, you figure out how you’ll get there.

That starts with learning about the types of paid writing projects out there. For example, some projects make more money than others but take longer to get established in, some are quick and easy but require the right instruction, and some can be launched and profitable and then put on hold for a period of time.

Here are a few different paths you can take to transition into a writing career…

Career Path #1: Transition from a full-time job to paid freelance writing

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

But really, it starts with your comfort level when it comes to communicating what you’re doing.

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.

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 till she was officially ready for her transition.

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 whom you tell when you decide to transition out of a full-time job. Sometimes telling your boss and coworkers can lead to future freelance writing jobs, depending on the nature of your current work. Someone you work with now could be a future client when you venture out on your own.

In other words, you can tell nobody… a few close coworkers… or everybody!

At the very least, we recommend setting a “goal date” for when you plan to leave your job.

We also recommend setting up your support system — whether that means friends and family members in your home circle or connecting to other Barefoot Writer Club members.

And while you’re transitioning away from your day job, it’s a good idea to get yourself set up online with a LinkedIn profile or a professional writer’s website, if you’re ready for that step.

Career Path #2: Become a part-time paid freelance writer

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

Because you can follow your own schedule, take on only work 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.

Career Path #3: 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 paid 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.

Career Path #4: Become a seasonal or “occasional” paid freelance writer

Many of our Barefoot Writer members are teachers, or they work in the educational field and have summers off.

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.

When you’ll 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.

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, as far as we’re concerned!

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.

See, we can’t say you’re not a writer until… because you may have been doing heaps of writing in preparation before you hit any benchmarks we can dream up.

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 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.

That’s because 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.

Writing is a pathway that changes as you go, but if you stay on it, as long as you keep trying and putting yourself out there till you succeed in paid writing…

Then you — at least in our book — can honestly call yourself a writer!

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 valid 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 writing career

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

  • Maybe you’ve hit an income ceiling at your current job and you don’t like the prospect of never earning more… There’s no income ceiling when you’re a paid writer.
  • Maybe you’re frustrated by never having enough time to spend with your kids or partner… The flexible schedule you have as a writer will solve that.
  • Or maybe you’re sick of having to ask a boss’s permission to take time off for a vacation, or even to leave the office early for a dentist appointment! As a writer, you’re the boss.
  • Could be that you love your current job, but you’d like some extra spending money. Because you can get paid to write on weekends and in your spare time, writing solves the problem.
  • Or perhaps you’d like to move across the country… or across the world! As a paid freelance writer, you can live anywhere you please — all you need is access to a computer and a stable internet connection.
  • Maybe you have a disability and can’t work in a traditional office. Paid writing means you can work from home.
  • Or maybe you want to work from home so you can care for a new baby or an aging loved one. Paid writing gives you the enormous flexibility you need.

Here’s the bottom line: A paid writing career path is the answer to 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 paid writing as quick and easy as possible, here are a few lessons on what not to do when you’re 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, as we call it — 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, you’ll be in a situation where you can offer your clients new ideas on projects they didn’t even have in mind, and they’ll jump at the chance to pay you something extra (it starts with being an idea machine).

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 to get paid 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, or used to be bad at it (like Barefoot Writer Sean McCool, who flunked high school English and still makes $200K+ today as a paid writer!).

It’s because the persuasive writing techniques we use as professionals can all be learned. 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 — but we’ve all been there! Don’t sweat it. Let it roll right off your back. 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. 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 to remind yourself, once you start studying persuasive writing, that you know more than your client. And that’s 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. (As a Barefoot Writer Club member, you get 24/7 access to our private Facebook group.)

Here’s what all of this means:

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

And it will 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.