What It Means to Be a ‘Pajama Writer:’ Take the Leap Into Freelance Writing

You guys. Freelance writing is so rewarding. Whether you’re in it for some side-hustle cash every now and then or you take the plunge to go full-time, there’s something magical about taking control of your financial freedom and doing something you love – writing. And it’s that feeling that drove me into writing, and, ultimately, to launch The Pajama Writer.

So, how do you know if you’re ready to take the leap and become a Pajama Writer for yourself? There’s some soul-searching and goal-setting involved. And it’s going to take work. This lifestyle isn’t for those who dream big and do little. You won’t be successful if you don’t actually enjoy writing and learning about how to improve your craft. But it will be a rewarding experience and journey, especially if you have a little help and direction to find your way to earn $300, $1,000, and even $10,000 every month with your content.

You Enjoy Writing 

There are plenty of side-hustle gigs out there, along with lofty promises of get-rich-quick programs to sign up for. Freelance writing as a self-employed contractor is much different. There’s a lot of work involved, since you’ll have to go find new clients, set pay rates for yourself, manage deadlines, and create great copy. None of that work will phase you if you love to write. 

If you ask any freelance writer, there are a million different motivators and journeys that led them to where they are today. And that journey is entirely yours to travel. Just make sure that it starts from a passion for writing compelling content.

We’re not writing werewolf and vampire novels here. That’s a different journey altogether.

We’re not starting our mom blogs. That’s a different journey altogether.

We’re not shooting for that-one-blog-post-that-goes-viral. That’s not a sure thing in any realm.

What we ARE doing is engaging businesses and individuals out there who DON’T love to write and are willing to pay someone else to do their writing for them. And that’s where the money is, along with the opportunity for you to realize your gift of writing.

It All Begins with a Decision

Starting this (or any new) journey begins with one critical moment: deciding to go for it. 

You have to have a “coming to Jesus” with yourself in an honest way. Can you do it? Sure. WILL you do it? That’s the commitment you have to make. Conduct an audit of where you are and compare that with where you want to be. 

Deciding to leap into freelance writing isn’t easy. You might question yourself a thousand times. “Am I good enough?” “What if I fail?” Those doubts are normal, but here’s the thing: success doesn’t happen by waiting for the perfect moment. It happens when you bet on yourself, even when you’re scared.

Take the leap. 

You don’t have to commit to full-time. Maybe you just want to side hustle in addition to your full-time job. 

You’re never going to feel 100% ready, but the first step is deciding to start anyway.

A Goal Fuels Your Journey

Freelancing without a goal is like driving without a map (or without the nav on.) You’ll end up somewhere, but it probably won’t be where you want to go. Goals aren’t just motivational posters. They’re the foundation of everything you do.

Ask yourself: Why do you want to freelance? Is it financial independence? More time with your kids? The freedom to travel or take on projects you’re passionate about? The idea is to discover that “where you want to be” and set that in stone. 

Your goal doesn’t have to be flashy, but it has to mean something to you. Write it down, say it out loud, and keep it in your line of sight when things get tough. When you’re staring down rejection or struggling with a difficult client, that goal will remind you why you started.

Thinking part-time writing side-hustle?

If you find yourself with time on your hands that you want to invest in doing something meaningful and productive, a freelance writing side-hustle can be a rewarding outlet. Stay-at-home moms, teachers on summer break, retired professionals, and college students all find incredible earning potential in part-time or seasonal writing projects. 

If your goal is to make an extra $300 every month, there are great resources and platforms out there to explore. It’s how you can connect to businesses and brands currently looking for contract writers and copywriters to help them with short-term writing assignments. 

Thinking full-time freelance writing?

Facing a full-time career change comes with anxiety, uncertainty, and even emotional distress in worrying about the financial and mental “what ifs.” 

Maybe freelance writing is an option for you because you’ve been laid off recently, considering your next move. Maybe you’re burnt out in your current job and eager to find something new. Or, it could be you have a mountain of medical bills or student debt to pay off soon. 

For me, I HAD to do something different after a corporate acquisition layoff. I knew I could probably make a few calls and get right back into the grind in a familiar role somewhere else. But I also knew that was the last resort. It would bring some financial stability, but it wouldn’t bring me peace. It wouldn’t spark my curiosity and creativity. And it wasn’t going to make a difference in how I was FEELING at this stage of my life. For me, it was now or never – and that was when I made my decision.

Leaving behind the comfort (or monotony) of a steady paycheck to build something entirely on your own is terrifying. Freelance writing isn’t some magic wand fairy dust where you snap your fingers, clients come flooding in, and you suddenly rake in six figures.

It takes work. A lot of work.

But here’s the good news. You don’t have to slog it out alone, blindly guessing where to find clients, how to improve your craft, or when the money will start rolling in. I’ve been where you are, and I’ve learned the hard way what it takes to succeed. Now, I want to help you skip some of the pain and go straight to the part where you build a freelance writing career that works for you.

Find Your Secret Sauce

With a commitment to a decision and goal in place, it’s time to build your roadmap for “how” to get there. You can take the long way, the short way, the uphill path, or the risky shortcuts. But the “how” is about finding your secret sauce.

Here’s the truth: the freelance writing world is crowded. There are thousands of self-proclaimed writers out there, all competing for the same gigs. Some are better than you with more writing experience. Many are downright terrible. So, how do you stand out? By finding your secret sauce.

Your secret sauce is the unique blend of skills, experiences, and voice that only you can bring to the table. Maybe you’re amazing at simplifying complex topics, or you have a knack for writing in a conversational tone. Maybe you’re an expert in a specific niche like healthcare, tech, or education. Whatever it is, lean into it hard.

Finding your niche isn’t always immediate. It takes some experimenting, some trial and error. But once you discover what makes you stand out, you’ll stop chasing clients and start attracting them.

For me, I found my niche by accident. There was a paying assignment on a content mill job board. It involved writing about cars. Nothing sexy about it – horsepower this, how to connect Android Auto that. But for a brief stint in my long-ago career, I sold cars at a dealership. So, talking about cars came easy for me. And I aced that first writing assignment that led to hundreds more over the next few years with that client. Since then, I’ve expanded my niches to include other areas and industries. But my journey can remind you as a new freelancer that your “I can write this in my sleep” niche doesn’t have to be passion-project-related or tied to hobbies.

Commit and Watch It Grow

Freelance writing isn’t a “set it and forget it” kind of career. You have to show up every day, put in the work, and keep pushing forward. Even when it feels like you’re getting nowhere.

There will be days when you doubt yourself. Days when a client ghosts you, a pitch gets rejected, or you can’t string two sentences together to save your life. Those moments suck, but they’re also what separate the dabblers from the doers.

The writers who make it are the ones who stay consistent. They pitch even when they don’t feel like it. They write even when the words don’t come easily. They improve their craft, market their services, and keep moving forward, one step at a time. And when you’re dead-tired, ten hours into your screen time for the day, you tell yourself you can accomplish one more task toward growing your little business.

The Rewards Are Endless

Let’s get real. The freelance life isn’t all sunshine and rainbows. But the rewards? They’re incredible.

For me, freelance writing has meant working on my own terms. It’s meant being there for my family, setting my own schedule, and making more money than I ever thought possible.

The beauty of freelance writing is that the rewards are personal. Maybe for you, it’s about leaving a toxic work environment. Maybe it’s paying off debt, saving for a dream vacation, or simply proving to yourself that you can do this.

The best part? Every day you invest in yourself brings you closer to those rewards.

You Don’t Have to Do It Alone

When I started freelancing, I didn’t have a guide. I didn’t have tools, resources, or anyone to tell me what the hell I was doing. I made writing mistakes, wasted time, and spent way too many nights wondering if I was cut out for this. And if you’ve spent any time researching “how” to side-hustle as a contract writer, endless hours of skimming blogs, coaching programs, and entrepreneur tips, you know what I’m talking about.

That’s why I’ve created real-world, no-BS tools and guides to help you. You don’t have to guess where to find clients, how to craft the perfect pitch, or how to build your portfolio. I’ve been there, done that, and put everything I’ve learned into resources designed to help you succeed faster.

Ready to Make the Leap?

Freelance writing is so worth it. If you’re ready to bet on yourself, embrace the challenge, and build a career that works for you, I’m here to help.

Download my tools and guides today and take your first step toward becoming a pajama writer. Let’s make your dream writing career a reality—one word at a time.