How to Plan Your Freelance Writing Business


It’s easy to dream about how great it will be to be a freelance writer someday.


Imagine it: you’ll be your own boss. You’ll choose the very best clients. You’ll set your own hours and work with people who know the value of what you do.


You can work in your pajamas. You can sit at your desk with a steaming coffee in one hand, and with the other hand you can apply your keyboard with surgical skill.


Or if you’re the type to get up at 4:00 AM and have the day’s work over with by noon, you can do that too.


With freelance writing, you’ve got the freedom to live life on your own terms. The only structure in your life is the structure you create.


And as long as you think about the freelance life that way, it sounds amazing.


You’ll never have to report to another boss. You’ll never have to go to a pointless meeting ever again. You’ll never even have to go to some boring office party where you have to pretend to enjoy yourself.


That’s freedom. But this freedom comes with a price.


Because as soon as you make the plunge and become a full-time freelancer, you’ve got a problem. It’s wonderful to daydream about how great it would be to live without a boss, but there’s a reason so many of us don’t make that choice.


The reason? Simple.


The flipside of being your own boss is that you have to be your own boss. The flipside of having no structure confining you is that you have to create your own structure. The flipside of having nobody there to supervise you is that you have to supervise yourself.


Let me say something personal: I have a friend who is clinging to a job she hates, because deep down she’s afraid of this very thing.


She’s afraid if she goes out on her own she won’t be strong enough, smart enough, or creative enough to make things work. She’s afraid if she leaves behind the structure her job gives her, she won’t be able to push herself to succeed.


I try to tell her it’s not as bad as she thinks it is. Heck, I try to tell her that once she gets used to it she’ll wonder how she ever lived any other way. But she’s still clinging to that job she hates. I think it’s because she doesn’t trust herself. I think it’s because her job is safe and familiar.


I hope she takes the plunge before it’s too late.


With this article, I want to talk about planning and goal-setting.


And I’m not here to tell you I’ve got all the answers. I’m still learning. If I had all the answers, I’d be a politician.


All I want to do is tell you a little of what I’ve found in my time as a freelancer and as a human being. I’m a young guy, but I think I’ve figured out a few things worth knowing. I hope they help you in your journey.


Let’s start with goal-setting.


Goal Setting

If you’re serious about freelancing, you have to set goals. Some people will tell you this is a stupid place to start. They’ll tell you goal-setting doesn’t matter. They’ll tell you things like “follow your heart and it’ll lead you right.”


(Disclaimer: there’s nothing wrong with following your heart. If I hadn’t followed my heart I’d never have made it as a freelancer. But if I’d only followed my heart I’d still never have made it as a freelancer.)


You have to set goals if you want to succeed as a freelancer. Those goals must be concrete. They must be measurable. They must be precise.


Before I go any further, I want to say something: some of this stuff will sound obvious. And it is obvious. This is stuff we all already know. So don’t be surprised if none of this stuff sounds exactly ground-breaking. We already know this stuff. But we don’t always act on it.


And unless we act on it, knowing it doesn’t do us any good.


So what’s so great about goals?


Better yet: what’s so great about measurable goals?


As human beings, we need to have something we’re working toward in order to feel like we’re making progress. This isn’t a business thing. This isn’t a cultural thing. It’s an existential fact of being human.


If we’re not aiming for something beyond ourselves, we fall apart. We slip into hopelessness. We slip into despair. We slip into saying things like, “What difference does it make? Life is meaningless anyways.”


Goals change that. Goals give life meaning. Goals give us a framework to understand ourselves and the world.


They allow us to feel good when we’re making progress, and they allow us to feel bad when we’re not making progress. As human beings, we’re either striving toward a goal or else we’re stagnating hopelessly.


That’s why we need goals.


Now, why do they need to be measurable?


We need measurable goals because if a goal isn’t measurable, A) we can’t tell if what we’re doing is working or not, and B) we can’t tell if we’ve reached the goal.


Let’s go into a little more depth about both of those:


  • We can’t tell if what we’re doing is working.

Let’s put this in broad terms. Say you’ve got two possible goals: you could have a vague goal like, “I want to be free and independent,” or you could have a concrete goal like, “I want to make $1,000 every week from freelancing.”


It’s good to want to be free and independent. That’s a major reason many people choose to be freelancers. But we have to work out specific, measurable, practical goals if we’re going to make it a reality.


Aiming for a specific weekly dollar figure is a good high-level goal. In order to reach a goal like that, you’ll have to develop a series of subordinate goals to take care of on a daily (or weekly) basis.


Most importantly: setting measurable goals forces you to change your actions when they don’t work.


It’s so easy for us to slip into routines. The good thing about a measurable goal is that it forces us to recognize when our routines are letting us down. A measurable goal keeps us accountable and forces us to change.


  • We can’t tell if we’ve reached our goal.

Why is it important to know you’ve reached your goal?


By the time you reach your goal, you’ll have come up with a sequence of actions that allow you to reliably meet that goal. Once you’ve got a system that works, you won’t want to change it all that much.


(This is known as the Principle of if it Ain’t Broke, Don’t Fix it.)


That means it’s extremely important to know when what you’re doing is working. And if you want to know that, you’d better be able to measure it.


When I first started freelance writing, my goal was to reliably reach an income of $1,000 every week.


I knew that if I could reach that goal, I’d have a system in place that allowed me to achieve that.


I also knew if I built a system that could make $1,000 a week, I’d be able to develop a system that made $2,000 a week.


The point is to set a goal and find the right sequence of actions that allow you to reach it. That’s what they call planning.



Every plan has three elements: a goal, a deadline, and a set of repeatable actions to be taken.


We’ve already talked about why you need a goal. Why do you need a deadline?


Well, I’m only going to speak for myself here, but if you’re like me you’ll be able to relate: I’m lazy. There’s nothing I hate worse than pushing myself any harder than I need to be pushed. I hate feeling rushed. I hate feeling like I have to be in a hurry to do anything.


If I’ve got a goal without a deadline, I’ll look at it and think, “That’s great. I feel so good about myself for setting that goal. I think I’ll go take a nap.”


But if I’ve got a deadline, I have to do something about it. I have to change what I’m doing when it’s not working. I have to figure out what I’m doing wrong, and I have to figure out how to fix it.


All that stuff takes a lot of effort and is massively inconvenient. The lazy part of me hates even thinking about all the work involved.


That’s why I need a deadline. It’s a club I hold over my own head to get myself to do the damn thing.


That’s why deadlines are important.


Now that we’ve got our goal and our deadlines in place, it’s time to get our actual course of action laid out.


Why do we need a repeatable sequence of actions? The short answer is that we’re always going to have a set of obstacles holding us back from our goals, and those obstacles never go away entirely. A freelancer’s work is never done.


You’ll always need more clients. You’ll always need to do some marketing. You’ll always need to do the client work.


The point of developing a repeatable sequence of actions is to organize yourself so you can take care of everything without any unnecessary stress. It’s about becoming as efficient as you can. It’s about keeping things as regular and predictable as you can. It’s about eliminating busyness from your business.


And if that all sounds seriously boring… it sort of is. You’re pretty much learning how to build and run your own small business. But when you’ve built the system and make your own decisions, it doesn’t feel oppressive.


That’s one of the things I couldn’t stand about working for somebody else’s company. I hated following someone else’s procedures and having someone else set the agenda. Freelance writing was a way to get free of all that.


So even though running your own business means you have to do a lot of organizing, it’s your own organizing. It’s your own set of solutions to your own problems.


And that makes it a lot better.


But you don’t have to come up with brand-new solutions to every problem under the sun. There are plenty of places online where you can find experienced freelancers who can help you learn how they do things. Find a few mentors, and you’ll be well on your way to running your own freelance business.


Let me know if you have any questions or concerns about freelancing. I’m always trying to tailor this blog to your needs, so I’d appreciate the help.


And I know some of you don’t like to post publicly, so feel free to contact me by email at if you’d rather do it that way.


Good luck, and good copywriting!