How To Be A Successful Freelance Writer

Every choice brings you closer to success. Or does it?

How To Be A Successful Freelance Writer
Photo by Anthony Fomin / Unsplash

Freelancing is the ultimate adventure. You get to set your own schedule, follow your own rules, and — most importantly — call yourself a founder.

But how does one get started? What’s the process? Is it even possible to make millions of dollars as a writer?

There’s a lot of advice out there. Like, an insane amount. Only you can choose what to listen to and what to ignore.

I think that’s the single best piece of advice: constantly think about how you could be doing things better and questioning yourself. Elon Musk

Luckily for you, I’ve poured 10,000 hours into developing a journey to freelance success. Choose your own adventure and become a millionaire!

Note: this is a Choose Your Own Adventure story, like the ones you probably read as a kid. Make your choice and click the appropriate link.

Good Morning!

Being a successful writer begins by simply waking up. If you don’t wake up, your only hope is to dream. Waking up at least gives you a shot at success.

When to wake up is the first choice on the path to greatness. Some suggest getting up super early to get a jump on all that freelancing. Others attest that sleeping in allows for ultimate creativity. It’s time to make your first choice.

What Do You Do?

Wake Up At 4am

Your alarm goes off and you lumber to the shower. Successful people take cold showers and so you do too. You ignore the pain and convince yourself it’s invigorating because you want to be a successful writer and this is obviously part of the process. Someone successful wrote it down so it must be true.

The shower is short. Five minutes of icy water is all you can handle at this unholy of hours. You dress for the day and move to the kitchen. It’s time for breakfast.

But What Are You Going To Eat?

Lite Breakfast

You read somewhere that chewing consumes precious time that could otherwise be spent writing. So for breakfast, and every other meal for that matter, you enjoy a glass of the latest liquid-only vitamin fad drink. Sure, it tastes like shit but it gives your body fuel. And just think of all the time you saved!

Breakfast consumed and the remains placed in the recycling bin, you take a moment to recite your daily mantra. Focusing inward, you close your eyes and quietly chant, “Today I will write. Today I will succeed.” You repeat these lines twenty-two times because you read somewhere that twenty-one times makes a habit so you add one more to be sure it sticks.

You’re Now Ready To Start Working. But Where Does That Happen?

Heavy Breakfast

Breakfast is the most important meal of the day. You live by this mantra and you take it to heart. Sure, it takes time to prepare three eggs, four strips of bacon, two waffles, half a melon, and an entire industrial carafe of coffee but this is the fuel you need to be successful. And bacon is delicious no matter what those hippie green people say.

You enjoy breakfast and take time to savor it. As you eat, you read the morning news. You pride yourself in diversifying your input, so as not to be biased. As such, you pull up AVC, 500 Startups, Growth Hack, and The New York Times. Of course you only read the Times’s headlines because their paywall is such a waste of money.

After cleaning up, it’s time to allow the calories and information to swirl around your brain for awhile. You meditate for exactly seventeen minutes — any less and you’ll get distracted, any more and you’ll fall asleep.

Now You’re Properly Ready For The Day.

The Office

Sure, you could save money and use a home office, but would you ever get anything done? And human interaction is nice. In moderation, of course. So you pay for a membership at a high-tech co-working space downtown.

There’s a few different membership levels, yet you pay for the top tier. This gives you a dedicated elliptical desk so you can burn calories while working. You also have unlimited access to the kitchen, a receptionist, and your own nap-pod. While you can’t afford any of this, it’s important to look like you can.

You turn on your desk, starting with the lowest setting. Easing into the day is important. Of course, you’ll forget to set the desk to a higher setting later but you could if you wanted to.

You put on your headphones to drown out the commotion a busy co-working environment brings. Your chosen playlist is a custom mix of whale noises overlaid on EDM. It’s a creation that took you weeks to get right. With the environment properly set, you’re ready to get to work.

But What Are You Going To Do First?

Wake Up At 9am

Setting an alarm is for losers. A truly successful writer let’s their body wake up naturally. The sun pouring through the window gently rouses you from gentle slumber. You smile and wonder why anyone wouldn’t want to wake up this way.

Next step is a long and luxuriously hot bath. The steam wakes up your capillaries and stimulates your brain. You’re going to be so creative today! After all, you read this on some VC blog and VC’s have all that money for a reason.

After The Bath, You Skip Breakfast And Head To Work.

Home Office

Sure, you have a “home office” as far as the IRS is concerned. But you are most creative, and most comfortable, on the couch. As long as you have an office, the IRS doesn’t care if you actually use it. Right?

Anyway, you’re ready to get down to business. You link your phone to your expensive bluetooth speaker and start the proper inspirational playlist — a mix of movie soundtracks and clips from TED talks. With the “office” set up, you are ready to get to work.

But What Do You Do First?

Review Your Notebook

All of your thoughts, ideas, and writing prompts are kept in a leather bound notebook. You know the kind with the cool leather rope that keeps everything concealed? That’s the one! You open it up to review yesterday’s additions.

Except you can’t read it. You can never read it. Your handwriting is atrocious. However, the mixture of colors, scribbles, and the occasional doodle is inspiring. This makes you feel great, but since you can’t read it you’re frustrated too. Frustration isn’t a pleasant feeling and does not help with creativity. You ignore your frustration and open a new internet tab.

Check The Internet

Sure, you could be writing but a little distraction can’t hurt. And maybe one of these distractions will provide new inspiration, or maybe even a new contact that could lead to new business. The internet is an endless sea of possibilities!

First stop is Twitter to check for new followers. Sure, Elon Musk hasn’t followed you back yet but that doesn’t stop you from retweeting his latest tweet and replying to the one before that with a, “Such great insight. I can’t wait to put this into practice.” Surely this will get Musk’s attention and when he eventually follows you, look out world!

Next up is Facebook. Of course, you don’t tell anyone you still use Facebook since it’s totally uncool, but you enjoy lurking. Plus there’s that one private group that you really like. Forty-five minutes later, you realize what you’re doing. Feeling ashamed, you move on.

You skim through Medium, bookmarking stories that sound interesting. Eventually you’ll read them, or at least throw a few claps to make it look like you read them. A check of the stats shows that your views are trending down. Must be time to publish something again. But what? You’ll come back to that thought later. Maybe.

A quick stop at MailChimp to check for new people on your mailing list before moving to UpWork. This is where the real work begins. Since you have no messages to respond to, you check the job feed.

The feed is full of gigs to write a thousand word essay for $5. While it’s well below your advertised rate of $1/word, money is money. Besides, the job posting says it could lead to a “long term” opportunity. So this listing might be the path to ultimate freelance success. Right?

What Do You Do Next?

Write On Medium

Sure, you don’t have any new ideas but why would you let that stop you from publishing something. And besides, all those new followers you pick up every day probably haven’t read everything you’ve published.

You open up your stats and scroll down far enough so that your entire history loads. Then you randomly scroll up and down with your eyes closed for a few seconds. When you stop, your cursor is on a story you published six months ago. That’ll do!

After copying the story and pasting it into a new one, you spend thirty minutes changing the content around a bit. You add a new insight and change the quote at the top of the story. After editing, you pull up a Dropbox folder of photos from your latest photoshoot and spend thirty minutes looking for just the right one to headline the story. Of course, don’t forget to give yourself a photo credit and link people to your Insta. You are such a smart entrepreneur!

When the story is ready, you schedule the publishing date. Publishing right away is for plebeians and you are not a plebeian! You spend another thirty minutes scheduling Tweets and Facebook stories to coincide with your chosen publishing time. Promotion is the name of the game, after all.

Feeling Accomplished, You Have To Decide What To Do Next.

Apply For The UpWork Gig

So $5 isn’t a lot of money for a thousand words, but an easy gig like this is great for that feedback rating. Making sure your proposal stands out in the sea is key here. You spend the next thirty minutes writing a kick-ass, five-hundred word cover letter outlining your strengths and your past experience in the healthcare field. Of course, you don’t actually have any experience in the field, but the client doesn’t need to know that.

After you’ve crushed the cover letter, you attach a CV for that extra little something. And, to stand out even more, you adjust your proposal rate to $4 to undercut all those other greedy freelancers. Sure, $4 is less than $5, which isn’t much to begin with, but this is what it takes to be successful. And noticed.

You submit the proposal and patiently wait. Of course, 99% of clients ghost freelancer proposals, but maybe this one will respond right away. After a few minutes, you lose interest.

What Do You Do Next?

Take A Nap

Let’s face it, you’ve worked hard today. Sure, things might not have worked out as planed but you’ve done a lot of work to set things up for the future. And that is justas important as a billable hour! You don’t just need a nap, you deserve a nap.

After putting on your fair trade sleep mask and setting the white noise generator on your phone, you pass out for a few minutes. Or an hour. Maybe even two. Who’s to say? Since you’re the boss, there’s no one to get mad over lost time.

Feeling refreshed, you decide to get in a workout. That Apple Watch activity streak isn’t going to continue itself. A quick wardrobe change and you’re ready for some physical fitness.

What Is Your Chosen Workout?


Everyone can use a little yoga now and then. After rolling out your yoga mat, you pull up the latest “Yoga with Adrienne” video on YouTube. When you see that it’s an active class, you quit that one and go to “Yoga for Relaxation”, which you’ve got bookmarked.

Relaxing yoga is more your speed. Slow. Low impact. Plus, you’ve worked hard today, so why work hard when you’re working out? Twenty minutes later, you’re properly stretched and feel great. You towel off and eat dinner.

The Evening‘s Possibilities Are Endless. What Do You Do?


After arriving at the gym, you’re greeted with a series of yells and instinctively start doing burpees. You throw a medicine ball at the ceiling as if your life depends on it — and it might the way the trainer reacts to your every move.

A few tire flips and rope flings later and you’re feeling good. Your arms might not be able to function tomorrow, eliminating the possibility of writing anything, but at least you’re healthy. This is healthy, right?

But you don’t have time to think about tomorrow right now, you’ve got a whole evening of possibilities in front of you. You down a protein shake before showering and going home.

Sitting Down On The Couch, You Weigh Your Options. What Do You Do?

Cruise Tinder

The night is young and full of potential. A world of opportunity awaits with just a few swipes. You pull out your phone and start swiping.

Your profile is meticulously groomed for optimal reception. The picture is one from a recent photoshoot. Your bio mentions that you’re a founder, but not outright because you don’t want to be super braggy.

After swiping a few times and sending a few messages, you wait for the inevitable responses. To pass the time until your phone starts buzzing, you decide to throw up a little Netflix.


Post workout you’re feeling great and the sun is at the perfect spot in the sky. You heard it called the “magic hour” at some point in the past and you fully support the name. Grabbing your camera and tripod, you head out to catch a few hundred shots.

You look longingly at an abandoned warehouse and pensively in front of a street art mural. You take an artsy, over the shoulder shot on a set of train tracks. You time a shot perfectly as strangers walk by to imply that you’ve got friends. These photos are going to look amazing!

The sun sufficiently down, you head home to edit the photos and upload them for future use. But it’s still early and you’ve got options.

What Do You Do?

Watch Netflix

You’ve done enough work for today. Sure, it wasn’t what you hoped to accomplish but there’s always tomorrow. And right now, there’s a back log of ER to watch. Again.

You put on the show and get lost in Dr. Ross and Nurse Hathaway’s relationship. At some point you drift off to sleep.

You wake when the sound cuts out. Netflix wants to know if you’re still watching. You are, of course. After getting frustrated at Netflix for judging your entertainment consumption, you figure it’s probably a good time to think about your plan for tomorrow.

What Do You Do?

Thanks to Quincy Larson for pointing out the Medium hack that made this possible, and to Oliver “Shiny” Blakemore and Ernio Hernandez for encouraging my insanity.

Justin Cox Justin Cox

Justin Cox is a donut-loving, word-writing, nonprofit consultant based in Orlando. He also runs The Writing Cooperative on Medium. Come say hello!