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Upwork as a Stepping Stone in my Literary Career

A Writer’s Life – Upwork as a Stepping Stone in my Literary Career

By Paul Deines

Where do freelance writers find work? I get that question a lot, and the answer is, of course, lots of spots. There are email lists and journals. There’s certainly plenty of networking, and there are also lots of websites that connect freelancers with clients.

My favorite of these sites, bar none, is Upwork.

A sharp, intuitive platform that includes easy profile and resumé setup, clear job parameters, messaging and work tracking – Upwork is the gold standard for freelancers. Its mobile app is so seamless, I can sometimes apply, draft and submit jobs on my phone. It also provides the best-quality client pool, in my opinion.

Upwork can be an integral stepping stone for freelancers looking to kickstart their writing careers. Here are a few benefits of the service:

 Engaging Another Party

 Writing, by its nature, is a solitary pursuit. Your words may be brilliant, but often you’re the only one who sees them. That’s not necessarily a bad thing. Writing alone allows you the freedom to write badly, sloppily … in a word, freely. But there needs to come a time when you present this work to someone else. That might mean a friend or partner. It might mean a writing group or editor.

The very act of handing your words to another person transforms writing from a diversion into something concrete. This is truer still when the other party is paying you. Not to diminish the value of non-transactional feedback, but you can’t deny that a client has a vested financial interest in extracting your best, cleanest work.

Having a good Upwork client is like having an editor who always prioritizes your work and desperately wants to improve it. Even better, a client won’t let you edit and refine endlessly. We writers are all prone to that vice!

Exploring Your Strengths

I’ve had a lot of different jobs in my life. I have worked in the arts, marketing, community organizing, education and the financial sector. I’ve also manned a steam table, a video store counter, and a women’s shoe department. My contention has always been that a wide breadth of life-experience makes me a better writer. So while I haven’t loved every job, I’ve taken valuable lessons from each.

My attitude toward my Upwork proposals is the same. I do marketing, blogs, short stories, mini-novels, and whatever piques my interest. Freelancing through the site has opened my eyes to skills and interests I didn’t know I had.

Every job is an opportunity for personal growth. So, don’t hesitate to send proposals for anything that interests you. You might discover a new strength, which might also be a new writing income stream.

Refining your Portfolio

When you start as a freelancer, your portfolio is razor-thin. Maybe you have some school work or the odd article you got placed in a journal. Sometimes, you find yourself including unpublished personal writing, hoping that a potential employer will read it and appreciate your style.

Of course, the only way to grow this portfolio is to write and have that writing picked up.

Upwork is a wonderful resource for developing and refining the work samples you send potential publishers and employers. Being able to tell someone that the writing in your portfolio was commissioned and compensated lends it an additional air of credibility. The folks that look at your samples will, at minimum, think, well, looks like someone paid for this applicant’s work.

Building Contacts

I have found, time and again, that the clients I write for on Upwork return to me for additional work. The site attracts serious, organized folks looking for quality content. Many draw from its freelance talent pool to eventually take on salaried creative employees. What begins as a series of one-off commissions can become a permanent job.

Moreover, plenty of publishers use Upwork for ghost-writers. This too can be a stepping stone. On more than one occasion, a satisfied client has inquired about my personal writing. After all, they’re happy with the words I produce, so they’re curious about my passion projects, too.

In the end, we’re all looking for regular employment that can meet our financial needs. As writers, we also look for something intellectually and spiritually fulfilling. Upwork is a huge resource to identify and secure high-quality contract employment. Every freelancer should be on it.



About Paul Deines:

Paul Deines is a New York-based writer focusing on beer and culture, sometimes together and sometimes separately. His work has appeared recently in SR-Mag, Brew Studs, and Hop Culture.

As a freelancer for hire, he ghostwrites novels, crafts marketing copy and contributes dialogue for video games and other digital content.

An occasional playwright, Paul’s plays have been performed both online and on stage around the country. In his spare time, he enjoys experimental cooking, classic cinema, watching football, attending the theatre, and constructing playthings for his daughter.

You can read more of his work at his website, The Curiograph ( or follow him on Twitter @thecuriograph.

You can also read recent articles by Paul Deines by visiting the links below:

Ashton Rice

The One Tool No Ghostwriter should be Without

The One Tool no Ghostwriter should be Without

By Ashton Rice

Ghostwriting is a way to hone your craft quickly. While getting a grasp of where your style fits in the world of literature, using your skills as a writer is the best way to get better and stay sharp. With constant assignments and the back-and-forth communication with clients, it can become difficult to maintain a healthy workflow. The work is something any aspiring author appreciates and most are ready to rise to the challenge. Let’s be honest though, it can be a lot to juggle.

At times, you’ll find yourself writing for one editor on weekends, and another one on weekdays. Each has slightly different preferences, so at the very least you’ll need to make sure that the grammar, spelling, and syntax of your work is correct and flawless. As your fatigue kicks in, you find yourself sending poorly reviewed writing to your editors, leaving them upset and confused as to why such a talented writer suffered from such simple mistakes.

Every writer should use automated editing software, like Grammerly:

One thing that every writer in the 21st century should be using is Grammarly (or any automated editing software, I’ll use Grammarly for convenience and consistency). This used to be a discussion and debate of skill and inadequacy, but now, it is simply the more efficient way to review writing. Grammarly is the most efficient way to get your tired writer’s eyes on mistakes that would be easily overlooked otherwise. This program saves you precious time on projects and highlights basic errors and mistakes as you write. That’s kind of the beauty of it. While Grammarly will catch most issues in your writing, it still leaves the option to correct to you. So, if you are a particularly stubborn writer, this is the tool for you. As opposed to automatically changing mistakes, Grammarly brings them to your attention and lets you act on them yourself. Even if the settings are too casual–or even too professional–Grammarly allows in-depth customization for writers of every level.

 This is a tool you don’t want to overlook:

Putting off installing Grammarly is a mistake. This is a free resource that doesn’t suffer from fatigue or apathy. This program is always on its A-game and gives you the ability and time to focus on writing the best content you can produce. Feeling like you missed something after re-reading your document for the twelfth time is a horrible feeling. It is even worse when you hear from the editorial staff that your review wasn’t thorough enough.

Let Grammarly do the grunt work of finding flaws in your writing. Again, it’s free and allows you to be less focused on straining your eyes because you missed an ‘i,’ and lets you worry about your style, and what makes your writing unique. Don’t send a poorly reviewed document to your editor; let Grammarly help you find those pesky little errors and give you one less thing to worry about.

About Ashton Rice:

As a sequential art major out of SCAD, Ashton began writing as an intern editing for The Borgen Project. He learned valuable experience as an editor and writer while taking on this role, and discovered a passion for writing and sharing information and ideas through written language.

Ashton now writes for SOLRAD Magazine and Write-On e-Publishing. His passion for comics still persists, and he continues to write and illustrate his own comics while studying up and coming alternative artists for reviews and interviews for the SOLRAD Magazine. Ashton favors writing science fiction as well as contemporary fiction in his personal work.

Follow Aston Rice on Instagram at:

Paul Deines

How I Make $3k Every Month as a Freelance Ghostwriter

How I Make $2k – $3k per Month as a Freelance Ghost Writer

By Paul Deines

No one is expecting to buy a mansion in the Hamptons with their freelance writing income, but we should aim to receive decent compensation for our work.

Using sites like Upwork, Guru, MediaBistro and Freelancer – as well as pitching websites and journals I find in the Writer’s Market and online – I have built an income of $2,000-$3,000 per month. It requires a fair amount for boot-leather, but here are some best practices I have discovered.

Keep a Diverse Stable of Clients

I pitch clients constantly. It’s a part of my weekly writing routine. Of course, the most important component in developing a steady freelance income is having clients that come back to you again and again.

The good news is that if you produce quality work, clients will come back. They don’t want to spend money and time posting jobs on freelancer sites when they have a consistent writer they already know. So once you’re getting repeat offers, you need to diversify your stable.

Right now, I have three regular clients that reliably return to me multiple times throughout the month. Each has a different deliverable and turnaround expectation:

  • One client expects a 20,000-word novella every two weeks.
  • One client expects a couple of 3,000-5,000-word short stories a month.
  • One client expects an Instagram caption every couple of days.

I can write for all three of these clients concurrently. I know what they expect and when they expect it. The first two require me to sit at my desk and type. For the third, I can produce Instagram content on my phone while my daughter eats breakfast.

What these clients have in common is a consistent rate. Combined, they guarantee a little under two-thirds of my monthly income. The rest I can fill in with one-off commissions.

Look for Work that Interests You

All writing takes time, but some writing will be easier on your time.

Obviously, we cannot always pick and choose, but I encourage you to seek out work that is as close to your interests as possible.

Early this year, I happened upon a contract for a 25,000-word story in the style of Ian Fleming. I’m a huge James Bond fan. I have read most of the Fleming books and have a sense of their appeal and, crucially, their shortcomings.

Never have I been so confident in a proposal, and sure enough, I got the commission.

I wrote the story in four days, with minimal revisions. Was this because I am some preternaturally talented writer. While I’d like to claim that, the reality is that I could write quickly and well because I loved the work. Six thousand confident words flowed out of me each day.

It’s a cliché but not untrue: if you love what you do, you’ll never work a day in your life. The same is true of finding writing you’re interested in.

Know and Build Your Value

It’s easy to say that you value your own time and work, but properly valuing your work can be a tightrope walk. I can insist that I be paid two dollars a word, and the work will never materialize. On the other hand, there are plenty of potential employers out there that want to pay you five dollars for 1,000 words. How do I thread that needle?

Unfortunately, I have found that sometimes I need to take a lower rate when pitching to an industry or on a genre I haven’t written before. Is that fair? No. I’m taking less money to produce the same amount of work.

But I think of these lower-commission jobs similarly to a paid internship. You know you’re being short-changed, but you are gaining some experience, a reference, a portfolio sample and a little cash. Once you’ve knocked out a couple of these, you’ll have something for the portfolio and can increase your rate.

I’ve had some incredibly nice, supportive clients that simply haven’t been able to match my increasing rate. I have to walk away from them. I always thank them for their continued confidence and ask them to think of me if their budget increases.

Queue Up Work for the Future

 Just because you’re booked solid with current projects doesn’t mean you stop pitching. Lots of employers set deadlines far into the future, so you should be doing the same.

Queuing up future work is imperative to maintaining a regular income. You may be killing it today with lots of lucrative contracts. If next month rolls around, and you have nothing in the pipeline, yesterday’s workload will be cold comfort.

So line up next month’s work today.

But remember: you have to maintain your clients’ expectations. If you won’t be writing word-one for a week, tell them. That way, they won’t be refreshing their inboxes, wondering why you haven’t submitted anything. You also won’t have to update them constantly when you haven’t started.

Set a Schedule and Stick to It

Being a freelancer requires lots of hustle and elbow-grease. I write, on average, fifty thousand words per month for my various clients. Much of this work flows quickly, but I’m still putting in a lot of time at the keyboard.

The only way to ensure you meet your deadline and don’t because overwhelmed is by planning your days ahead of time. Create a schedule with your most challenging work at your most productive hours. I’m a morning person, so I tend to write my research-heavy pieces first thing. If I’m writing something action-driven or salacious, I schedule that in the evening when I’m in a looser mood.

The point is, I schedule. Each day, I know what’s on my agenda and have blocks of time for each item. If I don’t get everything completed that day, I go back to my agendas and reschedule those words for later.

Remember that revision has to be a part of your schedule and incorporate that into your time. Reviewing, proofing and refining your words takes time. Don’t take it for granted.


I won’t guarantee that if you stick to this advice, you can immediately quit your day job. But I have found a modicum of success by holding to these tenets. I don’t plan to change course anytime soon.



About Paul Deines:

Paul Deines is a New York-based writer focusing on beer and culture, sometimes together and sometimes separately. His work has appeared recently in SR-Mag, Brew Studs, and Hop Culture.

As a freelancer for hire, he ghostwrites novels, crafts marketing copy and contributes dialogue for video games and other digital content.

An occasional playwright, Paul’s plays have been performed both online and on stage around the country. In his spare time, he enjoys experimental cooking, classic cinema, watching football, attending the theatre, and constructing playthings for his daughter.

You can read more of his work at his website, The Curiograph ( or follow him on Twitter @thecuriograph.

You can also read recent articles by Paul Deines by visiting the links below:

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