How I Made My First $10k as a Freelance Writer on Upwork

I just passed my $10,000 milestone on Upwork, time to pop the champagne and share some tips for those of you also looking to jump into the freelance writing world!

As I mentioned in my previous post (Day in the Life of a Freelance Writer) I do freelance writing full-time when I’m in-between writers’ rooms. It’s a great way to keep my skills sharp while doing interesting freelance writing for amazing clients all around the world, and a flexible schedule means I get to travel and have time to do other creative projects during the week (like the immersive theater event I’m working on with my writing partner!) It’s a luxury to be able to abscond to somewhere like Lake Tahoe to do some writing on a Tuesday.

I do most of my freelance work through this platform called Upwork, which connects freelancers with people who want to hire us.

So, here’s how I made my first $10k, and how you can, too!

Picking Projects & Clients I’m Passionate About

On Upwork, I get invitations to interview for different jobs on a weekly basis, but I don’t accept very many of those invitations. Why? Because I’m selective about the clients, companies, and brands I work for. I do my best work when I’m on a project I’m excited about, so I only accept offers for jobs that I believe in. This also prevents burnout and keeps work from feeling like “work.”

I particularly enjoy working with clients who have interesting life stories. Ghostwriting in particular lends itself to fascinating work: hearing people talk about the extraordinary lives they’ve lived is like fiction, but better because it actually happened.

I also collaborate with other freelancers on more complex projects, like writing Murder Mystery parties with 40+ characters and Escape Room stories. I started my own agency on Upwork to make this collaboration easier, and we’ve just started on some awesome scripted projects.

I Know My Niche & Don’t Let That Define Everything I Write

My focus is on projects that are storytelling-based, but I love to try my hand at every different writing project under the sun. I’ve been hired to write everything from immersive theater events to escape rooms to murder mysteries to memoirs, and I thrive when I can put my training and experience to use. I also do copywriting and blogging work for a variety of clients to mix things up: it’s nice to have some writing work that isn’t as intensive on the creative side to keep things fresh.

I’m versatile, and I love the variety of jobs that I’m working on at any given time. I think that’s the key to a sustainable freelancing career: constantly finding ways to mix it up and challenge yourself.

I Manage My Time & Don’t Overcommit

I’m careful to balance my workload, and communicate deadlines that give me plenty of time to turn in quality work. The common mistake most freelancers make is to overcommit ourselves — especially since a lot of the work we do ebbs and flows. While you do have to maintain a variety of long-term clients, it’s important to have time to rest and read and continue to learn. Having days where all I do is read books sometimes adds more value than doing anything else, because it leaves me recharged — and often whatever I’m reading or learning feeds into the work I do every day.

Nobody’s ever going to be perfect at time management — myself included — but I’ve learned a lot since I got started. I do my errands in batches and meal prep on Mondays to help cut down on time spent in the kitchen or doing housework, and when I really need to focus, I go to one of my favorite coffeeshops and don’t leave until I’ve finished the work I need to do for the day.

Recently, I’ve been experimenting with trying to figure out the best work schedule. Are my weeks more fun and productive if I take Wednesdays off and do a bit of work on the weekend? Do I still feel rested if I work for half of the day on Sunday so I can take Friday off to go to an art exhibit in the middle of the day? I’m still trying to figure out the right schedule, but I do avoid doing calls/skypes on the weekend if I can help it.

I Value My Time & Skills

I’ve spent a long time learning how to write for all sorts of mediums: screen, stage, novel, blog, Tweet — you name it, I’ve written it. I attended USC for screenwriting, so I’ve got training in storytelling that’s unique in the freelance marketplace.

So, I charge what I’m worth, and value my time and my skills. It can be intimidating at first to set your own rates, but think about what you’re bringing to the table. Your training, experience, and point of view are unique to you, and you should charge what you’re worth when it comes to assignments.

Also, don’t forget to factor in all the time you’re working outside of billable hours: submitting proposals for jobs, invoicing, researching, networking, learning new skills — most of that you’re doing on your own time. While all of this adds value to you as a freelancer, it’s something you need to factor into your weekly schedule and what you’re charging.

Taking Breaks & Traveling

In the periods of time that I’m full-time freelancing, I try and get out and travel as much as I can. This summer I went to Tahoe, San Fran, Santa Barbara, and am planning a trip in the fall to NYC and D.C. to catch up with some family and friends.

These breaks function as an important reset to keep me constantly learning and growing as a writer. That way, whenever I return to my work, I’m refreshed and with a new perspective.

I try and exclusively stay in odd and unique AirBnb’s that also are unique and interesting workspaces. In San Francisco, I stayed in a guesthouse on this beautiful ranch next to the sea with horses and incredible views. The property was so lovely and our host was amazing, so I’ll definitely find my way back there!

Staying Organized & Tracking Projects

The nature of freelance work dictates that you’re constantly working on several projects at once. This can be great, but it also means there’s a level of organization required at every step of the game.

As soon as I get assigned a deadline for a project, I put it on my calendar and add the item to my whiteboard’s to-do list. I keep an Evernote notebook for my freelance work, and take notes on every call I’m on so I can reference back to what I talked about with my clients if need be. This is critical with projects like memoirs that are very detail-specific, and where I need to organize a lot of different information.

Enjoy the Journey

Last but not least, enjoy every part of your freelance journey! I’ve had some amazing experiences working with some incredible clients. I’m lucky to be able to work on my own terms, and believe anyone who wants to should as well.

Happy freelancing, everyone!