My Freelance Writing Workflow: Billing, Invoicing, Contracts and More (How to Manage Your Freelance Writing Business)
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Like most freelance writers and people on the planet earth, I don't really enjoy things like contracts, billing, invoicing, and all that jazz. If it was up to me, I'd spend my days frolicking through the forest writing poetry on tree bark and learning how to whittle tiny figurines of pandas.
Okay, to be honest I'd probably get tired of whittling and end up finding my way back to society, and starting a whittling business or something. As it turns out, even as I sometimes fantasize about escaping to the woods (as I did on a month long remote work trip to Colorado during these Plague Years) I do enjoy the parts of my job that include working with cool clients with fascinating stories.
Enter: reworking my billing and contracts workflow so as a freelance writer I can focus on what I do best (writing and whittling, obviously.)
The Best Billing and Invoicing Platforms for Freelance Writers
I remember the very first time when, years ago, a client asked me to send them an invoice for my work.
I turned to the good ol' Google machine: "ummm... what's an invoice?"
If you are in the same boat I was, dear reader, you'll learn from said Google adventures that an invoice is simply a request for payment for services rendered, with your payment info on there so your client can mail you cold hard cash. Or a check. Or fax you a buried treasure map, whatever currency you're working with, I don't know what's up in your life Dread Pirate Rodgers. I'm just a woman behind a keyboard, okay?
Anyways, the ways in which you approach billing and invoicing communicates how much of a professional you are. If your client asks you how you prefer to be paid and you just shrug and say, "cash is fine, feel free to use my dead drop location in the abandoned library," then you might be a drug dealer with a very niche hiding spot.
If you're not a drug dealer with caches of money all over town, you should probably figure out a more solid strategy for getting paid for your work, unless intrigue is part of your appeal I guess.
Throughout my career, I've moved around a bit to try a few different platforms, and each has its own pros and cons.
I started my freelance career on Upwork, which I love because it helps me find clients who might not have otherwise found me. Upwork is nice because it has a built-in billing and invoicing system -- but you pay dearly for it (20% of your income, which ain't monopoly money folks.) There's also a delay in payments, two weeks for hourly and five days for fixed-rate.
As I started working with clients outside of Upwork, I began using a combination of Docusign and Paypal for my freelancing, but the problem with that is with recurring payments/long-term contracts, I'm not a fan of Paypal since you have to send invoices manually. Paypal also has a limit of money you can withdraw after a certain point, so it's not great if you're making a full-time living as a freelance writer and need to be able to process larger payments.
So, I've finally landed on my favorite invoicing and contract management software, HoneyBook. I love this platform for a few reasons:
I can store contracts and client documents all in one place. I can store client contracts, NDA's, and other documents all in Honeybook, and my client and I can edit and sign contracts together to land on terms that make sense for us.
I can set up recurring payments and automatic billing with my clients. This is one of the things that's made so much easier with long-term clients, as I can just set up recurring payments without having to remember to invoice every month.
It's easy to use. It's super intuitive and easy to use, and I feel much more organized rather than having to run around to multiple platforms to get things moving the way they should.
It integrates with Quickbooks and Calendly. I use Quickbooks for accounting and Calendly for scheduling meetings, and they all integrate with HoneyBook so I can see everything in one place like I have a very boring superpower, like an all-seeing eye but for my freelance work.
If you're interested in giving Honeybook a whirl, I have a 50% off coupon you can use via my affiliate link. If you do give it a try, I'd love to know what you think!
When Should Freelance Writers Get Accountants and Lawyers?
Since we're talking money and legal things, I'll touch on a question I get asked a lot by fellow freelancers: when and in what capacity should I hire an accountant and lawyer?
Answer: generally, as soon as you can.
Once you're making even a part-time income off of freelancing, you've got tax obligations and other business things you'll need to take care of. You can also write off a lot, and having an accountant to help advise you is critical for tax season at the very least, if not year-round.
Having an accountant handle your bookkeeping helps if you've got a lot going on, and I know that my brain melts when I look at spreadsheets so having support there helps a ton. The years I did my own bookkeeping and expenses tracking felt like I was in the Matrix and not in a good way and I probably spent a full month doing my taxes.
Math phobias aside, on the legal side you'll need to consider getting a lawyer at the very least to help you draw up basic contracts you can use with clients. Generally, my clients ask for a basic agreement and an NDA, so you'll want something similar depending on your work.
As you keep moving through your professional career as a freelancer, this stuff will start to fall into place, so take it one step at a time. Asking for help from people who do this for a living is worth the cost of avoiding tax pitfalls or legal mistakes.
Optimizing Your Freelance Writing Meeting Workflow
I’ve mentioned Calendly before, but I wanted to expand a bit on the meeting workflow.
If you’re a freelancer who takes on large, complex projects, you’ll almost always need to have at least two Zooms or phone calls: the first will be a free “discovery call” where your client will hop on a short, 30-minute call with you to interview you about your experience and share more about what they’re looking for. Then, after they decide to work with you, they’ll schedule a kickoff call that can be an hour or so (project dependent!) where they’ll go over more details and you’ll go through any questions you have to get started. From there, you may have weekly check-ins, or meetings after certain milestones or deliverables are hit.
That can be a lot of meetings, especially as freelancers need to juggle several clients at once.
That’s why you need to either use Honeybook’s meeting tool, or have a more powerful scheduling tool like Calendly to help you manage different types of events. I have my main scheduling page, and then I have a bunch of secret events of different lengths with different availabilities (i.e. 30-minute meetings for my discovery calls, 60+ minute meetings for clients, and 2-hour meetings for longer workshop days.)
I also follow a maker/manager schedule popularized by Paul Graham that I talk more about in my book Freelancing for Creatives, so I generally reserve just two days per week for meetings. I have a separate calendar link for urgent meetings that shows more of my schedule, but I only use that link for true, urgent projects.
As a freelancer, you need to take advantage of the fact that you control your schedule. You need to set boundaries around your time so that you are able to complete great work for your clients!
Other Tips for Managing Your Freelance Writing Business
Since I like blog posts that go on to infinity like the outer reaches of the universe, I'll drop a few more extra tips I've been thinking about in terms of managing the business side of your work as a freelance writer. (You can also find more tips in my recent post about how I earn $350+/hr as a freelancer!)
Here are some of my top tips:
Find ways to organize deadlines and manage clients. Different freelancers have different work setups. Some writers have a lot of short-term clients, others have fewer long-term clients. Figure out the best way to manage your clients and track and hit deadlines, especially if you're in the former category.
Set weekly objectives. Setting weekly objectives can help you stay on-track and know exactly what you need to get done when. I find that my weeks tend to be a blend of administrative work (ugh) and writing work/client interfacing (which I love!) So I find myself needing to figure out which days I'm going to tackle what.
Protect your deep work days. I've mentioned this before, but I'll say it again here: protect the days in which you do deep, uninterrupted work. The business side of your business can sometimes creep into days you've set aside to dig into your freelance writing work, and that's not good. As a writer, you need full days to focus, and you need to push meetings and admin stuff out of those days and into their own days in order to protect your energy and focus. This is generally why I try and reserve meetings to only Tuesday and Thursday so I can spend Monday/Wednesday/Friday doing deep work for my clients. One of those days usually gets sacrificed to the Admin Gods, but I do my best to keep them completely uninterrupted so that I can do the work I've set out to do and deliver high-quality writing.
Find ways to reach potential new clients. Every time some marketing guru says "sales funnel" I want to throw up, so I'm not going to use that godforsaken jargon here. Instead, I'll encourage you gently to find ways to authentically connect with new clients. For example, a lot of my clients found me via this blog (hey guys!) and that's pretty nifty because you can see all my secrets and wordplay magic tricks and know exactly what kind of writer I am and how I collaborate with clients to deliver high-quality work. So if you're a freelancer looking to grow your business, try and think about ways in which you can cultivate a presence on the World Wide Web that showcases who you are and what you like to write. For me, I love writing witty blog posts, complex memoirs, and TV/film/podcasts/literally anything in the entertainment space. You'll find that all here on the good ol' blog. That's my "brand" I guess -- well, that and artisanal coffee and dreams of becoming an infamous whittler. Yeah, I'm not letting that dream die yet, readers! My Siri is going to hear me typing about whittling and give me hunting knife ads for the rest of eternity, just you wait.
My last tip is one I'm doing right now: getting myself organized on a Sunday night. Before I start my week, I spend my Sunday cleaning, writing out my weekly objectives, saving pictures of Walden pond to a Pinterest board as I gaze longingly out at the Los Angeles smog, and prep for the week ahead.
So that's it, that's my spiel. If you're reading this and are like, "damn that writer is organized, I want to work with her!" you can check out my work with me page.
If you're a fellow freelancer and you wanna say hi and shoot the shit, I'm always down to talk about cats on Twitter. Like, anything about cats. Also coffee, or if you've tried to go vegan and failed, that's great let's talk about it because man not eating cheese sucks and I will never go to that place again unless something goes terribly wrong in my life.
This blog has gone on for way too long and my clothes I put in the dryer are starting to wrinkle, so I'm going to go move them from the dryer to the couch where they will further wrinkle because it's nearing midnight and I don't feel like folding laundry. Maybe I'll write a separate blog post instead about a more efficient laundry folding system, but until then:
Stay safe fam,
-Amy
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