While you might start by learning how to make an invoice in Microsoft Word, eventually you’ll want to transition to an invoicing software or invoice generator that automates some of the work.

But what’s the best invoice maker for freelancers? Between Freshbooks, ZoHo, Bonsai, Wave and more… there are so many choices available, it can be intimidating.

Invoicing software options for freelance writers

We went on a mission to find some good options for you, including several free invoice maker tools. Our goal here is to take the hassle out of choosing an invoice generator, so you can get on with getting paid.

To accomplish this, we signed up for trial accounts with 10 different online invoicing companies.

For each invoice maker, we set a time limit of 30 minutes to explore and create mock invoices. We used that time to note any immediately positive features (pros) as well as anything that stuck out as challenging or frustrating (cons).

We also checked out their cheapest and most expensive payment plans — and noted which software offered a free option — and we’re eager to share the results of our experiment.

Here are some recommended invoicing software tools.

1. Bonsai

Pros: Properly pronounced “bone-sigh,” this invoicing system is as well-manicured as the miniature trees it’s named for. We also love that “writing” is one of the top three options when the software asks “what do you do?” as part of the setup. 

With Bonsai (also known as Hello Bonsai because of its URL), you can quickly create one-time, recurring, and recurring auto-payment invoices, all of which allow you to easily add in specifics like discounts, taxes, peripheral expenses and even preferred payment method.

Bonsai also offers time tracking, expenses, and integrates a proposal and contract system — which we especially love for freelance writers, who all too often work without any formal agreements made in writing. You can easily have your client e-sign a contract or approve a proposed estimate before you start working, which can provide some much-needed stability to your freelance career.

Cons: Bonsai is clean-looking and easy to use, but you do have to pay for the privilege. However, plans start at a reasonable $21 per month and include unlimited projects, and there’s even a neat referral system that gets you a free month when you successfully recruit a friend. 

Free Plan: Not really… though they do have a cool referral program, as mentioned above. You can also test the waters with a free 14-day trial.

Paid Plans: $21 per month for the majority of the software’s capabilities, including unlimited projects, customizable branding, advanced reporting and chat support. You can upgrade to the $32 per month plan for white labeling, sub-contracting, and to add additional users, which will also require an additional $9 per person.

Best For: Freelancers who may be considering adding employees or colleagues to their team, and who want to be able to send professional proposals and contracts to solidify their relationships with their clients.

Our full review: Meet Bonsai, A Task-Management Tool Keeping Freelance Writers Organized

2. FreshBooks

Pros: We were immediately blown away by FreshBooks — it’s an invoicing website that truly does everything. They have a built-in time tracker, a team management system and even a way to connect your accountant to your FreshBooks account to make tax time easier!

From the moment we signed up, we felt like they “got” what we, as freelance writers, need: There were options for “content marketer” and “copywriter” (among other writing-related career choices) as Company options on the sign-up sheet. Nice!

The new FreshBooks also offers an invoice app for mobile, both iOS and Android, so self-employed professionals can run their businesses anytime, anywhere.

They also have an excellent referral/affiliate program.

Cons: Since we were basing this article on how “intuitive” the site was for new users with limited time on their hands, we have to say that the “bigness” of the site could be a bit overwhelming for new users just looking to invoice a client. 

Also, there’s no longer a free option; you’ll need to upgrade to a paid monthly plan to use the service after the initial 30-day free trial. That said, even when it existed, the free plan was pretty useless, only allowing you to invoice one client per month.

Free Plan: None, though you can check out the service with a 30-day free trial.

Paid Plans: Plans start at £6 a month, though the most popular option, which allows you to send unlimited invoices to up to 50 clients, is £11 per month. There’s also a premium plan, which is £17.50 a month, but that’s targeted toward businesses.

Best For: Just about any freelancer, to be honest! FreshBooks is popular in the industry for a reason.

Our full review: The Beginner’s Guide to Freshbooks: How to Create an Invoice

3. Zoho

Pros: Like Bonsai, Zoho is one of the only invoicing software tools we tested that integrates a digital proposal option. Called “estimates,” these documents automatically roll over into invoices if your client accepts your terms. They also allow you to send transactions by “snail mail,” though you have to purchase additional credits to do so. 

What’s more, Zoho had an extensive Reports page with more than 25 different categories. It wasn’t just organized, it was micro-organized! For someone like us — the tightly-wound physical embodiment of organization — the extra effort they put into their record-keeping is a welcome feature.

Cons: While Zoho’s invoicing software is pretty easy to navigate, be forewarned that if you go to the main Zoho page, you might be overwhelmed. The company also offers accounting services, IT management, and CRM software, many of which may be beyond the scope of your needs as a freelance writer. If you’re interested in its invoicing feature, we suggest navigating to that specific page for simplicity sake.

Free Plan: Yes. You get one user and you can invoice up to five clients. 

Paid Plans: £16 per month allows you to invoice up to 50 clients; £28 per month allows you to invoice up to 500 and also unlocks some additional features (and can be accessed by up to three users); £40 per month allows unlimited clients, up to 10 users and even a custom domain through the system. Note these are monthly prices. If you pay for a year upfront, you can get two months for free.

Best For: Because Zoho also offers a wide range of other business organizational tools, we like this option for freelancers who may expand their company in the future.

4. Harvest

Pros: The thing we liked best about Harvest was the finished invoice: it was easy to read and the total amount due was written both at the bottom in large numbers and in normal-size print within the invoice itself. Even if you have one of those clients who hates to read (we’ve all had them), there’s no way they could “accidentally” skip over the amount they owe you!

We also liked the variety of viewpoints Harvest gives you of your work. You can set up a variety of projects and access reports that show you exactly how much of your valuable time you’re using on different tasks and clients — which is key for maximizing your rates. 

Cons: Our original “con” for Harvest was that their time tracker was tucked away and hard to find on their site; however, they’ve since reconfigured the site and “Time” is now the very first tab at the top… so… no cons, really! 

Free Plan: Yes. You can have one user (yourself) and send invoices to unlimited clients with two active projects.

Paid Plans: $10.80 per month for one user and unlimited clients – which also allows you to use their apps and online extensions. Plus, you get a 10% discount if you pay for it yearly, and you can try it out with a 30-day trial (no credit card required).

Best For: Writers who regularly invoice the same client with similar projects (as the software easily allows you to set up reusable templates), as well as those who really want to key into where their time is going.

5. Quaderno

Pros: Quaderno was specifically made and marketed toward freelancers, and our initial impression was that they “got” us.

And by “got” us, we mean they understand one of the biggest freelancer struggles: taxes.

Quaderno’s whole schtick these days is that they make figuring out your taxes a whole lot easier, automatically calculating and adding your sales tax to your invoices (if you desire). When it comes time to file your return, you can access all the data in easy-to-read reports. And the invoices themselves are clean and minimal: they get the job done in an eminently readable fashion.

Cons: The main “con” with Quaderno is that it doesn’t have a free plan — and the paid plans they do have are pretty pricey (see below). Also, all that functionality comes with a bit of a learning curve, and you’ll need to click around a bit to get a hang of the software.  

Free Plan: None. You get a seven-day free trial and then you have to get a paid plan if you wish to continue.

Paid Plans: Plans start at the $49-per-month “startup” tier, which gets you up to 250 transactions a month. While that level would cover a lot of freelancers, if you need more, you’ll pay for it: upper tiers are $99 and $149 per month. Below the pricing options, it does mention a “hobby plan” for $29 per month for those with fewer than 25 transactions a month.

Best For: Quaderno is specifically set up to help you handle both domestic and international clients, so if you’re a remote nomad or your business is worldwide, this might be a great option.

6. Simplybill

Pros: Simplybill is exactly what you’d expect it to be: Simple. There were about four tabs to choose from and within each page, everything was written out in large letters and chunked into easy-to-understand sections. Simplybill was a no-brainer when it came to creating invoices — we didn’t even need a full half-hour!

We were also amused that a site that embraced simplicity so thoroughly had a total of 37 different template designs to choose from (hidden way in the “Settings”). Fancying up my invoice was optional, but discovering said option was a fun surprise.

Cons: Simplybill doesn’t do anything but invoice clients. While simplicity can be appealing, if you’re looking for other functions (like time tracking), this isn’t the invoicing site for you. Also, the site only accepts payment for subscriptions via PayPal, so if you don’t have a PayPal account, that’s an additional hassle.

Free Plan: No, but you can try it out for free for 14 days.

Paid Plans: $5 per month for unlimited clients (but you can only send out 25 invoices per month!); $15 gets you 100 invoices; $25 gets you unlimited invoices.

Best For: Solo freelancers looking for an uber-simplistic invoice generator.

7. Paymo

Pros: Whether you’re a solo freelancer or someone who regularly works as part of a team, Paymo is a great way to track your projects from start to finish, even allowing you to separate out sub-tasks in the implementation, planning and launch phases. The invoices themselves are easy to make and clean-looking, and the software offers all the other extras that are quickly becoming industry standard: time tracking, expense reports, etc.

But despite the extensiveness of functionality, Paymo still maintains a startup feel — in the good way. For example, the introductory email we received allowed us to send a direct reply to the CEO.

Cons: We love a lot about the way Paymo is set up on the backend, but the multiplicity of tasks and subtasks can make time reports look cluttered. (That said, you’ll get even more granular data on where your days are going, which could be super useful.)

Furthermore, with only three invoices allowed at the free level, you pretty much have to upgrade to a paid plan to use this system seriously.

Free Plan: While there is a free option, it only allows you to send three invoices per month. 

Paid Plans: $10.90 /user/month gets you unlimited invoicing capacity and extended functionality; if you work on a larger team, upgrading to $16.90 /user/month unlocks Gantt charts, resource scheduling, onboarding, training and more.

Best For: With its focus on multi-user management, Paymo is our pick for freelancers who are solidly team players.

8. Wave

Pros: If you’re looking for an all-inclusive invoicing platform that also integrates functionality like payment receipts, recurring invoices, expense tracking, and even the ability to run payroll, Wave invoicing has you covered. Honestly, it’s harder to find something you can’t do with this software… but even just on the invoicing front, it’s uber-detail oriented. I mean, you can use an actual hex color code to nail down your exact invoice accent color.

Better yet, this system is honest-to-goodness free at the basic level: you’ll get unlimited invoicing, top-of-the-line accounting software and receipt scanning for $0 per month, though invoices paid by credit card directly through the system are subject to a 2.9%+$0.30 fee (which is pretty standard). 

Cons: As with a few of the other invoicing systems we’ve reviewed here, the increased functionality is a bit of a missed blessing. There’s a lot to see, and even with its helpful launchpad and step-by-step guide system, you’re going to have to click around a bunch before you feel like you’re getting the full functionality.  

Free Plan: Yup — and it’s actually fully functional. Score. 

Paid Plans: You’ll pay an invoicing fee for credit card payments of 2.9%+$0.30 per transaction, as well as ACH transfer fees starting at 1%. If you need to use the program to run payroll, you’ll upgrade to a monthly plan starting at a $20 base fee and moving up depending on what features you need to implement. 

Best For: This system is our pick for freelancers who’ve been DIY-ing their accounting and want a free way to take their bookkeeping to the next level.

9. Invoicely

Pros: Yet another powerful platform offering multiple functionalities, including digital estimates, expense tracking, and the ability to hyper-customize your company’s branding and appearance. Invoicely really stands out to us because it’s one of the few systems we’ve encountered that offers unlimited invoicing for free (though some of the other functionality may be limited).

At upgraded levels, Invoicely offers an easy way to track mileage, so if you’re a freelance writer who frequently travels for work — such as, to interviews or reporting locations — it’s nice to have an easy way to calculate that deduction.  

Cons: At the free level, customization abilities are limited and you’ll have to accept payments through PayPal… in which case, it might be more parsimonious to keep everything on PayPal. (See: list item #10!) 

Free Plan: Yes. Win.

Paid Plans: Plans start at $9.99 per month for up to two team members and full access to Invoicely’s functions, and move up from there based on the number of users who need access.

10. PayPal

Pros: PayPal is an OG invoice maker for good reason: it’s easy to use, has a great search function for invoice records, and doesn’t come at any additional cost beyond the 5.4%+$0.30 fee assessed per transaction. 

These days, PayPal has stepped up its game with built-in estimates, recurring invoices, reports offering sales insights and more.

It makes sense to use PayPal for invoicing if all (or most) of your clients will be paying via PayPal anyway!

Cons: PayPal is really all about the money and doesn’t offer some of the upgraded business-organizational features the other platforms do, like time tracking. And the home page can be a little inscrutable for new users; it takes a while to figure out where all the functions you need access to live. 

Free Plan: Yes, in a sense. PayPal doesn’t charge any extra fees for sending out invoices; however, once your client pays, the usual PayPal fee will be taken out of your earnings.

Paid Plans: See above. Same percentage applies.

11. Xero

Pros: Xero is a widely acclaimed accounting software with several notable pros for freelancers and small businesses, including its user-friendly interface, comprehensive features such as invoicing, expense tracking, and bank reconciliation, as well as the ability to integrate with various third-party applications, providing a holistic financial management solution.

Additionally, its cloud-based platform allows for real-time collaboration and accessibility from anywhere, streamlining accounting processes and enhancing overall efficiency.

Cons: While Xero is praised for its extensive features, some users may find its pricing relatively higher compared to other alternatives, which could be a potential drawback for freelancers and small businesses on a tight budget.

Plus, as a cloud-based platform, users without a reliable internet connection may face challenges accessing their financial data or performing tasks in real-time.

Free Plan: No, potentially its biggest downside.

Paid Plans: Plans start at £3.75 per month and progress upwards in scale dependent upon the specific numbers of invoices sent, users etc. Full details and breakdowns can be found on their website.

12. Invoice Ninja

Pros: Invoice Ninja is an open-source invoicing and time tracking tool, offering a notable advantage with its self-hosted option, allowing users to have full control over their data and customization.

The platform also provides a range of features, including customizable invoice templates, expense tracking, and project management, making it a versatile choice for freelancers and small businesses.

Cons: While Invoice Ninja is a robust invoicing and time tracking solution, some users may find the learning curve steeper compared to more straightforward platforms, particularly if they are not familiar with open-source software.

Plus, as a self-hosted option requires technical expertise and maintenance, it might be less suitable for users who prefer a fully managed, cloud-based solution.

Free Plan: Yes. The free plan provides basic features for freelancers and small businesses, including unlimited invoices for up to 20 clients.

Paid Plans: Starting at $12 per month, paid plans allow for unlimited clients and a whole raft of extra features and functions.

Do you use an invoicing site to bill your clients? Are you using one of the 10 we reviewed? How have you enjoyed your experience?

This post contains affiliate links. That means if you purchase through our links, you’re supporting The Write Life — and we thank you for that!

This is an updated version of a story that was previously published. We update our posts as often as possible to ensure they’re useful for our readers.

Photo via Andrey_Popov / Shutterstock 

Freelance retainers, while not quite as thrilling as Jason’s hunt for the sheddings of a mythical beast, do have an air of mystery to them. And these types of freelance contracts are often just as hard to come by!

A “retainer” for a freelance writer usually refers to a retainer agreement. It’s a contract whereby your client typically pays you a set amount of money each month (or week or year) for a certain set of deliverables, a scope of work you agree on in advance.

Retainer agreements can either be really good or really, really bad. To decide whether a retainer agreement is right for you, I’m going to outline a few of the basic pros and cons.

Pros of working on a retainer agreement

Considering the amount of freelance writers who “swear by” retainer agreements, there must be something good about them, right? Well, yes.

If you know how to work them to your advantage, retainer agreements have several positives.

1. The pay is more reliable

One of the few downsides of self-employment is the income uncertainty that comes with it. The infamous “feast or famine” cycle has left more than one freelance writer running away in terror.

Your bills keep coming regularly, but your payment schedule is constantly up in the air. You might even earn more as a freelancer than you did in your day job, but not knowing when that paycheck will arrive can be stressful.

When you work on retainer, you typically don’t have that payment problem.

Provided your client pays as agreed, you’re guaranteed a steady flow of income. It’s the closest a freelance writer can get to a reliable paycheck and recurring work while still being their own boss.

2. You can get (and keep) better clients

Entering into a retainer agreement takes trust from both parties, but especially on the client’s part.

Typically only the “best” of your clients will suggest keeping you on retainer. These tend to be the clients you’ve worked with for a long time, who are most familiar with your dependability and general amazing-ness. Since you already have a working relationship, those clients are also already familiar with your rates.

Plus, you’ll also be able to work for a smaller group of “premium” clients – rather than a scattershot of “anyone who comes along” like you may do now.

3. Clients love retainer agreements

There are a few exceptions to this rule of course, but most clients would rather continue to work with a freelance writer they know they can rely on than scour the Internet looking for someone new every time they need a writer.

By setting up a retainer agreement, your clients have an added layer of confidence that your services will be there when they need them. In other words, it creates a feeling of security not only for you, but also for them.

Cons of working on a retainer agreement

Not everything about working on retainer is all it’s cracked up to be. You may encounter the following disappointments:

1. The pay can be lower

Some clients prefer retainer agreements because freelancers sometimes offer their services at a slightly decreased rate in exchange for steady pay.

While this can be a disadvantage, it can also work in your favor, depending on the rates you agree on. Why? Because when you’re on retainer, you no longer have to spend as much time pitching or trying to land work. Those aren’t billable hours!

If you know you’ll get paid consistently for a certain number of hours, it might make sense to take a small hourly pay cut; if you set your rates in a smart way, you’ll still make more in the long run.

2. Work levels can still vary

When you work on retainer, you may find that some client months entail little or even no work; while other months you’ll be overworked.

If a client expects you to be “at the ready” 40 hours per week, but according to your retainer, you only get paid for five, then your monthly rate quickly becomes less than you’re worth.

As a freelancer on retainer, you still have to be clear when you communicate about expectations, scope of work, and deadlines. Even though you have a steady work agreement, you may not be able to make assumptions about what’s headed your way in the coming weeks or months.

3. You’ll have to deal with scheduling conflicts

While working on retainer, you’ll always have a potential deadline hovering over you. And depending on the specifics and flexibility of your agreement, your deadlines may be highly inconsistent. Essentially you’re under contract to be at your client’s beck and call.

When you have a vague retainer project deadline looming over your head, it can be hard to accept and schedule other time-sensitive work. Even when your deadlines are clear, if your workload changes from month to month, you’ll still be left in the dark. You never want to risk overbooking yourself and, if you’re on retainer for an unpredictable client, it’s harder to judge when that’s a possibility.

4. Dependency issues are common — on both sides

Since your contract likely states you’ll be “at the ready” whenever your client needs you, you might be kept on a relatively short leash. Many of us left traditional work behind to be our own boss, so the expectation that you’ll always be available can be frustrating. This is something you might want to put limits on from the get-go.

However, personal frustrations aside, retainer agreements have a potentially more sinister side-effect: dependency. They encourage you to place all — or most — of your business eggs in one basket. And that almost always spells disaster for freelance writers.

Even with a retainer agreement, you’re still a freelancer and your client has the option to leave you at any time — so you can’t rely on a single client to get you from month to month. You still want to diversify your income sources!

Perhaps the best solution here is to have several clients on retainer, so you’ve both diversified your income and can rely on those paychecks month after month.

How to make the most of working on retainer

If you have amazing time-management skills and a little less freedom feels like a fair price to pay for steady income, then working on retainer might be for you.

But if this is a path you want to pursue, take heed of the following:

• Clearly define the scope of the work in your contract. Retainer agreements have a tendency to get out of hand. If your contract is poorly planned, there’s a good chance your client is about to take advantage of you — even if they don’t intend to do so.
  
  Make sure you understand clear definitions of not only what you’ll be paid, but also the type and amount of work. For example, rather than having “one blog post per month” listed in your contract, try more specific wording like “one blog post up to 2,000 words per month, with topic agreed upon one week prior to deadline.”
• Suggest a trial or probation period. If you’re unsure about working on retainer and need to get comfortable with the idea, suggest a shorter payment period over a probation period. Say, “Let’s start with __________ and see how we feel.”

Remember: you can always renegotiate with your client at a later date and sign a new contract with that updates each party’s responsibilities. Nothing is permanent.

• Choose a service that works well with your arrangement. The best retainer projects are exactly that: projects. If your client tries to offer “per hour” services rather than “per project” services, small details may eat up too much of your time.

Stick to project-based arrangements that can be done routinely: three blog posts per month, or a set number of social media posts, e-newsletters or other repeating content updates.

Above all else: Be realistic. If your schedule is already stretched to the limit, say “no.” Don’t let the lure of a steady paycheck fool you into thinking you can somehow materialize extra hours in the day through sheer will alone.

Have you ever worked on a retainer agreement? What advice would you add? Let us know in the comments!