The Best Invoicing Systems for Freelancers: A Writer Tries 10 Popular Options

The Best Invoicing Systems for Freelancers: A Writer Tries 10 Popular Options

Invoicing is something every freelance writer has to do. After all, earning money is what distinguishes us from the “writing just for fun” writers — but to earn that money, we have to invoice our clients.

While you might start by creating a simple invoice in Microsoft Word, eventually you’ll likely want to transition to an invoicing system or website that automates some of the work.

But what’s the best invoicing website for freelancers? The many choices available can be a bit intimidating, especially if you’re a newbie.

So we went on a mission. We signed up for trial accounts with 10 different online invoicing companies. For each one, we set a time limit of 30 minutes to explore and create mock invoices — imagining a scenario in which a decidedly unreasonable client had demanded we create and send an invoice from a specific invoicing site within that set time limit or we wouldn’t get paid.

With each site, we took note of 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. Here are the results of our experiment:

1. 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 that their Reports section was uncomplicated and easy to use. It has a search function similar to PayPal’s and it was simple to find exactly what I was looking for.

Cons: Our original “con” for Harvest was that their time tracker was tucked away and hard to find on their site; however, they recently changed that and it’s now easily found in the “Timesheets” section…so…no cons, really!

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

Paid Plans: $12 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!

2. Quaderno

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

Quaderno was simple and easy to use. Their Reports (“Numbers”) section was colorful and easy to read. They have a nice importer tool, offer several color choices and invoice templates, and even have an affiliate program for groups of freelancers.

Cons: The main “con” with Quaderno is that it doesn’t have a free plan. We couldn’t find anything else that really stuck out as terrible. However, the “pros” we found weren’t all that remarkable either. So perhaps Quaderno’s biggest “con” is that they’re fairly unremarkable in either direction. That said, we have high hopes for this company: they’re fairly new, and their middle-of-the-road-ness could just be growing pains.

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: $29 per month for one user (you) and unlimited clients; $48 per month for five users and unlimited clients.

3. Freshbooks

Pros: We were immediately blown away by Freshbooks — it’s an invoicing website that truly does everything. They had 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 a mobile app for 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. (Like, it’s super cool that you can register for GoDaddy domain names from your Freshbooks account, but it might be a bit overwhelming to some people – just sayin’).

Also, the free payment plan is a bit useless for busy freelancers, making paid subscriptions a must if you choose to use Freshbooks.

Free Plan: Yes, but you can only invoice one client per month.

Paid Plans: $15 per month for one user and five clients; $25 per month for 1 user and 50 clients; or $50 per month for one user and 500 clients.

4. 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. If you’re looking for other functions (like time tracking), this isn’t the invoicing site for you.

Simplybill also doesn’t have options for additional users or teams. So if you’re not a solo business, look elsewhere.

Free Plan: Sort of. You get one user and unlimited clients; however, you can only send out three invoices per month.

Paid Plans: $5 per month for one user and unlimited clients (but you can only send out 25 invoices per month!); $25 per month for one user and unlimited clients (and unlimited invoices).

invoicing for freelancers

5. The Invoice Machine

Pros: The Invoice Machine is another invoicing company that was made for freelancers and small businesses. Again, we found that comforting (if you’ve ever had to explain freelancing to a non-freelancer, you can imagine how edgy you’d feel if the company handling your billing didn’t understand your profession).

True to their name, The Invoice Machine ran like an efficient, well-oiled machine. It was exceptionally easy to create and send invoices using the clean, simple interface.

We also loved that we could export our invoices, estimates, templates, clients and other information as XML or CSV files.

Cons: The Invoice Machine only invoices. If you want additional features, you’ll have to look elsewhere.

Their Reports were also a bit too simple. Other than “Paid” and “Unpaid,” we didn’t see any records or stats. Or, if there were any, they were too hidden away for me to find (which is a problem in its own right).

Free Plan: Yes. You get one user and unlimited clients; however, you can only send out three invoices per month.

Paid Plans: $12 per month for two users and unlimited clients (30 invoices); $48 per month for unlimited users, clients and invoices.

6. Zoho

Pros: There were two things that really stood out to us about Zoho. The first was that they’re the only invoicing site we tested, other than Freshbooks, that offers a “Snail Mail” service.

Second, Zoho had an extensive Reports page with 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 recordkeeping is a welcome feature.

[Editor’s note: Zoho offers U.S.-based users an option to pay a 50-cent PayPal Business Payment fee, no matter the size of your invoice.]

Cons: We were a little annoyed with the four emails that were sent out to introduce us to the service, but were thankful they stopped coming after the initial four. We were worried they were going to start spamming us; however, that wasn’t the case. If you sign up, expect those four emails right away, and then you’ll be left alone to do your business.

Free Plan: Yes. You get one user and 25 clients.

Paid Plans: $7/month for 50 Customers and 1 user, $15/month for 500 customers and 3 users, and $30/month for unlimited customers and unlimited users.

7. Paymo

Paymo’s website and services have fully embraced the future and it’s glorious. The time tracker is great! They’ve also added Gantt charts, Kanban boards, and will soon be adding resource planning

Free Plan: No. After your 15-day free trial expires, you have to pay to continue the service.

Paid Plans: $8.95/user/month and you can expand that with flat rate add-ons, or $9.95/month for unlimited invoicing, or $19.95/month for the additional Gantt charts.

8. Ronin

Pros: To be honest, there weren’t many. Ronin was probably our least favorite of all the sites we took for a test drive. The only really impressive feature we found was the number of payment integration options they offered; however, payment integration is only an option for their pricier subscription plans (a definite negative!).

Cons: Before you can create an invoice, you must create a Client and a Project. If you’re selling Products or Services, you must add those into the system before they’ll show up on your invoice. Rather than writing in each project/product/service on the invoice itself, you select items from a drop-down box. It added an extra level of tediousness and inflexibility to the process.

In addition, you have to pay to see your Reports! Sure, the “free” plan is pretty much useless (most of us have more than two clients!), but we should be able to see our records for how much those two clients have paid us.

Free Plan: Yes. You get one user and two clients.

Paid Plans: $15 per month for one user and 30 clients; $49 per month for five users and unlimited clients.

9. Pay Panther

Pros: Pay Panther’s dashboard was one of our favorites: It was uncluttered and focused on the essentials — Paid, Due and Billable — with a calendar page and a “Feeds” box to communicate with your team (if you have one). Nice and simple!

Pay Panther was also very flexible with how you could bill your clients, with options for flat rates, item rates, user rates or per-project rates.

You can sync your Pay Panther account with your Google account (handy if you use Google Calendar!), Outlook, your iPhone/iPad or Mac Calendar.

[Editor’s note: Pay Panther offers an option to pay a 50-cent PayPal Business Payment fee, no matter the size of your invoice, rather than applying the standard PayPal fees to payments received. PayPal only offers this option to U.S.-based users.]

Cons: Other than the PayPal option only being offered to U.S. users, there weren’t really any cons.

Free Plan: Yes. You get one user and three clients.

Paid Plans: $24/month for two users and 500 clients when paid annually, or $39/month for 5 users and 5,000 clients paid annually.

10. PayPal

Pros: PayPal was also easy to use, had a great search function for invoice records, and didn’t charge any additional fees to send out invoices to clients.

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

Cons: The “Create Invoice” section of PayPal can be difficult to find for new users. It’s tucked away under the “Request Money” tab.

PayPal also featured no additional functions (like time tracking) and although clients can pay you via credit card, that’s not immediately obvious to users (and clients) who are unfamiliar with how PayPal works.

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: None.

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 originally ran in November 2014. We updated it in January 2017.

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!

Filed Under: Freelancing
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  • Sean Walsh says:

    I’d like to invite you to try

    It’s a time & expense tracking system for freelancers and project teams. You track your time on a daily time-sheet, add expenses as you incur them, and then you can generate professional invoices to your clients for the time worked & expenses incurred.

    It has a wide range of reports and charts that give you more insight into your billing performance, budget vs actual figures, and so on. I’ve attached an image showing the budget vs actual graph, which gives you an idea of how you are progressing through your budgets (as an amount or as a percentage).

    Give it a try. There’s also a demo version you can log into and play around with

  • Scott says:

    One new product that was not mentioned is ChronoBeans. This is specifically designed for one-person business with multiple/clients & projects. It only runs locally on your windows desktop – some people like to keep their clients, rates, and invoices stored locally and not in the cloud. ChronoBeans has a free trial and low monthly cost with free upgrades. More information can be found at Please consider ChronoBeans for your next product comparison. We’ve worked hard to create a product to meet the needs of freelancers and independent professionals.

  • Guillaume L. says:

    Great post Lauren!
    Have you ever tried Bonsai ( It allows freelancers to create invoices, but also to manage their contracts, proposals and payments directly from the platform.

  • Ric Evans says:

    Thanks for a very informative article. I chose Zoho and I hope it works out for me

  • Mark says:

    Any thoughts on the invoicing software Harpoon?

    I’ve been looking at some business banking accounts and some of them have invoicing software built in, which makes a lot of sense to me. I was previously looking at invoicing software but I’m not sure why it all can’t be streamlined. The catch I see is in setting up rates and such. Bank software probably isn’t that advanced

  • Claudia says:

    Hi guys,

    I like the article and the fact that you update it.
    Maybe for the 2018 update you will include elapseit also.
    This is a tool that integrated a lot of useful feature like time tracking, resource planning and project management.
    The time tracking is linked with the project, clients and invoicing in such way that it makes it easier to prepare and send the invoices whenever you need. Also, you will have the overview of what invoice is done, sent, paid and not paid yet.

    Just have a look,
    Claudia from Elapseit.