Finally, Apps Pull Their Weight by Keeping Track of Who Owes Us $$$

Sep 29, 2017 | Brian Merritt

What’s a major barrier to successful freelancing? The administrative stuff. Keeping track of who owes you what, and following up, and chasing people around. Being a sole proprietor means not having a secretary or accounting team. Luckily, technology has introduced a support network in the form of invoicing apps.

These pocket administrators can organize your working life so you’re free to hustle. But how good are they at helping you be a better, and richer, you?

1) Invoicely

Invoicely is focused on invoicing and invoicing only. You can track your mileage and earnings as well, but it’s all in service of invoicing as neatly and efficiently as possible.

With Invoicely, clients’ information is stored so when it comes time to send a bill, you just type in a name and their information autofills into the template. Your details autofill as well — name, address, email — and there’s the option of adding a customized line at the bottom. This might be where you state fees for overdue payments, or it might be where you add a thank you note. Either way, the personalization is appreciated. It makes clear that you’ve put your own touch on the document. You can link to a PayPal account, and accept payments directly through the app.

The only downside to Invoicely is that it’s a bit time-consuming to set up, depending in part on how many clients you have. But it’s worth it in the end.

Invoicely offers three plans based on how many users you’ll have. The basic plan is $9.99/month for up to two people; the professional plan is $19.99 for up to 10 people; and the enterprise plan is $29.99 for up to 25 people.

2) Paydirt

Paydirt offers a bit more than Invoicely: the program tracks your time spent working on projects in addition to creating invoices. But it’s not particularly intuitive at first, as the time tracker is a pop-up that appears on the side of each page. But for freelancers or businesses who bill by the hour, this can be a lifesaver. Enter your hourly rate, tell the timer which project you’re working on, and hit the start button. It automatically converts the time into a dollar amount, which you can then upload into an invoice later. That means no more forgetting to track your time and then trying to remember when you started; it’s all there for you.

Paydirt also features an invoicing program that is, again, particularly useful for those who bill by the hour, as the app does the math for you by calculating how much you’re owed based on how much time you clocked. The breakdown of invoice management isn’t quite as robust as Invoicely, but Paydirt casts its net a bit wider in terms of functions. You can link to PayPal or Stripe accounts to collect payments.

The app has six different plans, ranging in price from $8/month to $149/month, depending on what you want to use it for, and how many people will be on the account.

3) is a very comprehensive app. In addition to invoicing, time management, and linking to outside payment accounts, it offers readymade contracts, expense management, and a “Chief Operator” to provide personal attention. This all means that there’s another, secret function, which is that it keeps you from procrastinating.

Navigating is simple, with easy-to-follow language. You’re always given the option of not doing something (i.e., you don’t have to import your clients right away). The most impressive thing about is the contract-creation system: simply input a few pieces of information — what you charge as a late fee, for instance — and it creates a personalized contract. offers a free option, but it’s pretty limited; you can send only 2 invoices and track 20 expenses per month. Their monthly fee for unlimited use is $19, or $134.40 annually (which works out to $14 per month).

4) Invoice2Go

An industry standard, Invoice2Go streamlines the creation of invoices. Getting started with this app means customizing your invoice -— including selecting from a small pool of designs (no decision paralysis here) and adding a logo by choosing one of their stock clip-art images (I enjoy the tasteful moustache) or uploading your own — then sending to your heart’s content.

Invoice2Go allows customers to pay either through PayPal or using a credit or debit card, which is nice, but be aware that there is a charge for the latter option. It also tracks expenses for tax purposes and allows you to store photos of your receipts; never again will you dig through bins and stab yourself with multiple thumbtacks (why do you even have thumbtacks?) in search of a receipt from eight months ago.

Plans start at $19 a year for 50 invoices and 5 members, and go up to $399 a year for unlimited invoices and as many as 20 team members.