If you don’t track your time, you can’t bill the client. And if you don’t bill the client, you won’t get paid. You have to love the simple and logical nature of freelancing.

Fortunately most time tracking programs either include invoicing features or integrate with other applications for invoicing. In this post I’ll discuss programs I’ve used or evaluated, but I would like to hear from others about what they use to track time and handle billing.

Billings

After reading this great write-up by Veerle Pieters, I bought Billings 2 (Mac only, sorry PC users), and have been using it for all of my time tracking, invoicing and estimating ever since. It is a nice program, with an easy-to-learn interface, customizable templates and Apple Address Book integration.

Tracking your time is dead simple, thanks to the handy menu bar timer. You can even start new timers right from the timer window, if necessary, without going through the process of setting up a project or client. Then you can go back later to assign the time to the right client and project. The timer window can also handle multiple active jobs, so bouncing around between projects is very easy. The time also shows the dollar amount associated with a timer, which is helpful when working on a tight budget. At least for me, since I don’t like to do math.

One thing Billings does not do is make it simple to track estimated versus actual expenses, which so far hasn’t been a huge hassle for me. Billings also lacks support for multiple users.

There is a new version of Billings available, which has some interface and feature enhancements. It is definitely worth checking out (see Veerle’s review here). I’m hesitant to mention this, since it hasn’t been released yet, but Marketcircle (makers of Billings) have also announced a companion Billings iPhone application, so if that’s important to you, be on the lookout for it.

On The Job

On The Job 3 is an absolutely gorgeous Mac application with an iTunes-style interface that seems very easy to use. I haven’t used this program yet, because Billings 2 fits my needs just fine for now, but I am strongly considering upgrading to On The Job rather than Billings 3. The heads-up-display style dialogs look particularly nice and easy-to-use. As with Billings, the invoices are fully customizable, which makes the wannabe designer in me very happy. For more on On The Job, have a look at this review on The Unofficial Apple Weblog. Like Billings, On The Job is strictly for single users, not groups or teams of users.

Harvest

If you have more than one person’s time to track, aren’t on a Mac or you don’t want a desktop application there are several web-based time-tracking solutions, the most popular of which seems to be Harvest. If you have to do work on-site or from multiple computers, a web application is the way to go. Harvest was the first time tracking program I used when I started freelancing on the side. Harvest has a nice interface, strong reporting features, integrated invoicing, and a free desktop widget. Harvest also integrates with 37Signals’ Basecamp project management web application, allowing you to automatically import clients and projects.

Harvest has a free 30-day trial, after which you choose either a $12, $40 or $90 per month plan, depending on how many users, projects and other features you need. If you are a solo freelancer, it doesn’t take long to catch up to the cost of desktop apps like Billings and On The Job (both currently around $40). And if you have a lot of small projects, the project limit may be troublesome. But, if you have a team of users, Harvest may be worth it.

Other Time-Tracking Sites

If you don’t like Harvest, or just want to try something else out, there are several other time-tracking sites. One of my agency clients uses Timefox, from Functionfox (which, by extension, means I use it when working for this agency), which might have the worst interface of any time-tracking software or service I’ve ever seen, but works well enough.

When I mentioned on twitter that I was working on this article, I heard from fellow twitterer Bradley Joyce about a new service called TickStart, which looks to have nice features (including multiple users) and a very nice interface. TickStart doesn’t include invoicing, but Bradley tells me it will integrate with FreshBooks for invoicing. TickStart, which is currently in beta testing, hasn’t announced a pricing structure yet.

Shockoe is another new web-based time-tracking and invoicing service based here in Richmond and backed by the owners of Techead, a technology and creative staffing firm I’ve mentioned on this site before. Shockoe seems to have a similar feature-set to the other options, but its per-user pricing model may be better fit for small teams. Shockoe has unlimited projects and invoices for all price-levels. Shockoe is $4.99 per user, or $19.95 for up to five users (additional users are $3.99 each).

Invoicing

However you track your time, eventually you have to bill somebody. When it comes to sending invoices, there are even more choices, from Microsoft Word and Excel templates to full-featured accounting programs like QuickBooks. The first invoice I ever sent for freelance work was sent through Blinksale, a nice-looking and easy to use web service. Like Harvest, Blinksale includes Basecamp integration. With the free Blinksale account, you can send three invoices a month. Beyond that, you have to pay a monthly fee of $12, $24, or $49 for the ability to send 50, 250, and 1500 invoices a month. Though, if you are sending 1500 invoices a month, you can hopefully afford a bookkeeper to send your invoices for you.

Whatever solution you choose, make sure it fits your mental model for tracking and invoicing, because any barrier to tracking your time or sending invoices, however minor, will surely spell doom for your entrepreneurial adventures.