Tracking Your Expenses: Ready for Your UK Tax Return?

January is traditionally a time of renewal, as the New Year carries with it new perspectives, promise and ambition. Here in the UK, it’s also the time of year when the dastardly Her Majesty’s Revenue & Customs come to take your hard-earned sterling!

With the self-assessment deadline for the 2008-2009 British tax year looming this coming Monday, it seems like an opportune moment to round-up some useful tools and services for managing your business expenses. Each year, I find that I’m missing a receipt, I can’t account for a crucial purchase or that paper receipts have literally faded.

Though too late to help my preparations for filing my own tax return this year, the selection below is driven by what’s caught my eye lately and my preference for web-based, iPhone and Mac (s aapl) applications. For the 2009/2010 tax year, I’ll certainly be employing one of the following:


Midnight App’s beautifully crafted Cha-Ching almost makes me want to do my expenses! With a playful name, Cha-Ching is very much designed with Macs in mind, employing a gorgeous, intuitive interface and integration with iSync (for scheduling bill payment reminders) and an iPhone edition for mobile use.

I found Cha-Ching’s real strength to be the ability to tag individual expenses, and — like iTunes’ smart playlists — create dynamic standing searches that can, for example, pull out anything you bought from tagged as “Apple” and “business expense.”

ReceiptFarm & Shoeboxed

We covered receipt organisation service Shoeboxed a couple of years ago, finding it to be a great solution for uploading, storing and organising your paper receipts, via a mail-in service. In the time since we last wrote about them, they’ve added a DIY “self-scanning & data entry” plan to their service, along with an iPhone app.

More recently, ReceiptFarm has begun to offer a similar Shoeboxed-style service, based here in the UK. Both services are almost identical, feature-for-feature, though ReceiptFarm appears to be slightly more expensive than its competitor. Also, where Shoeboxed is confident their stored receipts meet IRS guidelines for taxes, its not clear whether UK authorities accept scanned copies of expenses.

Expensify & WebExpenses

We reviewed Expensify early last year; it’s a comprehensive solution for managing and tracking expense reporting. The service is oriented around importing expenses, scanning receipts and generating reports. The service’s killer feature is the ability to generate tax authority compliant electronics receipts for expenses below $75. Recently, Expensify also launched integration features with bookkeeping service Outright.

WebExpenses also offers a similar service here in the UK, and with the likes of E*Trade and Heineken amongst its clients, it appears to have traction within large as well as small organisations. Features are broadly similar, though the service offers an innovative SMS expensing feature, which enables users to expense items as and when they occur.


Finally, recent weeks have seen the launch of inniAccounts, a comprehensive accounting and bookkeeping service designed specifically for UK-based freelancers.

inniAccounts was created by a pair of engineering contractors, frustrated with the minutae of managing their fiscal data using Excel (s msft) or complex accounting software designed for large organisations.

The service helps manage timesheets, invoices and payroll, but also include some features for compiling, completing and settling tax returns as well as mileage and expense claims. Uniquely, the service also provides a real-time tax calculation, helping users understand their financial position immediately, rather than waiting to the end of the year.

With only five days to the 31st January filing deadline here in the UK, it’s likely too late to adopt and employ any of the applications we’ve covered here, but they may help streamline your accounting for the coming 2009/2010 tax year, with greater productivity and accuracy.

Personally, after tinkering with each of the options above, I’m leaning towards Cha-Ching, simply because of the playful interface (it makes a difference for such a dull task!) and the immediacy of booking expenses via an iPhone app. However, I suspect something like inniAccounts will be a better long term solution, though I’m concerned that much of this space is occupied by startups rather than established companies, raising questions and doubts about the continuity of your financial data if the company ceases to trade.

Do you have preferred services, applications or methodologies for tracking and managing your expenses and receipts?