For years, I’ve used a 5×7 piece of paper folded in quarters to keep track of my personal to-do list and weekly shopping lists. As Lifehacker recently commented:

There’s a reason there’s still so much paper around in this hyper-connected, everything-online age: the stuff is cheap, portable, compatible with all your applications, and everyone masters the interface by the time they’re out of the first grade.

Notwithstanding its simplicity, my piece of paper lasts about 2-3 weeks before it becomes so tattered and full of cross-outs that I need to start over.

Here are more of my paper-related issues:

1. Data entry: from week to week, I add new items, but I forget to cross off items like cat litter…so now I’ve got enough cat litter for a litter of cats
2. Data reuse: at the end of my piece of paper’s useful life, I re-copy 75% of the list I started with (not unlike my to-do list, but that’s a story for another day)
3. Multiple lists: invariably my wife or I find a recipe we want to try on the weekend so I end up creating a completely separate shopping list and juggling between two lists at the store
4. Sharing: to further complicate matters, we have a weekend home, so my wife and I will split shopping duties as we need to stock two places with purchases from different stores…

Even though I’m someone who is generally slow to change (and I certainly wouldn’t classify myself as a Web 2.0 techie)…I have to think there must be a web-based solution out there that not only addresses the paper-related issues but also provides even more value (like the ability to automagically add ingredients from recipes into my shopping list or proactively reminding me when I need to re-stock an item or the fact that the cat litter I usually buy is on sale, etc.).

So far, I’ve tried Backpack, Remember the Milk, Cozi and several other web based list makers – only to conclude that while they address some of my data entry, reuse and sharing issues – they’ve primarily replicated paper on the web. I’ve found that the effort required to keep them up-to-date, send to mobile, set recurring reminders, share with my wife, etc. takes more time than my current paper-based solution. Personally, I also find the blank slate nature of many of the new solutions to be off-putting…give me some guidance, a little structure or even better, anticipate my needs.

It’s these ideas – guidance, structure and proactively making the web useful – for tasks as simple as shopping lists that we’re focused on as a company and with the product we’re building.