Driving home from Baltimore, I was listening to The Tropical MBA Podcast and came across episode 437, The Two Tomato Strategy.

I was already feeling inspired by an idea for a side project for a couple weeks–so it was the perfect time to listen to this episode. The main idea behind the two tomato strategy is to spend an hour a day (M-F) on a specific project.

While not required, they recommended setting a goal for 90 days and committing to it.

I will be devoting one hour per day for 90 days to work on a product called Jonah (a working name for now).

One thing I’ve found especially challenging in a distributed work environment is setting long term deadlines and monitoring progress. Everyone knows that estimating software timelines is super hard. Jonah will live in the middle of your deadline(s) and the present day.

How Jonah Improves Your Workflow

If you are like me, you are probably juggling a dozen projects. Each product has a different scope, deadline, and priority. For example, you NEED to ship a feature by the end of the month but have five hot fixes you need to deploy over the next week or two. You also need to allot time for customer support, documentation, meetings, and the other normal daily activities.

Jonah will look at all of your projects and tasks and build a calendar to make sure you allot ample time day-to-day and week-to-week. Just tell Jonah how much time you expect something to take and it will block out your schedule so you can be confident you’re staying on track.

But…Estimating is Hard

More times than not, scope normally expands and you need to push deadlines back. The more you use Jonah, the more accurate it can be with estimating the average time you push projects back by. If you regularly extend a projects due date by 20%, Jonah can anticipate this and build this buffer into your schedule or alert you when you may be at risk of missing a deadline.

But…I’m just one part of the team

Jonah can connect with your calendar and everyones’ calendar on your team. It will look at everyones available time and work within those schedules to divvy out the appropriate time for each deliverable.

Sounds neat…but 90 days?

I’d love to ship all of this functionality in 90 days but realize there are quite a few unknowns between here and there. Additionally, as people use the product, things are likely to change based on feedback. So this is what I commit to deliver over the next 90 days:

  • A solution that helps individuals stay on track
  • A solution that works with the time you have available
  • A solution that is simple and easy to use
  • A solution that has a paid version for teams or more advanced functionality
  • An accompanying marketing site and collateral

The shape and scope is up the air, but I’ll consider it a success if I accomplish the above. If this project sounds interesting to you, please feel free to reach out on Twitter.