Creating a winning streak

Drawing roadmaps is one of my favourite things to do. It was also my biggest trap. I have a folder on my computer called “personal_projects”, which at this time has 165 folders. That means I’ve started 165 different projects in the last 4 years (the number of years since I got this laptop). If I counted the number of projects that I felt were “completed”, or “launched”, the grand total is 3. Now, I’m not saying that this in itself is a sign of wasted time, rather each of these projects has thought me something new - a new API, a new market, a new technology, a new language, etc. But what bothers is me the number of those projects I really wanted to finish and show the world, but were abandoned. The question to reflect on is: Why?

The answer is actually really simple, roadmaps are fun and awesome, but they’re long. They’re an infinite list of wants and needs. When the dust settles, and the pen is lifted off the paper, you realize the daunting task ahead. And that, I argue, is the first step to failure or abandonment.

One of the most important skills that I’ve learned is mapping our priorities and breaking them down to smallest tasks possible. These tasks act as a propeller and even completing the smallest of tasks will seem like a win. Then it’s just a matter of keeping the winning streak going.

Surprisingly, one of the places that’s nailed down this habit for me has been the gym. I’m pretty sure that the best athletes are already using “agile development” processes without even knowing it. The best agile development flows that I’ve been a part of have been successful at breaking down long, complex tasks into small bits that can be achieved in the smallest time possible. At the gym, that might look like getting another 90lbs added to a barbell, but knowing that taking incremental steps of 5lbs per week will get you there faster than trying to load up all 90lbs.

With this, comes the next most important aspect of this process: making sure you mark each small task’s completion as a success. Visually marking tasks as completed feels like success even though the whole tast list might not have been completed.

The size of the tasks I like to break down are in 30 minute chunks. I feel after 30 minutes, I usually need a break or I need some sort of conclusion. It’s important to understand that these task lists are not set in stone, they’re mean’t to be tweaked, and changed as you go. However, the large goal should remain the same.

Chain these tasks up, and you got yourself a winning streak. Even the smallest winning streak will keep you coming back another day.