Shawn Dahlen

Periodic updates on my software startup endeavor

Working Smarter, Not Longer

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This post discusses my challenge to work smarter, not longer, and the path that led me to build 4dashes — a productivity tool inspired by the Pomodoro Technique.

Frustration was mounting. I wanted continued success at work without sacraficing the value I place on family. Within the span of a few years, my responsibilities had increased significantly from an associate software engineer to a program manager overseeing multiple projects. Naturally, the pressure to work longer came with it — in fact, our culture demanded it — the number of hours we worked was viewed as a badge of honor. Frustration was mounting indeed.

As a newly minted manager, my first inclination was to become more organized. It seemed rational. The more organized I was the more in-control I felt. I tried several productivity tools based on GTD. They worked wonders for organizing my work but did little to help get things actually done. My inbox was zero but my todo list was a mile long. It seemed like I had to reset myself every few weeks to regain the illusion of control I craved.

After repeating this nasty cycle more times than I care to admit, I reflected on the situation and realized that my old work habits were becoming an impediment. With less responsibility, I was able to deliver perfect results while still handily supporting interruptions and socialization with colleagues. But as my workload increased, this became untenable.

The time I dedicated to delivering results was squeezed by an increasingly interrupt-driven work environment and I let it happen. Looking back, it makes sense. Constantly responding to email, helping colleagues, and putting out fires creates a short-term reward loop that is tough to break. Don’t get me wrong, I understand that much of this comes with accepting more responsibility. I simply refused to fall into this trap that so many around me did. I sought new work habits that would assist in setting limits so I could focus on what was important.

When I came across the concept of the productivity dash, and later, the Pomodoro Technique, I was immediately drawn in by the power and simplicity of the timebox. Select an important task to focus on and work on it uninterrupted for a small duration of time. By doing so, you become more mindful of the triggers for interruption and develop strategies to handle them effectively.

Unfortunately, changing habits is hard. While recording the completion of a dash or pomodoro does brings a small sense of accomplishment, I started brainstorming about gamification techniques that could be applied to the concept of a timebox. The objective was to replicate a compelling reward loop facilitated by challenges and leaderboards that would build a sustainable path towards mastery. The result was the product of my recent startup, 4dashes.

4dashes is a productivity tool inspired by the Pomodoro Technique that transforms your todo list into a game challenging you build more effective work habits. Habits that enable you to plan and accomplish important work in the face of urgent and unexpected activities. And with that in hand, you gain the power of truely managing expectations and the satisfaction it brings.