Maximizing time is a constant struggle. Motivational speaker and entrepreneur Chris Winfield knows this all too well, as he struggled for years to make proper use of his time. After countless research, trial and error, and a little banging of his head against the wall, Chris has discovered that the key to him living his most productive life is 25 minutes long.
Desperate for a way to improve his productivity, Chris eventually discovered and settled on the Pomodoro technique. Invented by Frances Cirillo in the 1980’s, the Pomodoro technique maximizes time and efficiency by blocking out 25 minutes of uninterrupted focus. From there, Chris cut his work week in half, transformed his career and, most importantly, balanced his life.
Chris admits to being a former workaholic who regularly clocked in 60 to 80 hour workweeks. Despite the excessive hours he put into co-founding one of his companies, a marketing agency, things didn’t go exactly as planned. Many of Chris’ worst fears came true as an entrepreneur, and in his own words “the company completely imploded.”
But the story doesn’t end there; in fact, it just begins. “Failing at something led me to look at it as an ultimate blessing because I realized I was completely miserable and inefficient,” Chris explains.
Chris now cites this failure as one of the best things that ever happened to him, because it motivated him to make transformative changes in how he approaches not just his work, but also his entire life.
“Looking back, I was so inefficient,” he admits. “I was spending 80 hours on something but not getting a lot done, because I really just didn’t understand how to work.”
A Pomodoro Pact
Chris researched all kinds of ways to work more productively before he finally stumbled on the Pomodoro technique. The Pomodoro technique is the practice of choosing one task and making the small commitment of spending 25 minutes completely focused on that initiative.
The name Pomodoro is derived from the tomato shaped kitchen timer that Francesco Cirillo, the movement’s founder, used while perfecting the technique.
Chris started small by resolving to accomplish one Pomodoro a day. He quickly found that adding a timed structure around his process forced him to focus in a way he wasn’t previously capable.
Chris began gradually upping his Pomodoro sessions, seeking to optimize his productivity and subsequently help him find more balance in his life. He now has a steadfast commitment to 40 Pomodoros per week, which equates to 17 hours. He asserts that he gets more done now, in 17 hours, than he ever did when he was regularly pulling 60+ hour work weeks.
“When your energy is focused on just one thing, then you become more powerful.”
- Chris Winfield
Chris uses a Trello board to break down big projects into small tasks, assigning each as an individual card. Then when he is ready to “Pomodoro” a task, he moves that card over to an “In Progress” list, starts the timer, and goes heads down into focus mode.
Battle Your Own Resistance Movement
Eliminating all distractions and dedicating time to one single initiative isn’t easy, and it takes practice. People spend an inordinate amount of time focused on why they don’t want to do something, or worrying that the end product won’t be of a certain caliber. Chris realized the only way to get past that was to give up on the finesse and just start.
“Give up perfectionism. Just do it anyway. Once you get started actually doing something, you will wind up finishing it. And you’ll typically do a good job,” Chris asserts. Sometimes the hard part is just getting going, but he stresses that simply getting something down, anything, even if it’s just jibberish, is crucial for your momentum.
One book Chris cites as influential to his philosophy is The War of Art by Steven Pressfield. It discusses the idea that we tend to talk ourselves out of doing something, however we have the power to fight the resistance inside ourselves. For Chris, he battles his own resistance by staying disciplined.
The Discipline Decision
One of the biggest questions that comes out of adhering to a highly specified process is how to stay disciplined enough to dial into the Pomodoro process. Chris’ advice is simple: Start by flossing your teeth.
No, seriously. Chris is the first to tell you that he didn’t come out guns blazing, tackling 40 Pomodoros per week at the onset of his productivity journey. It started with a simple decision to better his life. For him, this began with a decision to floss his teeth regularly.
“I timed it: it took me 53 seconds to floss my teeth. And I said to myself, “If I can’t spare 53 seconds to do something, then what hope is there that I can accomplish bigger things?’”
Chris realized that it was all about flexing his habit muscle, and building upon it. Now, he boasts 40 Pomodoro sessions a week, he exercises five times a week, and spends ample time with his wife and daughter. Oh, and he flosses regularly.