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How To Pomodoro Your Way To Long-Lasting Productivity

By | Published on | 5 min read
<span id="hs_cos_wrapper_name" class="hs_cos_wrapper hs_cos_wrapper_meta_field hs_cos_wrapper_type_text" style="" data-hs-cos-general-type="meta_field" data-hs-cos-type="text" >How To Pomodoro Your Way To Long-Lasting Productivity</span>

pomodoro technique for improved productivity

Maximizing time is a constant struggle. A fast and effective way to try improving your productivity is the Pomodoro Technique. 

Just how powerful is the practice of counting your pomodoros? The Pomodoro technique may just be the focus booster you need.

Motivational speaker and entrepreneur Chris Winfield struggled for years to make proper use of his time. After countless research, trial and error, failing at time management, and a little banging of his head against the wall, Chris has discovered that the key to him living his most productive life is a 25 minute block and a simple timer.

Desperate for a way to improve his productivity, get rid of distraction, and free up more of his time, Chris eventually discovered and settled on the Pomodoro technique because all he'd needed was a timer. Invented by Frances Cirillo in the 1980’s, the Pomodoro technique maximizes time and efficiency by blocking out a 25 minute interval to free yourself from interruption.

Thanks to this time management technique, Chris cut his work week in half, transformed his career and, most importantly, balanced his life.

Introducing The Pomodoro Technique

Before diving into Chris' story of major productivity transformation, here's a quick video tutorial for timing your tasks with the Pomodoro technique and timer:

Overcoming The Adversity Of Time

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 To Productivity

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 using a timer and spending 25 minutes completely focused on that initiative, followed by short breaks.

Here’s how this technique, pioneered by Francesco Cirillo, works:

  1. Choose a task to be accomplished.
  2. Set a kitchen timer for 25 minutes (preferably, a tomato timer).
  3. Work on the task until 25 minutes is up.
  4. Take a short five minute break (this marks the completion of one "Pomodoro").
  5. Repeat steps 1 to 4.
  6. After every four pomodoros, take a longer break such as 20 minutes or more.

francesco cirillo pomodoro technique

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 technique session 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 technique sessions each day, seeking to optimize his productivity and subsequently help him find more balance in his life. He now has a steadfast commitment with his timer for 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.

Chris Winfield headshot


“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 step-by-step 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. 

The Trello board also gives Chris a visual view of how many Pomodoros he has completed and how many more he has to go until he can take a break and clear his mind. While he uses another one of the Pomodoro apps for a timer, the Trello board has helped his technique.

Battle Your Own Resistance Movement

The Pomodoro method doesn't take much time, but it also doesn't come stress-free. 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 his mind games was to give up on the finesse and use a timer to just start working. Chris explained: 

“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. 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. That's his technique."

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 with his daily tasks and sticking to a time management structure to get them all done.

The Discipline Decision

One of the biggest questions that comes out of adhering to a highly specified process is does the Pomodoro technique work and how to stay disciplined enough to dial into this method. Chris’ advice is simple: Yes, it works. Just 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. He didn't start as a morning person or dedicate himself to grueling work sessions. 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.

Special thank you to Chris Winfield for sharing his tips and advice. Read more about his journey to working less and accomplishing more here

Good or bad, we'd love to hear your thoughts. Find us on Twitter (@trello)!

 Next: The Top 5 Blockers To Your Productivity (And How To Hack Each One)

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