(This is Part 5 in a series about My Productivity System.)

The Pomodoro Technique has become an essential part to my focus management system. If you haven’t used the Pomodoro Technique, I encourage you to do so. And if you’ve tried it in the past but have given up on it, I encourage you to give it another try as part of a more comprehensive focus management system like the one I’m writing a series about currently.

WHAT’S THE POMODORO TECHNIQUE?

The Pomodoro Technique is described by Francesco Cirillo:

1. Choose a task to be accomplished.

2. Set the Pomodoro to 25 minutes (the Pomodro is the timer*)

3. Work on the task until the Pomodor rings, then put a check on your sheet of paper.

4. Take a short break (5 minutes is OK)

5. Every 4 Pomodoros* take a longer break

*Francesco seems to call the timer a Pomodoro and also a 25 minute session a Pomodoro. For my purposes, I’ll call the timer a timer, and a 25 minute session a Pomodoro.

Here’s how I sum up the Pomodoro Technique: Use a timer to work in 25 minute sessions followed by 5 minute breaks.

1. GET SET UP WITH A TIMER

You can use a physical timer, or your phone, or whatever. I personally use My Little Pomodoro (mac app) which allows me to see the timer on my Mac desktop at all times.

To get the Pomodoro Technique really working, in my experience you really need to commit that you’ll use Pomodoros for all the work that you do (or at least for as much of the work day as possible).

Now that you’re set up, you’re ready to go.

2. START THE DAY WITH A POMODORO

It’s tempting to start the day by jumping into email and all the urgent tasks at the moment. Resist the temptation. Start your work day with your first Pomodoro (25 minute work session). During your first daily Pomodoro, the key is to organize your 3 Desired Outcomes of the day. This will allow you to get focused and will keep you accountable. I like to review my current notes regarding my daily focus area. For example, if I’m working on Product Features for Monday, I’ll review all my notes regarding Product Features. And then I’ll start listing out various tasks and things I want accomplished that day. I use a pen and pad for this. After I have about 10-15 tasks, I’ll then start to draft my 3 Desired Outcomes for the day. I’ll write them in past tense form; for example, “Login/Registration workflow drafted”. Usually a Desired Outcome ends up taking about 1-3 hours. Three Desired Outcomes usually takes me about 6 or so hours to do.

3. KNOW THAT GETTING STARTED IS ALWAYS THE HARDEST

I find this interesting phenomenon at work: the first 2-3 Pomodoros of each daily are usually the hardest to get through. This is when I have the most distractions. I want to reply to email, visit Hacker News & MacRumors, do other things, or just give up. The first 2-3 Pomodoros of the day I find myself fighting to keep focused. Without writing down my 3 Desired Outcomes of the day, I don’t know how I could break through this wall on a daily basis. The 3 Desired Outcomes gives me a goal that if I don’t reach by the end of the day, I’ll have to face my failure and the reasons why.

But here’s the other phenomenon: sometime after the 2nd or 3rd Pomodoro (roughly), I break into an extended time of extreme focus and productivity that surprises even myself. It’s like runner’s second wind. I feel like I can go on and on and on. And it feels great.

4. FOCUS ON YOUR 3 DESIRED OUTCOMES FIRST

I make sure to that my first 10-14 Pomodoros for the day are focused on my day’s 3 Desired Outcomes. And then toward the end of the day I’ll do another 3-4 Pomodoros on less important items like replying to email, organizing my desk, admin tasks, and other things unrelated to my daily focus area. Sometimes it’s a battle to keep focused on your 3 Desired Outcomes, but remember this: once you’ve finished your 3 Desired Outcomes of the day, you’ll know that you’ve finished the most important tasks for that day and you’ll feel great.

It’s a great challenge to know really what the most important tasks you need to be doing at the moment. I find that once I get started in my day, I start to inevitably face the challenges of the important tasks. Often, it’s discouraging and I’ll be tempted to do something less intense or less challenging. However, this is where the combination of the Pomodoro Technique and the 3 Desired Outcomes works miracles. I just keep plugging away. The 3 Desired Outcomes gives me my goal and the Pomodoros give me the means. If I just do one Pomodoro after another and keep focusing on the desired outcomes, I do some serious damage (in a good way). And before you know it, this behavior becomes a habit.

(Note: If something urgent comes up or I need to do something unrelated to my daily focus area, I might do less than 10 Pomodoros on my 3 Desired Outcomes, but this is rare. Also, if there’s an urgent deadline for a project, I might put in more than 14 Pomodoros on my 3 Desired Outcomes, but this is rare too.)

5. DON’T STOP THE CAR

Last month I was teaching my wife to drive manual (stick), and it’s amazing how easy stick shifting is if the car is already moving (ie., in 2nd gear). However, when the car is stopped and you need to get into 1st gear, it’s extremely difficult - too little gas, too much clutch, etc. Case in point: it takes a lot of energy to get something moving from a standstill.

The same is true with the work day. Once you get going, you want to avoid coming to a standstill and having to get yourself moving again. Even if you don’t know what you need to be doing, just start the timer and do your 25 minute work session. Sometimes (especially during the first few Pomodoros) I find myself just thinking about the task at hand for the entire 25 minute Pomodoro. And that’s ok. Actually that’s great. After I spend enough time thinking, I’m bound to find some kind of breakthrough.

Here’s the key to making the Pomodoro system work: Keep the timer going.

Don’t stop the timer, if possible. The timer is either counting down from 25 minutes (for a work session) or from 5 minutes (from a break)… or from 15-20 minutes for a longer break. Here’s a sample of from a typical day of mine:

9:00am - 1st Pomodoro (set daily 3 Desired Outcomes). 5 minute break.

9:30am - 2nd Pomodoro, 5 minute break.

10:30am - 3rd Pomodoro, 5 minute break

11:00am - 4th Pomodoro, 5 minute break (prep lunch)

11:30am - 5th Pomodoro, 20 minute break (lunch)

12:15pm − 6th Pomodoro, 5 minute break

So on.

The key though isn’t to schedule your Pomdoros. Rather, you let your Pomodoros schedule your day for you. Just follow the timer - 25 minutes work, 5 minutes break, 25 minutes work, 5 minutes break, etc.

If you do it right, your engine won’t reach standstill and you’re be in constant forward motion.

Hemingway had an interesting quote regarding how to avoid writer’s block:

The best way is always to stop when you are going good and when you know what will happen next. If you do that every day … you will never be stuck. Always stop while you are going good and don’t think about it or worry about it until you start to write the next day. That way your subconscious will work on it all the time. But if you think about it consciously or worry about it you will kill it and your brain will be tired before you start.

I think a similar principle applies here with Pomodoros. By taking forced 5 minute breaks after every 25 minute work session, you’re usually ending your work session in the middle of something. You might be in the middle of a design or a deep thought. And then you take a break. Part of you doesn’t want to take a break because you want to finish what you’re working on. But this is where you need to obey the timer, and just take the break. By taking a break in the middle of something, it will naturally help you get started easier in your next work session.

(Read more about My Productivity System. Check out my other series too.)