Pomodoro: Simple But Not Easy (And The Parts I Break)

I've Been Doing It Wrong for Three Years

For years, I thought I had Pomodoro figured out. Download an app, set a 25-minute timer, work until it beeps, take a 5-minute break. Rinse and repeat. Basic time management, right?

Except I kept forgetting to start the timer. Or I'd skip breaks because my dog was sleeping and I didn't want to wake him up. Or I'd abandon the whole thing for weeks.

Last month I read the book - The Pomodoro Technique by Francesco Cirillo. Turns out I was missing about 80% of the technique.

When I finally started using the complete system, my deep work hours jumped from 3 to 5 hours per day. Not because I suddenly got more disciplined (although that’s also part of the story). But because I was finally using the right tools.

What I Thought Pomodoro Was (& I Was Wrong)

Like most people, I focused on three rules:

• Work for 25 minutes
• Break for 5 minutes
• After 4 cycles, take a longer 20-minute break Simple. Except that's like saying "coding is just typing characters”. Technically true, but there’s much more.

The book revealed a whole system I didn't know existed:

The Daily Sheet:

Not a digital app. Actual pen and paper with columns for:

• Task name
• Estimated pomodoros needed
• Actual pomodoros used
• Internal interruptions (marked with ')
• External interruptions (marked with -)

Interruption Tracking

Every time you think "oh, I need to email Emanuel” or “did I order food for dog?” - mark it down. You don't act on it. You just mark it.

Unplanned & Urgent Section

A separate list for stuff that pops up during the day. When a pomodoro ends, you check this list. Maybe one of those things becomes your next pomodoro. Maybe not.

The Actual Rules:

• A pomodoro is indivisible (no pausing mid-cycle)
• It must ring (can't just stop when you feel like it)
• If you break during a pomodoro, you cancel it entirely
• Tasks less than 1 pomodoro get bundled together
• Tasks more than 5 pomodoros get split into smaller chunks

That’s not just 25/5 timer technique. This is a complete workflow for managing attention, planning work, and tracking what actually matters.

What I Actually Do (The Honest Version)

Let me be real with you: I don't follow all the rules. Here's my actual workflow on a typical Tuesday:

Morning Planning (5 minutes): I grab my notebook and write down 4-6 tasks I want to tackle today. Next to each task, I scribble a rough estimate: "Write first draft - 2 pomos”, "Fix bug in auth system - 1 pomos”, “Prepare POC - 4 pomos”. These estimates are usually wrong. That's fine. The point isn't precision. The point is to prevent me from stuffing 10 tasks and 25 pomos into an 8-hour day. I know I can handle up to 5 hours of deep work. So I can plan accordingly.

The 25/5 Cycle: I start the timer. For 25 minutes, that task is my entire world. Email can wait. Slack can wait. That random idea about extracting layout to reusable component? Let me write it down for later. When the timer rings, I take the break. This is where I mess up most often.

Where I Break the Rules:

Sometimes I'm deep in flow and the timer feels like an annoying interruption. I keep working. Big mistake. You know what happens? I finish the task, feel accomplished, then completely forget to start the next timer. Suddenly it's 2 PM and I've done three hours of unfocused work instead of structured deep work.

The domino effect: Skip break → Stay in flow → Forget next timer → System collapse → Feel guilty → Abandon Pomodoro for two weeks.

When i was writing, I understood that skipping break is my main issue. That’s why system collapses. But maybe I’ve found a fix. When I’m in the flow I’ll extend my working session to 50 minutes. But I’ll ALWAYS take the break after. Break is critical. It’s a reset for the system. Brain needs it so it doesn’t get stuck in the rabbit whole.

What I Do Keep:

• Pen and paper: Non-negotiable. Apps don't show interruptions. Paper sits on my desk and look at me whole the time.
• Interruption tracking: Every ‘ mark is a moment of "oh crap, I'm distracted again." It's like catching yourself drifting during meditation. The awareness itself changes your behavior.
• Single-task discipline: One pomodoro, one task. No multitasking. No "let me quickly check this other thing." This is the hardest part and the most valuable part.

Who This Is Actually For

Let’s be real. Pomodoro isn't for everyone.

This works great if you're:

• A maker, not a manager (shoutout to Paul Graham's essay)
• Someone who can actually block 2-4 hour chunks for deep work
• Working on tasks that require sustained concentration (coding, writing, design, analysis)

⠀This probably won't work if:

• Your calendar looks like Swiss cheese (4+ meetings per day)
• You're in a support role with constant interruptions
• You're a manager coordinating multiple people
• Your job is primarily reactive rather than creative

If you're constantly on Slack, jumping between emails, and putting out fires, Pomodoro won't fix that. The problem isn't your focus system; it's your role.

The hard truth is: if you're creating anything meaningful and your calendar is packed with meetings, that's the real problem you need to solve first.

Why It Works (Even When I Break It)

Here's my data, messy and honest: Without Pomodoro: About 3 hours of deep work per day. With Pomodoro: 5 hours of deep work per day.

Sounds like a bit gain!

Why does it work?

• Single-tasking compounds: One focused hour beats three fragmented hours. Every time. The compound effect over weeks and months is enormous.
• Interruption awareness changes behavior: Once you see yourself marking ’ five times in one pomodoro, you get annoyed at yourself. Next pomodoro, you mark three times. Then ones. You're not trying to be perfect. You’re trying to be better.
• The planning ritual matters: Spending five minutes deciding what matters today prevents you from spending five hours on stuff that doesn't. This seems obvious but how often do you actually do it?
• “Next pomodoro will be better": This mindset shift is everything. You're not optimizing for perfection. You're optimizing for improvement. Bad pomodoro? Okay. Next one will be better.

The Thing About Simple But Not Easy

Pomodoro is brutally simple. Set timer. Work. Break. Repeat.

But simple isn't easy (one of the best talks i’ve seen Simple Made Easy)

It's not easy to sit with discomfort when you want to check your phone.

It's not easy to see how many times you interrupt yourself.

It's not easy to admit that you can only do 4-5 hours of real work in a day.

It’s not easy to start when you have to tackle hard problem.

It’s not easy to start when you have boring task.

I still mess it up. I still skip breaks and forget timers. I still abandon it when life gets chaotic. But I always come back. Because those 5 hours of deep work. They're when the actual magic happens. When the code finally makes sense. When the writing flows. When the problem clicks. Everything else is just noise.

Try it for three days. Pen and paper. Mark your interruptions. See what happens. You don't need to be perfect. You don't even need to be good. You just need the next pomodoro to go a little bit better. What's the one task you're going to tackle first?