I've actually been actually working at this for the past few weeks. First, the caveat that I haven't implemented a good tracking system beyond casually jotting down Xs next to my task list to count the # of strict Pomodoros I allocated to each one. I'm also not strict about this and definitely don't compute statistics expect useful metrics. I'm much more interested in day-to-day rhythym improvements, interruption control, and focus training. For higher level scheduling, I've experimented following Cal Newport's recommendation to schedule every minute of my day (http://calnewport.com/blog/2013/12/21/deep-habits-the-import...). On days it works, it goes great, but I'm still working to integrate this method with the need for reactive changes of plans. With that, a few observations and outstanding questions about the Pomodoro side of things:

- Interruptions definitely affect my feeling of accomplishment and may affect my results. I find even the smallest external interruption or moment of weakness triggers my internal critic, resulting in an arguably more detrimental cascade of self-criticism. An avalanche of blog posts argue that these minor interruptions dramatically impact my productivity for other reasons. I totally buy this anecdotally but won't attempt to justify it since I suspect most people here agree anyway.

- Sometimes 25 minutes just doesn't cut it. I especially chafe at the forced 5 minute break during my 1.5 hour period pre-standup where I haven't eaten at all and am caffeinated. I know the creator of the technique and blog authors like Martin claim that I should be able to slice all of my tasks such that I don't need longer than 25 minutes, but I disagree. While I enjoy holding the state of a program in my head and occasionally finding the zone, I'm willing to acknowledge Martin's overstated but partly true point that the zone can induce tunnel vision and the downsides that go along with that. However, I've also observed that 3 break-interleaved chunks of work can zap my energy more one large block of work would have.

- How do people deal with waiting for things that take longer than a minute? I've recently been working with jobs that take multiple hours to run. It's difficult to both schedule my Pomodoros such that I have a free one to check the result of this job. Even worse, the validation of the job can take between a minute if it succeeded and hours if it failed. This makes budgeting hard.

- Should I budget Pomodoros for checking email and Slack or include that in my breaks? Ideally, I'd use breaks to recharge and not context-switch between communication platforms. But, while I'm not an always on, 10-minute to respond to any email guy, a consistent multiple hour time-to-respond to any communication is a recipe for face-to-face interruptions in the age of the open office.

- Should I include lower level planning in my break or 25-minute chunk? I often find going from high-level task statement to knowing exactly what I need to do requires a few minutes to orient myself. I'd be fine including this in my Pomodoros except this orienting can involve firing off a quick question to a colleague or searching through my emails / Slack messages. Maybe I just need to get better at gathering requirements beforehand...

To be clear, I'm not putting down the technique. I suspect any time management strategy would reveal the issues I described above and that we simply don't hear about the pains of actually implementing a system beyond a week of casual usage (see any blog post with a just-so title like "I Adopted <> and It Changed My Productivity Forever" as an example).

As I look back at my bullets, I've realized I'm mostly looking for wisdom from some seasoned Pomodoro veterans. I see one or two people on this thread who fit this description, but overall I'm disappointed with the ratio of people who want to sell the technique or have tried it to people who have used it consistently for months or years. This seems to be a common problem among productivity techniques.

Meta-comment: I recognize this comment could be condensed, and "if I had time I would have written a shorter letter" (http://quoteinvestigator.com/2012/04/28/shorter-letter/).