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08) Roadmap Revisited

“Designing a product is keeping 5000 things in your brain — these concepts — and fitting them together and kind of continuing to push to fit them together in new and different ways to get what you want.” — Steve Jobs

I spent last week on the 2nd most difficult software development task: detailed planning.  My first roadmap, made more than a year ago, described everything to the month level.  My next, made in December, planned things week by week.  This new March roadmap gets it down to the day-by-day.  Before me now stands 120 work days of development, split into eight milestone deliverables, one every three weeks.  Quite a lot was cut.

Earlier I wrote about timeboxing, which keeps things on track through the peaks and valleys of software surprises.  Often there comes a point where you need to “throw one away,” where incremental adjustments just won’t cut it, where you need to start fresh with a completely new plan.  Ripping up the floorboards can be stressful and confusing, particularly last week while swimming through the vertigo flu.   Somehow I made it through to this much cleaner plan, one that gives me both confidence and relief.

I wish I could describe this planning process.  With dozens of factors in play … this piece becomes easier when this piece is done, this piece needs to happen first so this audience can use it earlier, this one’s a nice-to-have, this one is risky … it’s a huge multi-dimensional puzzle with no easy answers.  Looking back, all the pieces fit where they need to be, but getting to that point is a true mystery.  It just happens, at least for me.

And so a new chapter begins, once again.  Now to focus on now.

One Response to “08) Roadmap Revisited”

  1. definitely sounds like a lot of work to be done, best of luck on it and hope the work gets done smoothly.

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