Timebox and Milestones

Updated: Jun 28, 2020

Make a daunting project more manageable by "timeboxing" it and creating milestones.

Sometimes, some projects seem so large and intractable that you may not even know where to begin. It’s daunting! So how can you go about this?


There are many techniques but one fairly straightforward method is to first constrain the problem by setting a timebox, that is to determine an end date by which the project must be completed. By setting an end time, you’ve at least constrained it such that you can now have at least a high level objective: complete the project before that end date. Note that even if this end date is arbitrary, as long as you set one, you can start actively working towards it.

“...first constrain the problem by setting a timebox, that is to determine an end date by which the project must be completed.

Now once you’ve time-boxed the problem, you can then break the project into milestones or “gates” that you want to pass that will indicate that you are making progress towards your end goal. When you choose milestones, try to make each one meaningful and interlink them such that completing one means that you can move on to the next one.


Let’s use the above two techniques in an example. Let’s say you want to plan your retirement...quite daunting especially if you are fairly young and it seems so far away! But what’s the first thing you should determine...basically at what age you want to retire which creates a natural timebox. Let’s assume that the age is 65. Now what do you do? Determine the set of milestones you want to hit to make sure you are on track towards hitting retirement. Well how do you do that? You backtrack and see the lifestyle you want to live in retirement and calculate how much income and savings you should accumulate by then to support that lifestyle sustainably. So then comes the task of creating milestones around how much your savings/investments/income streams should be increasing over the years to make sure you are on track...this is what a financial advisor essentially does.


In short, timebox the problem. Then break out the milestones.


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