In my previous post, I talked about the unique difficulties faced by a total newbie. At the end of that piece, I said that a beginners best friends were persistence, diligence, and awareness, coupled with a good dose of openness. That post got me pondering on the very fine balance between planning, learning, and adapting.

The crux of the matter is that not very much gets done without some sort of planning. At the same time, planning incites action and action incites learning. So ones plan needs to be constantly adapted in the light of new experience in order to remain relevant.

So, how does one plan effectively? While there is no one-size-fits-all method, I would like to share my planning strategies in this post.

I like to draw up daily to-do lists. I think planning on a day-to-day basis provides sufficient structure within which to act while at the same time allowing one to adapt quickly to new learning.

I find making daily to-do lists most helpful when starting something new. It forces me to think about what I learnt the previous day and makes me consciously choose what to do next. It brings attention to things which I have been putting off but should be doing. It forces me to commit to new experiments and also define expectations of those experiments before hand.

For example, in my current startup bootstrapping phase, I am navigating new worlds with respect to idea formulation, idea validation, product positioning, etc. So here are summaries of my recent to-do lists:

Etc.

These are brief summaries, and each task gets broken down further as I go about executing it. A task may occasionally spill over into multiple days. Sometimes my future (tentative) tasks get dropped or postponed if something else comes up that seems more relevant. The essence is that the targets are focused enough to inspire concrete action while at the same time are not binding in their detail.

It is extremely important to choose the granularity of the to-do list carefully. All planning is based on assumptions about your goals, your assets (money, skills, etc.), and the state of things outside your control (like the economy in general, your competitors, etc.). In a fast changing world with lots of uncertainty, keeping your assumptions minimal, simple, clear, and credible is crucial for the design of workable plans.

This is why I think detailed long term plans are not very useful. For instance, planning your time for the next six months down to the granularity of a day seldom produces anything of value in a highly uncertain world. Even setting a highly detailed goal which is six months out may not make any sense depending on the circumstances.

This does not mean long term planning is not important. If you are aiming to reach a definite goal, then you need to have a frame of reference within which to plan your days so as to ensure that you are actually building toward that goal. But the long term plans should not be very detailed. And they should not be set in stone.

Continuing with the startup bootstrapping theme, my long term goal is to have a fully validated feature set for a Minimum Viable Product (MVP) in a couple of months. That seems like a reasonable target to aim at. But it may change depending on what I learn in the intervening period. What I don't think is worthwhile is to define a weekly plan for that arriving at that goal --there are just too many variables in the picture to make any sort of credible weekly plan for the next two months.


Finding an approach to planning that works for you is learnable skill which you get better at with time. Some final points to keep in mind:

Constant revision and refinement is a necessary part of workable plans. Good plans should enable you to do concrete work every day. Good planning should never feel like an overhead. Your plans, taken as a set, should be building toward some tangible goal. (like a product release or milestone, improved facility with a certain skill, etc.) Without discipline in execution, the best planning process is useless. That said, oodles of effort pulling in different directions will take you nowhere. So good planning is well worth it.

Thanks for reading, Enjoy!