All Plans Fail

Rama Nimmagadda
4 min readSep 16, 2022


picture taken in 2021 by Prateek Kumar Rohatgi at Bighwan, India

“Travelers, there is no path, paths are made by walking.” ― Antonio Machado

Despite our meticulous plans for achieving goals in our life, they hardly ever play out. Even for the simplest of these plans, there are so many uncontrollable variables that plans end up changing all the time and in hindsight, what we end up doing inevitably turns out to be different from what we started out with.

I quit my corporate career about a year and a quarter ago. Having not attained financial independence yet, I had clear plans on how I was going to manage my finances. I knew that without monthly salary, finances could end up putting tremendous stress. So, I had a very well laid and thought through financial plan. My plan did not last even three months. As it turned out, I overhauled my entire financial portfolio, going from a relatively safe portfolio of equity mutual funds to a highly concentrated portfolio of small cap stocks. I moved from my version of “sanctity” to “blasphemy” in three months. This was no knee jerk change — I put in solid mental effort before getting convinced that this is the right way to go. What I was most amazed with was how quickly some of my long-held beliefs changed.

“The afternoon knows what the morning never suspected.” ~ Robert Frost

Few thoughts on plans

  • Plans work best when treated as maps (“plan-as-a-map” is a bonafide mental map). A map gives a good sense of what to expect on your journey but only during the actual journey do you realize the actual hurdles. A detailed plan is helpful in the sense that it will help you think through the path ahead in intimate detail and hence allow you to be prepared for what to expect
  • Plans could give a false sense of confidence because of the precise details they contain. Also, given that we get anchored to these details, we tend to waste efforts in constantly bringing our actions back to plan even though the original plan may not be as relevant anymore
  • Planning usually takes a static view of future and thereby creates enormous stress and strain as we try to bring future to align with our plans. It should be the other way around. An active and dynamic approach to planning allows for us to keep in alignment with future as it unfolds
  • Ironically short-term plans can be subject to more volatility than long term plans, particularly if large number of variables or resources are involved. In longer-term plans, we end up accounting for larger uncertainty (say, allowing bigger buffer in estimates) and hence our execution may end up more in line with planned estimates. In other words, in longer projects, we tend to create plans as if they are maps and in shorter projects, we may create plans as if they are paths
  • World seems to follow certain universal laws and this probably allows us to forecast with higher certainty of “what” may happen. However, it is impossible to predict “when” this may happen. For example, the correction following the stock market build-up immediately after COVID-19 was not hard to predict. My confidence in our ability to predict these corrections does not stem from being able to foresee the specific causes — e.g.,, printing too much money, doling out too many freebies or quantitative easing. Rather, my confidence is informed by universal truths such as “all (sustainably) good things take time to build”

So, are plans useless?

No, planning can be useful if done with the right mindset:

“Plans are of little importance, but planning is essential.” — Winston Churchill

  • Planning can help with management of the “controllables” in achieving specific objectives
  • Planning can lead to creating maps and getting familiar with what to expect
  • Planning can create intuition and ability to respond as opposed to react
  • Planning can be a tool to support execution which in turn, is about active risk management and passive project tracking
  • Plans can motivate action — they can provide a sense of purpose and progress

“Agile” planning methodology works (at least in theory) because it is more focused on planning capacities and creating byte sized outputs, thereby allowing for dynamism during execution. In reality, “agile” methodology fails when practitioners fall prey to (modern) human propensity to focus more on the output (uncontrollable) than the inputs (controllables).

“Chance favors the prepared mind.” — Louis Pasteur

Planning unlocks value when it is about taming chaos and is not about eliminating it. This is done by creating an approach that aligns your personality (personal traits) and available resources to your goals and conversely, not by detailed planning of the execution. So, make plans more about setting boundaries, contours and direction and then let the resources act and respond as things evolve.

“I always say don’t make plans, make options.” — Jennifer Aniston


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