In as much as I love Yoda-like sentences like this (Originating from Sir Winston Churchill), I tend to ask deeper questions like, what does that statement really mean?

The simplified way of looking at it is, yes as a matter of fact, failing to plan will lead to unproductive days or wasted time and life is like a sailboat, taking you wherever you’d like to go.
I don’t even want to go into the thousands of literature written about this. It’s a multi-billion dollar business in the guise of books, courses, software and more.
Our obsession with optimization, living life to the fullest (planned) way, micro-managing every bit of life seems like a necessity for urban living.
Whether it’s peer pressure, ranking up… or for personal fulfilment… the big question is:
Does it all really matter at the end of the day?
I don’t really know. Maybe some may say yes.
I prefer to have a lot more flexibility in this area BUT it depends on whether it’s personal or business.
In business, there are no two ways about it. The demise of ones business is soon to come if there’s no clear direction, goal or outcome.
In life, perhaps there’s some leeway but this too, is subjective.
The simple answer is, having some idea of planning or motion in place set with a deadline may actually help move things, make things fun and or even profitable if its a business.
I see planning as a solution to procrastination or lack of accountability, perhaps even as a reason to have a reason to do something.
Maybe it’s time to unplan everything.
Or maybe its time to plan a plan that’s an easier plan to work with.
Word twisters aside, I admittedly have to say that taking a few minutes to a few hours in a day to map some ideas is actually pretty useful.
My wife says that she has a bucket list. I used to have one and after she told me she has a bucket list, I had to create one for myself.
Given that I’ve actually achieved quite a few of my bucket lists in life so far, I’m not that adventurous but enough to have tasted the goodness of life.
I guess, I don’t have enough of a bucket list and so I’ve added 100s more to my list (which took some time to plan and prepare.)
When it comes to business and meetings, when there’s a bunch of scrums, sprints, meets, whatever six sigma, Edward Demmings, Ford related way of working more efficiently, I guess that’s how things are going to have to be, adapting to systems that create progress and moving people to move big ideas and goals.
And so, the million dollar question: Failing to Plan Is Planning To Fail?
(If we do not fail to plan to plan to fail.)
p.s I’ve used Trello and a few other popular tools for planning, but my recent favourite admittedly is Monday.com , though there are a lot more out there.
The only thing about Monday.com is the slight lag but otherwise it makes spreadsheet planning (for excel sheet lovers) a lot more versatile, fun and productive.
I’m not an affiliate but I think it’s worth a tinker for those who are interested in planning.