Recently, a good friend and I have been inquiring into the merits of ‘living life to a plan’ vs. ‘living life without a plan and let life reveal it.’

Planning isn’t my forte.  I confess to a bias towards spontaneity. I would choose a free-and-easy backpacking trip anytime over a planned holiday with a detailed itinerary.  I love the idea of ‘getting lost to find myself.’ 

The notion of ‘career planning’ is absolutely alien to me.  Perhaps I lacked ambition and a clear sense of direction.  What I lacked, was compensated by a natural tendency to follow my curiosity, resulting in a professional journey that is largely a product of serendipity and divine coincidences.  Whenever a trusted source drops me some breadcrumbs, I would follow.  

Fresh out of college, I bumped into a friend who said casually, “Check out Andersen Consulting. They do quite interesting work.”  That led me to my first job in management consultancy.  A couple of years later, whilst talking about a café I was about to start, a good friend who mistook the title of a book I was working on as the name of the café said, “Gone Fishing is a beautiful name.” That’s how the café got its name and our customers nicknamed me ‘The Fisher’ (ironically, I don’t even love fishing).

Another year later, over coffee, I shared with another friend about an epiphany on what I found brings me immense joy, meaning, and fulfilment, he said, “Hey, if your life is about helping others to live fully, check out this thing called ‘coaching.’”  With that, I meandered into the world of professional coaching, and subsequently, leadership consulting and organizational development.

Most recently, after seeing some random photos of Milo (our family cat ) which I shared on our team’s WhatsApp, a dear colleague said, “You should start an Instagram account for your cat.” I listened, and @The_Miloist was conceived.

Do I believe in the merits of having a plan? Oh yes! If we don’t plan our holidays ahead, block out the calendar, book the flights and make hotel reservations, it’s very likely that it won’t happen.  At work, if we try to execute a project without a plan, it won’t take long before disaster strikes.  “Fail to plan, and plan to fail” is a timeless wisdom that only fools would ignore. 

Structure and spontaneity are both needed in life, just at different places and at different times.  Have a plan when helpful, and let it go or go without one when it is not.  An avid explorer would not set forth on an expedition without adequate planning and would not expect that everything will turn out as planned.

Perhaps, the answer to the question “To plan or not to plan” isn’t about choosing one over the other, but learning to dance with them and living with the perennial tension between two equally essential elements in life. 

Follow your curiosity. Venture into the unknown. Explore the uncharted territory. Listen with your heart.  Let your soul be your pilot. And see where it takes you. Be warned that joyful discovery, risks, and challenges are all part of the journey.

“Life is either a daring adventure or nothing at all.”

Helen Keller