This memoir unravels the unconventional life of Dr. Man Mohan Kakar, whose life’s journey has been inundated with unexpected and unplanned turns that brought him to the peak of professional success and to its depressing lows. John Lennon observed that “life is what happens when you are busy making other plans,” which fits Dr. Kakar’s life. His steadfast determination to stay relevant, current, and open to new experiences have been guiding him through his personal and professional life – even when that goes against all conventional wisdom. He choose to forsake his seat in a prestigious university to serve the country by joining the armed forces, forego a secure, comfortable, and successful career to join a short-term stint with United Nations in Afghanistan, and then go to Seychelles as the telecommunication advisor to the then future President of Seychelles. However, while at its acme, family dynamics brought his career to a grinding halt. At nearly sixty years of age, he was forced to start life afresh from the bottom and learn to become an entrepreneur, and at eighty-two he started a technology startup.