05 Mar 2025
Lessons for the Road – with Ajay Gupta
Every time I speak to Ajay, my brain grows. I’ve been fortunate to count him as an investor and advisor since 2021.
Ajay Gupta is a McKinsey Senior Partner Emeritus, based in Chicago. Last week, he joined our monthly Team Learning session, to talk about his journey and his advice to young professionals starting out their careers in our firm. As often with Ajay, his advice was poignant and concrete – so much that I’m sharing it here in hopes it may inspire others too.
Ajay never had a big master plan for his career. But he followed a set of principles that helped him recognize and pursue opportunities. More on these principles shortly.
Ajay started his career somewhat unexpectedly for a would-be McKinsey partner: in oil-field exploration across Asia and in the North Sea. A hard-hat job in a rough climate, he thrived.
It was a very entrepreneurial culture; they dared betting on ambitious young people. The CEO of Schlumberger was this self-made Scottish guy, who had worked his way up from the shop floor. We all looked at him and thought, ‘That could be me!’.
After 5 years in the field, Ajay was talked into an MBA, where he in turn encountered McKinsey. At the time, the firm had just 3,000 employees (vs. more than 40,000 today!). Ajay initially hopped between different industries (“against the advice of my seniors, it took me a while to specialize. I did what I found interesting”).
His enthusiasm really showed when we got to this part of the conversation. Ajay likes to ask “why is is?”. A seemingly simple question, it has surprising depth. This question means you doesn’t settle with accepting worldly constraints as granted, but challenge their very existence with curiosity. Ajay effectively applies first principles thinking, where you keep drilling to the very root of any constraint or problem.
Following his curiosity, Ajay eventually gravitated towards healthcare and rose to become a Senior Partner in McKinsey’s Healthcare and Medical Products practices.
His advice to young professionals:
Enjoy the journey. Whatever you do for work, make sure you enjoy it. You have one life! If your job doesn’t inspire you, find out what does – and move on!
Whatever you do: be good at it. If you’re good at something, you tend to enjoy it more – and vice versa. But learning complex things requires you to:
Be resilient. Almost nothing that you do is going to go well at first try. Learning is hard and takes time. You must enjoy the learning journey, finding enjoyment in dedicated practice. It helps if you decide to:
Strive to learn from everyone around you. Intellectual curiosity is incredibly important. Be curious: how could we make things work better? Learn to listen well.
Finally, maintain relationships. The world is small, and you will meet people again. Don’t hold grudges. Show gratitude to those who have been generous or helpful to you along the journey.