One of Gokul Rajaram’s insight into successful founders struck a chord with me. The idea that one of their defining characteristics is perpetual dissatisfaction.
It’s a mindset that might seem counterintuitive in a world obsessed with positivity, but it holds profound truths about leadership, growth, and ambition.
This characteristic drives them to keep pushing, improving, and achieving more—not just for themselves but for their teams as well.
To me, this is the essence of a continuous improvement mindset and the philosophy of playing infinite games.
However, I believe there’s an important nuance to one of his statements:
This dissatisfaction / urgency / push transfers to the broader team, who pushes harder and stays hungry.
Gokul’s post on X
In the short-term, I believe most people will react positively to a dissatisfied leader and keep pushing. I’ve seen it work over and over.
But in the long term, for those who aren’t intrinsically motivated, optimistic, and growth-oriented, this approach can lead to burnout.
Derek Sivers, in his book Hell Yeah or No, captures this tension beautifully.
He contrasts the mindset of a Silver medalist, who focuses on how close they came to first place and feels dissatisfied, with that of a Bronze medalist, who feels gratitude for making it onto the podium at all.
The lesson? While perpetual dissatisfaction can be a powerful driver, gratitude and perspective are essential for maintaining resilience.
For leaders and their teams, perpetual dissatisfaction should be a happy place—a mindset of ambitious, disciplined growth.
But it’s equally important to cultivate gratitude and celebrate progress.
Leaders must balance urgency with appreciation and know when to switch gears. Above all, understand the game you’re playing and ensure your team is equipped and motivated to play alongside you.
For the individual, know yourself and what motivates you.
