The questions business leaders ask themselves reveal more about their generation than their balance sheets.
While previous generations of entrepreneurs focused primarily on survival and profitability, today’s business owners have the luxury of considering deeper questions about purpose, fulfillment, and life balance.
This shift represents a fundamental change in how we approach entrepreneurship and what we consider success.
The Traditional Owner’s Mindset
I had a very interesting conversation last week with a friend who is also a respected investor.
I asked him about one of his kids who recently started his own marketing agency. The question I asked: “Is he happy?”
My friend surprised me in his response. He said “Is he happy?” is a question non-owners deal with.
As a founder and owner, the questions he deals with are different: “Are we profitable?” “What’s my exit strategy?” “Should I delegate this or that?”
But happiness, he felt, is almost not relevant.
New Generation of Questions
I believe this striking contrast in perspective reflects a generational shift among business leaders in how they approach work, values, happiness, and freedom—with far more nuance and options than previous generations had.
Today’s business leaders are asking fundamentally different questions:
“Is the sacrifice of my time and energy worth what I’m getting from this business?”
“How is owning this business affecting my relationships with family and friends?”
“Am I building a business that aligns with my personal values and purpose?”
“Is this business making me happier and more fulfilled, or just busier and wealthier?”
The Luxury of Choice
These are all key questions new business leaders are asking, and I am grateful we live in an era that they have the luxury to ask and search for great answers to these questions.
This luxury didn’t exist for previous generations who were often focused purely on survival, building wealth from nothing, or breaking through barriers that today’s entrepreneurs may not face.
The economic stability and opportunities available today allow business owners to consider not just whether their business works, but whether it works for them as whole human beings.
Conclusion
The evolution from asking “Are we profitable?” to “Are we fulfilled?” represents more than just generational change—it’s a maturation of entrepreneurship itself.
While profitability and strategy remain crucial, today’s business leaders have the privilege of building companies that serve not just their bank accounts but their souls.
This shift suggests a future where business success is measured not just in financial returns but in the quality of life and alignment with personal values that entrepreneurship can provide.
The question isn’t whether this new approach is right or wrong—it’s recognizing that having the freedom to ask these deeper questions is a luxury worth celebrating and using wisely.