A lifetime of entrepreneurship, teaching, philosophy and reinvention—translated into conversations that challenge audiences to think differently about success, purpose and how we live.
Roger Kuperways has spent a lifetime exploring a deceptively simple question:
A Professor Emeritus at New York University, author, entrepreneur, philosopher, and former fashion designer and manufacturer, Roger brings to the stage something that cannot be learned from textbooks alone: the perspective of a life repeatedly reinvented.
His lectures combine philosophy, business, entrepreneurship, human behavior, and personal experience to examine the questions that shape both our professional and personal lives.
Roger believes philosophy should not remain in universities or books. Philosophy is most valuable when we can use it.
Drawing on ideas from the world's great thinkers—and on his own experiences building businesses, teaching generations of university students, surviving failure and loss, and beginning again—he makes complex ideas understandable, relevant, and practical.
His approach is conversational rather than academic. He challenges audiences to question assumptions, examine the way they think, and consider not only what they want to accomplish, but why it matters.
For decades, Roger has also spoken about entrepreneurship, leadership, management, organizational culture, ethics, creativity, and personal development. He believes that the culture of an organization ultimately determines not only its success, but the value of the legacy it leaves behind.
Today, his speaking reaches beyond business. His subjects include philosophy and everyday life, reinvention, purpose, happiness, fear, failure, aging, relationships, decision-making, leadership, entrepreneurship, and what it means to live a life well lived.
Meaning is not something we find waiting for us. We create it through what we love, what we contribute, whom we care about, and what we do with the time we have.
A meaningful life does not have to be an extraordinary life.
Sometimes meaning is simply knowing that because you were here, something—or someone—is a little better.
BACK TO QUESTIONS ↑Because we confuse “I failed” with “I am a failure.”
They are not the same.
I have failed many times. Some of those failures closed doors. Others forced me through doors I would never have opened voluntarily.
Failure is painful—but it is also information.
The greatest failure may be allowing the fear of failure to decide what we never attempt.
BACK TO QUESTIONS ↑We usually ask, “What is the right decision?”
Sometimes a better question is: “Which decision can I live with?”
We rarely have all the information we want. We make the best decision we can with what we know, our values, our experience, and our judgment. Then we accept responsibility for it.
Wisdom is not always knowing the right answer.
Sometimes it is knowing the right question to ask.
BACK TO QUESTIONS ↑I know the answer to this one personally.
Yes.
I have begun again more than once.
A new country. New businesses. New careers. Teaching. Tango. Philosophy. Writing.
Beginning again does not mean pretending the past never happened. It means refusing to believe that the past has already written the rest of your story.
As long as there is another chapter, the book isn't finished.
BACK TO QUESTIONS ↑Not the size of the office. Not the title. Not how many people report to you.
A successful leader creates an environment in which other people can become better.
Leadership requires competence, certainly—but also character, trust, judgment, humility, and the willingness to take responsibility when things go wrong.
A leader's greatest achievement may not be what people accomplish for him, but what they become because of him.
BACK TO QUESTIONS ↑Success can be measured.
Money. Position. Recognition. Accomplishments.
A successful life is harder to put on a résumé.
Did you love? Were you loved? Did you remain curious? Did you help anyone? Did you enjoy some of the time you were given? Did you become someone you respected?
I have known successful people who were deeply unhappy.
Success is what you accumulate.
A successful life is what remains meaningful when the accumulation no longer matters.
More than we might imagine.
The technology has changed. Human nature has not.
We still struggle with love, fear, ambition, jealousy, happiness, purpose, injustice, mortality, and the question of how we should live.
Socrates asked us to examine our lives. Aristotle asked what makes a good life. The Stoics asked us to distinguish between what we can and cannot control. Montaigne asked us to confront mortality. Nietzsche challenged us to become who we are.
The questions are ancient. We are not.
And perhaps that is why philosophy still matters.
It reminds us that although nobody can live our life for us, we do not have to think about it alone.
BACK TO QUESTIONS ↑Using enduring ideas to think more clearly about the choices and challenges of everyday life.
READ MORE →Beginning again after change, failure, loss—or when the life you built no longer fits.
READ MORE →Lessons from building businesses, taking risks, solving problems and turning ideas into action.
READ MORE →Why values, ethics and organizational culture shape success and legacy.
READ MORE →Looking beyond achievement to ask what makes work—and life—worthwhile.
READ MORE →Moving beyond the barriers that keep us from attempting what may still be possible.
READ MORE →Philosophy should not be something we only study.
It should be something we use.
The great philosophers wrestled with the same questions we still face: How should I live? What can I control? What makes me happy? How should I deal with fear, loss, uncertainty, and other people?
The world has changed enormously.
Human nature has not.
Practical philosophy takes ideas that may be thousands of years old and asks a very modern question:
How can this help me live better today?
BACK TO SPEAKING TOPICS ↑I know something about reinvention because I have lived it.
I have been an immigrant, fashion designer, manufacturer, entrepreneur, professor, tango teacher, philosopher, and author.
Some changes I chose.
Others life chose for me.
Reinvention does not mean erasing the person you were. It means taking everything you have learned and asking:
What can I become next?
You are never starting entirely from zero.
You are starting again—with experience.
BACK TO SPEAKING TOPICS ↑Entrepreneurship is not simply starting a business.
It is seeing possibility where other people see problems.
It requires imagination, judgment, persistence, and the willingness to act before you know exactly how everything will turn out.
I learned entrepreneurship by doing it—building businesses, making mistakes, taking risks, succeeding, failing, and beginning again.
A good entrepreneur does not wait for certainty.
He learns enough to take the next intelligent risk.
BACK TO SPEAKING TOPICS ↑A company can have an excellent strategy and still fail because of its culture.
Culture is what happens when the boss is not in the room.
It is how people treat one another, how decisions are made, what behavior is rewarded, and whether the values written on the wall are actually practiced.
Leadership therefore begins with example.
People listen to what leaders say.
But they learn from what leaders do.
And ultimately, an organization's culture becomes part of its legacy.
BACK TO SPEAKING TOPICS ↑We spend enormous amounts of time asking:
What do I want to achieve?
We spend much less time asking:
Why do I want to achieve it?
There is nothing wrong with ambition, money, recognition, or success.
But none of them automatically creates meaning.
Purpose begins when achievement becomes connected to something larger than ourselves—to people, contribution, curiosity, creation, service, or love.
Success asks, “What did I accomplish?”
Meaning asks, “Why did it matter?”
Fear is useful when it warns us about genuine danger.
It becomes dangerous when it prevents us from living.
Many of the barriers we face are real.
Others exist largely in our imagination:
What if I fail?
What will people think?
Am I too old?
Is it too late?
I have learned that courage does not mean being without fear.
Courage means refusing to give fear the final vote.
Possibility begins the moment we ask:
What if I tried anyway?
BACK TO SPEAKING TOPICS ↑“ANYTHING CAN BE DONE.”
Not because everything is easy.
Not because we always succeed.
But because human beings are capable of changing direction, learning, adapting—and beginning again.
Roger does not simply try to provide answers.He tries to leave people with better questions.
For speaking engagements, lectures, programs and inquiries.
Contact Roger