Get All Access for $5/mo

Getting at the Real Why The most successful entrepreneurs in history have been those acutely tuned to solving the most common problems.

By Derek Lidow Edited by Dan Bova

Opinions expressed by Entrepreneur contributors are their own.

Thomas Barwick | Getty Images

Editor's note: This article is an excerpt from Building on Bedrock: What Sam Walton, Walt Disney, and Other Great Self-Made Entrepreneurs Can Teach Us About Building Valuable Companies.

A strong core motivation, is always present with great entrepreneurs, but rarely with entrepreneurs who muddle through. Uncovering and understanding those deeper motives is the first step toward succeeding as an entrepreneur or discovering that you are not cut out for its punishing demands—the personal sacrifices, inevitable setbacks, relentless work, crushing time pressure, financial uncertainty, and sleepless nights faced by 99 percent of entrepreneurs. You need to know whether your motivations are strong enough to carry you through an experience that can certainly be exhilarating, but also exhausting, calling on your deepest reserves of personal strength.

You could of course invest a great deal of time and money in therapy, but most ordinary entrepreneurs have little time or money for that. Besides, you don't necessarily need to resolve whatever issues underlie your motives; you only need to know what those motives are so that you can guard against their excesses. You can start by undertaking a simple exercise that I often use with aspiring entrepreneurs and students.

First, ask yourself why you want to be an entrepreneur. You've probably answered this question many times before, either for yourself or friends and family, and you've also likely come up with the usual platitudes.

Nevertheless, write them down. Then ask and answer some deeper and far more specific questions:

What fundamental desire or fear would success as an entrepreneur satisfy?

This question, too, produces some answers that recur over and over. For example, many people fear being humiliated in the eyes of a parent or rival. Others discover that they have a deep drive for power or status, or to be listened to. They are deeply motivated by the wish to have no one ever telling them what to do, or to have a group of people become highly dependent on them. Many other people's deepest motives are driven by challenging childhoods—economic hardship, for example, or an alcoholic or abusive parent—and their deepest wish is to never again feel the way those challenges made them feel back then. Still others have had their deepest motives formed by any of the many possible permutations of family dynamics.

What makes me so mad I can't control myself?

Perhaps there are certain names or labels that make you flash into anger. Someone casually says something that suggests you're lazy or inconsequential and you erupt. That eruption is an indicator that you're getting close to a core motivation you don't fully understand. Suppose, for example, that you're infuriated when what you regard as your unfailingly diplomatic touch is seen by someone else as toadying or spinelessness. Your anger is out of all proportion to the offense. Why? Perhaps as a child you were the peacemaker in a highly dysfunctional family, a valuable role that you are constantly driven to recapture. Maybe there is some other deep reason. But the point is that your hair-triggers can tell you a lot about yourself, if you're willing to pursue the clues they provide.

What made me happiest when I was child?

Like anger, joy can point us toward our deepest motives. But if you ask people a generic question about what makes them happy, they will either name transitory things like a good meal, or long-term experiences like enduring relationships, family life, or spiritual satisfaction. Localize the question to childhood, however, and the indelible memory of specific situations that made you deeply happy and you can begin to home in on highly specific motives. Maybe it's as simple as constantly wanting to recapture the feeling you had when you made the winning goal in an important soccer game. Or perhaps it is as complicated as the enormous relief you felt when your parents reconciled after a trial separation. But whatever it is, it will get you closer to uncovering what really drives you.

How would I feel if I failed?

If the answer is "as long as I felt I had given it my best, I could accept failure," then the chances are your motivation is not strong enough. The psychological consequences of failure must be significant enough to drive you to overcome, without hesitation, the hardships and traumas you will encounter. There must be nothing that is more important; otherwise you are likely to abandon the effort when the going gets really tough. And it's far better to find that out about yourself before you lose money, waste precious years of your life, and destroy a lot of valued relationships along the way. That doesn't mean you shouldn't join a startup where you can exercise skills you're proud of in exchange for some kind of payback. It just means that you probably shouldn't be the leading founder.

Would someone whose wisdom and guidance I value see my motives the same way I do?

Once you have examined and recorded what you believe motivates you, seek out a trusted advisor, someone who knows you well, who has seen you in action in a variety of situations, who can be counted on for candor, and is willing to ask probing questions. Do their perceptions about what really drives you align with yours? If not, then revisit your self- questioning and try to resolve the difference.

As you will understand when you complete this exercise in self-discovery, your strongest motivations arise from the things that are the source of your happiness or that protect you from primal fears. You therefore inevitably find you have a totally selfish reason for wanting to be an entrepreneur.

There is no shame in that, and there is much to be gained by identifying it and admitting to being selfish. If you don't acknowledge it, you're likely to feel ambivalent about success and, as a result, sabotage yourself.

Does that mean you should adopt a "looking out for number one" philosophy and steamroller anybody who gets in your way? No, just the opposite. The most challenging requirement for entrepreneurial success is the constant need to change your leadership style as your business grows and changes. Without a powerful motivation you will not make the required changes within yourself, nor will you master the tricky balance of being selfish enough to be a driven entrepreneur and selfless enough to lead the people that sign up to help you achieve your dream.

Derek Lidow

Teaches entrepreneurship, innovation and creativity at Princeton University, author of Startup Leadership

Derek Lidow is a successful global CEO, researcher, innovator, startup coach and professor at Princeton University, where he teaches entrepreneurship, creativity and innovation. He was tapped by the University to inaugurate a campus-wide “design thinking” curriculum. Lidow is the author of Building on Bedrock:  What Sam Walton, Walt Disney, and other Great Self-Made Entrepreneurs Can Teach Us About Building Valuable Companies (2018) and Startup Leadership: How Savvy Entrepreneurs Turn Their Ideas Into Successful Enterprises (2014).

Want to be an Entrepreneur Leadership Network contributor? Apply now to join.

Editor's Pick

Growing a Business

New York News Anchor Rosanna Scotto and Her Daughter Jenna Ruggiero Share the Secret of Running a Successful Family Business

Fresco by Scotto restaurant co-owners Rosanna Scotto and Jenna Ruggiero break down their family's business, how they use social media, and the impact of their philanthropic efforts.


California's Fast-Food Minimum Wage Hike Is Already Impacting Franchises. Here's What a New Study Revealed.

Several chains have raised their prices — or closed locations — in response to the wage increase, which has now led to a noticeable decline in foot traffic.


Telling Better Franchise Stories Via The Narritive Arc

Storytelling triggers the release of oxytocin, a hormone associated with empathy and trust, fostering a deeper emotional connection with the brand. Let's dive into that.


Tennis Champion Coco Gauff Reveals the Daily Habits That Help Her Win On and Off the Court — Plus a 'No Brainer' Business Move

As Gauff prepares for the Olympics in Paris this summer, she's sticking to some tried-and-true routines for success.

Side Hustle

She Grew Her Side Hustle Sales From $0 to Over $6 Million in Just 6 Months — and an 'Old-School' Mindset Helped Her Do It

Cynthia Sakai, designer and founder of the luxury personal care company evolvetogether, felt compelled to help people during the pandemic.

Employee Experience & Recruiting

Follow These 5 Strategies if You Want a Thriving Mentorship Program

How your mentorship program can become a powerful force for growing your team and company image.