Get All Access for $5/mo

5 Questions to Help You Find Out Why You Really Want to Be an Entrepreneur Your strongest motivations arise from the things that are the source of your happiness or that protect you from primal fears. Explore them.

By Derek Lidow Edited by Dan Bova

Opinions expressed by Entrepreneur contributors are their own.


Ask would-be entrepreneurs why they are pursuing that path, and you're likely to get answers like these: "I want to do something good for the world," or, "I want to do something that's mine," or, "I want work that makes me happy."

Over the past five years, I've heard those answers -- or some variation of them -- from more than 250 students in my entrepreneurship courses at Princeton University and from many of the more than 100 entrepreneurs I've counseled about their startups. But these declared motives, worthy as they may sound, are rarely what really drives entrepreneurs who ultimately succeed. Dig deeper, and you'll often find motives that are far messier -- selfishness, revenge, fear of failure, a need to prove oneself to a seemingly unloving parent and many other things that most people would be reluctant to admit, if they were even aware of those motives in the first place.

Related: Entrepreneurs Turn the Classic Theory of Maslow's Hierarchy of Needs on its Head

An entrepreneur I know well failed at several startups, one after the other -- until he discovered the power of revenge and a thirst for recognition. Previously, he had launched each of his startups to capture opportunities, but he kept failing, because other entrepreneurs wanted those same opportunities more than he did. Subsequently, as an employee of an internet media company, he designed some software and devised a business model that would go on to revolutionize the company's business.

But after a year-long struggle with the CEO, he was fired and watched as the company took off, largely as a result of his contributions. Motivated now by a burning desire to avenge his treatment and to win recognition for his originality, he launched a company that competed in the same space as his former employer. Within five years, his new company captured a significant share of the global market and now has a value of over a billion dollars.

Uncovering and understanding those deeper motives is the first step toward becoming a successful 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 very little of either. 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 a successful 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.

1. 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. They are deeply motivated by the wish to have no one ever tell 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.

Related: 5 Signs From Childhood That You Were Destined to Be an Entrepreneur

2. 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 family ridden with conflict -- 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.

3. When I was child what made me happiest?

Like anger, joy can also 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 a sunset 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 hone 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's 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.

4. 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 a founder, but you can certainly be part of a team.

5. 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 clearly 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 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 it to yourself. 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 in yourself and master the tricky balance of being selfish enough to be a driven entrepreneur and selfless enough to lead people to sign up for your dream.

Related: 5 Antidotes to Overwhelm In Your Life And Business

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

Business Solutions

Increase Productivity with This Microsoft 365 Subscription, Now $25 Off

It can make the entrepreneur life a lot easier.

Business News

Apple Pay Later Is Ending. Here's What's Taking Its Place.

The program was available for less than a year.


This Artist Answered a Businessman's 'Powerful' Question — Then His Work Became 'the Poster Child for Juneteenth': 'Your Network Really Becomes Your Net Worth'

Reginald Adams was the executive director of a Houston-based art museum for more than a decade before he decided to launch his own public art and design firm.


Harvard Business School Professor Says 65% of Startups Fail for One Reason. Here's How to Avoid It.

Team alignment isn't nice to have -- it's critical for running a successful business.

Business News

Here's What Companies Are Open and Closed on Juneteenth 2024

Since it became a holiday in 2021, Juneteenth has been recognized by some major corporations as a paid day off.

Growing a Business

I Hit $100 Million in Annual Revenue by Being More Transparent — Here Are the 3 Strategies That Helped Me Succeed

Three road-tested ways to be more transparent and build relationships that can transform your business — without leaving you feeling nightmarishly over-exposed.