Even the World’s Most Successful Business Leaders Struggle With Self-Doubt—but You Don’t Have To

My mother once called me a spectacular failure.

She uttered the words on a particularly dark professional day. I’d built a business I loved from the ground up and invested everything I had in it. I’d mortgaged the house and spent days and weeks away from my young sons and was now watching it all fall apart.

When I had to declare bankruptcy, I was devastated. After that day, whenever I would walk into glass conference rooms at the tops of skyscrapers, I’d look at the other leaders in the room, assessing them.

Had they spectacularly failed too?

As it turns out, many of them had. I want to share with you the realization, the secret, that helped me overcome my personal fears: even the most successful business people in the world struggle with self-doubt. 

Let’s explore why. 

To be sure, some leaders follow a straight and predictable path.

Rose Marcario, the CEO of Patagonia, graduated top of her class. She got her undergraduate degree in finance, earned an MBA, and spent fifteen years at a private equity firm. She joined Patagonia in 2008 as the COO and CFO, and in less than five years was promoted to CEO. 

In the time Rose has been with Patagonia, she’s tripled the firm’s profits. She serves on several boards and has built a culture that functions as a beacon of social responsibility for other companies. Rose Marcario fit my mold of a well-qualified, confident leader.

Sundar Pichai is another prominent leader with what at first glance seems a direct path to the C-suite. Sundar is the CEO of Google and an alumnus of both Stanford and Wharton. He’s responsible for the development and distribution of the ubiquitous Google Drive and has been instrumental in shaping how the world thinks about search and document storage.

He also grew up in a two-bedroom apartment in India.

His family of four didn’t have a car and, as a child, Sundar often rode the bus for several hours a day. In 1984, when he was twelve, the family installed their first telephone, after a five-year wait. Sundar remembers the day their first refrigerator arrived. 

When he received a scholarship to study for his master’s at Stanford, his family withdrew nearly a year’s income from savings to pay for his plane ticket to California. When he first interviewed at Google, he was asked what he thought of Gmail. He’d never seen it.

When I learned about Sundar’s history, I wondered what he thought about when he first walked into the glass conference rooms at Google. 

Did he think about how he measured up to the others around the table? Did he compare his childhood self, on the bus or playing soccer in the park in Chennai, to the childhood selves of the other leaders? Did his path feel somehow less than those of his peers? He hadn’t had the advantages of private school and a game-day carpool. How did he reconcile his beginning with theirs?

I’ve since learned he did think about it. He describes his overwhelming early days in California: “I didn’t understand the internet. The change was too much for me. I think I was a little lost.” 

As well-educated and prepared as he is to lead, as much as he’s accomplished, Sundar Pichai, at least once, compared himself to his peers and found himself lacking.

The same is true for Rose Marcario. In 2006, she quit her private equity job after a crisis of conscience. She couldn’t reconcile her role in the private equity firm with her values. She traveled to Rishikesh, India, and spent weeks meditating on the banks of the Ganges. She returned to the United States feeling more centered but still very much unemployed.

I’ve seen this experience, at some level, with nearly every leader I’ve coached. All have moments when they feel disconnected, disingenuous, and alone. All wonder if they are enough.

These thoughts of self-doubt echo through most people’s minds, and I’ve concluded that the root of our fears is this: We are each privy to our full set of experiences, every misstep and failure and occasional success. That history is never perfect. Each of us at some point believes we aren’t the right or best choice for what’s ahead.

Everyone, even the world’s top executives, has experienced feelings of self-doubt and inadequacy. The difference is whether or not you will let your fears hold you back. Will you shy away from opportunities that seem like a long shot? Or will you put yourself out there, flaws and all?

When my first company went bankrupt, self-doubt devastated me, but I moved past my failed business to achieve even greater success. I remind myself, as I encourage you to, that if Sundar and Rose had given in to their self-doubt, Google and Patagonia might not be the industry-defining successes that they are today. 

Follow their example, like I did, and embrace the reality that we all experience doubt. Don’t let your doubt define you. Take risks, chase opportunities, and above everything else, trust yourself and your path, flaws and all. 

For more advice on improving your professional performance, find Naked at Work on Amazon.  More coaching is available at Avenue 8 On-Demand, on the topics of Spectacular Failure: The Secret to Success, The Power of Story, and more.

Danessa Knaupp is an executive coach, CEO, and keynote speaker, shifting the global conversation on leadership. She has coached hundreds of executives across every major industry and has developed a reputation as a candid, compassionate and courageous leadership partner. She is the author of the leadership manual, Naked at Work: A Leader’s Guide to Fearless Authenticity. She regularly addresses C-suite audiences on how to harness the power of real authenticity (not #authenticity) to drive measurable business results. Danessa earned her executive coaching credentials from Georgetown University, is credentialed by the International Coach Federation, and holds a B.A. in Psychology and Sociology from the College of William and Mary. She spent more than 20 years as an entrepreneur and a senior executive, and ultimately, CEO, before founding her coaching practice. Connect with her at danessaknaupp.com.