Dara Khosrowshahi was born in Tehran, Iran, in May of 1969. Less than a decade later, Khosrowshahi and his family would emigrate to the United States in the wake of the Iranian Revolution.
“We sure didn’t feel like refugees, but in hindsight I guess we were — my father and mother left everything behind to come here — to be safe and give their boys a chance to rebuild a life,” Khosrowshahi wrote recently in a company memo. “I remember my father taking us to meeting with lawyers, interviews with immigration officers, doing everything he could to get us that treasured Green Card — and the happiness, the sense of relief, when he finally did — we knew that we were welcome now, and we would be welcome tomorrow.”
The 9-year-old immigrant would eventually become CEO of one of the world’s largest travel companies, expanding Expedia’s presence to over 60 countries across the globe. Despite the company’s ascent deeper and deeper into the Fortune 500, Khosrowshahi has kept the company’s envied culture intact. Expedia has been consistently named one of Fortune’s Most Admired Companies, Forbes’ Most Innovative Companies and ranked No. 1 on Glassdoor’s Best Places to Work in the UK.
Looking back, Khosrowshahi shares his views on the different skills, personality traits and critical life practices that entrepreneurs and future executives should aim to develop by age 30.
From a substantive leadership and skills perspective, what were the key talents that you developed during your 20s?
Khosrowshahi: When I was in my 20s, I learned not only how to work hard, but about the importance of focus. I started in investment banking at Allen & Company in 1991. It was the go-go days of media mergers and we were incredibly busy with one deal after another. Unlike typical investment banking groups, even in the midst of merger mania, we didn’t have a formal face-time culture — and I felt empowered by that.
You should identify specific takeaways from your first few roles as a young professional that will prove relevant for a lifetime. Early on, I learned the importance of being acutely focused on my goals — and the importance of fostering a culture that avoids unnecessary restrictions.
From an emotional and human perspective, what do you think were the vital qualities that you developed during your 20s?
I learned how critical flexibility is. Learning to cope with endless demands on your time — at a young age — will both position and prepare you for advancement and growth. As you move up, business problems become non-linear and systems less predictable. A uniform approach just won’t cut it so you have to approach problems differently, with flexibility.
I remember a task I was given by Herbert Allen early on in my career. He was worried about certain financial products becoming a ticking time bomb. As you would within a startup, I was given the job of researching the subject and reporting back to him personally, with little guidance or direction. That’s how the day-to-day works at many early companies, and it’s a work setting you should become comfortable with. As I mentioned, the farther you move up, the tasks at hand often lack any structured precedence or linear roadmaps.
When you were in your 20s, what did you reflect on/think about most often? How did you come to understand your strengths and weaknesses?
Maybe it had something to do with my family having lost a lot when we emigrated from Iran to the U.S., but when I first began my career, I was a bit “Wall Street-obsessed” when it came to being financially successful. In the longer run, Expedia would teach me that passion and mission are much stronger motivators than money.
If you could go back and make one decision differently, what would it be?
If I could go back and make one decision differently, I’d travel more, but you knew I’d say that!
In what ways is serving as a leader of a company different than what people might assume?
Many people think that leadership is solely about communication — presenting, making speeches, motivating. Being a good communicator is certainly important, but I’ve found that one of the most important skills for a leader is being a good listener. The higher up in the chain of command you are, the harder it is to really know what’s going on, so you have to discover the right information out of your people. You have to be great at reading body language and asking questions. You have to engender trust to get to the real stuff. Leaders who are disconnected with reality are the ones who fail.
Looking back, if you could tell your 30-year-old self one thing or share one piece of guidance, what would it be?
If I could give my 30-year-old self one piece of advice, without a doubt it would be that it’s ok to fail. When I was younger, I was so afraid of being wrong, of being late, of being rejected. I was afraid of failing. But, the thing is, failure is so important in life, not only in terms of learning, but also in taking risks — both in your business and your personal life.
Believe me, it’s not fun to fail, but when it happens, you get up, you dust yourself off and you move on. A life without a fundamental fear of failure is way more fun than a life spent ducking for cover.