What 10 Incredibly Successful People Wish They Knew at 22

Thought leaders from Guy Kawasaki to Richard Branson reveal the surprising things they wished they'd known way back when.
May 23, 2014

When most of us started our careers, we had an idea of where we wanted to go and how fast we wanted to get there. But rarely does planning work out the way you, well, plan.

And it's not just you. The wisest, smartest, most successful people don't hesitate to admit they weren't capable of planning everything along the way to the top.

In a recently published series titled "If I Were 22," LinkedIn asked the most successful industry leaders to share what they know now that they wish they'd known then. The most common advice these leaders have for young people just starting out is to be more adaptable and resilient—the majority (86 percent) of the 50 leaders interviewed for the series are doing something they never thought they'd be doing when they were 22.

From Richard Branson to Rachel Zoe to Guy Kawasaki, we've highlighted some of the most helpful insights from the brightest minds around.

Richard Branson, Founder of Virgin Group

Richard Branson, founder of Virgin Group

"If I were 22 today," Branson says, "I would embrace the opportunities technology has given us. While I am in my sixties, I am incredibly excited about the transformative power of the Web and all sorts of new technology. From opportunities to tackle climate change to research to beat terrible diseases, as well as inventions to improve everyone's lives, I am sure the coming years will be a period of tremendous innovation.

"Most 22-year-olds today think that the way to make their fortunes is through setting up tech businesses," he adds, "and it is true that can be a fruitful direction. But other more conventional businesses shouldn't be forgotten. There are still plenty of different sectors that need shaking up. It is more important to follow your passion than going into tech simply to make a fortune. Not everybody is technically minded anyway, and if you don't really love what you do, you won't succeed."

Sallie Krawcheck, Owner of 85 Broads

Sallie Krawcheck, owner of 85 Broads


Krawcheck warns young people today that the road ahead isn't easy, but working hard will get you through it.

"Keep a running note of what works and what doesn’t work for you, what you like and what you don’t like, what you’re good [at] and what you aren’t, the work styles that suit you and what doesn’t, where your passions lie and what leaves you cold," Krawcheck advises. "The chance of the stars aligning on these fronts in your first job, or even your first couple of jobs, is very low, so you’ll have to keep searching.

"But it still won’t be easy once you decide what you want to do," she adds. Then she addresses her former 22-year-old self: "Over the months that follow, you’re going to be rejected by all of the major Wall Street firms—by Lehman Brothers three times (I guess they’ll want to make sure you know they really don’t want you there), by one firm after they give you an offer because they discover you have a baby at home, and by one director of research who doesn’t think you’ll work hard because you’re married. But you’ll eventually find the right firm, Sanford Bernstein, and you’ll be off to the races. It’s going to be a lot of fun. Not every day, but most days. You’re going to be rejected a lot. You’ll need thick skin to get through it. Oh, and work hard. That really matters."


Dara Khosrowshahi, CEO of Expedia

Corporate And Media Leaders Attend Allen & Company Media And Technology Conf.


"I am 22 times two now," Khosrowshahi says. "If I could do it over, I would plan less and take more risks. I wouldn’t be in such a hurry to grow up. I would realize that the consequences of mistakes are usually less than you realize. And loss and losing can be the most valuable lessons in life. I would realize that at the ripe old age of 44, I’d still have a lifetime ahead of me."

Julia Boorstin, CNBC Correspondent

Julia Boorstin, CNBC correspondent


Upon graduating from college, Boorstin already had her entire career planned out. She was going to get a master's degree at the London School of Economics and work at World Bank or a think tank. While waiting to hear back from graduate school, Boorstin got a job as a writer for Fortune magazine and decided to take a "fun year" off before launching into her "real career." As fate would have it, she never went to London or to graduate school. 

"From Facebook’s Sheryl Sandberg, who started her career at World Bank, to Twitter’s Dick Costolo, who after college tried to jumpstart a career in Improv comedy," Boorstin says, "it's hard to think of anyone who's passionate about his or her job who didn't try something unexpected."

Arianna Huffington, President and Editor-in-Chief of the Huffington Post Media Group

Portrait Of Arianna Huffington


At 22, Huffington wish she would've known that she could achieve all that she's achieved now, but with less stress, worry and anxiety.

"... The advice I’d give to young people today is this," Huffington says. "Don’t just climb the ladder of success—a ladder that leads, after all, to higher and higher levels of stress and burnout—but chart a new path to success, remaking it in a way that includes not just the conventional metrics of money and power, but a third metric that includes well-being, wisdom, wonder and giving, so that the goal is not just to succeed but to thrive."

Guy Kawasaki, Chief Evangelist of Canva; Former Evangelist of Apple

Andy Rubin Conversation With Guy Kawasaki - 2013 SXSW Music, Film + Interactive Festival


"Don't get married too soon," Kawasaki advises. "I got married when I was thirty-two. That's about the right age. Until you're about that age, you may not know who you are. You also may not know who you're marrying. I don't know anyone who got married too late. I know many people who got married too young."

Rachel Zoe, CEO of Rachel Zoe Inc.

Rachel Zoe, CEO of Rachel Zoe, Inc.


Zoe's advises all young people to "rise above the drama." "Conflict in the workplace is inevitable," she says, "especially when you work in a creative field and there are a lot of emotions or passions at play. If there is someone in particular who is weighing you down, my best advice is to kill them with kindness and smile your way through it. Ratting someone out or biting back will never get you anywhere."

Jim Kim, President of World Bank

Jim Kim, president of World Bank


"When I was 22, one thing naturally led to another," Kim says. "Even so, I wish I knew then what I understand better now about preparing myself for the future. I have three suggestions that I wish someone had told me when I was younger."

First, Kim says to work on your leadership skills, because this will always work to your advantage no matter what you do. Leadership is not about being in charge or the head of an organization but about the ability to make groups more effective. Second, he says to learn as much as you can about other people, especially the poor, because all of us, as he says, "will need to face the task of making the world more inclusive and just." Finally, Kim says he wish he would've understood the benefits of meditation or other practices that clear the mind.

Maynard Webb, Chairman of Yahoo

Maynard Webb, Webb Investment Network


"In my 20s, I was all about me," Webb says. "I wanted to be relevant; I wanted to be a shining star. I wanted success so badly that I took on special assignments hoping to get recognized. I preferred working on my own—it was so much easier and faster when I could do it all myself! But wow, I missed out on a lot. Collaboration makes everyone and everything better. I wish I knew that in my first decade at work."

Jonathan Bush, CEO and Co-Founder of athenahealth

Athenahealth's Chairman, CEO And President Jonathan Bush


"The biggest lesson I’d like to bring back to my 22-year-old self is to let my passions lead my career choices," Bush says. "I’d tell my younger self that what he saw broken in health care could be fixed if he worked hard. That is a real thing, I would tell myself. Everyone says they need a real job, but you can define what is real and worthy.

"I remember telling a well-connected family friend that I wanted my first job to be either as a medic or the right-hand man for a health-care business CEO," he adds. "He suggested consulting. I’d like to tell my younger self to not let my ambitions get clouded by those others had for me. I’d tell myself that being on the ladder is not a reflection of how hard you work." 

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Photos: Getty Images, Maynard Webb