Lessons Learned: The Art of Never Looking Back


Maynard Webb, the chairman of Yahoo, wishes that when he started out in business, he had been more collaborative and less focused on his own ambitions.

“In my 20s, I was all about me,” Webb told Linkedin in a 2014 article, If I were 22. “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.”

Webb is not the only iconic business leader who has some regrets about what they did, or how they did it, when they were first starting out. Fashion icon Rachel Zoe, CEO of the company that bears her name, wishes she did more to avoid office drama and politics. Expedia CEO Dara Khosrowshahi would like to have taken more risks. Former Apple Chief Evangelist Guy Kawasaki thinks young people should wait until their 30s to get married.

The point is that even the most successful people in the business world get to a point where they understand that they have learned things over their careers that would have been invaluable to them when they were starting out. It’s just part of human nature and the maturation process.

Could you somehow avoid this fate, and learn now everything that you need to know at the outset of your careers? Unlikely. Instead of worrying about accumulating wisdom prematurely, you should focus on applying the knowledge you acquire the moment you acquire it.

Most of us will end up working 30-40 years, and one of our biggest challenges will be finding the energy and willpower to make every day of our working lives meaningful and productive. One way to do that is to learn the important lessons about work and career, and incorporate the new wisdom into our daily routines.

The trick here is not to lament about what you didn’t know earlier in your working life. It is to realize it’s never too late to try new things or approach problems in new ways.

The reality is that we can never go back to the beginning of our careers and start over. And even if we knew then what we know now, we’d likely not take our own advice.

However, we can make every day a fresh start by applying gained wisdom immediately and forcefully.

  • That's an astute answer to a tricky qutosien

    4/27/2017 1:13 PM
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