We are told mistakes happen and that we should to get over them as soon as they occur which is pretty sound advice. But some career mistakes can haunt us for years and cause severe damage. So why not avoid them in the first place?

I make a lot of mistakes but one of my biggest happened over a decade ago when I was offered my dream job. It involved a move halfway across the world but an opportunity to head in an entirely different direction in my career. When the time came to talk about my salary, I didn't do the one thing you're supposed to do: negotiate. I was so frightened that the job would go to someone else or that I would be seen as a troublemaker that I jumped at the first offer.

Little did I know that this devalued me in front of my new employer. Years later, she told me that I had made a terrible mistake. She said she was ready to negotiate and that she had purposely given me a lower salary. I undervalued myself and I paid the price by living for many years with a below-average salary. This mistake cost me tens of thousands of dollars.

Looking back, I want to face-palm myself. But I'm not alone. I think we all have those moments, including the CEOs on Radiate who were gracious enough to share their own career blunders:

"I would have taken control of my career earlier" says Susan Lyne, founding partner of BBG Ventures. "For many, many years, I really said 'yes' or 'no' to offers that came in; and it was only after I lost my job at ABC, a job that I really adored, that I realized there was a hidden benefit here, which was that I was going to, for the first time in my life, be able to really step back and decide what I wanted to do, as opposed to what was being offered to me; and that was the beginning of something very new and very interesting."

"I've been crippled by opportunity for the last decade," remarked Gary Vaynerchuk, CEO of Vaynermedia. "Should I have gone on Top Chef and been the wine guy seven years ago, and then use that vein to create other opportunities. It's easy for me to say passing on Uber twice in the angel round, it's clear as day that I left a lot of money on the table. But the truth is even with that multi-hundred million dollar lost opportunity, I think there's a lot of other blind opportunities. Not taking that meeting, not going to that event and finding that person."

"My biggest career mistake has had to do with people," admitted Mellody Hobson President of Ariel Investments. "Either choices that I made that weren't right or sitting with an issue with a person for too long, not pulling the trigger when I needed to, maybe being too conservative about a person that I wanted to hire that seemed expensive." She continued: "Sometimes they were short-sighted or sometimes I let a relationship get in the way of a better decision. Sometimes it was really my drive and energy and ambition pushing people too hard, and I have to own all of that."

Now that you've read these CEOs' biggest mistakes, what are yours and what did you learn? Let me know in the comments below!

Published on: Dec 7, 2017