17 Successful People Share The Best Career Mistakes They've Ever Made

For his first job, Pickens decided to go into a lawn mowing deal with his grandmother, who owned six small rental houses at the time, but he failed to do any research on his business strategy:

"It would rain two days, then we would have sun for five days. I could see the grass growing – and growing. I hadn’t looked at the job very closely. I didn’t realize the lawns were as big as they were, or what a rainy summer would do to me.

"'This was a very bad summer, and you made a bad deal,' my grandmother told me. I couldn’t help but agree. Grandmother was right. Misjudging that bid was a small mistake, one that only cost me a few dollars. Yet the sting of that minor miscalculation created such a long-lasting impression that it has stayed seared in my mind throughout my entire career."

When he was still at Microsoft, Taneja, found himself in an elevator with an important executive and couldn't say anything more than "hello":

"After that elevator ride, I promised myself to make more of an effort to connect with people with whom I don’t normally interact. In many cases these serendipitous conversations add a whole new dimension to ones thinking ... For those who find themselves in similar situation as I did, my advice is to always take the opportunity to connect with others but the key is to be genuine in doing so. Put some forethought into what you’d want to talk with someone about if you had the chance — this will make for better conversation.

"This experience taught me that in business, you have to make the most of the moments you have and to not let a level of intimidation get in the way of making a good, and lasting, impression."

Source: LinkedIn

When Schiller started in the media industry, she was told that she should choose either the creative or business route, but she was interested in both, so she never chose:

"I loved the creative side — developing documentaries, editing scripts, constructing story narratives. However, I also loved the business end. I made distribution deals with foreign broadcasters, worked with ad sales on sponsorship packages and marketing extensions. I took some interesting detours: licensing and merchandising for Captain Planet and the Planeteers; marketing the Golden Globes for TBS. It was a rush. So I kept deferring the decision about what I wanted to be.

"Since I was not on a proven course, it was never clear how one job would lead to the next. But choosing my trajectory one crossroad at a time allowed me to enjoy both sides of the media business, and I collected eclectic skill sets that prepared me for unanticipated opportunities."

"I may have seemed to weave between jobs on different sides of the industry, but what I’ve walked away with is a 360-degree view of media. Having no set roadmap gave me a view in every direction. And I truly believe that success doesn't come with a set plan. It comes with patience, a little luck, and trusting yourself to choose the opportunities that are right — for you."

Source: LinkedIn 

In 2008, Twitter was a simple "bare bones" platform that allowed third-party developers to build on it. At the time, there was so much demand for mobile Twitter apps that Le Meur decided to build an entire company — Seesmic — just for this purpose.

When Twitter realized how much hype companies like Seesmic were getting, it changed its strategy:

When he was 22 and working at Google, Rosenstein had the idea for "Gdrive," which was developed to sync files across your computers, let you share with others and worked on Windows, Mac, Linux, and the Web. It was so "useful, it was amazing," but the program was turned down by Larry Page:

"Larry was so successful and smart, I just didn’t have the confidence back then to do what I wish I’d done in hindsight: Put together a clear, coherent presentation on why Gdrive was the time to make a rare temporary exception to Google’s product integration strategy ... maybe I still wouldn’t have convinced him, but, in hindsight, I think I just didn't try hard enough. I didn't have enough confidence I was right. I also didn't have the organizational capital to influence the Google Docs team, and so when Dustin asked me in 2007 to join Facebook, I left Google without completing the project. Google eventually launched an integrated Gdrive five years later ..."

"So what did I learn? If you’re managing a project inside of a company, living and breathing it, the onus is on you, not upper management, to understand and articulate the marketing positioning and strategy that’s unique to your project. If management still disagrees with you, I wouldn’t fight them, but have enough confidence to make your case with conviction."

Source: LinkedIn

When starting her career, King wanted to move to California to become "the ultimate modern gonzo journalist," but her car broke down in Albuquerque, New Mexico along the way. Here, she heard about a job opportunity with America Online and decided to stay for the job. That's when her "education in the complete spectrum of human behaviors" began.

At the time, King thought it was a mistake to stay, but years later, back in New York, she was able to pitch her story to the Village Voice. It eventually became the cover story called "Terms of Service: Sweaty Scenes from the Life of an AOL Censor":

"Not only did this serve to launch my career as a journalist, but it also created an unexpected side-effect. I became a specialist in understanding identity shifts in the digital realm, as well as the role of corporate culture in society. I've continued to work on digital identity on projects around the world."

"I’m glad my car broke down. I’m glad my family never gave me the kind of financial support that might have forced me to justify my unusual career decisions or made me less ambitious or willing to take risks or weird jobs. And I’m glad I made that huge mistake, staying in Albuquerque, when I wrongly believed that my destiny demanded Big Sur."

Source: LinkedIn

In 1995, Agassi was working on a project for Apple that was dropped because it relied too heavily on the Internet, which at the time was still a new concept to the public.

When that project ended — along with a few other failed portfolios — Agassi was left with very little cash, so he worked fast and put together a prototype for a product to market within months:

Source: LinkedIn

In 1995, Geerdens had just started her first job at a recruitment company. At the time, investing in IT was still a new thing and when her boss said that she didn't think the company would be investing in "expensive IT," Geerdens communicated her disappointment and was fired a few days later:

"I started my very own tech-savvy recruitment company. Not to prove [my boss] wrong; I just felt very strongly about my vision on the future. In just 5 years I built a strong brand and I sold it soon afterwards, focusing even more on the opportunities the Internet has on offer with a new company and my very own online recruitment solution.

"Looking back on this episode, I’m even grateful. It's amazing how things turned out. Every mistake and every choice you ever make has an influence on your path in life. Nothing is written, but I truly believe it is worth following your guts. I fell and stood back up stronger. What I learned? Nobody is too young to have a vision for the company."

Source: LinkedIn

"Many folks criticized the Warriors' management for this move. We were projected to finish in the lower quarter of all the NBA teams. Lin, at the end of the year, on his own choice moved on to a very, very lucrative contract back to Houston where he’s performed well enough to be a significant contributor to that team this year.

Source: LinkedIn

"I was in my mid-20s at the time — my editor, David Snyder, called me into his office" and "handed me a small piece of a paper with a name and number on it and suggested I give the person a call." 

"I don't remember exactly why I never called the person David suggested I call. Some matter of weeks later David called me into his office again, this time to show me an article in the Wall Street Journal on precisely the topic he had suggested I contact his source to discuss. He didn't yell at me, but he did let me know in clear language that I had screwed up. I was humiliated.

"After that moment, and to this day, when my boss suggests I contact someone, out of principle I treat this as the highest priority. I literally drop what I'm doing and pick up the phone — or, unlike then, write an email. Any number of things can and will still go wrong, but if you don't make the call you're not setting up yourself up for success."

Source: LinkedIn

Openshaw was heading into the local CBS station in Los Angeles to appear as a guest on the live morning show when she spilled coffee on herself. She didn't know what to do and realized she wasn't prepared:

"OK, so maybe this isn’t serious stuff, but you get the idea. We've all been there. Haven't you had scenarios where you didn’t prepare as well as you should have? Or, worse, didn’t prepare at all? It’s one of the most common mistakes we make and, friends, it quite frankly does a huge disservice to us. Failing to prepare comes in all shapes and sizes and can be avoided.

"For my drive that morning into the Channel 2 station and for all of my TV appearances, I probably should have had a backup outfit on hand. Maybe you don’t spill coffee on yourself like I do, but no matter what you’re doing — wherever you are in life or your career — please always remember be prepared. Focus on what is in front of you, and don't forget to ask yourself: Am I prepared for this, and what’s my backup plan?

Source: LinkedIn

At 28, Kellman was running products for a company he co-founded when he was called in for a meeting because the board wasn't happy with his performance:

When Berger decided to spend a semester abroad in college, he handed the keys of his successful company over to the CFO and asked him to run things until Berger's return. But his staff had other plans:

Source: LinkedIn 

After selling his company to CNET, Rosensweigg was offered a job with Yahoo, but turned it down because he wanted to stay and help his team transition under new leadership. Soon after his decision, the stock market crashed and Rosensweigg lost a lot of money.

His decisions seemed like a "giant mistake personally, professionally, and scariest of all, financially," but one year later, "that mistake would turn out to be one of the best decisions of [his] career." At this time, Yahoo changed its management team and needed a new COO, a position offered to Rosensweigg:

"A year after walking away from a generous offer, I ended up joining Yahoo in a much higher position, with a new leadership team, a new board, and what I believed to be a huge opportunity. Sure, there were still great risks to making the leap to move my New York based family out to Silicon Valley. It was a costly move, in many ways, that my family wasn’t initially thrilled about. But together my wife and I decided this time the reward seemed to outweigh the risks; and the outcome of making that move was the most magnificent professional experience I have had to date."

"I took the risk to do something for the right reasons at the right time and fortunately that brought about great results ... You can never know the road not taken and at the time I didn’t know my big mistake would turn out to be such a great life changing experience."

Source: LinkedIn

When a venture fund that's known to be "rapacious" offered to lead Fertik's second round of fundraising, the two parties agreed to honor the price for a two-week period while Fertik shopped around for a better deal.

However, in the end, the company decided not to adhere to the agreement:

"At this point, the worm turned. Smelling my diminished leverage, and going expressly against their word, the original fund insisted that the deal required new terms, claiming that market conditions had changed so much in that two-week period that the adjustment was justified. Of course, as you can imagine, there was no material market condition change in that fortnight of any kind at all, either on the public or private markets."

"And they had pushed me to my limit. For the first time in my working relationship with them, I decided to stand up squarely for myself. I quietly and firmly told them that that I would not accept those terms. I went further. I told them that if they went back on their word to me, I would make sure every single young entrepreneur inside and outside New England would know what they had done."

"Bottom line: there’s just a way to be a human being, even and especially in business, and being around people who plunder your good intentions doesn’t interest me. It’s also why I’ve made it a personal mission to educate young entrepreneurs. At least when they make mistakes – as we all inevitably do starting out – their eyes will be wide open and watching for the biggest pitfalls."

Source: LinkedIn

After appearing on FOX’s hit reality television show, Paradise Hotel in 2003, Kerpen dealt with public backlash:

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