Many of the most successful people didn’t have a straightforward or easy path to the top. They made big mistakes, missed big opportunities, and suffered harsh setbacks.
What distinguishes them is the way they responded.
LinkedIn recently asked more than 60 of its influencers what their “best career mistake” was — something that seemed like a disaster at the time that ended up being incredibly beneficial.
For example, Asana co-founder Justin Rosenstein failed to get an early version of Google Drive off the ground because he didn’t push hard enough for the project. “Larry [Page] was so successful and smart,” he said. “I just didn’t have the confidence back then to do what I wish I’d done in hindsight.” But that mistake has made him a better leader today.
We’ve pulled out some of the most compelling and interesting stories that show no matter how bad things seem at the time, it’s usually not the end of the world.
T. Boone Pickens didn't do enough research on a lawn mowing deal he entered into with his grandmother, and had a terrible summer.
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 realise 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.'
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.'
Loic Le Meur, CEO of LeWeb conference, was too dependent on Twitter when he was running Seesmic, one of his six startups.
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 realised how much hype companies like Seesmic were getting, it changed its strategy:
'The end of the story is well known: some developers were acquired, others like us had to change strategy from one day to the next and many disappeared. We were finally acquired by Hootsuite.'
'Here are my two cents for entrepreneurs betting on someone else's success: be careful that everything can change from one day to another and all the rules will change. I will never be that dependent on anyone anymore.'
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.'
When Science House's EVP Rita J. King's car broke down in Albuquerque, she stayed and took an odd job.
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 behaviours' 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.'
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:
'I called a good friend from Apple, who called a few good friends he knew, and all of a sudden the mythological stories about funding a business in Silicon Valley became my reality. Within two weeks we had the capital lined up. We were looking for $500,000, but raised $800,000 from 14 individuals.
'As for TopTier Software, the company that went through this near-death experience in the summer of 1996. Well, we sold it 18 months later, for the whopping sum of $110 million. I stayed on for three more years as CEO, and in 2001 sold the company again to SAP. This time for $400 million. I stayed at SAP, too. It became my next home.
'And the lesson from my mistakes? Trust no one but yourself with the fate of your company. Don't tie yourself onto a troubled ship nor should you tie your fate to a bunch of small boats. Neither of these options will take you in the right direction ... That and hard work will make you very lucky in life.'
Inge Geerdens, CEO CVWarehouse, was fired because she had a different vision than the one her boss had for the company.
Peter Guber, CEO of Mandalay Entertainment and co-owner of the Golden State Warriors, decided not to sign Jeremy Lin last year.
'Many folks criticised 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.
'The dialog and the chagrin from the naysayers disappeared when our team this year, having engineered these changes, secured its first all star selection in 17 years and made the playoffs for only the second time in over 20 years, with the last 30 games being total sellouts.
'What all this proves is that you shouldn't worry about the naysayers. Follow your convictions and don't be driven off course by idle gossip and media speculation. They are peripheral opponents. Hits and wins turn naysayers into yeasayers.'
'The most dramatic episode took place in frustration, given that we weren't listening to the customers' preferred choice of hardware for a specific environment. More precisely, the tech customers had one preference, but their executive chose the expedient route. Things were moving really slowly, but I tried hard to be a team player, until I lost my patience one day at a customer location, visible to a number of people on both teams.''Doesn't matter that I was right, and that the project failed ... That started in the early eighties, and I didn't quite ... understand and modify my behaviour until the early nineties. Probably what really got me going right was starting to do serious customer service, and it's been eighteen years of that.'
Adam Lashinsky, senior editor at Fortune Magazine, missed an opportunity when he didn't call someone his boss told him to.
'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.'
Money expert Jennifer Openshaw spilled coffee on her shirt right before appearing on live television.
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 realised 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?
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:
'Every firing happens differently except in this one respect: the person being fired can't believe how fast it happens ... the chairman explained why I was being fired. I listened to him like I had never listened to anyone in my life. In 45 seconds, he did what almost no one paid to be your manager usually has the guts to do: he explained what was wrong with me as plainly as if I were a dented car.
'At the end of it, I said I wouldn't leave. I promised to change. I cried. 'Glenn,' the chairman said, looking away. 'Please.' Then he said, 'We're going to give you one more chance.' He never said why.
'I went back to work. I changed. All the things I imagined my successor doing, I did. The company went public. The CEO and I became good friends. I was able to look on my eight years there as a success, not a failure.'
'Since then, I've never stopped feeling lucky. It's important for a CEO to feel lucky ... Feeling lucky also fills you with love. Most CEOs walk around the office like we own the place, without realising that the place itself isn't worth owning: a business's value comes from the people who walk out the door every night, who have to decide each morning whether to walk back in. One of the simplest things you can do as a leader is honour their choice, and appreciate their work.'
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:
'After I left, the group met and decided that me running the organisation in absentia wasn't going to work. Turns out I had underestimated how critical it was to be on the ground with my team. I had changed my plans, and that was fine, but they had decided to change theirs as well. They fired me.'
'I was devastated. This organisation was my life. I had sunk all my creative energies into it and now I was just supposed to walk away? But I did. It was hard at first, but I started looking for something else to focus on. I had just read the book The Tipping Point, and decided I wanted to learn more about trends and why things catch on. A professor in the business school was doing some related research, so I asked if I could help.
'Eleven years later I'm a Marketing Professor at the Wharton School at the University of Pennsylvania. We've studied the science behind word of mouth, discovered why popular things become unpopular, and even published a popular press book on why things catch on.'
'Getting fired was the best thing that ever happened to me. If I hadn't been booted, I'd never have discovered the career path that took me to where I am today. Sure, getting fired hurt; it always does. But setbacks are just that. Setbacks. They're not the end of the story; they're the start of a new chapter.'
Daniel Rosensweigg, CEO of Chegg.com, turned down an opportunity at Yahoo because he felt like it wasn't the right move.
Reputation.com's Michael Fertik didn't listen to his gut when he chose a venture firm to finance his company.
When a venture fund that's known to be 'rapacious' offered to lead Fertik's second round of fundraising, the two parties agreed to honour 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.'
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