8 LinkedIn Influencers Reveal Their Best Career Mistakes…Ever (Must Read)


What is the worst career mistake you ever made? Sometimes we wish we could take it all back and go back to the way things were before that life changing decision that changed everything for you and the people around you.

There are days you wish you had made that decision to start a company. There are times you also wish you had not quit that job. And sometimes you just wish you had quit your job sooner. It’s a different story for everybody, but in the end, make the most of even your worst decision and come back stronger.

These are  8 LinkedIn Influencers who wished they had done things differently in the past. You can also check out some of the best advice..ever from 8 other LinkedIn Influencers.

1. Cyrus Massoumi, CEO / Founder at ZocDoc

–My Best Mistake: Starting a Company

In 1999, I set out to solve the problem that my size 13 feet have long posed. I was buying countless pairs of shoes online, but returning just as many. The returns process was as painful as too-tight sneakers in the early days of e-commerce. To solve this, I started a company called OneSizeTooSmall, which was going to change this forever.

On paper, everything seemed great: I built a team of great people who had dedicated a lot to making the company a success. We had raised some capital and attracted some high profile board members.

Things were looking good. And yet, as you’ve probably deduced, OneSizeTooSmall is no more. My first company was a failure. What happened? Well, the e-commerce industry collapsed.

Of course, I look back on the failure of my first business with pangs of regret and sadness, but it’s mixed with a healthy dose of gratitude, as well. I never would have had the foundation to start ZocDoc without this painful failure.

2.  Mark Hull, Director of Product Management at LinkedIn

–My Best Mistake: Ignoring What Really Matters

My biggest career mistake was choosing a career opportunity for the wrong reasons. I realized too late that my series of bad work days was going to be a Groundhog Day experience — a never-ending cycle until I left.

There were plenty of signs at the office that the company’s values weren’t aligned with my own. My coworkers commiserated about daily executive screamathon meetings that pitted us against each other in an exercise of deflecting blame.

Others were surprised when a leader said not to worry about a deal’s details because “a contract doesn’t mean anything once it’s signed.” There was rarely interest in addressing cracks in the company’s product and business foundation.

Undoubtedly, you will have your own horror stories at work. But if you choose career opportunities that are authentically aligned with your values, you’ll have the rewards and incentive to carry you to the next brighter day.

3. Justin Rosenstein, Co-Founder of Asana

– My Best Mistake: I Could Have Launched Google Drive in 2006

I led the development of an early fully-working version of Google Drive, but failed to ship it under some pretty crazy circumstances. In the process, I learned about the importance of clear, confident communication.

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.

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

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.

Now that I’m in a leadership role as the co-founder of Asana, I think twice before disagreeing with one of my reports when they look like they’ve really thought something through in their area of expertise and are passionate about their conclusion.

5.  Shai Agassi, Founder, Better Place

–My Best Mistake: Betting On Apple and Others—And Nearly Going Under

Back in 1995, my small startup was contracted by Apple to work on a special project within Apple’s Advanced Technology Group. Mind you, this is pre-“Jobs’ second coming” Apple. So, while still counting as working inside the holiest part of the church, we weren’t working in the great Apple of the 21st century.

I moved myself and a team of seven engineers from Israel to Cupertino, Calif., and we started coding an educational platform. Within a year the project got canceled.

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. Unless you find a smart partner that shares your vision, avoid the temptation. You are better off setting your own course through life.

6. Vivian Schiller, Head of News at Twitter

– My Best Mistake: Forgetting the Five Year Career Plan

Here is my most dreaded question: “Where do you see yourself in five years?” I have never been able to answer that one. Still can’t. And that failure to map out my life in advance has been the best career mistake I ever made.

When I first started working in media in the pre-internet era, I was told by my elders that there were two ways go: the “Creative” direction or the “Business” direction.

I was told if I wanted a career I had to choose one of those paths, but I had to lock in soon. I was in my 20’s and apparently getting old fast. But I didn’t pick. I loved the Creative side — developing documentaries, editing scripts, constructing story narratives.

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.

7. Jon Steinberg, BuzzFeed President and COO

–My Best Mistake: Thinking Education Beat Experience

I made career mistake after mistake for the first 8 years of my career. I’ve taken the dirt road, a long-and-winding, unpaved path filled with diversions. I had an amazing internship as aDisney Imagineer at the age of 15, which was the culmination of a dream I had had since the age of 10, see above.

We I met Jonah Peretti and the team behind BuzzFeed, I knew this was a team of great people that I could trust, enjoy working with, learn from, and collaborate deeply with. I could correct the mistake I made in leaving Jerry many years ago.

And when I learned about what they were building, I realized I could get back to the world of ideas and innovation that had been so magical and inspiring from my Imagineering days and time with Trevor.

And finally, in taking leaps first to Google and then to BuzzFeed, I was able to do what I wanted to do, correcting the mistake I made in not skipping college and staying on at Imagineering.

8. Gary Vaynerchuk, Entrepreneur, Investor, Best-Selling Author, Speaker, Jets Fan

–My Best Mistake: Too Much Success

The biggest mistake in my career was actually during an enormously successful period, circa 2003-2008. That was a five-year window where I accelerated the Winelibrary.cominfrastructure, my wine store grew from 4,000 to 40,000 square feet, and I solidified my place as the leader in the wine retail e-commerce business.

Then in 2006 and 2007, I began my journey as a wine blogger, built my personal brand, started investing in companies like Tumblr, became “internet-famous” and a New York Times best-selling author.

I will tell you that I look at 2003-2008, a period that many people look at as a signature growth and winning experience, as a losing experience.

I look back at those five years and tremendously regret not having better balance between that success and spending time with my wife Lizzie.  I sit here, even as I write this, and really regret not finding 50 days in those five years to go to Paris or Japan; to go to the beach; to just stay home and watch movies.

Work-life balance is always the most difficult thing for someone as hungry and as ambitious as I am. However, the saving grace of that five-year period is the fact that it taught me — in hindsight of 2009 as I thought back to it — the balance that I was looking for, and the mistakes I’d made. I’m not replicating those mistakes in this new chapter of my life.

Do share your mistakes with others to help young professionals make the best decisions now and tomorrow.