What Was Your Biggest Mistake & What Did You Learn From It?

Mistakes, experimentation, and failure are the hot topic in education and creativity circles these days. Here at 99U, we’ve covered Tim Harford’s new book on the importance of making mistakes and adapting, rounded up tons of creatives talking about the fringe benefits of failure, and heard bestselling author Joshua Foer talk about how we must step out of our comfort zones. And if you don’t believe us, the NY Times Magazine just did an edition on why failure may be the key to success.

So when I stumbled on this Dilbert cartoon that spoofs the common job interview question, “Describe your biggest mistake and what you learned from it,” I couldn’t just laugh it off. It actually felt like a question worthy of deep consideration. So that’s what I’d like to ask you to contemplate today:

What was your biggest mistake, and what did you learn from it?

Is making mistakes really all that bad? Can we demystify our fear of failure? I’d love to hear your perspective. Please share your stories in the comments below.

To start the thread, I’ll share mine:

One of the biggest mistakes I made was a poor job transition in 2007. I had been working for an exciting startup called Flavorpill for a little over 4 years. When I joined in 2002, the company was expanding, and I had the opportunity to assemble an editorial team, collaborate with the founders on growing the brand, and work closely with our wonderful design partners to build and launch new products. It was a great job and I learned a ton. But eventually, I knew it was time to move on.

A friend connected me with the CEO of a massive music website that wanted to reinvent its coverage for a new, hipper audience. He was looking for an editor with a vision. I didn’t like their current website, but the allure of having carte blanche to reinvent the site was strong. I was also offered more money than I had ever made, and the opportunity to relocate to Los Angeles. I was ready for a major change, and this seemed like the perfect way to shake things up.

As a result, I probably didn’t do as much homework on the position as I should have. After just a few weeks on the job, I realized something was amiss. To name just a few of the problems:

  • My immediate superior and the primary person I was excited to be working with quit shortly after my arrival.
  • I recognized that this was not a startup environment. Decisions were hampered by bureaucracy and fear of upsetting what was already a good thing.
  • The people whose support I needed were not all on board with the CEO’s thirst for reinvention. Not everyone wanted change.

Recognizing all of the above, it quickly became apparent that the possibility of thinking (and acting) creatively within the organization would be slim, and consequently so was the possibility of affecting any kind of major change.

The people I worked with were lovely, despite the dysfunctions of the larger organization, so I tried to make the best of it for awhile. After it became clear that I wasn’t going to get anywhere, and I decided to get out.

Less than 10 months after I had moved to LA to take that new job, I moved back to New York and started working as a freelance consultant. Within a year, I was working with Behance, and we were planting the seeds for the research that would evolve into this website, 99U.com. In other words, everything worked out great in the end.

Four years after my ill-considered move to LA, I hardly even remember the negative aspects of that experience. What sticks with me are the crucial lessons and relationships that came out of that “failure”:

  • I learned that I love the freedom, flexibility, and creativity of startup environments.
  • I learned that having enough money is important, but more money will never motivate me if I lack passion or belief in a company’s larger vision.
  • I learned that removing myself from my normal environment (in this case, New York) was a great way to reflect on next steps for my career. Even if I did it during a time when I had just made a bit of a career misstep!
  • I met a bunch of great people (who all moved back to New York, too) that have made a great impact on my life.

When I look at it this way, it doesn’t feel much like a failure. It just feels like a very necessary learning experience.

What’s Your Story?

What was your biggest mistake, and what did you learn?

More insights on: Career Development, Failure

Jocelyn K. Glei

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A writer and the founding editor of 99U, Jocelyn K. Glei is obsessed with understanding how work gives our lives meaning. She has authored three books about work, creativity, and business, including the Amazon bestsellers Manage Your Day-to-Day and Make Your Mark. Follow her @jkglei.
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