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.
load comments (62)
  • student

    college student:(girl)
    my biggest mistake i did was,
    i am 21 years old and my parents thought to make me get married and they asked about it to me. But i was not yet ready for marriage but they convencied me for marriage and so i agreed. But as a girl i was in a great confusion that i am getting married to a person weather he is good or not and in order to know about him i created a fake face book account and sent fiend request to his friend in order to know about him but as i realised my mistake and i told his friend total truth about me and stopped talking to him. Isaid total matter to my best friend and he stopped talking to me he thinks that i am a bitch what to do now i don’t know what to do now i can’t live if he stop talking to me. I lost my total impression on him what to do

    • ali

      You just tell him what were you intending to do, that you cared about him , his company etc, if he is smart enough he should believe you. Try to make friends and dont depend your happiness on him for sometime .

  • Rashid Ntalaluka

    Am 28 old. My two biggest mistake that are still killing me. One: I trusted a wrong people/Friends. Second: I made a wrong discussion after getting a job. I have learned from it, but i think is too late. Now i think am depressed: Man with No friends,Sleepless, Not eating well, Lonely, over-thinking. BAD THING IS AM FROM POOR FAMILY……!..
    I’M totally confused.
    Anyone with some helpful idea, welcome: rancotz@hotmail.com

  • Jasmeen Kaur

    mh biggest mistake is i choosed maths carrer without knowing about that i can do or not. now year is passessd hardly 1 month r left i don’t know 1 chapter about maths . i will be fail in 12 :'( pls anyone can tell me the solution

  • Natalie!

    thank you valentina, i want you to know that you have brought new hope into my life in a time where i am struggling to find myself. thanks.

  • Jay

    How do you study for a lie detector test? Either you lie on the test or don’t.

  • Ria

    My biggest mistake was going to college thinking I was on a full volleyball scholarship, but found out months before I finished my Freshman year that it wasn’t and that my sister had to pull a loan under my name to pay for part of my schooling, which was not covered by my scholarship. Now, my student loan is back to bite me in the behind, but I’m now married and have a daughter. And it’s really complicating things more because I’m trying to join the Air Force, but my student loan had landed me on probation with my processing because I had know idea that half of my student loan went into default. Now, I have to write a waiver statement to plea my case to their officials on why the Air Force should grant me this opportunity. (sigh)

    What the hell happened to my other payments I’ve been making? Where are those payments going to? I’m freaking out because the Air Force is basically our only option to a better life. SMH. If only I had known financial information during high school, but that is of my own fault.

    I’m really lost and feeling completely vulnerable and defeated because I don’t know what else to do to provide for my family. Please, if anyone out there can help, let me know as soon as you can. Other than that, God bless.

  • Aman

    My biggest mistake in life was helping a person. Yes helping a person at a wrong time. After gradation I had joined a MNC as a software developer and all was going fine. During my training period I made lot a of friends, some special, some normal. As in the company we had reviews, so one of my friend was lagging in the review and it was his last chance to clear it, If he was unable he was sure to be fired from the company. We were sitting on our workstations and suddenly a call came out for him for the review. He just asked me to help him in the review or he will loose his job. I made a stand to help him. I helped him in the review but unfortunately I was caught helping him. Due to this, we both was fired from the company. Now the problem is that I had only 3 months experience and its 7 months I had left the job. I am scared to mention these 3 months experience in my resume and if I did not I will be caught but any IT company for my experience through the NSR profile. The company which I had left had not mentioned any thing wrong on my profile on national basis. So, guys how should I handle the question that what have you done till now after you had done your graduation. Your comments are welcome at amandang007@gmail.com

  • samantha1980

    My biggest mistake is falling in love with someone who already had a girlfriend. I was in highschool and my best friend had recently started dating a girl, and I had fallen for him hard, so I told him with the expectations that he’d either tell me he didn’t feel the same, or he would reciprocate my feelings and then we could be together. But I didn’t realize what would really happen: being led on with the belief that he would end things with her “soon, but now is a hard time”. 3 years later and I was still head over heels in love, passing up opportunities to date other guys, and feelings terrible about myself because he cheated on her 4 times with me. I have tried to have a mindset that I learned from it, and I’m not as naïve as I once was, but that’s not what happened. Now I feel like a terrible person constantly, I don’t feel like I’m worthy of a nice man to love, and I am cynical and distrusting of love and relationships. I regret every decision I made regarding him. If I could take it back I would. But instead, I am just constantly trying to learn to live with the HORRIBLE mistake(s) I have made.

    • Nelson

      I know how that feels. I went through a similar experience with a girl who I knew at the time I wanted to marry and have kids with. But she had trouble telling me she did not feel the same way and thus just led me on. I put her too high on a pedestal which resulted in me getting hurt and then comparing every girl that I dated to her. That was the last time I ever like that for any girl.

  • Guest

    It was through the eyes of an HR representative that I found
    the company irresistible. The promise and hope of a fulfilled career move was
    just beyond my imagination; I could not have chosen the best time to make a
    transition from banking to health care.

    The thrill and prospects to ‘run’ my own projects, learn and
    adapt into new and promising organisational culture could not allow me to
    consider my employer’s counter promise of a better salary, a better role and an
    established mandate for the integrations.

    The turning point was meeting the two ladies I, at the time,
    felt they would afford me the platform to demonstrate my business acumen,
    technical skills and people skills by taking ownership of projects to be
    undertaken. I planned nothing less than to drive these projects to success at
    all costs.

    I was offered the role and I could not stop bragging about
    the prospects of the future of health care in South Africa since I firmly
    believed in the culture of innovation, allowing a project to dictate its destiny
    and needs without being coerced into the state of ‘template zombie’.

    And then I met the two ladies who sold the prestige of the
    brand of the company making me believe I could never meet a company that seemed
    to be so much in line with my views and my chosen profession. The interview was
    exciting and somewhat deep to say the least.

    I’ll forever treasure meeting those ladies; they stroke me
    like gifted and very senior professionals sharing the exact sentiments about
    the direction of the Analysis profession primarily in South Africa as well as globally.

    It honestly felt the feeling created by going through the
    spec was underselling the value of the role I was being interviewed for – a
    reason for me to brag to my wife saying “I have finally found people who
    understood the intricacies of my profession”. What an exciting journey it
    promised to be!

    The offer, I definitely knew, I could not turn down came
    through entitled “Verbal Offer – My Full Name – Senior Business Analyst Role” The
    first line after the salutation read as directly quoted from the original email
    below: ”It is with great pleasure that we extend a
    verbal offer to you for the Senior Business Analyst Role of…” The letter also
    had a mock payslip attached…

    I, soon afterwards, received another letter which seemed to
    be formal this time around but the title had been revised to “Letter of Offer –
    My Full Name – Business Analyst Role” nothing else had changed on the letter
    except for ”It is with great pleasure that we extend a verbal offer to you for
    the Business Analyst: Associate Specialist Role

    This confused the living life out of me as a result I did
    not meet my deadline to accept the job; I contacted the HR representative to
    understand what this meant to which it was confirmed it meant the same thing as
    the original letter entitled Verbal Offer
    – My Full Name – Senior Business Analyst.

    The unfortunate thing was that I had originally made it
    clear what type of a role I was looking for because I know just how challenging
    it would be to share my experience for the benefit of the company. Her
    demeanour was very convincing – How could I not believe her explanations!

    I firmly believed I was going to be part of those
    responsible for ‘questioning’ established norms within the profession. I was adamant
    the people I had met, that made me fall in love with the company, would not
    deliberately change my role and HR knows this it just made sense that the role
    was what we discussed; besides they gave me an impression they needed to quell
    a number of established practices that hinder seamless IT project delivery. I
    genuinely felt I was welcome!

    However anticipation of something is almost always different
    from actual experience. I arrived in an environment that, in my opinion, did
    not live half of the impression it created through the job specification which
    was originally printed and handed to me by the HR representative.

    I was prepared for anything the company could throw at me
    because I believe in my passion for IT. I believed that, together with the
    people I had met my interview, I could take any punches and can count on their full
    support. Was I bluffing myself?

    …It is only six months since that hype I am now in my
    seventh month; serving notice. However I am still optimistic about South
    Africa’s future and that of the company – I just do not think it would be
    worthwhile to be part of this establishment’s future.

    I can see just how much I bluffed myself because I desperately
    wanted to believe in the promise of an inclusive South Africa. I’d soon be
    joining what seemed like a young team of gifted architects prepared to devise a
    winning formula to demystify IT projects challenges.

    I wouldn’t wish my experience to my worst enemy. Learn from
    me; trust your guts – if people change anything for some reason do not to trust
    them; review your decision there and then.

    Do not allow the overwhelming feeling of excitement take
    your rational thinking out of the equation. Inconsistency equals lack of credibility;
    press the delete button and move on!

  • alishu faisal

    i do many mistake in our life the big ,mistake is that i heart someone and then i go and ask for forgiveness. then i realise that if we heart somethink soo we also not be easy to doing something

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