I’m a recovering perfectionist, and some thoughts about failure.

May 9, 2016 |  Category:   life me rambling


As an (overly) ambitious and driven person, accepting failure is hard. Finding the lessons to be learned from those failures, however, is not too difficult to do. The truth is – and this may sound ridiculous – I have not “failed” at very many things in my life and in a way I felt I was overdue. I know this is a really weird way to look at things, but hear me out. It’s an important lesson that I need to pass on to my daughters and one that’s taken me nearly a lifetime to learn. We can’t live in fear of failure because failure is a part of life. If it’s not something you’ve gone through and experienced, you won’t necessarily learn the coping skills to pull yourself out to the other side.

But while I’ve not experienced failure in my professional life on any grand scale (perhaps up to now), I feel like big success has eluded me as well. I write this rather tentatively because I know I’ve gotten flack in the past for being critical given everything that I have, but I don’t take anything in life for granted. More now than ever. Being driven can leave you unsatisfied with current and past successes because it’s often not enough, but success is subjective and it means different things to different people. Your definition of success isn’t necessarily the same as others – and it shouldn’t be. Why? Because we wouldn’t have leaders and dreamers and entrepreneurs making great things – big things – if the definition of success was the same for everyone. So while I’m working on loosening the grips of all the little aspects of being a life-long perfectionist that are unhealthy, I’m reluctant to totally let go of this part of my personality because it is what drives me, despite what I have achieved so far. Sometimes I get tired of being told that the constant seeking of bigger successes is the root of unhappiness. I see the value in the power of contentment, but it’s also often at odds with my ambitious nature. I guess this is where the struggle lies and the key, as with everything, is finding that elusive balance between healthy and obsessive.


So…back to failure. Our startup failed. The fact is, the vast majority of startups fail. We failed to raise our next round, but I don’t think our product failed. I was floored by the community response around our closing and the words that were thrown around in tweets, messages and videos: Innovators. Pioneers. A company that listened to their users and cared about the community till the very end. In that sense, we did not fail and our team should really feel proud of that. I remember a few years back, talking with a friend and saying that I really wanted to be a part of something, to be part of a team and have the experience of building something great. I can now check that off my list and this is an experience that not everyone gets the opportunity to have. So perhaps the biggest disappointment is not getting the chance to see how far we could take it. I certainly didn’t expect to mourn the closing of this company so deeply. That story might be over, but what I take from it will carry over far.

Photos from Dia Beacon.

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  • Becky Kremer May 9, 2016 at 5:09 pm

    Well said 🙂

  • Vanessa May 10, 2016 at 12:02 am

    I don’t think it is human nature to be content, unless we are talking about an afternoon at a time. It’s built into us to strive, celebrate, reconsider, strive. It does seem like there should be a finish line, or perfect weather, or the right shade of pink, but I don’t ever see it happening. I am curious at what age I will stop looking forward and start looking back.

    • Jenna May 10, 2016 at 2:09 am

      I actually do think being content is something that is more natural for others. It’s really a matter of personality, I think. I’m curious too, at what age I stop striving for more. If I’m anything like my mother, it could be a while 🙂

  • Linda May 10, 2016 at 12:51 pm

    To me, you don’t sound like you’ve been a perfectionist. You sound like an impressive doer and tryer. Perfectionists are often the opposite of ambitious. They are non-doers and procrastinators, so stymied by their vision to get things right, they don’t even start. There is never enough time, enough money or the right conditions, so they put things off and are stuck in inaction. Their vision remains perfect in their minds because they never put their dreams and ideas into motion.
    I think it’s natural and healthy to mourn your loss and feel disappointment, but you *did* something. You did something you were proud of and were part of a team you were proud of. You put yourself on the line and you believed in it. Best wishes as you go forward, as it seems to this regular reader (and rare commenter) that you are made of good stuff!

    • Jenna May 13, 2016 at 2:42 pm

      Linda, thanks for taking the time to write this out. Kind words. Although I don’t think I can take 100% credit. There are plenty on internal and private moments of procrastination and inaction. I’m definitely not immune to that! I don’t know that I can ever erase self doubt completely – and maybe this is part of being an artist, but I do hope to take some more action on some of the visions I have in my head that have never made it on this blog or publicly anywhere. Thank you again.

  • yj May 11, 2016 at 12:18 am

    Hi, I learned it pretty late too; but I have to say, Brene Brown’s The Gift of Imperfection REALLY helped me as I was going through it.

    There was something very freeing about learning to be okay with not being perfect. I’m still not perfect at it, but I’m learning it and learning to practice it. I’m currently working in a professional environment where my bosses know that nobody is perfect and don’t expect it, so it’s been much easier to practice imperfection.

    • Jenna May 13, 2016 at 3:22 pm

      Yes, it’s ok with not being perfect. Nobody is, nor should anyone expect to be 🙂

  • Kika May 11, 2016 at 5:24 am

    I love the way you write. As a fellow freelancing designer with two daughters, thank you!

  • MCC May 12, 2016 at 10:06 am

    But what about rethinking our definition of “failure”. As I evolve my own identity, and as someone who finds it easiest to stay comfortable and safe, I’m trying to tell myself failure isn’t not achieving the results you hoped for, failing is never trying.

    I left a very stable job that I had for 8 years in 2015 for a startup. I learned a lot and really challenged myself. The person hired to lead the project quit which prompted the shut down of the project. My knee-jerk reaction was “see, i should have never left job A.” but that isn’t how I honestly felt/feel. I’ve since found a great opportunity that I would have not have been qualified for had it not been for the knowledge I gained at the startup. I’m trying to take more risks. Not because they’re easy or comfortable or results are guaranteed, but because I actively seek growth, knowledge and improvement. Failing is not trying — being a sideline critic. Our children are watching and how wonderful to show them sometimes we try, it doesn’t work and we try again. It’s ok.

    Onward we go.

    • Jenna May 13, 2016 at 3:24 pm

      I like this – rethinking what failure means. Thank you for introducing that perspective.

  • Prajna May 23, 2016 at 12:04 pm

    I can feel you as I experienced the same thing eight years ago. I left my job as an announcer on a radio station and joined a team to run a new jazz radio station which is my obssesion since I love jazz so much. In the beginning there was a hope. Our jazz radio had a lot surprising responses and fantastic feedback. We gained many fans and listeners and the numbers grew so fast in just one year.

    But as our main ” bussiness “, jazz music turned out failing to make promising revenues. The ectasy of getting epic feedback didn’t go equally with the profit. On the year of fifth, the investor decided to close it down. I remember that day, we got home with an emptyness in heart. It was just something precious pulled out of our soul.

    It’s been eight years now, but the failure is still haunting me. Some of my friends moved on. Some of us loose our passion (including me). I never thought that this failure can affect me deeply. I even refused some job offering in other radio station, because the passion was burnt with that jazz radio station.

    Some people may think I’m wasting my time for not moving on. But like you said, it’s just hard to accept failure. I want to be able to do that though. Maybe some another time.

    Aah I’m sorry for blabbering here. I just feel relieved to meet a ” friend “. Thanks for sharing and thanks for allowing me to write this down

  • Rachel June 3, 2016 at 10:37 am

    I’m 29, and I still haven’t experienced what I would consider to be true failure (disappointments, losses, sadness, yes; actual failure, no), and I definitely think it’s been a hindrance to my growth. I had the best childhood ever, no issues getting good grades or graduating, finding jobs…I sometimes feel like things have been too easy. I’ve worked hard, don’t get me wrong, but I often wonder if I’m weaker because of my lack of trials and tribulations. And I, too, have big ambitions…but that damn fear of failure, and not knowing how I’ll cope with it, keeps rearing its ugly head and pushing me in the opposite direction from the one in which I want to be moving. And don’t even get me started on perfectionism! Anyway, all of this is to say that I can relate. Still really enjoying your writing =]