The Failure Experiment


I know, intellectually, that failure is part of life. But it’s not something I’ve had much experience with. My life has never been messy, or far from the beaten path, or out of synch with my own expectations for myself.  My first 30+ years have provided stability and many rich experiences, but it is not quite the wild and precious thing that I want for the next thirty.

I am in the middle of a change. I’m at the point where I know something is happening, but my ultimate destination is murky. Even though I can’t visualize it (or maybe because I can’t), I am worried that I might fail to arrive in this new place. And that terrifies me.

I recently cut back to a 4-day workweek and now have Mondays to myself to focus on writing and explore an alternate career: becoming a career coach. I’m taking a coaching class and am practicing with friends. I am putting effort into this exploration, but it’s still firmly in the realm of safe. I am exploring without having to commit to quitting my current job or starting a real business. I cling to the word “exploring” when I explain what I’m doing. It is gentle and implies a survey of the surrounding terrain without needing to find a destination. “Exploring” is appropriate since I don’t really know my end destination, but I also take comfort in being vague.

Truthfully, I’m afraid. I’m afraid to go beyond the things that feel safe and under my control, like completing class assignments and reading books on communication and positive psychology. To really to move forward in this new endeavor, I need to do things that are scary, that risk rejection and failure. The potential for failure here feels very personal. In my current job, I can hide behind the complexity of being part of an organization that is trying to make changes in the world. Failed projects can be blamed on circumstance, lack of budget, or lack of coordination with stakeholders. I never feel that it’s all on me.

To work independently is to construct something (a business?!) wholly of myself. The daily tasks are personal (will I be a good coach?), as are the business decisions (what products should I offer? when and how do I look for clients?). These are choices that I must make alone, limited by my own ideas and ability. I must risk that my ideas will go horribly, embarrassingly wrong. I will risk that no one will pay me, or not enough, that I might find out that I’m not good enough, or that it’s not even actually want I want to do. I have no one to please but myself, a far cry from my current project-based work, and even farther from graded school assignments.

If I’m serious about trying something new in my career, I know I need to find I way to move forward, despite this fear of failure. In an interview, composer Marcos Balter described his desire for failure. He points out that all great composers wrote pieces that didn’t work, but history erases those mistakes and highlights the great works. You might be able to hum Beethoven’s 9th Symphony, but most people haven’t heard his first. Everyone has failures, even people who make it.

But Marcos goes further, suggesting that failure is intertwined with greatness. That is, people who create great music do so because they fail. To reach this level of success, you must push boundaries to find the place where your work is new and wonderful. In the process of trying, you will certain head in the wrong direction. Many efforts will not work; you will fail.

You will not necessarily *be* a failure though. The difference, I think, between being a failure and being someone who tried and failed is how much of your own worthiness and esteem you hitched to the wagon of accomplishment, and how you can rebound after the failure. Do you quit, or can you learn from it? Can this just be one failure, one trial run in a larger experiment?

My fear of failure runs deeper than those adorable, little fears behind lazy. These fears are significant. They threaten my livelihood and cut to the core of how I think of myself. But I’m trying to convert failure from big, scary and bad, into a sign that I’m pushing on boundaries and exploring courageously. It is time to experiment, and like in any scientific experiment, I will likely fail many times before I find the right solution.

So I’m psyching myself up for this. I am looking to fail. Whatever happens, I will aim to enjoy the experience and exploration. I hope to find the resilience to pick up and try again, and chalk it up to just one trial run, one data point.


Image: “Gravity” by Patrick Kramer (re-published with permission from the artist) 


  1. Nick Nelson

    Great piece! It’s important to approach the idea of failure (and, really, the word failure itself) in this way–especially when you’re traveling into unknown life territory.

    It’s also interesting how prevalent the thought of failure is when you start your own venture and head down a different, more independent path. When everything hinges on you, failure is so much more terrifying. That’s why it’s important to stop, take a long look at that idea of failure, and realize it’s not that scary after all.

    That way, in the occasions where failure does happen, you know it won’t be the end of the world. You almost start to embrace the failure as a key driver in the future growth/success of your business, your music, your art, or your whole darn self.

  2. Hi, thank you for sharing this. I started a business, and the nights of staring at the ceiling contemplating what I felt to potentially be a public failure ~ this was definitely one of my biggest challenges. After having only one student sign up for my first class, it has gone well, after ups and downs, and those meditations to get through those feelings have impacted me for the better. I think you will be a great coach, as you are so open and brave to share your feelings. Thanks!

    • steph

      Hi Alexa– thanks so much! I really appreciate your confidence, and your insight as someone who is farther down the path! It definitely takes patience and persistence to keep going.

  3. Years ago I left my law firm, which no longer felt like a fit for me, to start a publication. It was an area where I saw a need but had no assurance of it succeeding, and there were times of real anxiety — borrowing, selling a painting to keep things going. And amazingly it did work out quite well.

    Now, years later, after a period of relative inactivity, I’m doing something similar — a cyber pub; website + email — but the field has become crowded, very crowded. Younger and very talented people. It’s exciting. I’m not making money this go-around, but I’m engaged and enjoying it. And if i could just find someone to help me market it, there’s every chance it would do well.

    There’s a carrot in front of my nose, I guess. It may work out, or not, in the next few years, but I’m enjoying the buzz of it all. The ideas. The wordplay.

    • steph

      Robert– good for your for multiple rounds of uncertainty! Thanks for sharing your experience and good luck with your current venture!

  4. Clare De Mayo

    Just struck me as strange that you have decided to be a career coach, when it doesn’t seem you actually have much experience in this area, as you say, you’ve ‘played it safe’. But you’ll be encouraging others to take ‘a leap of faith’.
    I’m all for ‘learning together’, but if I pay someone for expertise, then I do expect them to have it. Sorry if I have missed out on life experience you have, but haven’t documented in this article. It just felt like you were planning to do for others what you really needed to do for yourself.

    • steph

      Hi Clare– thanks for your comment. This is definitely something that I am testing out! I do have years of work experience and training in coaching that I bring. That said, I don’t see coaching as expertise– that is, I’m not the expert, but can hold a process to help clients figure out what they want to do next and how to get there. I definitely didn’t document that here since this piece is intended to be about the risk of failure (not really on coaching specifically).

  5. Eddie Marritz

    These are great questions you’re entertaining. A couple of things occur to me…Failure doesn’t feel like a choice. In fact, in trying to avoid failure, clinging to getting everything right, we actually cultivate failure. It’s so true about the artists and scientists we admire. We only see their successes, their masterpieces. I’ve actually shot documentaries about scientists who encourage their fellows to be guided by Samuel Becket’s words:
    “Ever Tried. Ever Failed. No matter. Try again. Fail again. Fail better” or the Mississippi blues artist Otha Turner said.”Nothing fail but a try”

    Part 9 of 9: Rising Star Fife & Drum Band at Othar Turner’s farm (1978)

    It’s how we discover, and it often involves discomfort.

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