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Failure is shaped like a fork

Failure has been on my mind a lot lately because I am launching my own business. I feel optimistic and excited, but I have no idea what I'm getting myself into. I vacillate between "How could I fail?" and "How will I pay my mortgage?"

My business is called Rain Content Solutions, and I am helping professional services clients develop content marketing strategies. It was a very difficult decision to start the business, and it took me a while to figure out why. For all of the talk among entrepreneurs about failure being a net positive, it scares me to death. I've conveniently forgotten that I've already failed in a fairly spectacular fashion in my professional life. For some reason I had never seen my failure in such stark terms. Thanks to the forgetting that comes with age, many sleepless nights and tears, I now see my failure as a fork in the road. I want to share it because I think it's so important for us all to remember that failure is inevitable, and we could all use a bit of empathy, encouragement and reframing what failure actually means. So here is my failure story.


As I sit backstage at the Orlando Opera in 1998, I think about this moment and the many directions it could take me. I am in the finals of the Orlando Opera Young Singers Competition. First prize will land me a paid singing job with the Orlando Opera for one year. This would be a perfect next step for me in my journey toward being a full-time opera singer. Building a singing career is like building a massive pyramid one brick at a time. Every brick is essential to the whole. The base of the wall is much easier to put in place, and as the wall gets higher, fewer bricks are needed and they are harder to reach. This job's brick is getting close to the top of the pyramid.

I love singing because I never feel more connected to the world or more free than when I am performing. In Orlando, I would perform small roles with the company, do community outreach and occasionally sing in the chorus. The drawback: I would have to move to Orlando, and I live in New York City. To some, this might seem like a fun diversion. To me, it represents my mixed feelings about my chosen career. Living for an entire year in a place that doesn’t feel at all like home is enough of a deterrent, but I hesitate for other reasons. After so much wandering, dating and loneliness, I have finally found a life partner, and he does not live in Orlando. He lives in New York.

I am 28 years old and so far, my entire life has been moving toward this moment. From the discipline and musical skills I learned as a preteen in the San Francisco Girls Chorus, to the roles in the high school musical, to my two degrees in music, this is why I’ve trained so hard. I have sacrificed the stability of my hometown in California and moved across the country to New York City for moments like this.

I step on stage and perform three arias in front of a very forgiving audience of opera supporters. Nothing feels right, and I've instantly convinced myself that I couldn't win or maybe it's that I didn't want to win? I can't really tell the difference. Something just feels off.

You might have guessed that I didn’t win the competition, and I went back to New York knowing that this time, my failure was a big fork in the road. I missed the next rung in the ladder, and it became emblematic of the choice that was really in front of me: Continue singing, and possibly give up my relationship or give in to failing at something I had worked toward for so long.


Failure is something that most of us truly dread (unless you’re one of those Silicon Valley startups that likes to “fail fast” and get funded at a new company the following week). I was so scared to fail, and I believed that it couldn’t happen to me because I had worked so hard and been so committed to being a professional musician. The thing is, life sometimes gets in the way, and there is always a lot of luck involved in succeeding. For me it was very important to listen to my feelings about succeeding and my feelings about failing. In the case of this competition, succeeding felt so much worse than failing. Of course, failing also threw me into turmoil because I had to figure out what my life was going to look like next.

In hindsight, I can see that my chosen career and I were not a good match. I'm a homebody, and I like my creature comforts. I'm a bit nervous about the unknown, and I've never had a trust fund. I also felt such a strong drive to start a family of my own. Being an opera singer would have kept me on the road for most of the year, probably not making very much money and missing my family and friends. So what really happened here is that I embraced failure. I stopped pushing so hard. I agreed with the fate that had befallen me rather than fight, fight, fight, a requirement for professional musicians. I happened upon a fork in the road, and I chose my path.

I tell this story because I think we all have the power to get past the terrible feeling of rejection when we don't reach our goals. Do I regret my choice to embrace failure? Sometimes. But mostly I’m proud that I was able to start over. Right after Orlando, I started working in marketing in a law firm, and I poured myself into learning a new field, without any training or experience. Proving to myself that it is possible to learn from my failures and look for something new was a huge lesson. It was also a lesson to realize that I could be happy and thrive even though I wasn't living the dream that I had laid out for myself. We are constantly confronted with these types of disappointments and the inevitable choices that follow. We dream, pursue, strive, struggle, fail and adjust. But maybe sometimes what we want is not going to make us happy. Our failures allow us to uncover new strengths and new lives within our lives.

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