• Caitlin Ouano

How to Thrive on Failure

I remember getting into my first choice university when I was seventeen. I had worked so hard to do so; it had been my goal every single day since I was eleven years old. I loved school, I loved learning; I thrived on getting A’s. I thought getting admitted was the first success in a long path of future achievements.


As it turned out, that was the last successful acceptance I would have for a while.


University wasn’t difficult for me, but I found that trying to do several things wasn’t as easy as it was in high school. I liked literature and economics, but found it hard to balance the rigorous economics coursework, so I had to drop the major and minor in it instead. I considered that a huge failure and a blow to my confidence as a straight A student. I applied for eighty paid internships and was admitted to one unpaid one. I didn’t make the club basketball team. I tried to direct a play, something I’d never done before, and received a small budget and no assistance. I was “failing college.”


Through those failures, I found purpose. I realized that applying to internships in economics related fields didn’t make me happy. Directing the small budget play with no help at all, for some reason, did make me happy. I tried applying to a screenwriting internship that had 150 more qualified applicants lining up with their reels and resumes. I immediately got a response: please call me for an interview, you show real passion. My boss from that internship is still a friend of mine to this day. Plus, it was paid.


When I graduated, some mild success came! I secured a production job in Los Angeles faster than all my friends, so I decided to work in production; I used that job to make a few short films and wrote copy for websites. I was thriving, I was successful. Then, I found myself in a miserable low-paying job at a production company, none of my scripts that I pitched to producers were getting good feedback, several of my friends moved away, and freelance work stopped rolling in. The success had made me complacent; I had no fresh material, my perspective in meetings was stale, and I had neglected my friendships in the name of work. I was now “failing in my career.”

I sat in the failure for a while. Everything I thought I was doing right wasn’t making me happy, and I was not productive at work. I examined my mistakes. After a few months, I hit restart again and moved home to New Jersey. I used my failure to rediscover a new purpose, one that I didn’t foresee at all.



I remembered that I liked tutoring in college, so I started doing it again to pay the bills, and then found long term work as a teacher. I found real joy in it. I loved watching students grow in their understanding of something they were passionate about, and remembered how much my high school tutors had inspired me and helped me through some tough moments; it was a way to give back.


Education ended up being a better fit for me than production work, but it additionally gave me a flexible schedule so that I could write and work on film projects I enjoyed. I didn’t have to work long production hours to pay rent and pitch work to producers that “would sell.” I could develop work I was truly interested in making. Now I couldn’t be happier with some of the New York films I’ve developed in the past year, and I formed strong friendships with several collaborators and film crews, something I didn’t think to do before when I was strictly hiring people. The first short film I made since my extended year-long “failure” rut went on to be officially selected in five major festivals in 2020, and was nominated for a few awards. My films before then? One festival appearance, zero awards.


I can name several colleagues off the top of my head who switched careers at the same exact point in their lives: the moment their boss offered them a promotion. They realized “heck no; I don’t want to keep doing this.” Success without purpose perpetuates apathy and leaves us on a plateau, as we chase reinforcement from others rather than ourselves. Success motivates us to replicate the original outcome. Failure and dissatisfaction force us to focus on our own goals and desired achievements. If I had become a successful economics research associate, it would have taken me years to finally become a filmmaker and teacher.


Working in a career or going to a certain school because you are “supposed to” or because you did well in school and “should do” what smart kids do, isn’t an optimal decision (to use some economics terminology!). By achieving for achievement’s sake, or staying in a school or a job we don’t really care about, we are taking the place of someone who would truly find meaning in that position. My replacement at the miserable production company job went on to revamp their whole website and demo reel; something I would have never bothered to do if I had stayed.


I am now quite far from the achievement-driven person I used to be (though I’m still a Type A workaholic). Just a few months ago, I interviewed a young student as part of his application process for my alma mater. He had started his own business at fifteen! I was impressed until I asked him why he started the business and he responded, “I wanted to show colleges I could do it.” Until this young man fails at something, he will likely keep achieving for others' reinforcement.


I hope I instill in the next generation the desire to cultivate a habit of personal growth. Find your own interests as early as possible, and chase them until they shift and evolve into something else for you to chase. You only have this one unique life to live, and there’s no sequel. Investing in your core purpose and drive makes you more resilient, persistent, and efficient—an economist’s favorite word.


I used to think failure was the worst thing that could happen to me. I thought it was something to be ashamed of. Now, I’m addicted to it. Mistakes suck, but I work to find the kernel of wisdom in them. The best advice I give my students is the same advice my tutor gave me: Fail Big and Fail Fast. The deeper the rut you fall into, the more momentum you have to propel forward.

Caitlin Ouano is an academic coach and business development professional at AscendNow. She graduated from Georgetown University in 2017.


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