Confronting Failure By Drowning In It
It’s not productive in the short term and there are probably better options.
Three years ago, I went back to school because I worked in tech and felt that product strategy was, more often than not, being defined by people who had consulting and business operations backgrounds. I didn’t like it. No offence to you if this describes you. But I felt that if a product vertical in your organization is being led by a product manager that doesn’t have a background in design, engineering, or analytics, you are optimizing for process and productivity. You are not optimizing for expertise and user experience.
My work experience was in analytics but I wanted a more hands-on experience with development - designing and building both physical and digital products. I did a grad program in design engineering where I struggled a lot. I learned slowly and my peers in the program were younger, smarter, and more talented than me. There were days that I called in sick because I was embarrassed by my final product and I did not want my peers to see it. The shame actually caused physical symptoms so I wasn’t being totally academically dishonest. I finished the program with a capstone project where I worked on every part of the product development to produce something I was not embarrassed by.
After grad school, I took some time off before actively starting my job search which probably made it harder to get the role I wanted. I eventually got a job somewhat related to product strategy and development where I was doing product marketing for a 3D printing company. I struggled a lot. I did not have the project management or soft skills that someone with a consulting or business operations background has mastered to successfully keep multiple stakeholders aligned, marching towards a common goal. I was calling in sick again and avoiding the people I was responsible to. There were small wins and incremental steps in the right direction, but not enough. I was fired.
For the few months since this, I’ve been working on a project independently. The experiences of struggle and success have been similar to the ones I had in school and my product marketing role; the feeling of failure is prolific throughout where a good day feels like treading water after weeks of drowning. By contrast, the seven years before going back to school working in different analytics roles felt like lying down on a rudderless raft. I wasn’t struggling or thriving. I was living very comfortably and a good day didn’t feel very different from a bad day.
It took me a while to realize that this period in my life since going back to school, professionally, has been a blown out version of the experience I have every day as a stand up comedian. There is a consistent feeling of failure. I am imposing myself into a space that nobody wants or needs me in. But sometimes, there is a moment where I can take a gulp of fresh air and see that I’ve done something good. All of these things are happening repeatedly within a five-minute set I’m on stage for. The difficult part is when that breath of fresh air is not the last feeling at the end of the night. It makes the feeling of drowning not worth struggling against.
It may sound insane to continue this way and not return to the comfortable steady-state I had working in my analytics roles. And even more outrageously, I used to criticize people wanting to live in that comfortable steady-state. It’s partially because of the sensitivity I have to earning my privilege which makes me indulge struggle. But in large part, it’s because drowning underwater is where I craft something new and worthwhile that propels me out to take a breath of fresh air. And I appreciate that single moment more than the years of comfortable steady-state that, for me, were rudderless. Without direction and self-indulgent.
This isn’t for everyone and I have moved on from condescending at the idea of a person wanting to live in that comfortable steady-state. I even envy it at times because not everyone has to experience how low the lows can be and how infrequent the highs are to be doing something worthwhile. Some are able to do the things that give them purpose in that comfortable steady-state. The main benefit for me has been a lot of learning and growth. I have a little more familiarity with the path to a high to make them a little more frequent. And conversely, I know now that when I am drowning, the feeling won’t last forever. It doesn’t make the lows any less low. But it helps put drowning into context so I can sooner get back to crafting something new and worthwhile.
What this looks like in real life is that I used to think entrepreneurship was stupid. I still think it is stupid. At least the culture of it - the way people post on LinkedIn is very annoying. But I’ve been able to learn cool things going through starting my own business that has helped me discover that growing something matters more to me than the steadiness of a pay check. At an everyday-scale, it’s made me a little more resilient to facing the silence of an audience I’m performing a joke to that I’ve spent a year working on. That literally happens every damn day. It also helped me develop the project management and soft skills that I was lacking yada, yada, yada.
So if any of this resonates with you, try failing. A lot. Drown in your own mediocrity. You may learn that you are also a masochist. You may also find the things you’re willing to struggle for. For me that is my partner, stand up comedy, and building things.
Coincidentally, I started doing stand up when I went back to school. Probably not a coincidence, actually. I’m still not good at it but if you laughed a lot while reading this, from start to finish, you’ll really enjoy my stand up.