Wandering to inspiration, pt. III
Part three in a series about the journey to build something, starting from the moment inspiration struck
As my fiancee and I embarked on the next chapter of our lives in Los Angeles, I faced a funky situation with my career search. While there are many challenges one can face while job hunting, one of the biggest is the mystery of rejection. In most cases, feedback from those rejecting you is rare, so you are left to ponder and cautiously iterate on something you might have, possibly, maybe done wrong. As someone who prides himself on self-improvement, this system is incredibly frustrating because you don’t know if you’re iterating toward further frustration or future success. Eventually, I ceded to my fiancee’s advice and connected with a career coach to help arbitrate between me and my tome of cover letters, resumes, and ‘tell me about yourself’ speeches.
Really, the seeds for changing my opinion on career coaches (‘I can figure this out on my own’) began in the summer of 2019. I began digging into old episodes of the Gimlet Media podcast, Startup. It’s a fascinating journey from co-founder Alex Blumberg’s awkward pitch meeting with investor Chris Sacca to to building a company all the way to their acquisition by Spotify in 2019. In one episode, Alex receives some difficult feedback from his team and discusses it openly and honestly with Jerry Colonna, a professional coach occasionally dubbed ‘the CEO whisperer.’ Jerry has become famous for espousing ‘radical self inquiry’ and for making people cry (in a good way).
In fact, Jerry Colonna appears in a few episodes of Startup. He even has his own podcast, called Reboot — which is also the title of his book, as well as the coaching organization he co-founded. I know all of this because Jerry Colonna, in his podcast appearances and his book, made me believe in the power of coaching — and also myself. Radical self inquiry, a core tenet of Colonna’s beliefs, is about compassionately asking and answering hard questions about yourself to understand what makes you tick and how you got that way, as a way to empower you to take control of your ‘ship.’ It’s an incredibly powerful mission, and while there is much more to what he teaches, radical self inquiry made me feel good. It made me feel empowered again. And so I went into my own coaching experience with an open mind and heart, ready to break some bones to reset them in a strong way.
From our first meeting, I knew my coach and I would get along. Akin to ‘game recognizes game,’ it was ‘mega-empath recognizes mega-empath.’ One of the biggest struggles of my job search was the feeling that people never gave me a chance, or never saw past the gaps in employment, or imperfect application materials. When someone sees you, I mean really sees you, it’s earth-shattering in the best way. For so long, I indulged feelings of self-doubt, shame, and frustration. It needed to be shattered, and her support gave me the hammer.
Early in our consultation, I mentioned that I enjoyed thinking about user experience. For instance: why do some states have highway signs that are illuminated at night while others do not? What is the optimal layout of a bank for maximum space efficiency while balancing customer experience? Which colors inspire people to click on an ad, and which don’t? I find the design of an interaction, digital or otherwise, fascinating. It calls back to my time as a student of environmental history, which I describe as the study of the relationship between the built and natural world — how they interact, and how one affects the other. Being able to understand relationships between something that exists and a construct that affects it informed my perspective on UX design. Applying that understanding in a UX design context and guiding users to a specific goal through color, shape, and space felt like a super power. And I didn’t know it, but I coveted that power (in a non-super-villain kind of way). Through a bit nudging, my coach encouraged me to pull at that thread and pursue UX design.
It started with connections to people my coach knew who had transitioned into the field, then me reaching out to people in my life who were already there. Until then, I had never conducted informational interviews like that. I never imagined I’d find such a supportive, encouraging, and enthusiastic group of people. It felt like they were the first to discover how to make fire, and couldn’t help but share the knowledge rather than keep it for their own gain.
Armed with encouragement from those around me and a strong wind at my back, I took a confident step toward UX design.
