Overcoming indecision

A story about pursuing an entrepreneurial career in design

For the last five years, I’ve grappled with a crippling obsession with making the rightdecision. This is despite knowing, intuitively, that life doesn’t have right choices. The onset of this condition was likely an overconsumption of content about what is now known as “hustle culture.” Following a severe dissatisfaction with my undergraduate education, I embarked on a journey to find a career in the gap left by academia. What I discovered were the blogs of technologists and entrepreneurs who flaunted their highly optimized workflows and mental models. Each shilled their own tools or routines that got them to where they were (in positions that seemed desirable given how pleased these writers were with themselves). I obsessively took notes and downloaded the different apps in search of a way to optimize my own decision making, as I was lost and looking for an efficient way to find answers.

I went about building my career by testing different approaches and integrating the lessons I learned from these magical blogs. I tried freelancing, but the experience was far too lonely for me. Add a note in a new to-do app about freelancing. I got well-paid positions in organizations of various sizes, ranging from well established to months-old startup teams. Eventually, the need to forge my own…