Cross Road In July 2023, I find myself at a crossroads: whether to continue pursuing a job, knowing full well that I might just become another cog as most people drag their feet to their laptops every morning for five days a week, or dive back into the unknown, knowing full well that I might just live out the fantasy of being a founder and building a great startup. I want a road where these two paths converge so I can strike a balance — a balance that allows me to do both. However, I know these paths may never converge, and I have to make a choice. It’s a choice between stability, to pay my bills, and the instability of doing something I truly enjoy. As a child, I never understood why adults were always angry. Perhaps growing up in a struggling lower-middle-income household made me realize that being an adult isn’t fun — it’s always an adventure as a child, constantly learning new things, seeing new places, and dreaming new dreams, that’s fun and exciting. Fear When I was a kid, I promised myself that I would never have a desk job working 9–5 because I found it boring. However, in my last seven years of my career in Product Management, I have found myself doing exactly that. Not that it’s boring, but it involves tasks such as JIRA, documentation, and metrics. Of course, the job of a PM involves more than that, but I’m not here to write about its details. In June 2023, I find myself in a similar position of fear, experiencing mental anxiety, itchiness, and stress that all feel very familiar. I fear unemployment as my Employment Pass in Singapore is expiring, and I don’t have another job lined up. Out of fear, I have been mass applying for jobs. At the same time, I’m building a product with hopes that it will turn into a successful startup. This brings another type of fear, the fear of not achieving anything. I am currently caught in a pendulum swing of fear, moving from one fear to another. As a curious and problem-solving person, and as a PM, I seek to understand my fears and have considered scenarios in both cases: if I succeed in getting a job and if I start a venture. The first scenario leads to another fear, the fear of going back to the desk job that I hate, as for the second scenario it’s the same fear. If it were my wife, she would ask me to make up my mind. In this case, I want to make up my mind. Among all the fears I have, the fear of going back to a desk job shakes me to the core. I know I need to figure ‘Why’ if I’m going to survive this and be fully convince this is why. This is ‘Why’ “In trying to get this venture up, I kept asking myself, ‘What’s my ‘Why?’ Was it to make money? Sure, we all need money to pay off our bills and have income stability. Was it prestige? Sure, I want to be recognized for my work. Was it to prove naysayers wrong? Hmm, perhaps. In all my search for my ‘Why,’ I wanted to bundle it all up, but I know that in tough times, these narcissistic material needs aren’t going to cushion me; they’ll drag me down. I know I have to dig deeper. After watching a clip of Anthony Bourdain strolling the streets of Haiti in his documentary (I’ve always been a fan of Tony), something clicked in me. His world and adventure resonated with me. He lived an amazing life, traveling and experiencing different parts of the world as an adventurer. He had struggles and darkness, just like everyone else, but the sense of adventure was magnetic. I realized I had a rough idea of my ‘Why’. My ‘Why’: I want to live a life knowing that I’ve enabled adventure for those of us yearning for it. While some may be saving for their ‘adventure,’ we can help them dream it. I want to allow people to reconnect with the sense of exploration and adventure they once had when they were young.” To myself: Answering the question of ‘Why did we build this?’ “We want to get people to dream what their adventure could be, get excited on their office desk at 9am as they drink their coffee ruminating of that adventure so they can imagine, plan and pursue them and hopefully just hopefully do it forever.” I would accomplish my ‘Why’ if the following below happens: If a user emails me: Kit, I used to be an office desk person day in day out and now I’m living my dream traveling the world because this product enabled me to live this life. I’ll be able to rest knowing we’ve done something great. To myself: Answering the question of ‘What problem are you solving?’ The problem we’re solving is to enable people to imagine, plan and pursue their dream adventure full-time. The solution we’re providing is a product that combines UGC content discovery to build a travel guide for their adventure.