4 Months in Down the Start-Up Rabbithole

Fresh off of 2 weeks of vacation, I’ve finally had some time to garbage collect my many thoughts about my recent career transition from the stodgy corporate world to the Wild West frontier that is Startupland, which were splayed fragmented throughout my brain like my many half-written Medium posts. The purpose of this post is to pull some of them together and to provide some coherence that might be useful to others at this stage, or considering it.

Buffalo Bill, an exaggerated and heroic figure, was an important piece of American propaganda evangelizing expansion into the Western frontier of the continent.

Or was it down the rabbithole of Startupland, as the title suggests? Well, allow me the mixed metaphor, because I’m still sorting through my many conflicting thoughts about the recent move!

Down the rabbithole we go!

When I was making the decision, I think I was aware of most of the tradeoffs between the two worlds, but it is different to experience them than to consider them intellectually. Roughly speaking, the trade-offs are:

• the Big Company World provides higher, guaranteed pay, which means, if you can survive it longer, you can save up some guaranteed positive profit; the Startup World is much more higher variance.
• the Big Company World has tons of inefficiencies, but these don’t matter as much to you because you’re basically paid a flat rate; in the Startup World, inefficiencies directly cause you lost personal opportunity, so you become much more sensitive to them and manage strategies to avoid them.
• the Big Company World (at least the part I’ve seen) encourages quarterly-targets thinking and, especially in the Philippines (or greater SEA too, I expect), is mostly a game of optimizing your image with your bosses/stakeholders; in the Startup World, while it can have some of the same elements, good intentions are generally assumed among co-workers, value creation is rewarded over perception, and, if you can survive to reap the benefits, longer-term strategy and execution is allowed (and, in fact, seems to deliver higher returns).
• it’s very difficult to get real ownership in Big Company World, there are many opportunities for it in Startup World, but they come with inherent responsibility

I also found this talk on Imposter Syndrome very accurate of my personal experience in the start-up hustle and grind: https://www.youtube.com/watch?v=ZkwqZfvbdFw&t=12s. We all experience it, and I think it’s important to be honest about it. I kinda think Imposter Syndrome is how perfectionist or achievement-oriented people process (to their detriment) working on hard, open, new problems, which has inevitable, predictable challenges. You just gotta remember — it’s OK to be a beginner, it’s OK to only have half the answer right now, etc. as long as you maintain the growth mindset, healthy habits, and actively keep in your mind that long-term focus that got you starting dreaming in the first place.