A handful of quotes. I promise they are related.
From Andrew Yang's Smart People Should Build Things:
From David Graeber's On the Phenomenon of Bullshit Jobs:
"If you work in professional services you will be paid handsomely and have a brand-name firm on your résumé. You’ll gain skills, confidence, and exposure. But you may also become heavily socialized and specialized, more risk averse, and accustomed to operating in resource-rich environments with a narrow set of deliverables. You’ll be likely to adopt an arm’s-length relationship with your work. You won’t build anything; instead, you will compartmentalize and put the armor on each day as deals, clients, and colleagues come and go."
From Nassim Taleb's How to Legally Own Another Person:" [...] productive jobs have, just as predicted, been largely automated away (even if you count industrial workers globally, including the toiling masses in India and China, such workers are still not nearly so large a percentage of the world population as they used to be). But rather than allowing a massive reduction of working hours to free the world’s population to pursue their own projects, pleasures, visions, and ideas, we have seen the ballooning not even so much of the 'service' sector as of the administrative sector, up to and including the creation of whole new industries like financial services or telemarketing, or the unprecedented expansion of sectors like corporate law, academic and health administration, human resources, and public relations."
"Evidence of submission is displayed by having gone through years of the ritual of depriving himself of his personal freedom for nine hours every day, punctual arrival at an office, denying himself his own schedule, and not having beaten up anyone. You have an obedient, housebroken dog. [...] (However), there is a category of employees who aren’t slaves, but these represent a very small proportion of the pool. You can identify them as the following: they don’t give a f*** about their reputation, at least not their corporate reputation."
"Our point of departure must be the conception of an almost childlike play-sense expressing itself in various play-forms, some serious, some playful, but all rooted in ritual and productive of culture by allowing the innate human need of rhythm, harmony, change, alternation, contrast and climax, etc., to unfold in full richness."
Starting a startup: Failure
This was rather interesting. To convince myself and others that quitting my job was a good idea, I grabbed my biggest hammer and started looking for nails. And so everything in the process looked like a nail. Translation: I jumped into something to "play entrepreneur" and not actually build anything.
I spent two months talking to current and former teachers, school administrators, principals, parents, students, investors, other entrepreneurs. I tried to convince a great friend to leave his job at Uber to join me (so douchey of me). I applied to Y Combinator for funding for a nonexistent product that had one founder (me), getting mentors to vouch for my application. I wrote some code and spent too much time trying to make it perfect. I hung out at WeWork because that felt pretty cool.
This fizzled out pretty terribly. I had nothing delivered, no pre-sales; I hadn't even validated the idea. I was running around trying to convince people my idea was awesome and totally worth investing $$ in. I was scared, so I just did things that looked like success; this was my old brain still at work. But I learned a lot about myself during these two months. The epic failure was totally worth it.
Diving into technical concepts: Success
I realized from my failures that I didn't have enough confidence in my engineering, design, and sales skills to do anything. So the following month, I devoted each week to an intense, project-based exploration of technical concepts. Each week, I had to deliver a product and a blog post walking through what I built. During this month, I learned how to (and now ensues some largely unintelligible technical jargon): deploy a load balanced app to AWS, incorporate a fully Dockerized development-to-deployment workflow, write a simple virtual stack machine in Java, learn functional programming and math fundamentals via the Haskell programming language, and use bit manipulation and Hamming distance to crack repeated-XOR-encrypted messages in Node and Python.
(Edit: Also important note here is that I started learning how to code a little under 2 years ago. Discussion for another day: strangely, we overvalue our short-term selves and undervalue our slightly less short-term selves.)
There's a common piece of wisdom that goes like "The antidote to fear is hustle." To integrate that idea into constantly working on things that I knew nothing about, I broke each week into three 2-day sprints. Every 48 hours, I needed to be able to tangibly do a new thing. By doing this, I would force myself to focus only on what was vital and only go down rabbit holes that were necessary. Hat tip to Hack Reactor for teaching me this technique.
Building shit fast: Success (and ongoing)
Finally, it was time to get to start getting things out the door. My confidence in my coding skills had risen tremendously in just a short month. I have a Google Doc of around 500 small seeds of ideas, so I began picking a few to work on. In one month's time, I built: a Chrome new tab extension called "Do One Thing" (a to-do list capped at just one thing every day); a Slack bot called "Hack Genie" (who answers your code questions for you); and a book recommendations list called "Bookswell".
Each of these had varying levels of success. The Chrome extension took one day to write, but it didn't appear to be something many more people would find uniquely interesting, so I moved onto my next project (though I still use this extension every day). The Slack bot also took one day, and I still use it fairly often, but it also wasn't something that I felt many people would fall in love with.
Bookswell project was pretty awesome. Before writing any code, I simply shared a book recommendations spreadsheet that I had been passively working on for a year. The response was overwhelming, so I spent a few weeks building a web version of it, which itself has gotten thousands of visits in just a week or so of being live. My next steps with this are to just get it more exposure.
The cool part with each of these projects was that the only calculation running in my head was whether they were immensely useful or not. I wasn't worried about whether I had the chops to get them done or not, because the previous month had ingrained in me that I could now build almost anything I wanted to.
Most importantly, I wasn't evaluating projects based on "What will this lead to?" or "What's the long-term vision?" (This required some pretty intense unlearning of old habits.) It's this type of thinking that squashes seeds before they have time to bloom. Many amazing things arrive in this world ugly, slightly deformed, and with no clear sign of why they made it that far. Despite all that, they managed to make themselves useful, for reasons yet unclear to their makers.
Projects moving forward (update: December 3, 2016)
Given the sprawled shape of this calendar year, I ended up further sprawling. My mentors Myles and Oz invited me to join them in SF for ~10 weeks to eat/breathe/sleep computer architecture & operating systems. The amount of learning done here cannot be overstated.
However, my most profound experiences in SF revolved around building a daily practice of meditation, prayer, running, and writing.
I'm now back on the East Coast ready to move from opportunistic maneuvers to more deliberate, principled, craft-driven decisions. Programming is a lot of fun, and it can deliver pretty outsized value to society (in some cases). I'm excited to dig in and focus on this for the upcoming years.
The Secret Sauce
Writing has without a doubt been the secret sauce over the past few months. Every project and every concept that I was struggling with required a blog post of some sort. This forced me to be able to appropriately explain what I had learned. Oftentimes, we say we've learned something when we are able to do it right once, but it is in being able to explain it coherently that the concept finally gets internalized.
Beyond that, writing has helped me organize some of the more esoteric ideas and thoughts I've been having learning about (which is essentially the purpose of this Posthaven blog). I highly recommend that everyone keeps their own personal blogs with this express purpose. The mini-trends in what you choose to write about will teach you more about yourself than almost anything else.