In 2018, I got a job in sales at a great startup in Proptech. The only problem? I’m not a good salesman. With no prior experience, and a heavy aversion to techniques surrounding laws of power or influencing people, I did everything I could to learn how to be effective and consultative in my new role.
After some months of stressing about my hourly moves up and down the leaderboard, I hit my stride and became a serviceable rep. But as much as I worked on my craft, sales was not for me. But what was? I was the first in a big family to go to college - as well as the first to drop out. My dad and four brothers are all mechanics, but I could barely hold the flashlight without getting yelled at. Then, as if from on high, several sacred texts fell into my lap at the perfect times.
It all started with noticing a bright orange book with big text on a co-worker’s desk, So Good They Can’t Ignore You by Cal Newport. In it he argues that the conventional wisdom of finding what you’re passionate about, and then finding a career based on that, is dead wrong. Research shows that it’s the other way around. Building a skill through deliberate practice makes you passionate about what you do. The resulting autonomy, competence, and relatedness with others that are associated with the types of careers that require this continual craftsmanship are what makes people most enjoy their work. He suggests software engineering as a path that checks all these boxes in the white collar world, but in my mind, I was wholly disqualified to ever be employable in that field. That was for people with degrees and Mensa level IQ.
I enjoyed Newport’s work so much, I picked up a copy of Deep Work. The crux of this book is that one of the most valuable skills that people can develop in our current and future economy is the ability to deeply focus on difficult tasks for hours at a time. In today’s attention economy, this skill is becoming more and more rare. Every time we get a quick dopamine hit from social media when we are bored, this skill is actively deteriorating. He tells the story of Jason Benn, a young lawyer who quits his job and locks himself in his mother’s guest room for months with nothing but Ruby on Rails textbooks, learning syntax on flash cards. I found Jason’s website where he outlined his recommended path for a self-taught developer, and started working my way through Zed Shaw’s Learn Python The Hard Way.
Over the next 6 months, with a wife and young kid at home, I stayed after work for several hours every day and worked my way through an open source curriculum called The Odin Project. I flipped a coin and picked the Ruby on Rails track, for which I am eternally grateful. Then ol’ Cal blessed me again with Digital Minimalism. Following up on his prior work, he dives deeply into the psychology that today’s digital world is creating. Blown away by his research into what goes on in big tech to grab and keep our attention, I got rid of my smartphone and bought a Nokia 3310 with 300 texts and 100 minutes per month. This strengthened my resolve, crystallized my focus, and freed up time for study.
This schedule continued largely for the next year and a half. Though I was becoming more and more competent, there was still another major deficiency holding me back. I still had the mindset that I was unworthy and that I’d be lucky for some schmuck to take a shot on me. I’d hoped desperately to move into engineering at my current employer. Not only would coming from sales be a great story and accomplishment, I knew our internal applications as a user and was studying specifically our tech stack. However, my feeble attempts at getting my foot in the door were getting nowhere.
When things looked the bleakest, I stumbled upon Rejection Proof by Jia Jiang. This unearthed my deep fear of failure and rejection. It was the final piece of the puzzle to overcome and unlearn what was holding me back. He helped me see that I’d been conditioned to run away from any hint of failure, instead of building the character to run towards it without fear, knowing that rejection always has a number - that is there can only be so many no’s until the one yes you need. This shifted my attitude and gave me the confidence to know it was just a matter of time until someone gave me a shot and I proved them right. I put myself out there and began the necessary process of learning how to interview and letting rejections roll off my back.
Ironically, a few fortunate occurrences at work paved the way for the VP of engineering to take a meeting with me and subsequently offer me an engineering role before I ever hit the open market. To bring it full circle, they also paid for me to take a Data Structures and Algorithms course at Bradfield School of Computer Science - an integral institution in the development of a young Jason Benn.
I have to thank my mentor, Jay Dorsey, who helped guide and encourage me through those uncertain times throughout the career change. I ended up landing with a great team that leveraged my end user experience and helped me ramp up quickly. But if the empirical data Newport puts forth regarding happiness in work is strong - and it is - let me throw one more anecdotal data point in his corner. A year and a half later, I still wake up every day looking forward to work in a way I hadn't experienced in my career for the 15 years prior. Thank you, Cal!