Right now
I’m leaving the courtroom behind, building useful online things, and stumbling into whatever. Throughout 2027, I’m slow-traveling through Asia and Latin America while teaching online and developing a new app to expand my business. You can’t break into my house or steal my car while I’m gone; I don’t have those. I’ve sold almost everything.
During the year, I’m creating a next-generation advanced learning management system (LMS). It will empower subject-matter experts to prepare candidates for high-stakes credentialing exams. Both learners and educators benefit from artificial intelligence, spaced repetition algorithms, audio-video tools, and practice assessments. Any subject-matter expert can build and monetize a rigorous online test-prep program.
I also sometimes work as an Adjunct Professor of Law, and have spent the past decade running LexBar, an online program that helps law students pass the Virginia Bar Exam.
Some history
Growing up in the 90’s, I was often browsing cassette tapes for music, wandering physical Blockbuster aisles for a VHS film, and getting lost in bookshops or libraries for hours. Born right on the boundary line between Millennials and Gen Z, I was promised that digital streaming and instant online purchasing would simplify daily life and optimize our choices, and mostly that held true.
Like most people I use apps and the internet to fine-tune virtually everything. Picking a restaurant means consulting crowdsourced ratings and asking ChatGPT. Choosing a movie means opening Netflix so it can tell me what I like. Picking out a book is as easy as going to Amazon.com and letting its algorithm take control. In chasing total digital efficiency, I turned into a maximizer. I compulsively fine-tune every single decision knowing that if I do enough research or use the right technology, I will arrive at the perfect decision. But what might I like that the algorithm never gives me?
Selecting a movie to watch isn’t exactly the same as more significant and life-changing decisions. But underlying all of those choices, no matter the scale of the decision, is the idea that we can arrive at a perfect destination. In David Epstein's book, Range, he describes the arrival fallacy as the mistaken belief that once you achieve a goal you will be happy. But in reality, once we achieve the goal we don’t feel the satisfaction of having “arrived,” but instead we desire to reach another milestone or strive for a different outcome. In other words, when we set a goal we think achieving it will be the ending we’ve always wanted but when we get there, it only leaves us wanting more. Epstein suggests this:
“Make sure to appreciate aspects of the journey, not just the destination; lower your expectations for the arrival itself; and diversify your identity.”
It doesn’t matter whether the choice is as inconsequential as where to eat dinner or as life-altering as going back to school for a major career change. Meeting the goal never provides that sense of finality. Pursuing the goal, however, always brings immense joy and satisfaction.
What do you do?
In social gatherings, when someone asks what I do, the easy answer makes me most comfortable. “I’m a lawyer.” Since that is everyone is familiar with, it leads to a some small talk and requires little effort. I know I should try harder.
In reality, my professional life exists in some amalgamation of video editor, pastor, recreational pilot, teacher, traveler, technology nerd, car wash technician, developer, defense attorney, prosecutor, small business owner, and law school professor. I’ve loved the journey to those accomplishments much more than achieving them. Not once have I regretted learning something new.
Join me
Some decisions for the journey ahead:
- Embrace serendipity. I wander. I accept good-enough decisions, and avoid optimizing everything. Algorithms take a back seat; I stumble onto new things I like (and don’t).
- Love the process; accept the outcome. I’ve quit my job and bet on building something new. Will it work? Maybe not, but I’m happily trying and I know I won’t regret that.
- No final destination. I’m working from a new country every 60 to 90 days. You can join me. Whether I know you or not, you are invited to pick a location where I am and take a trip. We’ll meet up for some weekend coffee and sightseeing.
