I Don’t Usually Like Vacations
Currently flying back to SF from Fort Lauderdale. After spending the holidays home, I left the midwest for a week to go fishing.
I recently wrote how vacations never made sense to me and how it always felt that I was just doing the same things in a different location. I’ve developed a better understanding of vacations with age. I now see their value in resetting. There’s no shame in taking a big step back.
The First Good Vacation - A Break From NYC (War)
When I came home from NYC for the first time, it felt like I had returned from war. The city was such an amped up transactional machine, and I hadn’t realized how much it had weighed on me. This culture pushed me to perform, but it imprisoned the questioning side of the mind. Re-reading essays from this time period, it is interesting how urgency and structure even manifested in my writing. I felt suffocated. I was working so hard, but why? I am an ideologically driven person. If my work isn’t aligned with my view of the world, it cripples me. I need to have a “why” to march forward.
The Second Good Vacation - A Break From SF (Peace)
In contrast, my long visit home from SF felt like a relief for an opposing reason. Where NYC was over-structured to remove the need to think and execute, SF feels the opposite. People’s minds have wandered so far looking for answers that they’ve lost their grounding in the core essence of their work. People forget they need to build something other people want.
There’s something about technology as a “means” to create more with less that it’s easy to lose sight of the end you are chasing. I had a million prototypes but zero customers. Although San Franciscans are defined by their differences, the sheep-like tendencies of the city draws you in just like any other, and I was losing sight of my individual belief system.
Midwest Simplicity
Both the midwest and Florida pushed back on overthinking. In both places, few people care about ideas. High school was the foundational experience that cultivated my bias towards hustle. It taught me that hustle is the most important ingredient in success, at least in determinate environments. Overthinking is a losing strategy.
The goal is to reach some level of determinacy and then act simply.
There’s a lot of wealth flowing around Ft. Lauderdale, and many of these companies are a reminder of simplicity—think like generational wealth coming out of a fish & chips brand. Simple is good. I am drawn to complexity, but complexity still needs to be simplified. Where I thought I had reached relative clarity of vision, being forced to present my ideas to Midwesterners showed me I have some work to do, especially with such esoteric ideas. But these conversations help you ground yourself. You prune your old ideas and reduce them into their core essence.
Jean Demo - GenAI Collective, Chicago
My presentation at MHub in Chicago. There was a short time limit so this is high-level.
My Ideal Environment
I find myself missing the culture of Grainger library at the University of Illinois. Focused problem solving and execution in an engineering and technology context. I could sit and work for 18 hours a day, every day. I can’t find any places like this in SF and can’t afford an office. I can’t get myself to execute at all—the city makes you lazy towards execution in favor of making sure you are working on the right ideas. This is good, but I’m likely at the stage of my arc where it matters that my wedge into entrepreneurship is grounded in simple practice.
It really just needs to work right now.
Coming Back to California
Every place has a unique feeling associated with it that makes you miss it.
Absence has made my heart grow fonder towards the unique openness to ideas of San Francisco. There is no other place that has pulled inspiration from me like SF. Where in the midwest, I had simple thoughts on my own life, and in Florida it was impossible to string together two cogent thoughts, SF somehow keeps you in a trance-like state thinking about the same ideas over months at a time.
While here in California, I’ve built complex software architectures, even with little technical background. However, I’ve likely exhausted these threads. At some point you need to ground yourself in execution and structure, and the part of SF I am dreading returning to is the lack of both.
Grounding in 2025
I am first and foremost interested in ideas and “why”, so San Francisco is as good as it gets for me. The remedy for 2025 will be being more clear and simple on direction, making sure to touch grass, implementing purposeful structure, and exercising an east coast sense of urgency.
Lastly, what was amazing about being in the midwest is you remember who you really are. You are fooling yourself to try to be anyone else. Just be really good at being you. In startups, you have 10 problems that are promising and 10 angles to attack each from. To last the distance, the unconsidered variable is finding the route which you are most aligned with. What change do you want to see in the world?
Reminding Vision
The reason I left finance was to pursue these important changes. To try to ground myself in some random B2B software would be missing the whole point. But at the same time, operating entirely in the world of ideas has made it very difficult to actually accomplish anything.
There is a common, simple, midwestern thread in our destiny. Unearth it and focus directly on those pursuits to live true to yourself. Then, extract the better traits of both coasts for actualizing your pursuits.
Traveling can be a lot of work. lol