Pausing for cartography

I've started and stopped writing a bunch of different posts over the last few months – dozens, if you count all the topics I mapped out in my head that never made it to the keyboard. It's less a function of losing interest in topics and more that I want to write about too many things, all at once. Naturally, that results in the number of posts I've made since December: zero.

All of these liminal topics fit together, parts of a much bigger territory of values and experiences that I was exploring scattershot. I have a general sense of the shape of this metaphorical landmass, but I've never thought about it in its entirety. I have had occasion recently to think hard about what I want to do next – more on that in a future post – which is further motivation to explore its geography and terroir.

The territory I am mapping is the set of desires that drive me. These are made up in turn by my experiences and constraints as filtered through my core values and beliefs. What do I want to do and be and why? For who? (When is a whole other topic, but the second best time is now.)

If you could quantify every one of your desires, everything you want and need, every decision could be represented as an equation. Should I move for this job offer? Let's look up how much I like where I live, how close I am to my family and friends and how important that is to me, and how much of a hassle I would find it to move, and compare it to how much I'd like the new job and new location and the financial rewards – it's just math.

Realistically, these weights are not fixed but are constantly changing based on external factors and how I internalize them. Rather than trying to derive a perfect snapshot that is immediately outdated, I can gain a general sense of the things that are most important to me. Heuristics will suffice where math is pointless, which is why I'm mapping and not quantifying – after all, the map is not the territory, and while all models are wrong, some models are useful.

Let's start drawing the map.

My main driving value is helping people do and be better. I've had wonderful and valuable life experiences from childhood through today and have had the privilege of being around and learning from so many incredible people, and I feel obligated to share that where I can. I gravitate to similar roles in most social settings (I've been nicknamed Dad by several unrelated groups), and I feel drawn to leadership and mentorship-focused positions. The key insight here is not "I want to lead and be a mentor", but rather "I want to share what I've learned to help others, and leadership and mentorship are ways to do that". I don't want to lead for leadership's sake, I want to lead so I can teach.

My main motivator is solving problems. Growing up, I loved math and science, and later programming, statistics, and eventually data science and AI. I've always loved solving the hardest problems, and while there's certainly an element of competitiveness involved, it's mostly for the joy of figuring something out. I've learned that more abstract problems still fascinate me, like how to assemble the right group of people to complete a task and how to guide them to finding a solution faster than anyone could on their own. The harder something is, the more I want to be the person to figure it out. (There's the ego coming out.)

I'm also strongly driven by creativity, which I see as a complement to problem-solving. I'm equally fascinated by evoking a specific emotion in an audience, designing the perfect architecture for a software system, and communicating precisely and usefully. Creativity inspires me, both energizing me and revealing oblique solutions to seemingly unrelated problems. I've figured out how to motivate a team while thinking about the use of pressure and release at a live music show, and I've been reminded to simplify a project while contemplating art in a museum. It's all connected.

I have constraints. I need income to support my family, including my son who is about to attend a very wonderful and very expensive college. I need to stay in Chicago, at least until my daughter is off to college herself. I need to retain the energy and time to be present for my family and friends and my creative pursuits.

I have preferences. I enjoy having the space to find problems whose solutions unlock value, but also don't mind being handed a list of problems to solve. I really, really dislike doing things that don't create value or have some other purpose, although I understand institutional inertia. I can play politics if required but find it to be a massive misdirection of energy with high marginal cost. I like remote work, disprefer a long commute, and enjoy working for a company that creates something positive in the world, broadly construed. I do best when I'm surrounded by brilliant and creative people who aren't afraid to tell me when i'm wrong.

Underlying everything are my core values. Integrity is critical, and I have great difficulty working with people who lack it. I will always speak up when I think it's important to, even though that's repeatedly hurt my career. I won't lie about the status of a project, or to my team, although I understand there is sometimes information I can't share. I believe in equality of opportunity, which sometimes means nurturing someone who hasn't had as many advantages as someone else. And I think it's important to be nice unless there's a good reason not to be.

I think I know how all these factors align with the roles and companies I should be targeting, but I don't want to collapse the wave function by narrowing my focus. A map is a compressed representation of the territory and therefore a flawed tool, but it helps me understand the territory, which is the ultimate goal. A map can't account for everything, but if I can understand the territory, I can determine which career paths belong within it and which would take me outside its boundaries.

Armed with my new map, I'm more prepared to set out and explore career paths.