202109060825 My next level

I'm 30, what do I want to do by the time I'm 40? 10 years is a long time, but will be here before I know it.

Some candidate ideas that have consumed mind-share before now:

1. Continue down the tech leadership path
2. Blaze an entrepreneurial trail of my own
3. Research and create something completely new
4. Write a book

• Are any of these what I want?
• What would it take for me to pick one and follow it relentlessly?
• Is there a way to do more than one in a meaningful way?

The first thing is 202205231130 Knowing when to leave.

• Leave
• Stay

After that our paths diverge:

• If I leave, where do I go, how do I decide, what would I want to work on, what areas would I want to grow in?
• If I stay, what do I want to work on, what areas do I want to grow in, what is my future, what goals do I have?

A note on open-ended work

For much of the ground-breaking work, the challenge lies even in figuring out what to do. Not just how to do it. Breaking things down and checking things off a list day in and day out isn't satisfying looking back on a year's time span or more. If things can be broken down that easily and checked off, it must not be all that interesting.

This involves a murky sense of progress (202104291528 Leaders have to accept a slower feedback loop). Did I make progress today? Was today a good day or a bad day? Will today's work pay off in the long run? Do I have any idea what direction I'm heading in or whether this work is aligned with the direction I hope to be traveling?

One of the most consistent ways to perform knowledge/creative work is just to put your butt in the chair and spend time doing it. Spend time thinking, spend time tinkering, spend time experimenting, spend time trying and failing and iterating. That's one of the reasons that 202107272242 The Art of using a Zettelkasten relies on spending time like this. We gradually build, tinker, iterate and expand our knowledge by spending time doing just that.

We should still try to figure out what is actually valuable, and steer ourselves in those directions, but we're on the right path with a "butt in chair" work ethic. This brings up the need to plan mid-term error correcting goals that can be objectively evaluated. If I want a book written by the end of the year, regardless of what I'm writing in the chair every day, I need to at some point pick one idea and go deep on it. That's driven by the deadline. Goals like these can kill creativity, so it's good to leave these for less frequent check-ins.

Define a big project

In tech, a huge project is a year or more. In research, it could be a decade. Really diving deep on a problem in tech is tens of hours probably, maybe hundreds. In research it could be thousands or tens of thousands of hours thinking over a single idea. They both are optimized for the type of work and insight they're producing, but which do I value more?

Consider Pasteur's Quadrant.¹ Would I be happiest with pure science for furthering our understanding without potential use? Or would I prefer to work on immediately useful things without furthering insight? Or somewhere in the use-inspired, still furthering insight realm?

Am I wrong?

Should I trust my instincts on these "why are we working on this, not this" questions? Am I not seeing the other value involved in these things vs what I feel needs to be done? Is there a better way to dig deep down the five whys and yet still work in the system more? Am I too quick to see new opportunities as better than iterations?

How much should I listen to my self-doubt (202110212231 Differentiate between self-doubt and idea-doubt) and how much should I blaze a trail brightly ahead in 202112201317 The solitude of leadership? This question is posed in 202109060816 Do your own thinking regarding the level of expertise that one needs to be able to trust their thinking.