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Greg Kroleski

doer of hard things

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Through a Glass, Darkly: Pt. 1 – The Most Efficient Learning System We Know

This is the first post in a series I m calling Through a Glass, Darkly: Brains, Machines, and the Stories That Shape Us . In this series, I will explore the thesis that brains, AI systems, and cultures are all different kinds of information compression systems, and that , like all information compression, they pay a price for the efficiency gains. I sat down to write this after noticing a…

2026 Focus: (en)courage

At the start of a new year, I take the time to set my focus for the coming year. By being selective about where I direct my energy, I believe I can achieve results that are exponentially greater than if I split my attention. More details about the process are in this blog post and you can review the results from past years here. 2026 Theme: (en)courage Of all of the en words, this one is my…

2026-2032 Sabbath Cycle Vision: Giving Others Good Gifts

This is not only a new year, but it is also the first full year of my next sabbath year cycle. As such, before I define the focus for this year, I also need to define the guiding vision that will serve me for the next seven years. Sometime over the past few years and idea stood out to me words that had a version with an en or em prefix encourage, empower, enrich, enable, enjoy, embolden, etc. En…

Technology Predictions – Winter 2026

This post is part of a series where I talk about technologies and make guesses about how they ll deliver value in the future. One of my goals in life is to be a great technologist an expert at identifying technology that can deliver value and improve the human condition. I hope that writing this blog series and reviewing what I write will help me with that. Updates Since Last Time Winter 2025 was…

Yearly Focus – v1.7 Release Notes

Each year I focus my attention on a few named goals as a way to be more intentional about the pursuits I direct my energy towards. The way in which I do this has evolved over time and these release notes serve to document the current state of the process and changes I ve made recently. Review Of v1.6 I made a few changes to this process back in Jan 2019 as part of the v1.6 version. Those held true…

Random Things I’m Thinking About in December 2025

Is being a corporate employee just an inefficient way to be a node in a spark cluster? The effectiveness of the brain as a biological computer and how much of that can be recreated Where does value accrue as six-figure+ white collar knowledge work transfers to computer systems? The hardware layer? The software? The stitching? Or does the entire value chain greatly diminish? Can I build an agentic…

2018-2025 Sabbath Cycle Review: Preparing For My Calling

I ve been living my life in seven year chunks since I was 24 and began my career in earnest. I work hard for six years and attempt to rest in the seventh year (to varying degrees of success), recalibrate and refocus. It is a practice that dates back thousands of years but isn t followed much anymore. I find there is often wisdom in old traditions though. Back at the end of 2018 I wrote a vision…

What does FIRE mean to me?

Ten years ago I wrote about what it meant to be to be able to afford something and that financial independence meant the state of being able to chose to work where I wanted, doing what I wanted, or not at all if that is what I wanted. I was thinking about a sort of independence the lack of a dependency on others for a sustained meeting of needs. The lack of a need to conform to their rules in…

Reflecting On Three Years At Databricks

Three years ago I wrote about why I decided to join Databricks and each year since then I ve reflected on the year (here are the 1st and 2nd years). Once again, I d like to take a moment now to reflect on how things have gone in the last year and what I hope to accomplish in the next one. How Was My Third Year at Databricks? My third year at Databricks was an interesting one. The most surprising…

You’re probably changing PM roles too often

Over the past decade of advising, managing and mentoring PMs, the most common piece of advice I ve given is simple don t change teams, yet. I ve found that sticking power is one of the things most directly impactful on my success and believe the sweet spot for PM roles is about 4-6 years in an area. I see many PMs want to change teams after 1.5-2 years though, which I believe is too early. I think…