Archive - The Caring Techie Newsletter

The Real Efficiency Bottleneck Isn’t Planning, it’s Thrash

Why planning aversion isn’t productive and how to find the sweet spot

Sep 22 •

August 2025

How to Think Like a VC When Evaluating a Startup Role

A venture capitalist inspired checklist for choosing your next startup role. The questions to ask before you invest your time and energy.

Aug 12 •

and

July 2025

Lessons in Leadership from Formula 1: Christian Horner vs Toto Wolff

High pressure is a given in F1 and Tech. What changes everything is how you lead.

Jul 10 •

June 2025

High Performers and The Cost of Relentless Self-Critique

If you want to perform at your best, you need to fire your inner critic and hire your inner friend instead.

Jun 20 •

May 2025

Getting People to Listen is a Skill → Here’s Where to Start

A practical guide to understanding why your message isn’t getting through and what to do about it

May 15 •

April 2025

How to Avoid Sleepwalking into Irrelevance in the Age of AI

Let’s be real: most people in tech are still too chill about AI.

Apr 23 •

March 2025

What High Performers Know About Doing Hard Things

The mindset, habits, and brain science behind pushing through

Mar 27 •

The Key to Asking Great Questions

Hint: It’s not just about what you ask, but how you ask it.

Mar 11 •

February 2025

8 Guaranteed Ways to Annoy Your Senior Engineer

A comprehensive list of things that grind the gears of most software engineer, especially the seniors

Feb 12 •

January 2025

#nojs-banner { position: fixed; bottom: 0; left: 0; padding: 16px 16px 16px 32px; width: 100%; box-sizing: border-box; background: red; color: white; font-family: -apple-system, "Segoe UI", Roboto, Helvetica, Arial, sans-serif, "Apple Color Emoji", "Segoe UI Emoji", "Segoe UI Symbol"; font-size: 13px; line-height: 13px; } #nojs-banner a { color: inherit; text-decoration: underline; } This site requires JavaScript to run correctly. Please turn on JavaScript or unblock scripts