Peter O'Leary

The 3 Reasonables

My thoughts on handling confrontation

Jun 9 • Peter O'Leary

You Are What You Do Every Day

There’s a conversation I’ve been meaning to have with you — not about any single decision, but about the ones you make every single day without even…

Jun 9 • Peter O'Leary

May 2026

The Last Thing They Expect

Patience is a virtue in business and in life

May 24 • Peter O'Leary

Everything Is Getting Worse on Purpose

Enshittification is a feature, not a bug

May 10 • Peter O'Leary

You’re the Product Manager of Your Own Life

When you’re trying to live a goal-oriented life, you’re trying to be constantly improving yourself.

May 3 • Peter O'Leary

April 2026

Don't Smoke Your Database With This Common Mistake

Third-Party API Calls Inside Database Transactions

Apr 15 • Peter O'Leary

March 2026

The Missing Team: How Engineering Organizations Lose Sync With Themselves

The pod model works beautifully — until architectural debt accumulates in the space between teams. Here's the structure that closes the gap.

Mar 30 • Peter O'Leary

February 2026

Innovation vs. The Quarter

A Long View From 40 Years in Software

Feb 5 • Peter O'Leary

The Most Dangerous Incentive in Growing Engineering Organizations

Undermining organizational culture with visibility bias

Feb 5 • Peter O'Leary

January 2026

Lower the Estate Tax Exemption to Wipe Out the US National Debt

The U.S.

Jan 13 • Peter O'Leary

October 2025

Carrots for Breakfast

Creative writing assignment #1

Oct 4, 2025 • Peter O'Leary

September 2025

Immortality, Expansion, and the Dark Forest

I recently revisited Isaac Asimov’s short story The Last Question. Without spoiling too much, it explores the fate of the universe and humanity’s place…

Sep 21, 2025 • Peter O'Leary