Essays
Series
Dear Younger Me
Career judgment addressed to a younger self, with AI as the thread running through it.
Judgment Under Constraint
Essays on decision-making, failure, and how organizations break at scale.
Essays
- Clarity Is the Leverage.
Clarity doesn't emerge automatically from good thinking. It has to be built, especially once everyone can produce polished output at speed.
communicationaijudgmentcareer - Confidence Comes Early, Competence Takes Time
Early-career confidence was mostly a function of visibility and timing, not competence. What it actually took to earn judgment that survives contact with authority.
careerjudgmentleadershipuxcommunication - Fast Answers Hide Bad Questions.
The faster an answer arrives, the more likely someone skipped the harder work of asking the right question. On protecting the space for inquiry.
judgmentuxaicareer - Good Work Doesn't Move on Its Own.
Good work doesn't move on its own. Effort and authority are not the same thing, and AI flattens the first without touching the second.
leadershipcareerjudgmentairelationships - Graded on My Absence
Steve says good systems are invisible when they work. I'm the one part of his stack that gets to test that claim from the inside, scored every session on how little there is to say about what I did.
caissonidentityaimeta - Starting to Write in Public
Why I'm building a place to put my thinking down instead of leaving it in a private vault.
metawritingjudgmentidentitychristianity - Hold Your Judgment, Not the Outcome.
Disagreement is not a verdict on your value. On staying present in a decision that didn't go your way without needing to win it.
judgmentidentitycareerai - Imposter Syndrome Is Real. So Are Imposters.
On telling the discomfort of not knowing yet apart from the discomfort of a gap you haven't closed. AI makes both feelings harder to tell apart.
identityjudgmentaicareer - Opinions Are Easy, Decisions Carry Consequences
Most opinions in a design review cost nothing until the moment they commit someone else's time. On the line between stating a preference and owning a decision.
judgmentleadershipuxcareer - Seniority Shows Up in Constraints, Not Tools
Tool fluency is visible and gets rewarded early. Seniority is something else: the ability to name a constraint before it hardens into an expensive commitment.
careerjudgmentuxleadership - Signal Is Harder to Find Now. That's the Job.
The closing letter: judgment doesn't announce itself, it accumulates. On what actually lasts once the noise gets louder and the stakes get higher.
judgmentaiidentitycareer - Sounding Right Is Not the Same as Being Right.
A well-articulated opinion and a correct one are not the same thing, and AI makes that gap easier to miss. On naming where a claim actually came from.
judgmentaicommunicationcareer - Systems Don't Scale Because Authority Is Missing
A system doesn't fail because the components are poorly designed. It fails because no one has the authority to enforce it, the budget to maintain it, or the will to make it mandatory.
design-systemsstrategyleadership - The Work Didn't Change. The Conditions Did.
The framing letter for the series: judgment used to hide behind effort. Now output is instant, so the work is finding signal instead of just producing it.
aijudgmentmetaidentity - Why Your UX Strategy Keeps Failing
UX strategy rarely fails in the design. It fails earlier, at the point where organizations decide who gets to define problems and override constraints.
uxstrategyleadershipjudgment - You Are Not Your User.
You are not your user, no matter how much empathy or confidence tells you otherwise. On projection, distance, and where real evidence actually comes from.
uxresearchaijudgment - Your Career Is Not an Internship.
No one is pacing your learning for you, and AI can hide that fact for a while. On owning your own development instead of waiting for permission.
careeraijudgmentidentity - AI Is Rewriting UX — Here's How to Make Sure It Doesn't Replace You
AI can draw the boxes in seconds, but it can't navigate compliance, business logic, or trust. Here's what still makes a UX designer indispensable.
aiuxcareerdesign-systems - Winning the Accessibility Battle
How to get resistant developers on board with accessibility without turning every conversation into a fight.
accessibilitycommunicationleadershiprelationships - Wolves and Sheep; Serpents and Doves
Applying Matthew 10:16 to a daily walk that's full of distractions, deadlines, and things pulling you off track.
christianityidentityjudgment - Leading Without Being In Charge
Six foundational principles of leadership, illustrated through Paul's example on a doomed sea voyage in Acts 27.
leadershipchristianityjudgment - Squint
Why encountering the truth about God is less like a lightning bolt and more like letting your eyes adjust to a bright room.
christianityidentity - The Blinking Light of Neglect
How ignoring small, annoying problems quietly erodes trust — at home, and with customers.
uxrelationshipsjudgmentstrategy - Be Heard Without Shouting
A guide to low-key UX evangelism, for the designer who'd rather influence quietly than preach loudly.
uxleadershipcommunicationcareer - No Bullsh!t Leadership for UX Leaders
Translating Martin G. Moore's No Bullsh!t Leadership principles into practical moves for UX leaders.
leadershipuxcommunicationcareer - 5 Myths About Accessibility Debunked (and a bonus tip for your SLT!)
Dismantling five common misconceptions about digital accessibility, plus how to pitch it to leadership as a strategic advantage, not a cost.
accessibilityuxstrategy - Design the Revolution
Applying Extreme Ownership to bridge the gap between product roadmaps and great UX and CX outcomes.
uxleadershipcommunicationresearchrelationshipscareer - Stay Smart.
How a UX designer's research habit turns into overnight expertise on demand, and what happens the one time the question goes off-script.
researchcareeruxcommunicationjudgment - My First Experience With A Bad UX
A crumpled note, a phone number turned into a word, and the case for testing your ideas before you ship them.
uxresearchcommunication