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Allen Bailey
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Sep 24, 2025
More info about @allenbailey25
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I Designed a Money System I Couldn’t Return To
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Feb 13
I Designed a Money System I Couldn’t Return To
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2 min read
I Thought More Tracking Would Calm Me
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Feb 13
I Thought More Tracking Would Calm Me
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2 min read
My Finances Failed When Life Got Messy
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Feb 13
My Finances Failed When Life Got Messy
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2 min read
I Built a Budget That Worked Only on Good Weeks
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Feb 13
I Built a Budget That Worked Only on Good Weeks
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2 min read
My Financial Stress Came From Maintenance, Not Scarcity
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Feb 13
My Financial Stress Came From Maintenance, Not Scarcity
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2 min read
I Didn’t Lose Money — I Lost Flexibility
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Feb 13
I Didn’t Lose Money — I Lost Flexibility
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2 min read
When AI Sounded Confident, I Stopped Asking Why
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Feb 13
When AI Sounded Confident, I Stopped Asking Why
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2 min read
I Didn’t Realize AI Was Narrowing My Options
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Feb 13
I Didn’t Realize AI Was Narrowing My Options
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3 min read
AI Simplified My Process — And Hid the Tradeoffs
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Feb 13
AI Simplified My Process — And Hid the Tradeoffs
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2 min read
I Trusted AI More When the Work Felt Familiar
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Feb 13
I Trusted AI More When the Work Felt Familiar
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2 min read
AI Gave Me Answers Faster Than I Could Evaluate Them
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Feb 13
AI Gave Me Answers Faster Than I Could Evaluate Them
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2 min read
I Didn’t Lose Control to AI — I Deferred It
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Feb 13
I Didn’t Lose Control to AI — I Deferred It
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3 min read
Why My Money System Worked Better After I Missed a Month
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Feb 5
Why My Money System Worked Better After I Missed a Month
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3 min read
I Didn’t Need Better Discipline — I Needed Fewer Decisions
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Feb 5
I Didn’t Need Better Discipline — I Needed Fewer Decisions
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2 min read
My Finances Improved When I Stopped Aiming for Precision
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Feb 5
My Finances Improved When I Stopped Aiming for Precision
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3 min read
I Reduced Stress by Designing for Bad Weeks
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Feb 5
I Reduced Stress by Designing for Bad Weeks
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3 min read
I Thought My Money System Was Simple — It Wasn’t Forgiving
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Feb 5
I Thought My Money System Was Simple — It Wasn’t Forgiving
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3 min read
My Finances Didn’t Collapse — They Became Harder to Maintain
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Feb 5
My Finances Didn’t Collapse — They Became Harder to Maintain
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3 min read
How I Learned to Interrupt AI Before It Finished Thinking for Me
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Feb 5
How I Learned to Interrupt AI Before It Finished Thinking for Me
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3 min read
I Didn’t Question AI Because It Sounded Certain
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Feb 5
I Didn’t Question AI Because It Sounded Certain
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3 min read
What Broke When I Let AI Define “Good Enough”
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Feb 5
What Broke When I Let AI Define “Good Enough”
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3 min read
I Realized AI Was Answering Faster Than I Could Frame Questions
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Feb 5
I Realized AI Was Answering Faster Than I Could Frame Questions
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3 min read
AI Didn’t Replace My Thinking — It Reordered It
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Feb 5
AI Didn’t Replace My Thinking — It Reordered It
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3 min read
I Trusted AI Most When I Should’ve Slowed Down
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Feb 5
I Trusted AI Most When I Should’ve Slowed Down
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3 min read
I Didn’t Argue With AI Enough at First
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Feb 5
I Didn’t Argue With AI Enough at First
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3 min read
My Financial System Worked — Until Life Got Faster
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Jan 30
My Financial System Worked — Until Life Got Faster
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2 min read
I Reduced Anxiety by Making My Finances Less Precise
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Jan 30
I Reduced Anxiety by Making My Finances Less Precise
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3 min read
My Money Stress Came From Assumptions I Never Questioned
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Jan 30
My Money Stress Came From Assumptions I Never Questioned
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2 min read
I Didn’t Need a New Budget — I Needed a Reset
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Jan 30
I Didn’t Need a New Budget — I Needed a Reset
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3 min read
I Thought My Finances Were Fine Until My Routine Changed
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Jan 30
I Thought My Finances Were Fine Until My Routine Changed
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3 min read
My Finances Didn’t Fall Apart — They Slowly Drifted
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Jan 30
My Finances Didn’t Fall Apart — They Slowly Drifted
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3 min read
I Didn’t Lose Skill Overnight — It Slipped Gradually With AI
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Jan 30
I Didn’t Lose Skill Overnight — It Slipped Gradually With AI
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3 min read
AI Helped Me Move Faster — But I Missed Important Signals
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Jan 30
AI Helped Me Move Faster — But I Missed Important Signals
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2 min read
I Learned More From Reviewing AI Errors Than Successful Outputs
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Jan 30
I Learned More From Reviewing AI Errors Than Successful Outputs
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2 min read
I Thought AI Was Neutral Until It Changed My Defaults
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Jan 30
I Thought AI Was Neutral Until It Changed My Defaults
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2 min read
Using AI Felt Smooth — Until I Had to Explain My Choices
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Jan 30
Using AI Felt Smooth — Until I Had to Explain My Choices
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2 min read
I Didn’t Notice AI Replacing My Judgment Until I Checked My Decisions
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Jan 30
I Didn’t Notice AI Replacing My Judgment Until I Checked My Decisions
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3 min read
I Realized AI Was Editing My Thinking, Not Just My Work
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Jan 30
I Realized AI Was Editing My Thinking, Not Just My Work
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3 min read
What I Now Review Manually Every Time I Use AI
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Jan 30
What I Now Review Manually Every Time I Use AI
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3 min read
How I Rebuilt Trust in My Own Judgment While Using AI
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Jan 30
How I Rebuilt Trust in My Own Judgment While Using AI
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3 min read
Why AI Felt Helpful Right Up Until It Wasn’t
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Jan 30
Why AI Felt Helpful Right Up Until It Wasn’t
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2 min read
I Stopped Expecting AI to Think Like Me — Results Improved
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Jan 30
I Stopped Expecting AI to Think Like Me — Results Improved
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3 min read
What Using AI Revealed About My Decision Blind Spots
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Jan 30
What Using AI Revealed About My Decision Blind Spots
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2 min read
How I Learned to Spot Weak AI Outputs Before Shipping Them
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Jan 30
How I Learned to Spot Weak AI Outputs Before Shipping Them
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3 min read
Why My AI Results Improved When I Slowed My Thinking
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Jan 30
Why My AI Results Improved When I Slowed My Thinking
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2 min read
I Didn’t Lose Control to AI — I Gave It Away
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Jan 30
I Didn’t Lose Control to AI — I Gave It Away
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2 min read
What Changed When I Started Treating AI as a Second Opinion
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Jan 30
What Changed When I Started Treating AI as a Second Opinion
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3 min read
I Thought I Was AI-Skilled Until My Decisions Were Tested
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Jan 30
I Thought I Was AI-Skilled Until My Decisions Were Tested
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3 min read
I Built Stability, Then Had to Learn How to Keep It
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Jan 23
I Built Stability, Then Had to Learn How to Keep It
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3 min read
I Didn’t Fail Financially — I Stopped Maintaining
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Jan 23
I Didn’t Fail Financially — I Stopped Maintaining
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3 min read
My Finances Didn’t Break — They Drifted
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Jan 23
My Finances Didn’t Break — They Drifted
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3 min read
I Learned Stability Was a Maintenance Problem
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Jan 23
I Learned Stability Was a Maintenance Problem
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3 min read
I Learned More From AI Mistakes Than AI Wins
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Jan 23
I Learned More From AI Mistakes Than AI Wins
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3 min read
I Built an AI Workflow That Didn’t Survive Feedback
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Jan 23
I Built an AI Workflow That Didn’t Survive Feedback
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3 min read
I Learned to Question AI Outputs Before Trusting Them
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Jan 23
I Learned to Question AI Outputs Before Trusting Them
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3 min read
What AI Couldn’t Help Me Decide — And Why That Mattered
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Jan 23
What AI Couldn’t Help Me Decide — And Why That Mattered
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3 min read
I Slowed AI Down Instead of Speeding Myself Up
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Jan 23
I Slowed AI Down Instead of Speeding Myself Up
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3 min read
My Money System Worked — Then Life Changed
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Jan 23
My Money System Worked — Then Life Changed
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3 min read
My Money Got Easier When I Added Slack
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Jan 14
My Money Got Easier When I Added Slack
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2 min read
I Stopped Chasing Optimization and Felt Safer
Allen Bailey
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Jan 14
I Stopped Chasing Optimization and Felt Safer
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2 min read
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