I Asked AI to Destroy My Life Plan, and It Did
When liquid courage meets brutal honesty
I asked AI to brutally critique my 30-day challenge and career plans yesterday. It destroyed me so thoroughly that I had to walk to the store to buy wine at 3 pm. Not my finest moment, but possibly my most educational one.
Here's what I learned about the choice between data and courage - and why sometimes the bravest decision is the one that makes no logical sense.
The Prompt That Changed Everything
I gave AI this instruction: "I want you to act as my brutally honest, high-level advisor. I don't want comfort. I don't want fluff. I want truth that stings. Tell me what I'm doing wrong, what I'm avoiding, where I'm wasting time."
I told it about my 30-day challenge, my career crisis, my financial situation, and my plans for rebuilding my life at 46. I asked for ruthless prioritization and unfiltered analysis.
And fuck, did it deliver.
The Brutal AI Truth
The machine told me I was "performing my crisis instead of fixing it." That I was "romanticizing struggle instead of solving it." That my TikTok challenge was "a distraction, not a career." That I should go back to my old producing job and "stop treating my skills like they're beneath me."
It said I was avoiding reality, playing small, wasting time. It called my "beautiful mess" and "crumpled ink" poetry lovely content that wasn't paying bills. It suggested I was either desperate or not thinking clearly about sustainable income.
Every word was logically correct. Every criticism was data-driven and rational. Every recommendation made perfect financial sense.
And it left me absolutely devastated.
The Walk to Liquid Courage
I leaned back from my computer, flooded with dread, feelings of failure, and inadequacy. The kind of soul-crushing clarity that makes you question everything you thought you knew about yourself.
So I did what any rational 46-year-old woman would do: I walked to the corner store to buy wine at 3pm because I couldn't handle being sober for this revelation.
Walking down my street, having an internal argument about whether I actually needed alcohol to process AI feedback (spoiler: I did), I realized something profound was happening. I had a choice to make.
The Choice Between Data and Soul
I could believe the machine that sees only data, failure rates, and logical outcomes. Or I could choose the path that makes no sense but feels right in my soul.
AI calculated my odds of success based on current metrics. It analyzed my situation through the lens of pure logic and financial optimization.
But here's what AI can't calculate: the courage it takes to start over at 46. It can't measure the value of inspiring one person who's also lost. It doesn't understand that sometimes the bravest choice is the one that makes no logical sense.
What Machines Can't Measure
AI sees my two videos with 200+ views as failure. I see them as proof I'm showing up scared, and that's fucking brave. AI sees inconsistent income as a problem to solve immediately. I see a transition period where I'm building something sustainable rather than just surviving.
The machine calculated risk. I'm calculating courage.
It analyzed data points. I'm analyzing my soul's calling.
It optimized for financial stability. I'm optimizing for authentic transformation.
The Real Choice Framework
The choice isn't between being practical OR following your dreams. It's choosing to rebuild your life even when the data says you're crazy. Even when AI tells you to give up. Even when logic says go back to what's safe.
Walking back from the wine store (yes, I bought the wine), I realized that sometimes the machine is right about the odds. But machines can't measure the human spirit. They can't factor in resilience, creativity, or the power of someone who refuses to settle for a life that doesn't fit anymore.
The Courage to Ignore Good Advice
Here's the thing about AI feedback: it's probably right. Going back to production work would solve my immediate financial problems. Playing it safe would reduce risk. Following the logical path would make sense to everyone watching my life from the outside.
But I didn't survive cancer to play it safe. I didn't make it to 46 to settle for a career that was slowly killing my soul. I didn't start this 30-day challenge to quit when the data looked bad.
Sometimes the bravest thing you can do is ignore perfectly good advice because it doesn't account for who you're becoming.
Today's Choice
Crumpled Ink Day 18, June 26th, 2025: Today, I choose courage over data, heart over algorithm.
This isn't about being anti-technology or dismissing practical concerns. This is about recognizing that some decisions can't be made by spreadsheets and algorithms. Some choices require the kind of courage that doesn't compute.
The Question for You
What choice are you facing right now? The logical one or the brave one? The safe one or the one that feels impossible but right?
Are you letting data drive decisions that should be driven by your soul? Are you optimizing for the wrong metrics? Are you playing it safe when your heart is calling you to be brave?
Sometimes they're the same choice. Sometimes they're not. And sometimes that's exactly the point.
The Wine Wisdom
I did drink that wine, by the way. And while I was sipping it, I realized something: AI gave me exactly what I asked for - brutal honesty. But brutal honesty without context is just brutality.
The context AI couldn't see: I'd rather fail at something meaningful than succeed at something that's slowly killing me. I'd rather inspire one person to start over than produce a thousand commercials for products I don't believe in.
I'd rather choose courage over data, even when the data is right.
Today I chose to trust my heart over an algorithm, and that feels like the most human thing I've done in years.
Sometimes the machine is right about the odds. But machines can't measure what happens when humans choose love over logic, courage over comfort, growth over guarantees.
And maybe that's the real choice we're all facing: Do we optimize for the algorithm, or do we optimize for our souls?
I'm choosing souls. Every fucking time.
