Hey, beautiful human -

Here's something nobody tells you about starting over at midlife: the weird, terrifying freedom that comes when your old life stops making sense.

Eighteen months ago, I got laid off from Accenture. I've had a contract gig, unemployment insurance, and now I'm building something entirely new while my bank account practices limbo and my business has made exactly $800. And somehow? I'm happier than I've been in years.

Plot twist: uncertainty teaches you things that stability never could. I've learned I don't need as much money as I thought I did - turns out I was spending to compensate for doing work that drained me. I get to do things that give me energy instead of things a company pays me to do. And here's the big one: I'm starting to realize I have value as a human whether or not I actually produce anything.

Speaking of figuring out who you are when your old life stops making sense - I built you something for exactly those moments when "follow your passion" feels like terrible advice...

This week’s freebie

THE CLARITY KIT

5 Prompts for When You Don't Know What You Want

No jargon. No overwhelm. Just playful experimenting.

ROCO Tip O’ the Week

AI has been my unlikely companion in this reconstruction project. Not for productivity hacks or content calendars, but for the deeper work of figuring out who I am when I get to choose what matters.

I'm discovering I'm pretty good at seeing the bigger picture while also diving into the weeds and navigating them well. Still learning to handle the middle ground, but that's okay - I'm building as I go.

One Practical AI Tip: The Identity Archaeologist

When your old sense of self gets disrupted, AI can help you excavate what was always true underneath.

First, a quick reminder about ROCO - the prompt structure that gets you better results:

  • Role: Who should AI be?

  • Objective: What outcome do you want?

  • Context: Background info, tone, or limits

  • Output: What form should the answer take?

Role: Be an identity archaeologist helping me rediscover core parts of myself
Objective: Help me identify consistent patterns in my values and interests across different life phases
Context: I'm in a major life transition and feel disconnected from who I used to be. I want to find the through-lines that remain constant regardless of job title or circumstances. Ask me questions one at a time and build each question on my previous response.
Output: Start with one gentle question about a time I felt most like myself, then follow up based on what I share

This isn't about finding your "one true calling" (pressure much?). It's about noticing what lights you up when nobody's watching.

Here's the complete prompt to copy and paste:

Be an identity archaeologist helping me rediscover core parts of myself. Help me identify consistent patterns in my values and interests across different life phases. I'm in a major life transition and feel disconnected from who I used to be. I want to find the through-lines that remain constant regardless of job title or circumstances. Ask me questions one at a time and build each question on my previous response. Start with one gentle question about a time I felt most like myself, then follow up based on what I share.

Just for the heck of it

Bonus Delight: The Permission Slip Collection

Try this: Ask AI to write you a permission slip from different versions of yourself.

"Write me a permission slip to start badly, signed by the version of me who already built something beautiful."

"Write me a permission slip to change my mind, signed by the version of me who stopped trying to be consistent and started being honest."

Sometimes we need to give ourselves permission to be exactly where we are.

What’s coming

Join me for "AI Confidential: Once More with Feeling!" - a free one-hour session for anyone new to AI or still unsure what to do with ChatGPT or Claude. Grab your spot here. No jargon, no shame, pajamas welcome.

And I'm putting the finishing touches on my website with some exciting offerings: custom GPTs built in your voice, the first paid AI Confidential cohort, premium 1:1 coaching, and a paid Joy Prompt Club membership for those ready to go deeper.

That’s it for this week.

Building in public is vulnerable and weird. But it's also honest in a way that corporate life never was.

Keep being brave,

💜 Deb

PS - If this resonated, hit reply and tell me about your own "nothing left to lose" moments. I read every single one, and your stories remind me why this work matters.

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