Issue #13 For immediate release - You've been upgraded


The Work in Progmess Team

June 17, 2025

💌 From the Editor’s Desk

Welcome to Work In ProgMess — where every meltdown is just risk management in disguise.

This week, we’re giving out trophies for:

  • Doing a Premortem instead of losing your mind mid-trip
  • Faking confidence until you make eye contact
  • Downloading the latest patch for your internal operating system (includes bug fixes and boundary upgrades)

Your inbox deserves more than AI-generated LinkedIn fluff. It deserves the real stuff: laminated coping mechanisms, boundary firewalls, and parenting plans so tactical the Pentagon might call.

Let’s go.

— The Mess

📊Messy Metric of the Week

68% of employees say they’ve experienced imposter syndrome at work.
Only 25% have ever told anyone.
And exactly one brave soul made it a “fun fact” on their onboarding slide.
(Source: American Psychological Association + a truly off the wall team icebreaker.)

But here’s what’s real:
👉 Employees who feel psychologically safe are 76% more engaged, 50% more productive, and 67% less likely to leave.(Source: McKinsey, 2021)

So yeah, faking it ‘til you make it is a thing, but maybe feeling it while you fake it is where the real win lives.

📰Headline Shocker

📰 BREAKING: Mom Saves Family Vacation by Expecting Total Chaos, Prepares Accordingly

"I just assumed someone would vomit, someone would cry, and someone would try to pet a wild animal. So I packed for all of it."

ORLANDO, FL — Against all odds—and three overtired children—local mom Angela Ramirez pulled off the impossible last week: a family vacation with zero catastrophic meltdowns and only one minor injury (self-inflicted, her husband, emotionally).

Her secret?

“I did a Premortem,” she said, calmly unwrapping a granola bar from her fanny pack. “I imagined every single thing that could go wrong—and packed like it already had.”

Disaster? Pre-canceled.

Angela’s family of five had planned a four-day trip to Disney World. Historically, this ends in tears, blood sugar crashes, and someone Googling “how to get out of a family group chat.”

But Angela had laminated an itinerary, staged an emotional evacuation plan, and packed:

  • Ponchos for all weather patterns
  • An OTC pharmacy in quart-size baggies
  • Snacks with a zero-drama rating
  • And color-coded mood trackers labeled “MELTDOWN LEVEL: GREEN TO MAROON”

When their flight was delayed, she whipped out card games and a power bank.

When her youngest sobbed through the Haunted Mansion, she handed him noise-canceling headphones and a juice box.

When her husband suggested going “off itinerary,” she blinked twice and handed him the backup itinerary.

“She predicted me,” he said, still shaken.

Premortem Thinking: Anxiety’s Classy Cousin

“I just assumed we’d be one lost plushie away from collapse,” Angela explained. “That’s not negativity. That’s risk management.”

Local parenting groups are calling her a “logistical savant.” TSA agents referred to her toiletry packing as “art.”

A random dad in line for Pirates of the Caribbean saluted her with a juice box and whispered, “We’re not worthy.”


Angela’s Next Adventure: Teaching the Rest of Us

Angela now offers a free workshop titled:

“Vacation, Not Evacuation: How to Prepare for Joy Like You’re Bracing for Chaos.”

Her downloadable Premortem Trip Toolkit includes:

  • Family Risk Matrix™
  • Emergency Snack Flowchart
  • And a printable sheet called: “We’re Not Leaving Until I Say So”

The Family Reacts

9-year-old Lucas: “No one yelled. It was weird. I liked it.”

13-year-old Ava: “She had plans for moods. Moods. Respect.”

Husband Javier: [No comment. Still recovering from suggesting they “just wing dinner.”]

💡The Sports Page

🌽 SPORTS PAGE

🗞️ YOU 1, IMPOSTER SYNDROME 0: Rookie Shocks Veteran in Sloppy, Beautiful Upset

—From the Work In ProgMess Sports Desk, Where Confidence Is Optional

Tuesday, 8:47 AM — Self-Doubt Stadium

In a gritty, mistake-filled, emotionally unstable showdown, You pulled off the upset of the season, outlasting #1 seed Imposter Syndrome in a brutal mental matchup nobody saw coming—including You.

Down early after Imposter opened with its signature combo of “You’re not ready for this” and “Someone’s about to find out you’re a fraud”, You appeared rattled. They fumbled the intro, forgot half their talking points, and blacked out for most of the first quarter.

But then—something shifted.

Halftime locker room speech highlights (unauthorized transcript):

“You’ve done harder things. You’ve survived worse.
You belong here. Or at least you’re already here, so let’s fake it aggressively.”

The second half saw You come alive with bold, erratic plays:

  • The accidental good idea that made the Slack chat go quiet in a good way
  • A spontaneous head nod of leadership energy
  • Eye contact with a decision-maker (the crowd gasped)

Imposter Syndrome tried to rally late with a surprise whisper campaign: “You just got lucky.” But it was too little, too late.

Final Score:

You — 1

Imposter Syndrome — asking to “circle back”

🎙️ Postgame Quote from You:

“Honestly, I thought I blew it. But then I remembered literally no one knows what they’re doing and I’m allowed to take up space. So I did.”

📊 Game Stats:

You vs Imposter

Self-doubt turnovers 3-0

Tiny brave decisions 5-0

Eye rolls at own résumé 2-1

Actual proof you’re unqualified 0-0


Next Matchup:

You vs. Sunday Scaries.

Experts predict a slow start, with possible fourth quarter laundry.

🤝 Release Notes

🧵 New patch available for the operating system known as You.

If your internal software’s been buggy lately—glitching out during meetings, buffering when asked “how are you,” or spontaneously crashing mid-email—don’t worry. The latest release is here.

🚨 RELEASE NOTICE: YOU 2.0.2.5

Now rolling out across all under-caffeinated devices.

This update includes bug fixes, emotional performance improvements, and minor security patches. If you’ve been experiencing lag, burnout, or an inability to make basic decisions like what to eat for dinner, this release may offer temporary relief.


🛠️ Bug Fixes:

  • Fixed a glitch where user agrees to everything in meetings, then rage-slams laptop shut and mutters “cool cool cool” through gritted teeth.
  • Resolved issue where “I’m fine” auto-translated to “I’m in crisis but still answering emails.”
  • Calendar app now accurately reflects the amount of energy required to attend a 15-minute Zoom.

🧠 Feature Updates:

  • Boundary Firewall 2.0: Now blocks energy vampires, vague calendar invites, and group texts with 27+ people.
  • Notification Triage Mode: Auto-snoozes anything that starts with “Just circling back…”
  • New App: GutCheck™ — consults your instincts before committing to anything that might destroy your soul.
  • Do Not Disturb Enhancement: Silences Slack, internalized capitalism, and that one coworker who always asks “what’s your five-year plan?”

⚠️ Known Issues:

  • Still defaults to people-pleasing under pressure.
  • Occasional system crash when asked “What do you do for fun?”
  • “Quick break” feature can still unexpectedly turn into a full 3-hour scroll through Zillow listings in Vermont.

📥 Download Instructions:

  1. Take a breath.
  2. Say no once today.
  3. Unsubscribe from that productivity podcast that makes you feel broken.
  4. Forward this release note to one other human who needs it.

💡 Coming in YOU 2.0.2.5:

  • “Authenticity Settings” toggle.
  • In-app career panic translator.
  • Inner peace (beta).

💌 Dear Work in Progmess

💌 Dear Work In ProgMess,

How do I manage my time without becoming a productivity cult member?
—Overbooked & Underwhelmed


Dear Overbooked,

You don’t need a new planner. You need permission to stop pretending your calendar is a personality.

Try this:

  • Decide once. Taco Tuesday? Inbox Zero Friday? Default settings save brain cells.
  • Name what matters. Protect it. Let everything else fall off without guilt.
  • Plan like a person. Add buffer time. Snack time. “What was I doing again?” time.
  • Start small. Like, insultingly small. Open the file. Light the candle. That’s a win.
  • Rest on purpose. Blank space isn’t failure. It’s strategy.

Time management isn’t about doing more. It’s about making time feel like it belongs to you.


Whistle Whistle:
"If your calendar makes you want to punch something, it’s not a schedule. It’s a hostage situation." —Roy Kent

📩Until Next Time…

You’re doing great. Or you’re doing barely. Either way, it’s progress.

If no one’s told you lately:

  • Your chaos is valid.
  • Your color-coded meltdown chart is elite.
  • You’re allowed to prep for joy like it’s a fire drill.

Now close your 27 tabs, delete one meeting, and forward this to the person who once said “let’s just wing it” before a family trip. You know who you are, Javier.

Snarkily yours,
The Progmess Editorial Team

P.S. Since you made it to the Bitter End, we found this test to see if you could survive an extended (or an undisclosed amount of time) stay stuck in an airport with a "friend." Quiz carefully here.

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