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đ From the Editorâs Desk
Where productivity is a marketing campaign, burnout is a badge, and âcareer strategyâ is just your coping mechanism with better fonts.
This week, weâre covering:
- đ§ The science of emotional âwalksâ that are actually escape attempts
- đ€ AI bosses who never blink but definitely judge
- đ A Kentucky Derby filled with legacy hires and one horse who actually tried
- đ Ten-day career experiments for anyone allergic to five-year plans
- đ© And a reader question that asks: what happens when your ambition updates but your workplace doesnât?
If youâve ever opened your laptop, stared into the void, and thought, âAm I innovating or disassociating?â â youâre in the right inbox.
Letâs go make a beautiful, strategic mess.
â The Mess
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đMessy Metric of the Week
đŻ Emotional Evacuation Index
72% of employees say theyâve âjust stepped out for a walkâ during work hours.
Of those, 94% were actually walking to avoid crying on Zoom. The other 6%? They were crying during the walk.
đ Source: National Bureau of Deep Sighs and Unscheduled Breaks
But hereâs the twist⊠đ Forbes, February 2025:â 66% of American employees are experiencing some form of burnout.
Among younger workers, itâs worseâ81% of 18â24-year-olds and 83% of 25â34-year-olds report feeling burnt out.
Translation?â Burnout isnât a personal failure â itâs a workplace signal flare. Are you in a leadership role and still measuring output over wellbeing? Then you're not leading⊠you're just lighting the match.
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đ°Headline Shocker
BREAKING: Your Manager Has Been Replaced by a Printer with Feelings
And other signs weâre living in a Black Mirror episode co-written by HR and IT.
By Work In ProgMess Staff Writer
May 6, 2025
SACRAMENTO, CA â In shocking-but-also-not-shocking news, California has introduced the No Robo Bosses Act â a proposed law to keep real humans in charge of hiring, firing, promoting, demoting, and all the other joyful workplace rituals we pretend donât hurt.
The gist?
đ€ Robots = helpful tools. đŒ Robots = terrible bosses.
The bill would ban companies from using fully automated systems to make high-stakes decisions about your career without a human being saying something like:
âHey, maybe letâs not fire Marissa because she didnât use enough exclamation points in her emails!!!!!â
State Senator Jerry McNerney basically said:
âYou can use AI, but you can't let a robot run your business like it's an automated checkout line.â
Side note:â Imagine getting fired by a slightly condescending, auto-corrected email that says: âWe're circling back to let you know your service was⊠appreciated.â
đš Why It Matters (to anyone still keeping their camera on in Zoom calls)
If youâve ever:
- Been labeled âdisengagedâ because you donât smile during status meetings
- Had your rĂ©sumĂ© rejected because you didnât sprinkle it with trending buzzwords like âagile,â âsynergy,â and âLinkedIn influencerâ
- Been deemed a âculture mismatchâ by software that thinks pastel avatars = team spirit
Then congratulations â youâve already met your Robo Boss. And guess what? Itâs just as empathetic as your office printer during a paper jam.
Automation without empathy isnât efficiency. Itâs negligence with better branding.
đŁFrom the Editorâs Desk:
AI can predict which ads youâll click.
It can predict your next Spotify song.
It can even finish your email before youâve decided if youâre passive-aggressive or just tired.
â
But it shouldnât predict your worth.
It shouldnât decide if youâre a âgood culture fitâ because you didnât pick the right stock photo for your rĂ©sumĂ©.
Humans are messy.
Leadership is messy.
(Spoiler: Thatâs why the robots canât actually do it.)
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đĄThe Sports Page
đ Descendants of Secretariat Disappoint GrandlyâExcept One
By Staff Writer, Work In Progmess Sports Bureau
LOUISVILLE, KY â In a move described by some experts as âdestiny fulfilledâ and by others as ânepotism on hooves,â every one of the 19 horses in the 151st Kentucky Derby shared something in common: they were all descendants of Secretariat.
Naturally, 18 of them lost anyway.
Despite the storied bloodline, the majority of contenders appeared to suffer from what racing analysts are now calling âlegacy-induced complacency.â
âHe had Secretariat in his DNA,â sighed one trainer, watching Tiztastic finish 15th. âBut apparently he also had a LinkedIn Premium account and a penchant for feels over fast hooves.â
đ§Ź Everyone Had the Same Genetics. But Only One Had the Juice.
Most of the Derby field was stacked with horses who looked great on paper, gave strong interviews, and said all the right things in the pre-race pressers. But when the gates opened, it quickly became clear: pedigree is not performance.
Contenders like East Avenue, Coal Battle, and Sandman broke from the gate with the energy of a Monday all-hands Zoom. Publisher, widely expected to finish in the top five based on algorithmic predictions and a flurry of Medium posts, was ultimately buried in 14thâblaming âlow visibility and a lack of engagement.â
âI guess I peaked during my TED Talk,â Publisher admitted post-race, posting a reflective carousel: â3 Lessons from Finishing in the Bottom Third (And Why Iâm Grateful for It)â.
đ Sovereignty Wins by Mindset. Journalism Files a Strong Second.
While the pack was busy brand-building and checking Slack, Sovereignty stayed locked in and blew by rivals with a final burst of independence and self-assurance.
âSovereignty didnât try to crowdsource their race strategy,â said retired jockey-turned-life-coach Kip Gallup. âThey just ran. No podcast. No merch drop. Just grit.â
Close behind was Journalism, who appeared briefly tempted to fact-check the odds but ultimately committed to the race, finishing second and issuing a clean, unbiased post-race recap.
Third place? Baeza, who ran like they were one connection short of 500 LinkedIn connections, followed closely by Final Gambit, Owen Almighty, and Citizen Bullâeach of whom claimed victory in internal retrospectives but were, in fact, not Sovereignty.
đ§ Work in Progmess Analysis
In a world where everyoneâs got the same access, the same advice, and the same â5 AM Routineâ saved to a Pinterest board, the Derby reminds us: itâs not what you inherit. Itâs how you run.
â
When the track gets sloppy, the real pros arenât the loudestâtheyâre just the ones still moving forward, while the rest are checking their follower count and waiting for a repost.
Final Results (Select Highlights):
đ„ Sovereignty
đ„ Journalism
đ„ Baeza
đ Publisher (14th, but already scheduling a âLessons from Losingâ webinar)
â Chunk of Gold (19th, but âplanning a comebackâ on Substack)
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đ§Ș MicroDares & Career Flares
đ€ The Top 10 Ten-Day Experiments for Job Seekers
(Because life plans are exhausting and youâre out of highlighters)
đŁ Delivered in full David Letterman countdown style, complete with commentary you didnât ask for but definitely need.
#10: Apply to Jobs Without Editing Your Personality Out
For 10 days, write your cover letters like you talk.
Bonus points if you use the word âbananaâ in a sentence and still get an interview.
#9: Stop Starting Emails With âJust Following Upâ
Replace it with literally anything else.
âHope your inbox hasnât eaten you aliveâ is a fan favorite.
Track responses. You might be shocked by how many humans still exist out there.
#8: Schedule One Awkward Conversation Per Day
Old professor. Former coworker. Ex-boss who maybe still thinks youâre 22 and âfull of potential.â
You donât need a TED Talk â just a calendar invite and low expectations.
#7: Document Your Job Search Like Itâs a Reality Show
Day 1 Confessional: âTried to update my rĂ©sumĂ©. Got distracted by font choices.â
Day 6: âApplied to a role Iâm 60% qualified for. Feel 87% powerful.â
Day 10: âStill unemployed, but now Iâm entertaining.â
#6: Try Saying âNoâ to a Job That Makes You Flinch
Youâre allowed to pass. Even if itâs âgood on paper.â
Even if your aunt thinks itâs âa great opportunity with benefits.â
Even if it has âninjaâ in the title.
#5: Ask for Help Without Apologizing for Existing
One LinkedIn DM. One Slack message. One email.
Not âSorry to bother you.â
Try: âI admire your work and would love your thoughts.â
(Then breathe deeply and donât delete it 14 times.)
#4: Pick One Skill. Actually Try It. For Real.
Ten days of Canva. SQL. Cold emailing. Public speaking.
Not reading about it.
Actually doing it.
Yes, that includes clicking ârecordâ and watching yourself talk.
#3: Write Down Every Job You Think You Might Hate Slightly Less Than Your Last One
The bar is low. The honesty is high.
Youâll be surprised what floats to the top.
Looking at you, âmuseum gift shop managerâ and âremote spreadsheet whisperer.â
#2: Apply for a Job You Secretly Think Youâre Underqualified For
Youâre not underqualified.
Youâre under-confident and over-coached.
Send the application. Then go eat chips. Thatâs the ritual now.
And the #1 Ten-Day Experiment for Job SeekersâŠđ„
#1: Do One Brave Thing a Day, and Reward Yourself Like Youâre Five Years Old
Sent the email? Gummy worms.
Scheduled the coffee chat? Movie night.
Asked for feedback? You get two stickers.
Tiny bets.
Low stakes.
Possibly Chipotle.
âïž Closing Argument:
Letâs be honest: the job search isnât a journey â itâs a scavenger hunt with broken clues and way too many pop-up ads.
These ten-day experiments arenât magic fixes. Theyâre tiny rebellions against the soul-sucking norm. Theyâre how you remind the world (and yourself) that youâre not a keyword-stuffed rĂ©sumĂ© or a networking event survivor.
Youâre a human. With ideas. And potential. And possibly gummy worms.
So ditch the five-year plan. Pick the weird challenge. And remember: your next job might just be one experiment away.
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đ©Dear Progmess
đ Dear Progmess
"What Do You Do When Workplaces Say Theyâre Evolving... but They Arenât?"
Dear Progmess,
The mission statements all say âflexibility, wellness, innovation.â
The actual benefits still say âYou can have PTO⊠if you file a formal request in triplicate and promise not to actually use it.â
I want to grow my career. I want to believe in the companies I work for.
But it feels like Iâm being asked to run a modern marathon with a map from 1997.
How do you build your future when the systems youâre stuck in havenât caught up yet?
Signed,
Ambitious but Annoyed
Dear Ambitious,
First of all, welcome to those of us paying attention.
(And probably allergic to 17-page employee handbooks that were last updated during the Blackberry era.)
Hereâs the hard truth:
You canât always wait for the system to evolve.
Sometimes you have to evolve yourselfâand your strategyâfirst.
Hereâs your Work In Progmess career advice playbook:
đ 1. Treat your career like a product, not a loyalty pledge.
You are allowed (encouraged, even) to upgrade your career goals faster than your companyâs benefits department can schedule a committee meeting about it.
Stay grateful. Stay growing. Stay mobile.
đ 2. Get clear about what âsupportâ actually means to you.
Is it financial coaching? Mental health benefits? Real flexibility?
Know your non-negotiables nowâbefore the next shiny offer tries to distract you with ping pong tables.
đ 3. Invest in skills, not just titles.
When companies are slow to evolve, the most valuable thing you can stockpile isnât promotionsâitâs portable skills.
Build the rĂ©sumĂ© youâd want to take to a better offer, even if youâre not looking (yet).
đ 4. Ask better questions. (And donât be afraid to walk.)
When interviewing, donât just ask âWhatâs your culture like?â
Ask:
- âHow have your benefits evolved in the last three years?â
- âHow do you support employees navigating real life changes?â
- âWhatâs one way your leadership has changed in the past year?â
If the answers are all about casual Fridays and free snacks⊠you already know.
đ 5. Remember: Loyalty isnât about staying. Itâs about growing together.
If your companyâs idea of âsupportâ still looks like a faded poster in the break room, you owe it to yourself to find (or build) something better.
Youâre not selfish for wanting that.
Youâre smart for planning for it.
Bottom line:
Donât wait for the system to catch up to you.
Move at the speed of your own growthâand invite leadership to keep up.
(If they donât? Thatâs not your failure. Thatâs their lagging software.)
Stay stubbornly hopeful,
â Work In Progmess
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đ©Until Next TimeâŠ
Before You Pretend That Walk Was "Restorative"...
Just a few reminders to carry into your next "quick sync":
đ· Being busy isnât a personality trait. Itâs just a socially accepted form of hiding. đ§ If your âAI-enhancedâ workflow feels like a group project with a robot who hates youâyouâre not imagining it. đ Legacy doesnât guarantee leadership. Sometimes it just means you were born into the Google Drive folder.
And if this issue made you laugh, nod silently, or reconsider giving your résumé a wellness section, forward it to:
- A teammate whoâs lapping the virtual watercooler for the third time today
- A boss who insists burnout is a mindset
- Or that friend who applied to 47 jobs and now identifies as a productivity blog
Help them laugh. Help them cope. Help them unsubscribe from hustle culture, one exclamation point at a time.
Until next week,â âThe Progmess Editorial Team
P.S. We are embarrassed to even ask this... but how do you make a tissue laugh? (You put a little boogie in it... so since you suffered through that bitter end - here's a little boogie woogie.)
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