Just Because You Can Doesn’t Mean You Should
This week, I saw a LinkedIn post that honestly stopped me in my tracks.
It was from a recent college graduate, proudly describing part of their interview process. To protect anonymity, I’ll keep the details vague, but essentially, they were asked to search for something as part of the “assessment.” The prize? A job.
The comments were glowing: grit, hustle, commitment, “this is what it takes.”
And all I could think was: that could never be me.
🍰 The Cheesecake Test
The post immediately reminded me of that infamous episode of Making the Band, where Diddy sent aspiring artists from Manhattan to Brooklyn (on foot) to fetch him cheesecake.

The point wasn’t really the cheesecake. It was a test of obedience, endurance, and how far people were willing to go to “prove” they deserved a shot.
It was a power move disguised as a lesson in “grit.”
Watching that episode years ago, it felt absurd. Seeing versions of it play out in hiring in 2026? Even more concerning.
So I keep coming back to the same question: Are we testing skills, or are we just testing how much people will tolerate?
🚨 What’s Becoming “Normal” in Hiring
What bothered me most about that LinkedIn post isn’t that one candidate went along with it. It’s that this kind of thing is increasingly celebrated instead of questioned.
Over the last few years, the bar for interviews has quietly shifted:
First, it was multiple rounds.
Then, case studies.
Now: multi-hour assignments, scavenger hunts, simulations, and “challenges” that blur the line between evaluation and unpaid labor.
The interview process is starting to look less like assessment and more like performance, where the most compliant, not necessarily the most qualified, “win.”
📬 What You All Reached Out to Tell Me
After last week’s issue on skills assessments, my inbox (and DMs) blew up.
Dozens of you who are currently in the job market wrote in to share what you’re experiencing in real time. Some were frustrated, some were exhausted, and a few were downright angry.
What struck me most wasn’t just the volume of messages, it was how similar your stories were.
It wasn’t “one bad company.” It was a systemic pattern.
Many of you used almost the same language:
“It felt like free labor.”
“I did hours of work and never heard back.”
“The assessment had nothing to do with the actual job.”
In other words… This isn’t anecdotal. This is becoming the interview process!
If this sounds familiar, don’t sit on it, feel free to reach out and share your experience. I’m listening, email me at: [email protected]
🧠 The Bigger, Smarter Move (what seasoned operators do)
If you want to stay ahead in this new world of assessments, don’t just do the work better than everyone else.
Reframe the assignment so you look like a senior operator, not a desperate candidate.
Here’s how:
Treat every assessment like a real business deliverable, and make that visible.
Before you submit anything, include a one-page “How I Thought About This” cover note with three parts:
1) Your Assumptions
Be explicit about what you assumed because the company didn’t clarify it. Example:
“I assumed your priority was speed over perfection.”
“I assumed this role focuses more on execution than strategy.”
This does two things:
Shows critical thinking
Protects you if their expectations were unrealistic or unclear
2) Your Decision-Making
Briefly explain why you made key choices, not just what you did.
This signals maturity, not compliance, the difference between an IC and a senior operator.
3) Your Time Box
State clearly:
“I spent approximately X hours on this.”
This subtly resets power dynamics. You’re not desperate, you’re professional with boundaries.
In a world where companies are increasingly asking candidates to “prove” themselves, your edge isn’t just doing the work, it’s showing how you think, how you decide, and how you set boundaries.
🎯 What We Cover in our Proof of Work Workshop
If the “cheesecake test” era of hiring is here to stay, then your edge isn’t hustle, it’s how you approach the work.
In the Proof of Work Workshop, we don’t teach you to jump through hoops faster. We teach you how to control the process.
Here’s what you get:
🔹 How to decode any assessment (before you start)
You’ll learn a simple framework to:
Identify what the company is actually testing
Separate “busy work” from real evaluation
Decide when to engage, and when to walk away
🔹 A repeatable playbook for take-home assignments
We break down exactly how to:
Scope the work like a senior operator
Clarify expectations without sounding difficult
Time-box your effort so you don’t burn out
🔹 How to present your thinking like a pro
You’ll get a template for a one-page cover note that shows:
Your assumptions
Your decision-making
Your boundaries
So you look like a seasoned operator, not a desperate candidate.
🔹 Real examples (what “good” actually looks like)
We walk through sample assessments and show:
What strong responses look like
Common mistakes candidates make
How hiring teams actually interpret your work
🔹 Power dynamics & boundaries (the part no one teaches you)
We cover:
When to push back (and how)
What questions you should be asking employers
How to avoid doing unpaid labor disguised as “opportunity”
🔹 Your own private cohort Slack channel (this is the good part)
Each cohort gets access to a dedicated Slack space where you can:
Ask questions throughout the program
Rewatch session recordings anytime
Share your drafts and request feedback
Learn from (and with) your peers in real time
Think of it less like a class, and more like a mini community + support system for your interview process.
🔹 A toolkit you can reuse
You’ll leave with:
Checklists
Templates
Email scripts
A clear decision tree for future interviews
So whether you’re facing a 30-minute case study or a 6-hour project, you’ll know exactly how to approach it, strategically, confidently, and with your time intact.
📅 Starting February 25
Live, practical, and built for real hiring scenarios.
The Astro Alignment Report: Intuitive guidance for Executive Assistants
What if I told you using astrology to tailor your communication style to match your executives birth chart would strengthen your relationship with them? In fact, you might actually get the answer to that question you asked in slack instead of a vague “ok” that makes your soul shrivel all because you changed your messaging to align with their natural wiring!

I’m Cat, an executive assistant and professional tarot reader with a minor in hyperfixating astrology. Since 2018, I’ve studied how planetary transits affect our day to day and utilizing that knowledge has made me a more emotionally intelligent EA, strengthened relationships with my execs and colleagues, leveled up my career, and so much more. Astrology is an asset to my life personally and professionally and I’m passionate about educating other EA’s on how to make it work for you!
We’re in the final week of Capricorn Season. Capricorns are born between December 21st and January 19th. Spoiler alert: I’m a Capricorn. 😎 We are earth signs (yes, I need to touch grass or preferably a tree) and I can confirm we are considered the CEOs of the zodiac.
Ruled by the planet Saturn which represents time, discipline, and responsibility, we understand better than anyone that strategy combined with vision and consistency will set you up for success. Often we can be found excelling in leadership positions as either public figures or quietly pulling strings behind the scenes raises hand.

Like Gerri from Succession, a Capricorn knows that true power isn't always the person at the podium—it’s the person who knows exactly where the bodies are buried, always reads the room, and has the know-how to keep the company spinning.
Strategic Alignment:
Perform audits, take inventory, cut out waste. No, you’re not actually going to use that guidebook…or are you?
Capricorns value time above all. If your update takes more than 30 seconds to read, you’ve lost them. Use bullet points and lead with the 'ask'. Remove filler words (my personal Sisyphus, but whatever).
Remove one habit or workflow that doesn’t suit you or your exec anymore.
You can’t be at your best if there's no room to breathe and neither can your exec. Make space, name your “why” and refer to it every time you’re tempted to book over it.
Where does your Exec balk at structure or investing? How can you help or delegate?
Assess where you’re investing long term. And where you aren't.
Prep materials for salary negotiations (cuz a Capricorn stays ready to talk money)
Ask your exec questions related to longevity: 'What do you want people to say about this project in five years?’
Thanks for reading. I’m looking forward to sharing monthly astrological tips and insights for 2026 at Office of the EA!
Cat (they/she) is a full time Executive Assistant, Tarot Reader, and Intuitive Consultant based in Philadelphia, PA. To contact, follow on LinkedIn or email [email protected]
Where I’ll Be This Month
AI Outlook 2026 with Dapple AI
I’ll be joining a panel with Dapple AI for AI Outlook 2026: More Signal, Less Noise, a candid conversation about what’s actually working (and what isn’t) as AI reshapes how we work.
📅 Jan 22 | ⏰ 2:00 PM EST
OOTEA Free Virtual Events
Office Hours ft Molly Medvecky
For our next Office Hours, we’re welcoming Molly Medvecky, founder of EA Enneagram, for a live session on the Enneagram and how it shows up in our work.
Molly will share a foundational introduction to the Enneagram and practical ways EAs and operators can apply it to communication, stress, boundaries, and day-to-day work dynamics.
🗓️ Date: February 4th 12pm ET
🌐 Free & virtual
⏰ 45 minutes
💬 Cameras optional; coffee mandatory-ish (tea is fine, we guess)
Community
💬 Join the conversation
If you’re navigating this in real time, come talk it through with us in The Inner Office, our free Slack community for operators.
Workday Anthem
🎶 Song of the Week: “Don’t Start Now” — Dua Lipa
For anyone who has decided: I’m not chasing you, negotiating my worth, or fetching metaphorical cheesecake just to be considered.
Follow our Spotify playlist for inspo! 🎧

