Introducing Cubicle to Corner Office

Why I wrote the guide I wish I had — and how it fits into the First 90 Days OS.

Most people don’t struggle in their first job because they’re “not smart enough.”

They struggle because the work comes with invisible rules:

how to communicate progress without sounding unsure
how to ask for help without dumping the problem on your manager
how to navigate meetings, priorities, and the subtle politics
how decisions actually get made

If you’re an intern/new grad, it feels like everyone else got a handbook.

If you’re a manager, it feels like you’re re-teaching basic workplace operating skills on repeat.

Scene

At some point you realize there are two kinds of work in an office:

the obvious work (the spreadsheet, the deck, the ticket), and
the invisible work (alignment, updates, follow-through, not surprising people)

School trains you for (1).

Most first jobs assume you already know (2).

That gap is where a lot of early-career anxiety comes from — and it’s why managers end up “micromanaging” even when they don’t want to.

What this site is

This site (and the book behind it) is meant to be the handbook I wish I had.

Not “be confident.”

More like:

here’s the exact template
here’s the script
here’s the system

So you can copy/paste your way to competence while you’re still nervous.

What prompted this

You can see the invisible-rules problem in the wild — and the comments are always spicy because people are arguing about “professionalism” without defining it. Two examples: the Reddit thread on unwritten office rules (https://www.reddit.com/r/work/comments/15oad7z/what_are_some_unwritten_rules_and_etiquette_for/) and Ask a Manager on a younger employee missing professional norms (https://www.askamanager.org/2022/08/my-younger-employee-doesnt-know-professional-norms.html).

Why I wrote this

I started my career about 20 years ago in the mailroom at William Morris.

I’d done all the “school preparation” stuff.

What I wasn’t prepared for were the skills nobody grades you on.

Over time — especially after business school and a career pivot — I realized I was spending a big chunk of my life coaching new hires on the same handful of problems:

they were doing work, but not showing progress
they were asking questions, but not asking them well
they were working hard, but not aligned

So I wrote Cubicle to Corner Office: The Ultimate Survival Guide to Your First Job.

Not as a motivational “believe in yourself” book.

As a practical guide for the parts of work that are real… and rarely explained.

Why another career book?

Because technical competence is table stakes.

In real workplaces, the gap between “smart” and “successful” is usually:

clarity
consistency
judgment
communication

If you can’t write a crisp update, run a clean 1:1, or summarize a decision, you end up looking unreliable — even when your work is good.

And if you’re a manager, you end up micromanaging — not because you want to, but because you don’t have signal.

The 3 things I wanted to make painfully practical

1) Build tangible skills (beyond your degree)

Your degree helps you get in the door.

Your operating system helps you stay employed and get promoted.

That looks like:

setting goals you can actually hit (not “crush it” vibes)
prioritizing your calendar and protecting focus
communicating progress without rambling
flagging risks early (so you don’t surprise your manager)

2) Build meaningful work relationships (without being fake)

Nobody ships alone.

Early in your career, relationships do three things:

they speed up answers
they reduce rework
they create advocates (when you’re not in the room)

So the book gets practical about:

working with your manager
collaborating cross-functionally
networking without being weird about it

3) Demonstrate motivation the right way

Motivation isn’t “working late.”

Motivation (the kind managers trust) looks like:

learning fast
asking good questions
delivering what was asked
making your manager’s life easier

Do those consistently and you become low-drama and high-trust — which is basically the cheat code.

What you’ll actually get (examples)

I tried to make this feel like having a slightly older coworker whispering, “Do this, not that.”

So it’s full of practical artifacts and scripts, like:

a clean status update format that works in email or Slack
a 1:1 agenda so your manager meetings produce decisions (not rambling)
“how to ask questions” phrasing that gets you answers without sounding helpless
meeting follow-up templates (so decisions don’t evaporate)
how to manage up without being political or fake
how to build relationships without “networking” cringe

Two quick notes, depending on where you sit:

Early-career: you’re not behind. You’re just missing the operating manual.
Manager: the goal isn’t to “fix the kids.” It’s to create repeatable systems (templates, norms, examples) so new hires ramp without constant re-teaching.

Edge cases

Some workplaces are genuinely chaotic and under-documented. In those environments, “write it down and share it back” is a superpower.
If you’re coming from a different country or culture, the invisible rules are even more invisible. That’s not a personal failing — it’s just context.

Next step

If you want the backbone of the system, start here: Start here.