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You Were Never Meant to Climb Their Ladder
The Strategic Assistant Revolution Continues
Joshua Washington
August 07, 2025
💬 Quote of the Week
There is no failure except in no longer trying.
💼 A Personal Note from Joshua
Hey EA-Pros Community,
This week, I want to tell you a story.
For years, the world’s brightest minds insisted human flight was impossible. “Experts” had the math to prove that heavier-than-air flight couldn’t work.
Then two bicycle mechanics from Ohio ,with no formal engineering education, proved them wrong.
What separated the Wright Brothers from the rest wasn’t money, connections, or advanced credentials.
It was the refusal to accept the limits others accepted as fact.
And I’ve seen the same story play out with senior-level assistants.
The most gifted EAs often accept invisible ceilings as if they’re permanent fixtures:
“This is how far an assistant can go.”
“Strategic roles belong to someone else.”
“Chief of Staff is the best I can hope for.”
But what if that career ceiling isn’t real?
What if it’s just waiting for someone bold enough to challenge it?
Let’s flip the script.
This week’s newsletter is packed with ways to reframe how you show up, communicate your impact, and start shaping a career path that reflects your actual value, not just your title.
We’ll end with a powerful invite to this week’s Breaking the Career Ladder training.
But let’s earn our way there first.
🧠 Feature Insight
The Invisible Asset: How to Build Influence Before You Need It
At the strategic level, success isn’t just about what you do; it’s about the influence you’ve built long before the critical moment arrives.
This week’s power insight is simple:
You don’t rise to the level of your work. You rise to the level of your influence.
Here’s how senior-level assistants quietly (and consistently) build that influence behind the scenes:
✅ Pre-Position Your Ideas
Before big decisions hit the table, plant seeds in casual 1:1s, pre-meeting chats, or hallway convos. Influence starts in informal moments, not just in high-stakes meetings.
✅ Become the Executive Filter, Not Just the Funnel
Don’t just pass along information; distill, frame, and prioritize it.
Say, “Here are the top 3 implications I see,” or “Here’s what might land wrong with our stakeholders.”
You become the lens through which your exec sees the business.
✅ Backchannel Strategically
Build trusted relationships across departments. When your name comes up, your reputation should already be vouching for you, even in rooms you’re not in yet.
✅ Operate from the Balcony
Step back weekly and ask:
“What’s the bigger play here? What patterns am I noticing across people, meetings, and momentum?”
That’s how you stop reacting and start advising.
This isn’t about being louder. It’s about being seen as the essential lens that brings clarity when it matters most.
🎯 BREAKING THE LADDER [Summer Training Series]
A Free Training for Senior-Level Assistants Only. We’ve received tremendous feedback, so we’re going to keep this going all summer long!
If the traditional path doesn’t fit, maybe it’s time to break it.
On Wednesday, August 20th, I’ll walk you through a proven framework that helps assistants:
Break through stagnant titles and plateaus,
Get their companies to recognize and invest in their strategic value,
And finally feel like they’re building a career they want.
You’ll also hear how one EA used this approach to increase her compensation by 20% in just 6 months, without changing her role or burning out.
The seat is free. The shift is real.
And the career you want? It’s not just possible. It’s within reach.
✉️ P.S.
Here’s to rewriting the rules! And finally flying on your own terms.
With deep respect,
Joshua