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Hey All!

From the conversations I’ve had lately, one uncomfortable truth keeps popping up: the older you get, the harder it can be to land that next EA role.

  • Several seasoned EAs have told me they’ve been on the hunt for months, one for over a year.

  • Some say age bias is real. Others point to shrinking executive budgets. Remote and hybrid roles attract thousands of applicants.

  • One EA I spoke to finally decided to stop waiting for the market to cooperate and launched her own virtual assistant business. Now she sets her own rates, chooses her clients, and hasn’t looked back.

This isn’t a pity party, it’s a wake-up call.
If the traditional job search isn’t working for you, this newsletter will help you:

  • Diagnose why your search is stalling

  • Spot new opportunities outside of “apply and wait”

  • Position yourself to stand out in a competitive market

  • Build a backup plan that doesn’t leave you at the mercy of job boards

📊 What’s Happening In The Market:

  • LinkedIn data shows that administrative job postings have dropped in certain markets over the last 12 months!

  • Senior-level EA postings are trending toward hybrid or in-office, fewer remote-only senior roles exist than in 2021–2022.

  • Companies are experimenting with fractional or project-based EA support instead of hiring full-time.

📋 EA Job Search Self-Audit (3 minutes to find your gaps)

Check off everything that’s true for you:

✅ My resume clearly shows measurable results from the last 12 months.

✅ My LinkedIn headline positions me as a specialist, not just “Executive Assistant.”

✅ I’ve reached out to at least 5 people in my network this month.

✅ I’ve explored fractional or contract roles, not just full-time postings.

✅ I’ve posted something value-driven on LinkedIn in the last 30 days.

If you missed more than 2 checks, you’ve just found your action plan.

Job boards are dead. Your network is alive.

You don’t need another job board.
You need a signal in the noise.

Indy AI, a new feature by Contra, helps independents find career-defining opportunities through the networks they’ve already built. It connects to LinkedIn and X, then quietly surfaces warm, high-fit opportunities hiding in your extended network, including from people you didn’t even know were hiring.

No cold outreach. No endless scrolling. No pitching into the void.

This is work that finds you. Real opportunities, backed by real people you already know.

It’s not hustle culture. It’s human signal.


And it’s how independents grow without burning out.

Let Indy AI do the searching, so you can focus on the work that actually matters.

Let work find you

💡 The Pivot Playbooks

If your current approach isn’t working, try one of these, here’s exactly how:

1. Go Fractional

  • Make a list of 3 industries you know best.

  • Draft a 3-sentence pitch to execs/founders on LinkedIn: “I help [industry] leaders streamline [specific pain point] without the overhead of a full-time hire.”

  • Offer a flat-rate monthly package (e.g., 10 hours/month for $X).

2. Specialize

  • Pick one niche (legal, VC, healthcare, etc.).

  • Rewrite your LinkedIn and resume to highlight only that niche’s wins.

  • Join online spaces where decision-makers in that niche hang out.

3. Productize Your Skills

  • List 3 templates, checklists, or SOPs you’ve built in past roles.

  • Package them as a mini toolkit (Notion, Google Docs, or PDF).

  • Sell them online or use them as a lead magnet for potential clients.

4. Work Your Network Like a Job

  • Schedule 2 virtual coffees a week with former colleagues.

  • Ask “What’s the biggest operational pain point your team has right now?”

  • Offer a specific solution — not just a resume.

🎯 This Week’s Challenge

Before Friday: Send one message to someone in your network asking for insight, not a job. Example:

❝

“Hey [Name], I’m exploring my next move and would love your take on where you’re seeing demand for senior EA skills right now.”

Opportunities follow conversations, not just applications.

💬 Inside The Inner Office

This month, we’ve got Lauren Bradley from The Officials joining us for a members-only AMA.

Lauren will be sharing some of her favorite tech hacks that will simplify your life — whether you’re a G-Suite wizard, an Outlook loyalist, or somewhere in between. Think inbox zero tricks, automation shortcuts, and clever ways to shave hours off your week without breaking a sweat.

If you love this newsletter, you’ll love our community. For just $20/month, The Inner Office gives you:

  • Monthly expert AMAs (Lauren this month, Job Market AMA next week)

  • Exclusive templates, checklists, and resources

  • A private Slack brain trust of top-tier EAs for 24/7 answers, ideas, and wins

It’s everything you get here, but on tap all month long.

Join The Inner Office.

🛠 Tools for Your Next Move

If the EA job market has you thinking about your options, here are a few platforms to explore:

  • Contra – Build a portfolio and find freelance/fractional gigs without paying fees.

  • Welcome To The Jungle– Curated job board with clear, postings and a free candidate profile to get tailored role recommendations.

  • Teal – Track applications, organize your job hunt, and optimize your LinkedIn profile.

  • Boldly – VA network hiring experienced admins for remote support roles.

Bookmark these now, you never know when you’ll need a Plan B (or a better Plan A).

🎵 Song of the Week: Despacito, Luis Fonsi, Daddy Yankee Feat Justin Bieber

Because sometimes the job search (and life) feels like it’s moving at this exact pace… but at least we can dance to it.

👂🏼 Follow the playlist on Spotify.

Despacito - Remix

Luis Fonsi, Daddy Yankee, Justin Bieber ¡ Despacito Feat. Justin Bieber (Remix) ¡ Song ¡ 2017

open.spotify.com/track/6rPO02ozF3bM7NnOV4h6s2?si=6384c6e5f370409f

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