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Why Your Remote Job Search Is Taking So Long
The 5 mistakes that turn a 2-month search into a 6-month nightmare
INSIDE THIS ISSUE:
This week's hot & vetted remote job picks
Why 3+ months means something's broken in your approach
The 5 reasons your search is dragging on forever
The reset strategy that fixes everything
What to change right now if you're stuck
Hi Freedom Seeker,
If you've been searching for a remote job for more than 3 months with minimal results, something is broken.
Not you. Your approach.
I see this constantly: Someone applies to 100+ jobs over several months. Gets a few responses. Maybe one or two interviews. Then nothing. And they keep doing the exact same thing, expecting different results.
The truth? A healthy remote job search should produce results within 4-8 weeks. If you're past that and still stuck, you're making at least one of these five mistakes.
Here's what's actually keeping you in job search limbo - and how to fix it fast.
🚀 Weekly Vetted Remote Job Picks
1️⃣ Company: Modern Health
🔷 Role: Client Success Manager
🔷 Location: UK
🔷 Type: Full-time, fully remote
🔷 Perks: Remote-first, asynchronous work
🔷 Salary: Competitive
➡️ Apply Here
2️⃣ Company: Twilio
🔷 Role: Senior Social Media Manager
🔷 Location: US
🔷 Type: Full-time, fully remote
🔷 Perks: Remote-first, competitive benefits
🔷 Salary: $104,000-$153,000 per year
➡️ Apply Here
3️⃣ Company: Apollo
🔷 Role: Sales Operations Manager (Outbound Sales)
🔷 Location: Canada
🔷 Type: Full-time, fully remote
🔷 Perks: Remote-first, asynchronous work
🔷 Salary: Competitive
➡️ Apply Here
THE 5 REASONS YOUR SEARCH IS TAKING FOREVER
MISTAKE #1: YOU'RE APPLYING TO THE WRONG LEVEL
Applying to jobs you're overqualified for? You look like a flight risk. Applying to jobs that want 2+ years more experience? You're getting filtered out immediately.
👉 The fix: Apply to roles that match your experience level exactly. If you have 3 years of experience, stop applying to both entry-level and senior positions. Stick to mid-level roles where you're the perfect fit.
MISTAKE #2: YOU'RE ONLY USING JOB BOARDS
LinkedIn, Indeed, FlexJobs - everyone uses these. Which means every posting has 500+ applicants.
👉 The fix: Spend 50% of your time on direct company websites. Find 20 companies you want to work for and check their career pages weekly. Apply directly. You'll compete against 50 people instead of 500.
MISTAKE #3: YOUR RESUME ISN'T OPTIMIZED FOR REMOTE
If your resume doesn't scream "I can work remotely," you're invisible.
👉 The fix: Add these to your resume right now:
"Remote Collaboration Tools" in your skills section
Mention of async communication in job descriptions
Any cross-timezone work experience
Home office setup in your contact section
MISTAKE #4: YOU'RE WAITING TOO LONG TO APPLY
Applying to jobs posted 3+ days ago? You're application #300.
👉 The fix: Set up job alerts and apply within 24 hours of posting. Early applicants get 5x more attention than late ones. Make this your daily routine: Check alerts in the morning, apply immediately.
MISTAKE #5: YOU'RE APPLYING TO TOO FEW JOBS
"I applied to 30 jobs over 3 months and heard nothing."
That's 2-3 applications per week. Not enough volume.
👉 The fix: Apply to 10-15 quality positions per week minimum. That's 40-60 per month. You need volume AND quality. Anything less means you're not really job searching, you're casually browsing.
THE RESET STRATEGY
If you've been stuck for 3+ months, here's your reset plan:
WEEK 1: AUDIT
Look at your last 50 applications
What level were the roles? (Too junior? Too senior?)
When did you apply? (Within 24 hours? After 5 days?)
Where did you apply? (Job boards only? Company sites too?)
WEEK 2: FIX YOUR MATERIALS
Update resume with remote-specific language
Add remote collaboration tools to skills
Rewrite your summary to emphasize remote capabilities
WEEK 3-4: NEW APPROACH
Identify 20 target companies, check their sites directly
Set up alerts for job boards, apply within 24 hours
Aim for 12-15 applications per week
Track everything: where you applied, when, response rate
THE REALITY CHECK
Most people searching for 6+ months are making multiple mistakes at once. They're applying to the wrong roles, too late, on oversaturated job boards, with resumes that don't mention remote work capabilities.
Fix one thing and you might see slight improvement. Fix all five and you'll start getting interviews within 2-3 weeks.
Your search is taking so long because you're doing the same thing over and over. Change your approach, and your timeline changes too.
👉 NotSo9to5 Premium Membership
If you're tired of spinning your wheels, Premium gives you direct access to vetted remote opportunities before they hit public job boards. You'll also get my personal help reviewing your approach and fixing what's broken.
Premium includes:
✅ high-quality & hand-vetted remote opportunities weekly
✅ Early access before public posting (less competition)
✅ Application strategy review specific to your situation
✅ 1:1 support to diagnose what's keeping you stuck
Stop guessing what's wrong with your search. Let me show you exactly what needs to change.
Ready to end the job search limbo? Reply with "YES" for Premium access.
Remember, a long job search doesn't mean you're not good enough. It usually just means you're approaching it the wrong way. Fix the approach, and everything else falls into place.
Until next week,
Sami
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