
Edition #17
Remote Work Is Like Dating
What's Inside:
Why treating your job search like desperate dating keeps you stuck. Clarity beats volume every time.
How to define your non-negotiables before you waste time applying. These aren't “preferences”, they're your filters.
Why "hardworking" makes recruiters yawn. Lead with what you actually solve, not buzzwords.
The scattergun approach exhausts you without results. Five intentional applications beat twenty random ones.
This Weeks Remote Roles. Fully vetted remote roles for Senior Professionals.
You wouldn’t marry the first person who swiped right on you.
So why are you treating your career decisions like a desperate Friday night on Tinder?
The way people date badly is eerily similar to the way they job search badly.
Swiping right on every remote job posting.
Saying yes to roles they don’t actually want.
Hoping something, anything, sticks.
It’s panic more than it’s a strategy.
Let’s fix that.
1. Get clear on what you’re actually building
Not every career move is meant to last forever.
Some people want flexibility and variety. That might mean contract or project-based work.
Others want depth, stability, and long-term growth. That usually points toward a permanent role.
Neither is “better.” And pretending you want both at the same time, when you don’t, guarantees frustration.
Clarity comes before applications.
If you don’t know what you’re aiming for, every option feels wrong.
2. Define your non-negotiables before you apply
Wanting good pay doesn’t make you greedy.
Wanting time with your family doesn’t make you unambitious.
But you do need to decide what matters most.
Write it down:
Schedule flexibility
Type of work
Manager style
Mission or industry
Growth expectations
Then use that list as a filter, not a wish list.
If a role violates your core priorities, no amount of rationalizing will make it a good fit.
3. Position yourself with intention (not buzzwords)
Recruiters don’t read resumes.
They scan them.
If your resume sounds like everyone else’s, it fades into the background and doesn't stand out.
“Hardworking” and “looking for my next challenge” tell them nothing.
They’re the professional version of “I like traveling and food.”
Instead, lead with:
What you actually do well
The problems you solve
The environments where you perform best
What make you unique
Specific beats impressive. Every time.
4. Show up as yourself… AND strategically
You don’t show up to a first date in pyjamas.
But you also don’t pretend to be someone you’re not.
Interviews work the same way.
Be honest about what energizes you, as well as what drains you.
Ask questions. Pay attention to how they answer.
Because if you have to fake your personality to get the role, you’ll burn out trying to keep it.
Rejection can be such a good source of information.
5. Ditch the scattergun approach
You wouldn’t go on hundreds of dates without filtering them first, would you?!
Applying to 20 roles a day you don’t care about may feel productive, but it’s not effective.
A smaller number of intentional applications with:
A tailored resume
A personalised cover note, where relevant
And basic company research
…will outperform mass applications every time.
The companies worth working with can tell the difference.
This Week's Remote Jobs
🎯 Fully Remote Jobs (No "Fake Remote" Here):
What this really comes down to
You have more influence over your career direction than you think.
But influence requires clarity.
And clarity requires a plan (with no room for guesswork)
If you’re tired of scrolling job boards, getting vague rejections, or feeling stuck despite “doing all the right things,” the next step isn’t more applications.
It’s better decisions.
That’s what we help with.
We work with professionals to:
Get clarity on which roles/companies to target
Strengthen positioning and messaging
Build a structured approach to pursuing remote opportunities
If you’d like an outside perspective, you can book a free 45-minute conversation with our team.
Stay Rebellious,
Michelle & The RR Team
Resources to Support Your Journey
Here are our top resources to help you take the next step:
🔒 Download The Remote Connection System. Your playbook to build warm company connections and avoid your application making it to the graveyard with the other 97% ghosts! Get instant access here
📋 Take 90-second Diagnostic Quiz – Learn personalized insights about your situation and discover the real bottleneck holding you back. Start the quiz
📞 Apply for a Consultation Call – Ready for one-on-one guidance? Book a free strategy session! Apply now
