One Step Closer: Get Ready to Go Remote Without Quitting Everything
Want to go remote but not ready to upend your life? Here’s one simple way to start earning remote income without leaving your job (or your sanity) behind.
Welcome to One Step Closer, a no-fluff series to help you take small, intentional steps toward a location-independent life—without burning out or starting over.
If you’ve been fantasizing about remote jobs or dreaming of earning remote income from a cabin, a café in Lisbon, or maybe just wherever you are and whenever it fits… welcome! You’re definitely not alone.
But for a lot of midlife professionals, the idea of suddenly quitting everything to “go remote” feels like a leap off a cliff with no parachute. There’s mortgage math, family dynamics, identity shifts, and, oh yeah—actual bills to pay.
Here’s the good news: You don’t have to start over to go remote.
You just have to start somewhere. And for many of us, the best place to begin is with what we already know.
Instead of searching for your “forever remote job” right away, start by building a bridge opportunity… something that helps you test the waters and transition gradually.
Here are a few options that make sense in midlife:
Freelance a skill you already use in your day job (writing, project management, coaching, marketing)
Consult within your industry for former employers or colleagues
Package your knowledge into a workshop, template, or paid resource
Negotiate a remote-friendly shift in your current role or within your org
This isn’t about abandoning your career; it’s about repurposing what you’ve built into something that supports more freedom.
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Try this step today: Make a remote income inventory
Before you scroll job boards or rebrand yourself on LinkedIn, pause and take stock of what you’re already carrying. Your career capital—skills, experience, networks, and knowledge—is often more “remote-ready” than you think.
Start a simple list:
What do people already ask you for help with?
What have you taught, led, or created?
Which parts of your current or past roles could be done from anywhere?
You’re not reinventing yourself. You’re identifying what’s already in your toolkit, and seeing how it can be repackaged for remote income or freelance work.
Test it out before you transition
Start with a limited offer—one service, one project, one client—and see how it fits. The goal isn’t to replace your full income overnight. It’s to prove to yourself that:
You can earn income remotely
You like working this way
You know how to structure your time and energy differently
These early experiments will build both skills and confidence, and help you decide what kind of remote income truly works for your lifestyle.
You don’t need to burn it all down to go remote. You need to be strategic, honest about your bandwidth, and willing to start small to build something sustainable.
This isn’t the fantasy of “ditch everything and move to Bali.” It’s the real work of building a new chapter that actually fits your life, so you can put yourself first.
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