One Step Closer: Get Ready to Go Remote Without Quitting Everything

Want to go remote but not ready to upend your life? Let's take your remote skills inventory and find ways to start flexible 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.

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.