Rainy Monday, Yelapa on the Brain (and a Plan to Work From Anywhere)

After seven days in Yelapa, Mexico, coming home to a gray, rainy Monday feels like a cruel joke. One minute you’re waking up to the sound of waves lapping against the shore, sipping coffee on a balcony with a view straight out of a travel magazine. The next, you’re fumbling for an umbrella, dodging puddles, and trying to remember how to log back into your work computer.

Yelapa has a way of slowing life down. No cars, just cobblestone paths and sandy beaches. My wife, our two daughters, and I spent our days exploring the village, hiking to waterfalls, and eating fresh-caught fish prepared just a few steps from where it was pulled from the water. Every sunset felt like it was competing with the one before it, and every morning came with that easy pace you wish you could bottle up and take home.

Then Monday hit. The kind of Monday that’s not just a Monday—it’s a rainy, gray Monday. The kind that makes you start Googling “remote jobs” or fantasizing about buying a little palapa by the beach and running a tiny café just to avoid putting on real shoes ever again. The transition from barefoot on the sand to dress shoes on wet pavement is brutal.

It’s on days like this you start thinking about what life would be like if you were independently wealthy, free to work—or not work—from anywhere. The dream isn’t about never working again, it’s about working where your “office” could be a hammock with Wi-Fi. Yelapa reminded me that’s possible for some people. And on a day like today, that “some people” feels like it really should’ve included me.

Make It Location-Independent

Maybe the real takeaway isn’t just daydreaming about a different life—it’s figuring out how to build one. Make your work travel with you, whether you’re on a balcony in Yelapa or a dock on a lake in Missouri. Do solid work, shut the laptop, then step outside into whatever view you’ve chosen. That way, it’s not just vacations that make life feel full—it’s Tuesday, too.

What You Could Do (and How to Pitch Your Boss)

You don’t need to reinvent yourself to work from anywhere. You need honest skills, clear deliverables, and a plan.

Independent options

  • Freelance what you already do: writing, design, video, web, marketing, project management, ops, customer success.
  • Consulting: package your expertise into fixed-fee offers (audits, playbooks, setup + training).
  • Products: digital goods (templates, courses, checklists), or a small niche store.
  • Service + product combo: retainers for steady income, products for leverage.

Keep your current job—remotely

  • Start with proof. Ask for one day a week remote. Track output. Over-deliver for a month.
  • Document results. Show metrics: response times, tasks closed, projects shipped, cost savings.
  • Propose a policy, not a favor. Suggest clear hours, SLAs, meeting windows, and availability rules.
  • Solve their worries up front. Offer a communication plan (Slack/Teams cadence), coverage plan, and a simple KPI dashboard.
  • Make it a win for them. Lower overhead, stronger retention, no commute drag, focused work blocks.
  • Ask for a trial period. 60–90 days with a mid-point review. If it works, formalize it.

Sometimes the beach is closer than you think—you just have to show you can carry your weight from anywhere.