Laptop & Flip-Flops: The Definitive Guide For Remote Work

I've spent the last few months remote working in Costa Rica, and believe me, there’s a right and wrong way it. Here's everything I learned from the experience so you can do the same!

Author

PATRICK FRANK
March 16, 2025

In partnership with

(Total read time: 6 minutes)

THE APPETIZER

Well if you couldn’t tell by the topic of this newsletter, my time in Santa Teresa, Costa Rica is coming to a close. A wrap on Season 3 of remote work. During this time, my co-founder had his 4th child, my co-worker ended up in the hospital which left me and my 4 VA’s running our companies, while the town had rolling blackouts……. How did we end up? Just fine. That being said, there were about unlimited times where I thought to myself… I wish I brought this, or did this, or prepared for that. So I figured I would outline it all here for you all so you can learn from my mistakes and nail your remote work experience.

To my Santa Fam reading this…. See you next season. Pura Vida Ya’ll. 

Now, grab a coffee, a Pina Colada, an Imperial cerveza, and as always, enjoy my sauce, 

- Patrick Frank

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PAT’S SNAPPLE CAP

  • FOMO-Inducing Stats:
     40+ Fascinating Remote Work Statistics (2025):  LINK

  • Will You Actually Be Able To Work Remote In The Future?:
     Top Trends For Remote Work In 2025:  LINK

  • Top Places To Remote Work Ranked:

  • Economics 101:
    Tired of reading about tariffs? Here’s everything you need to know:  LINK

  • Cool Tool Alert:
     Instantly copy the exact design code from ANY website: LINK

  • Health Hack:
     Stop paying for blood marker testing. Use this instead: LINK

❝

My twist on the famous quote of the 1:60 rule: An error of only one degree would put you almost 500 miles off course… or it might just land you right where you are supposed to be… not where you were planning to be.

Before I came to Santa Teresa Costa Rica, I was supposed to land in Mangua Nicaragua for a surf trip…..Roughly 500km away. 

Not where I planned to be, but where I was supposed to be. 

And with that mic-drop…. It’s time for the main course. 

THE MAIN COURSE

🧠 The Remote Mindset Shift

First off, remote work isn’t an endless vacation, it’s a discipline, not a location. If your mindset sucks, your remote work will too.

Here’s how you shift into gear:

  • Set a Schedule: Freedom without structure is chaos. Block your time, guard your focus, and stay accountable to your schedule but don’t forget to have fun.

  • Build A Routine: Get into a rhythm of a new routine. Find your working hours, your fun hours, your new work spots, your gym, and get familiar with the commutes between them all.

  • Boundaries Are Your Best Friend:
    Set clear work hours but know when to be flexible. Is the surf firing? Go out for a quick session for recharge in between meetings and make up the work later that day. Guard your productivity to maximize the experience in your free time.

  • Embrace The New Location: Dive in deep when you are not working. Meet locals, have new experiences, get off of Netflix and away from your computer when you are not working.

    • Saucy Tip: Pick one ritual that signals your brain the workday begins and when it is over. (I couldn’t start work until I after I touched the ocean, and I stopped to make sure I always caught the sunset.)

🛠️ Non-Negotiable Remote Softwares & Resources 

  • Communication:  Slack, Zoom, or Teams. Don’t try to run your empire from email alone.

  • Project Management: Notion, Asana, Trello enhanced with Loom. Your memory is good, but not that good.

  • Automation: Zapier, IFTTT: Anything that removes repetitive crap from your life.

  • Security: For any secure work you are doing invest in VPNs. ExpressVPN if you have heavy security requirements like at a large corporate job or the FREE option: UrbanVPN for solo-preneurs and start up nomads.

  • Password Managers: Like LastPass. You don't want your entire business hijacked by some random café hacker.

  • Portable Wi-Fi & Cellular: Keep a portable hotspot or phone tethering plan ready. Go big with a portable solar powered Starlink or be smart and get a sim-card BEFORE you get to your destination to avoid heavy phone plan fees. 

  • Nomad Health Insurance: Avoid the massive healthcare costs like what we went through by rolling an atv. There’s 100’s of options for any plan you need to make sure those “oh shit” moments are covered.

🛠️ Non-Negotiable Packing List:

Backup Tech Hardware: Laptop, phone, tablet and hard drives. Trust me you don’t want to be scrambling offline trying to find a way to get back online. Things break (This happened to me) or worse, they get stolen. (Also happened to me) It’s worth the suitcase space. 

Solid Luggage & Nomad Ready Gear: Pays for itself day 1. Enables you to pack light and remain mobile instead of packing like a Kardashian. 

Portable Desktops: Have a corporate set up on the beach with awesome tech like the dual monitor attachment for your laptop paired with a sunshade to be able to have your toes in the sand while you crank away. 

Portable Chargers: You never know when the power is going to go out. Make sure you are charged up all the time. Max out the wattage to ensure you can power more than just your headphones.

Notable Mentions: 

  • Noise canceling headphones to be able to lock in and free yourself from distractions.

  • Kindle or equivalent so you aren't weighed down by books.

  • Tech organizers so you aren’t literally getting tangled up everywhere you go.

  • Go-pro or content camera to capture the moments.

  • Apple air-tags to make sure your luggage isn't getting lost at the airport.

  • Mini-first aid kits… Because you never know. 

HOW TO ACTUALLY MAKE FRIENDS WHILE WORKING REMOTELY

Working remotely doesn’t have to mean working solo. If you want a social life beyond your screen, here’s your playbook:

  • Choose Social-Friendly Workspaces:

    • Coworking spaces: WeWork, Selina, or local co-working spots.

    • Café culture: Skip Starbucks, find places frequented by other locals or nomads (Workfrom).

  • Be A Part Of The Community:

  • Strategies & Icebreakers:

    • Become a local at one location and befriend the owners and staff for local insights and credibility. 

    • Offer to buy the first coffee for a new connection. Instant icebreaker.

    • Host a casual gathering or dinner, people always will gather for free food.

    • Don't be afraid to ask for intros. You’re only one message away from a new friend, lover, or wingman/woman.

🗺️ HOW TO PICK THE BEST DIGITAL NOMAD LOCATIONS

Choosing your next remote-work paradise isn't just about beaches or Instagram likes. Ask yourself:

  • Internet reliability: Check average speeds on Speedtest.

  • Cost of Living: Tools like Numbeo break down costs by city.

  • Community Vibes: Verify on NomadList for insights from other nomads.

  • Safety & Comfort: Research crime stats and travel advisories (U.S. State Department Travel).

    • Saucy Tip: If you're planning to stay more than 30 days, try to visit first for a week before committing long-term. Also remember, some countries have limitations for how long you can be there without a return flight booked. Just photoshop a return ticket for customs and you will be good to go. THANK ME LATER FOR THIS AND DO NOT FORGET TO DO THIS.

🖥️ RESEARCH YOUR REMOTE WORK LOCATIONS & GROUPS

Don't go in blind, tap into these invaluable communities and resources:

🏨 BOOKING YOUR DIGITAL NOMAD STAY

Forget generic hotels. These platforms are your new best friends:

  • Hostelworld: If you are solo traveling, this is a must. Put yourself in a position to meet others on the same journey. Instant network and community.

  • Airbnb: If traveling with others, book something a bit outside your budget to be able to have a gathering spot after you meet others in the ocmmunity.

  • Selina: Coworking and co-living spaces designed specifically for digital nomads. Basically the best of both worlds.

  • Booking.com: For the classical travelers I had to put something generic on here for ya’ll.

    • Saucy Hack: Maximize and combine credit card and travel points with this amazing resource I use for ALL my trips to never actually pay for flights. Also skyscanner for all flights to empower you to bop around your main hub on the cheap.

🌎 COUNTRIES ROLLING OUT THE DIGITAL NOMAD RED CARPET

Want a warm welcome (and sometimes even tax breaks)? Here are a few standouts that are set up for you to plug and play and still give you an experience of a lifetime.

📅 HOW TO ACTUALLY TIME-BLOCK LIKE A PRO (AND NOT MISS THE FUN STUFF)

Remote work means discipline, not deprivation. Here’s your productivity roadmap:

  • Schedule Deep Work: Block 2–3 hours daily of distraction-free productivity. Use Focusmate for accountability.

  • Time Zones Are Your Friend: Leverage time differences for deep work, uninterrupted by slacks, unimportant emails but be sure to have your away messages timed and ready to go.

  • Batch Similar Tasks: Don't scatter your tasks throughout the day. Emails, calls, creative tasks, group them. My go-to here is reading and data digest in the morning, responses to team, then handle my most important initiatives before lunch. Creative thinking in the afternoon complimented by a nice beach walk/surf at sunset for decompression.

Patty’s Pro Tip: Plan your day backward. Schedule fun FIRST, then build productive time around it. You moved to paradise for a reason.

🎯 LOOK LIKE YOU’RE IN THE OFFICE, EVEN IF YOU’RE ON THE BEACH

Nothing screams “slacker” like beach backgrounds and cocktails on Zoom calls. Here’s how you keep your professional cover:

  • Consistent Backgrounds: Virtual backgrounds (Zoom Virtual Backgrounds) or minimalist walls. No beach shots during meetings.

  • Availability: Clearly communicate your schedule and availability via Slack or Google Calendar. Again, leverage away messages and your email signature.

  • Over-Communicate Updates: Regular check-ins via Loom videos or daily Slack updates create visibility.

  • Prompt Responses: Stay timely, even if it's “I'll get back to you by tomorrow.”

YOUR DO-NOT-DO LIST - (DON’T SAY I DIDN’T WARN YOU)

  • Don’t ignore time zones: Set them in your calendar immediately. Have both your HQ time zone and your new location’s time zone in you google/outlook calendar.

  • Don’t assume Wi-Fi works everywhere: Check speeds beforehand. Bring backup hotspots or Starlink.

  • Don’t forget backups: Gear, internet, power, everything needs a Plan B.

  • Don’t show up unannounced: Register for co-working spaces/events beforehand.

  • Don’t overshare your location on socials: People will get jealous and start to question if you are actually working.

  • Don’t isolate yourself: You didn’t move around the globe to live alone in your Airbnb.

HOW TO DIVE INTO LOCAL CULTURE: (WITHOUT LOOKING LIKE A TOURIST)

Immersing yourself isn't complicated unless you let it be. If you are in a digital nomad hotspot, chances are there are many others doing the same and looking for community as well. Let go, be open, make friends.

  • Local Cafés & Bars: Become a regular. People remember consistent faces.

  • Leverage Social: Look up the location on instagram or its hashtag to find others who are tagging it and reach out to them.

  • Learn The Slang: Research common phrases in the culture and drop them from time to time. The locals will get a kick out of it and respect you more.

  • Follow Local Businesses: Find insider events by following local hot spot’s social accounts to find out what events they are promoting in the community and show up!

  • Tip Big & Give Often: Chances are you are going somewhere that is not as privileged as the US. A little goes a long way to the workers and gets you VIP status out of the gate.

  • Volunteer Locally: Giving back instantly connects you with community (Workaway).

Working remotely isn't just about escaping, it’s about enriching your life, career, and connections. Keep it structured, social, strategic, and fun. And when in doubt, remember why you left the cubicle in the first place.

****If you want to know more about Santa Teresa, shoot me a response and I will send you my complete insiders guide to the town build from 20 others who have traveled there as well.****

As always, stay saucy,
- Patrick Frank

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