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Working Remotely from Anywhere in the World

For the past six years, travel planner Cassandra Santoro has split her time between New York and Italy. She spends summers on the Amalfi coast, travels throughout Italy in the fall, and then returns to the U.S. for the spring.

Sounds pretty great, right? 

Cassandra isn’t on vacation 24/7/365, though. She’s a successful entrepreneur and CEO of Travel Italian Style. She’s become an expert at working remotely from all over the world.

Now that the pandemic has opened up remote work opportunities for so many people, this lifestyle is more and more feasible. But to make this work, there are more than a few logistical challenges to address. 

Cassandra joined me on my live-streaming show Inside Scoop to share how she does it:

Bring your own WiFi

You might think there will be internet access wherever you go — but Cassandra says that’s actually not the case. She says bringing your own WiFi can help the transition to go smoothly, ensuring you can always log on when you need to. Cassandra recommends buying a Skyroam hotspot.

If the home rental where you’re staying advertises WiFi, Cassandra says you should always check with the host to make sure the internet connection is strong and reliable. Better safe than sorry!

I have lots of other remote office tips in my LinkedIn Learning course “Organizing Your Remote Office for Maximum Productivity” as well. 

Making the space work

Even if you’re in a beautiful part of the world, huddling up in a dark room to work will kill your mojo.

When you’re working remotely from somewhere new, Cassandra recommends buying fresh flowers or even a basil plant to make the space feel homey. She also prioritizes light-filled rentals. 

Consider time zones

When you’re figuring out the logistics of working away from home, Cassandra says it’s important to consider time zones. Will you have to get up in the middle of the night for client meetings? It’s important to ensure that you can do your job without having crazy hours.

When in Rome…

When you’re working from someplace new, Cassandra suggests really immersing yourself in the local culture. For her, that means an aperitivo!

If you want to hear the rest of Cassandra’s suggestions, you can watch our full conversation here!

Checklist to Take Your Remote Office on the Go

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BONUS FREEBIE: Want even more ways to stay organized, productive and less stressed? Click here to get access to my List-Making Starter Kit. It will boost your efficiency and get you back to doing more of the things you love.

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If you’ve been working remotely because of the pandemic, by now you’ve probably got some of the basics down — where in your home you work, what your hours are, and what you wear. (Although I have my opinions about the Zoom shirt…)

Read more

Four Steps to Taking a Real Vacation

BONUS FREEBIE: Want even more ways to stay organized, productive and less stressed? Click here to get access to my List-Making Starter Kit. It will boost your efficiency and get you back to doing more of the things you love.

I was recently browsing LinkedIn when I came across this BBC story, that I first thought had to be a joke. Apparently employees in the UK are taking vacation time to catch up on work! 

Isn’t that insane? 

I’m not really sure what’s happening on the other side of the pond. Are you guys okay?

All kidding aside – burnout is a real problem faced in the workplace.

In fact, the World Health Organization now recognizes it as a real condition. I write all about ways to combat this in my new book, Listful Living: A List-Making Journey to a Less Stressed You

And although I’m all for efficiency and hard work  – I would NEVER recommend taking vacation days to do more work! 

Your vacation time should be used as a way to break out of your workplace mindset and come back feeling refreshed. 

That’s the whole point!  Read more

Plan Mini Destination Trips to Recharge and Rejuvenate

I recently wrote a post on the importance of making time for myself now that I work from home. When your home is also your office it’s not easy to make as clear boundaries with your time. In the comments section of that post a friend and regular reader, Sandra Keros, wrote  that she likes to plan mini destinations to get out of her head and out of her apartment. What a great idea!

Since I loved it so much I got in touch with Sandra to talk more about her mini destinations and what she does. This is what she had to say:

“As an entrepreneur, it’s easy to get caught up in thinking about and working on your business around the clock. From time to time, a little recreation is necessary to give yourself a break, have some fun, and “recreate” your thinking on projects you’re working on. Read more

Wouldn’t it be nice to make some money off delayed flights?

I belong to a mastermind group for entrepreneurs and business owners and they meet twice a year in a great locations. This time it was in Tucson, Arizona.

Of course the day I was leaving NYC there was a snowstorm and I was connecting through Atlanta. Because of a tiny bit of ice…the whole city of Atlanta closed down 🙂

I was stuck in O’Hare airport for 5 hours. It wasn’t fun but since I’ve started meditating I found that I was a little less upset than I’d normally be.  Plus I went directly to the Delta Sky Lounge. I have a Delta Amex card and you can get in for $30. Well worth it!  I recommend getting a day pass if you ever get stuck! It’s a much more civilized way of hanging around an airport. Read more