I am fortunate/lucky/brave/bold/wild/crazy enough to have been working remotely and traveling for over three months now.  That in and of itself is a mouthful.  I make things happen to make this work for me every day.  Every day I’m working.

I am blessed with countless friends and family following me along for the ride, and even visiting (Dad’s coming next month!!!).  I’m blogging and sharing on Facebook and posting pictures on Instagram and writing emails and sending texts and enjoying FaceTime phone calls.  As I hit Stop #4 and passed my 100th day of traveling with Remote Year, I realized I still have so much more to say.

I notice sometimes that the conversation with a loved one back home can grind to a halt.  I haven’t seen you face-to-face in months, and our catch-ups may not be very lengthy or deep.  Maybe I’ll tell you about my most recent weekend but we haven’t chatted in six weeks.  Maybe you tell me about your day, but that’s it.  How do you connect on a deeper level?  How do I share the craziness of travel without completely dominating the conversation?  How do I explain what an AMAZING time I’m having without making your life seem dull or ordinary (because I never think that!  Travelers crave routine and home comforts too!).  How do I get you to open up and share with me?

I struggled myself when talking to friends who took side trips to other countries.  How was Stockholm?  It was great!  …… Cool!  …….. Now what do I say?

I started to form a list of questions to help myself and hopefully help all of you who know someone who travels.  It could be a weeklong vacation, or a semester abroad in college, or a permanent life of travel: everyone wants to share.  Here’s what to ask.

• What was the best food you ate in THIS CITY?
• What was your favorite moment this week?
• Tell me about where you stayed.  In a hotel?  Apartment?  With a friend?  Did you like it?
• Does THIS CITY have a signature drink or food item?  Tell me about it!
• Tell me one thing that you did and don’t regret.
• Tell me about the local culture in THIS COUNTRY.  How is it different from back home?
• What’s the weather like?  Did you pack appropriately?
• Did you feel like a local or like a tourist while traveling?  Why?
• Could you ever live there for a long period of time?  Why or why not?
• Tell me about a time you found peace and quiet.  Where was that?
• What moment made you feel the most alive?
• What moment made you wish you were back home?
• Have you connected with any locals or expats?  Who?
• Do you recommend me putting that on my bucket list?
• Do you have pictures you could send me?