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What happens when a six-month backpacking trip changes the entire trajectory of your life?

In Episode 9 of Roam Alone, I sit down with Donovan Pacholl, co-founder of Embark Exploration Co., the outfitter behind my very first summit: Mount Kilimanjaro.

Donovan shares how a backpacking journey through Europe and Africa evolved into a global trekking company that now leads adventurers up some of the world’s most iconic mountains. We revisit my experience climbing Kili with Embark, talk about what makes a trek beginner-friendly for first-time solo travelers, and unpack one of the biggest fears holding people back: safety.

If you’ve ever wondered:

• Is the world actually safe for solo travelers?
• Are people inherently good?
• What’s the best first “big” adventure if you’re going alone?

Donovan answers with the grounded confidence of someone who’s spent decades exploring remote corners of the globe.

Time Stamps:
00:00 – The backpacking trip that became a lifelong calling
16:30 – The best Embark trip for your first solo adventure
22:41 – Safety tips and why the world isn’t as scary as it seems

This episode is for anyone craving adventure — but waiting for reassurance.

Check out all of the treks YOU can join with Embark Exploration!!

Roam Alone is hosted by Theresa Stephens.

Instagram: @theresaannstephens

Facebook: /theresastephens

Facebook: /RoamAlone

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What if solo travel started with a concert ticket?

In Episode 8 of Roam Alone, I’m joined by Molly — the ultimate concert queen — who travels solo to cities across the country (and now internationally) to see her favorite artists live. I first met her at a Jon Batiste show, proof that live music and solo travel are powerful tools for connection.

Molly shares how traveling alone came about organically and how planning trips around concerts became her gateway into confident, independent travel. For her, attending concerts solo isn’t lonely — it’s one of the easiest ways to meet new people, build community, and create meaningful travel experiences.

If you’ve ever hesitated to travel solo or attend an event alone, this episode will inspire you to buy the ticket — and trust yourself to go.

Time Stamps
00:00 Meeting Molly at a Jon Batiste concert
04:43 How solo travel came about organically
07:02 Developing new friendships while attending concerts solo
09:20 First international solo trip to celebrate turning 50
13:00 Molly’s best solo travel safety tips

Roam Alone is hosted by Theresa Stephens.

Instagram: @theresaannstephens

Facebook: /theresastephens

Facebook: /RoamAlone

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What happens when a shared dream outlives the person you planned it with?

In Episode 7 of Roam Alone, I’m joined by Anne—a traveler who embodies wanderlust in its truest form. After the death of a close friend, Anne made the brave decision to take the trip they had always dreamed of together: the Amalfi Coast. What began as a tribute became the start of a lifelong solo travel journey.

From a chance encounter with a stranger in Paris to practical safety strategies that help her navigate the world solo, Anne reminds us that travel can hold both loss and beauty at the same time.

Time Stamps:

• 00:00 Introduction to Anne and her intrepid wanderlust
• 02:10 Taking her first solo trip to the Amalfi Coast as a tribute to a friend
• 12:48 A powerful encounter with a stranger at a Paris restaurant
• 26:21 Anne’s solo travel safety tips, including the famous “don’t mess with me” face

Annie's Nuggets

Rick Steves' tours

Roam Alone is hosted by Theresa Stephens.

Instagram: @theresaannstephens

Facebook: /theresastephens

Facebook: /RoamAlone