Behind the Scenes: What Being a Program Leader Really Looks Like

By Dianna Velasquez | July 4th 2025

Being a Program Leader has transformed me in ways I never expected. It’s one of those jobs that stretches you, surprises you, and leaves you speechless, in the best possible ways. Sure, it’s not always easy. But it’s the kind of “hard” that builds you, challenges you, and gives you stories worth telling.

Let me take you behind the scenes…

1. You Become More Responsible Than in Your “Normal” Life

You carry your essentials everywhere: the medkit, the binder with medical forms and budget, your phone always charged, you name it. If you forget any of it, you feel… well, naked. Like a soldier without a weapon.

And just when you think, “I won’t need this today,” someone asks for aloe vera… on a rainy mountaintop… because somehow they got a sunburn.

 You also learn very quickly never to forget your own stuff. One forgotten poncho and a cold later… you won’t make that mistake again. I now travel with my own personal mini-medkit; gum, ginger chews, and emergency chocolate included (yes, those are my essentials 😂).

2. Superpowers You Didn’t Know You Had

I swear I used to complain about carrying groceries up three floors, but as a Program Leader? I can carry 25 things at once, walk miles, and still lead a group with energy. Being “on” for others brings out a whole new level of strength.

You also discover skills you didn’t know you had:

● Active listening that helps you truly connect with a student’s emotions, even when they don’t know why they’re upset.

● Finding the right words to help someone feel seen, heard, and safe.

● Collaborating with someone completely different from you — and doing it with kindness, adaptability, and honest communication.

● Packing and unpacking in under 15 minutes! Yup. You become a master at folding clothes impossibly small and re-packing multiple times a week; pro level unlocked.

3. Learning from the Learners

The students teach you so much. I’ve learned new card games, handmade jewelry, and sports I never thought I’d try, all from the teens I guide. Watching them light up when they share their skills and passions is a gift in itself. 

4. Early Mornings… and Unforgettable Moments

Yes, there are 5a.m. wake-ups to prep for ziplining or boat excursions. And yes, sometimes you’re running purely on willpower (and coffee). But then you find yourself flying over a lush forest on a zip line… or standing on a remote island surrounded by turquoise water. And in that moment, you pause and think:

“I’m getting paid for this.”

And just like that, you fall in love with your job all over again. 

5. People Who Inspire You

I’ve met incredible people along the way, teachers and chaperones doing amazing things, like running accounting programs for Indigenous communities in Alaska. And then there are the students, some shy at first, who end up surprising us all with the best dance moves ever!

 You start to realize: the world is so much bigger than we think and yet, we’re so deeply connected in our beautiful differences. Learning to embrace those differences is what makes us truly human.

6. The Reward That Makes It All Worth It

There are days when your group doesn’t quite engage with your most passionate workshop whether it’s about sea turtles or the challenges faced by rural communities. Days when you wonder if your energy is making a difference. But then… you spot that rare bird you’ve always dreamed of seeing. You hear a student laugh like they’ve never laughed before. You get a heartfelt note from the one kid you thought wasn’t paying attention.

And you realize: Half the things on your bucket list have come true because of this job.

✅ Traveling

✅ Meeting people from all over the world

✅ Seeing wildlife up close

✅ Making a difference in someone’s life

✅ Supporting real change in communities and ecosystems

All of this has been possible because I said yes to becoming a Program Leader. This job allows you to grow while helping others grow. It challenges you, fulfills you, and reminds you of the beauty of being present, open, and human. It’s a win-win: I get to chase my dreams and become a guide, a spark, for others who are discovering their path, their strength, and their voice.

If you’ve ever thought of becoming a Program Leader…

Do it.

It might just change your life, like it changed mine in ways I couldn’t possibly fit into one blog post.

Dianna Velasquez

Dianna is proudly from Santo Domingo, Dominican Republic, and brings a vibrant energy to every program she leads. A passionate traveler and educator, Dianna has been part of the Offbeat Travel team since 2023, guiding groups across the Dominican Republic, Puerto Rico, and Costa Rica. Her love for culture and connection is matched by her enthusiasm for fitness — when she’s not leading trips, you’ll likely find her boxing or working out.

In addition to her work with Offbeat, Dianna runs a language school and teaches English, sharing her love of language and learning with students from around the world. Whether she’s introducing travelers to the rhythms of Caribbean life or helping them master a new phrase, Dianna is deeply committed to creating experiences that are both educational and empowering.

Next
Next

Staff Training Season: The Heartbeat of Offbeat