A Workation with Purpose: Discovering Our Shared Journey

When we first set out for our workation, the idea of blending work and relaxation sounded like a welcome break. But as soon as we arrived, it became clear that this trip was going to be about something much deeper.

We weren’t just here to unwind or brainstorm; we were here to reflect on our paths, recognize the diversity of our experiences, and think about how we could contribute more to the world beyond our work.

The Seed of an Idea

The idea for this introspective activity came from our founder, Samyak. He didn’t just pluck it out of thin air—it was something that had shaped him years ago, back when he was a fresh-faced student at IIT Delhi. In his first year, he participated in an exercise that made him pause and think about where he’d come from and where he was headed.

The activity wasn’t just an icebreaker; it was an eye-opener. It stayed with him throughout his journey from student to entrepreneur, and when it came time to plan our workation, he knew this was the perfect opportunity to share it with us.

The Activity: Stepping into Our Stories

We gathered in a wide-open field on the first day of the workation. Samyak asked us to close our eyes and listen as he read a series of statements. If a statement resonated with us, we were to take a step forward.

Simple enough, right?

But what started as a seemingly straightforward exercise quickly turned into something much more powerful.

Round 1: Recognizing Our Roots

The first round focused on where we came from—the opportunities and privileges that shaped our beginnings. Statements like “I grew up in a household where both my parents were graduates” and “I never had to worry about having basic necessities like food and clothing” floated through the air, each one a gentle prompt to reflect on our past. As we took steps forward or stayed in place, we were silently acknowledging the foundation that had been laid for us, without judgment or comparison.

When we opened our eyes, the sight was striking. We were all part of the same team, yet our starting points were so varied. Some of us had moved far ahead, while others stayed closer to where we began. But instead of feeling divided, there was a sense of unity—a shared understanding that no matter where we started, we were all walking this path together.

Round 2: Celebrating Our Achievements

In the second round, the focus shifted to what we had built with our own hands—our personal milestones and growth. Samyak read statements like “I have mentored or helped someone else succeed” and “I have taken a risk in my career that led to significant personal growth.” These weren’t just about professional achievements; they were about the lives we’ve touched and the chances we’ve taken.

As we opened our eyes after this round, there was a new energy in the air. Some of us had pushed ourselves beyond the opportunities we were given, while others realized there was still much more to achieve. It was a moment of collective recognition—not just of how far we’ve come, but of how much further we could go, especially when we looked beyond our own goals and started thinking about how we could give back.

The Ripple Effect: More Than Just a Workation

What made this activity truly special wasn’t just the personal insights we gained—it was the conversations that followed. As we sat together, we talked about the areas we wanted to grow in, not just for ourselves, but for the impact we could have on others. We set goals, not just for the next few months, but for the kind of people we wanted to become—both in our work and in our communities.

Activity Prompts for Your Team

If you’re planning to try this exercise with your team, here’s the list of prompts we used!

Round 1: Background

I grew up in a household where both my parents were graduates.
I never had to worry about having basic necessities like food and clothing.
My family owns the home I grew up in.
I attended private school for most of my education.
I had my own room while growing up.
My family owned a car when I was a child.
I had access to a computer and the internet at home during my school years.
I used to have regular medical check-ups growing up.
My family used to celebrate birthdays and special occasions with elaborate gatherings.
I come from a city or town where I had access to various extracurricular activities like sports, arts, or music.
I come from a family where I used to eat food in a restaurant more than 2 times a month.
In my childhood, I used to go on at least one family trip a year.
I had access to a wide variety of books or knowledge content via the Internet at home.
I was able to take music, dance, or art classes as a child.

Round 2: Personal Achievements

I have mentored or helped someone else succeed in their career.
I have built meaningful relationships outside of work.
I regularly practice mindfulness, meditation, or journaling.
I have volunteered my time to teach or coach others.
I have received recognition or an award for my work or contributions.
I have taken on a leadership role in a team or organization.
I regularly contribute to a cause or charity that I believe in.
I have traveled alone to a place outside my comfort zone.
I have taken a risk (of more than one year) in my career that led to significant personal growth.
I have completed a challenging hike or trek.
I have successfully started and sustained a side business or project.
I have written a blog or published an article.
I have completed a marathon, triathlon, or any other sport achievement.
I have given a session/public speaking to at least 100 people.
I have taken a break from any technology/platforms for more than a week.
I regularly work without money for a cause I'm passionate about, or I have organized or led a significant event or project at work or in my community.
I know how to play a musical instrument.

These prompts are designed to help your team reflect on their backgrounds and personal achievements, encouraging them to see the unique paths they’ve taken and the potential they have to contribute more to their communities.

Why Your Team Should Try This

This activity wasn’t just a nice break from our usual routine; it was a transformative experience. It reminded us that while we’re all working toward personal and professional success, we’re also in a unique position to contribute more to the world around us. It’s easy to get caught up in the daily grind, but taking a step back to reflect on our backgrounds and achievements helps us see the bigger picture.

If you’re thinking about organizing a workation or a team retreat, we can’t recommend this exercise enough. It’s not just about introspection—it’s about building a more connected, self-aware team that’s motivated to make a difference. The experience stays with you, sparking a sense of purpose that goes far beyond the office walls.

So, the next time your team is looking for a way to bond and grow, consider guiding them through an activity like this. It’s a simple yet powerful way to encourage reflection, foster unity, and inspire everyone to aim higher—not just for their careers, but for the impact they can have on the world.