The Art of Saying Goodbye: How Contract Work Shapes The Self and Relationships

I’m incredibly good at goodbyes. Sometimes I wonder what my friends, family, or new people in my life think about this. I can miss birthdays, skip Christmas for three years straight, and say goodbye to close connections with hardly a tear. But I wasn’t always like this. There’s an art to saying goodbye, and when you’re a contract worker, you get ample time and opportunity to master it. In fact, it’s practically a skillset.

Finding “Good” in Goodbyes

My career has mostly revolved around contracts. My first contract was on the seven seas, split between two very different locations—warm Caribbean waters and a much colder coast. On ships, every crew member arrives and leaves on different days. Teams don’t come or go together, so each return to our home port brings a rotation of crew members arriving and departing. In the beginning, saying goodbye felt nearly traumatic. We’d gather at the crew bar the night before someone left, toasting with friends I’d maybe only known for a month. If they were especially close friends, I’d take the early shift the next day just to say goodbye one last time as they walked off the gangway.

When my own time came to leave the ship, my friends gave me an extravagant send-off—cards, gifts, and a celebration at the crew bar. But soon enough, I was off to Alaska, missing my Caribbean “family” and left to start all over again.

Adapting to Change and Finding Anchors

Each new contract brings fresh surroundings and people, which forces you to adapt quickly. In Alaska, I faced the new challenge of being more alone. I took long walks along the chilly seashore and dined alone at local spots, getting to know myself in a way I hadn’t before. Sometimes, anchoring oneself in this transient lifestyle means finding mentors or grounding activities.

During a week-long assignment as tour assistant for the Rome New Year festivities, a seasoned manager, Ella, shared stories of her global travels. I asked so many questions and found such beautiful gems while talking to her. She also mentioned that for her, working during Christmas, New Years and any special holiday or occasion was “just another Monday”. Ella became an anchor—someone I aspired to emulate, whose vibrant yet easy-going energy grounded me.

In other cases, anchors were simple routines: journaling, taking quiet walks, or finding a guitar to play. These small practices bring consistency and help root me in each place.

Navigating the Connection and Release Cycle

Contract work in the entertainment industry is intense, with each contract like a mini-life of its own. Work, partying, friendships, and often romance all move at high speed. If you’re not careful, this intensity can lead to physical and emotional burnout. For months, you live and work in close quarters with the same people, adopting unspoken routines and flows.

Not everyone develops the awareness required for meaningful short-term connections. Some people lack the tact to handle relationships that form and end quickly. The key is maintaining a sense of self—knowing your boundaries and sticking to them. This lets you enjoy experiences without overcommitting emotionally, which keeps burnout at bay.

Approaching each new relationship with openness, instead of expecting others to fit your mold, makes it easier to connect meaningfully while still letting go when the time comes.

Rediscovering Solitude

Being alone becomes an act of self-care. In new places, connecting and making friends isn’t always easy, and sometimes the local culture feels foreign. These moments can feel isolating, making us cling to the few friendships we do form. Learning to embrace solitude has been a transformative experience.

On the Alaskan leg of my first contract, I found myself ziplining alone in the Tongass rainforest, joining a tour without any friends to back me up. It was the best decision I could have made. I had freedom to do what I wanted and the experience of a lifetime. This newfound embrace of solo adventures opened me up to more “yes” moments, making each contract less about clinging to others and more about personal growth.

Contract Work
Megan atop a glacier, dogsledding in Juneau, Alaska, 2017

Conclusion

Contract work in the entertainment industry doesn’t just teach you to say goodbye; it forces you to master it. With each new team, location, and connection, you learn to let go gracefully, carrying only what nurtures your growth. Each contract becomes a chapter in the book of your life, shaped by moments of closeness and the inevitable partings that follow. And perhaps that’s the real beauty of this work: knowing that every goodbye is a step forward, another story added to your journey.

Contract Work
Megan on the contract of a lifetime in Antarctica, 2023

 

All photos provided by Megan Gill
Megan Gill
Musician, Producer -TRINIDAD AND TOBAGO
Megan is a Creative Industries Professional from the Caribbean twin islands of Trinidad and Tobago. She is a versatile musician, producer and singer/songwriter with a rich audio/visual and technical theatre background. With over 16 years in live entertainment, Megan blends her talents with advocacy to empower the new generation of young creative professionals as well as underrepresented groups. A global citizen, Megan draws inspiration from her diverse networks and extensive travels. She holds a Master in Arts and Culture Management (hons), BFA in Performing Arts and Certification in Digital Media Studies- Music Technology. She is passionate about the Arts, coaching creatives, performing live and connecting with people of all cultures, living her life to the rhythm of ocean waves.

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Megan Gill

Megan is a Creative Industries Professional from the Caribbean twin islands of Trinidad and Tobago. She is a versatile musician, producer and singer/songwriter with a rich audio/visual and technical theatre background. With over 16 years in live entertainment, Megan blends her talents with advocacy to empower the new generation of young creative professionals as well as underrepresented groups. A global citizen, Megan draws inspiration from her diverse networks and extensive travels. She holds a Master in Arts and Culture Management (hons), BFA in Performing Arts and Certification in Digital Media Studies- Music Technology. She is passionate about the Arts, coaching creatives, performing live and connecting with people of all cultures, living her life to the rhythm of ocean waves.