Educator Gary Stewart travels the world in one year of soul-searching

Educator Gary Stewart’s travel to 23 countries over the past year has taught him to be grateful for life – “the presence of mind, self and body” and for the sacrifices his ancestors made.

A vice principal with the Toronto District School Board (TDSB), he has been working in the school system for 25 years and recently took a year off to fulfil his wanderlust.

Taking advantage of the board’s Four Over Five Plan which allows educators to teach for four years, while foregoing 20 per cent of their annual salary and being paid 80 per cent, he planned his world tour strategically. During the fifth year (the year of leave) teachers are paid 80 per cent (20 per cent accumulated during each of the four years).

“Really, the thought came to my mind even 10 years ago. It took a long time to plan, a lot of research, and coordination with friends and family to make this happen,” said Stewart who is now at Crestview Public School in North York.

To ensure that he had the barest of expenses in order to afford his trip, he paid off his mortgage and car loan. Stewart also rented his home while he was away to cover costs, and tried not to spend too much while on trip.

After graduating York University in 1999, the Clarendon-born educator taught at Wexford Public School, Jack Miner Senior Public School and Highcastle Public School – all in Scarborough.

He subsequently shifted to the role of guidance counsellor and then moved to Etobicoke where he taught grade 8 class during the pandemic. In 2022, he was promoted to the role of vice principal and taught at Lawrence Heights Middle School.

The journey to that promotion was challenging and just as he was about to give up, after trying seven times, a superintendent encouraged him to try one more time.

Citing details of his journey, he shared that navigating the education system as a black person has been difficult. In fact, after getting his principal qualification in 2006, he applied for the role of vice principal in 2011, but did not get that job until eleven years later in 2022.

SPIRITUAL AND MOVING

Stewart, 51, started his year-long travel in August 2023 in eastern Canada where he visited New Brunswick, Prince Edward Island and Nova Scotia, then the West African countries of Ghana, Sierra Leone, and Togo. He also travelled to England, Wales, Scotland, Netherlands, Germany, Poland, Turkey, Singapore, Malaysia, Thailand, Cambodia, Vietnam, Japan, Australia, Sri Lanka, Qatar, United Arab Emirates, United States of America, Trinidad and Tobago, and Jamaica.

“One of the reasons I took this year off was to regroup, find my roots, ground myself in my culture and my history. Many Jamaicans, like me, don’t know much about our African connection. In my family, we never talk about it,” said Stewart who only knew that his grandmother was a Maroon. He said many Jamaicans, if they traced back their African heritage, are from Ghana.

“Honestly, going to Ghana I felt the presence of my ancestors, it was like a homecoming. It was something I needed to do to prepare for life as I progress here in Canada.”

While in Ghana, he visited Cape Coast Castle which is the largest of the buildings that contain the legacy of the trans-Atlantic slave trade and is a UNESCO World Heritage Site.

“I had a tour there and it was very spiritual and moving,” he said. “I touched the wall in gratitude and a presence came through me that is indescribable. I knew that I was feeling my ancestors.”

FORM OF HOMECOMING

His visit to Scotland was to explore his father’s family history there, the Stewarts. He said his father was born in Jamaica, but raised in England as part of the Windrush Generation and would visit Jamaica to see relatives who remained in Clarendon. This is how his parents met, and Gary became their offspring.

It wasn’t until he was in his early 20s that Stewart learned about his father, and it took a long time for him to connect with that side of the family. Unfortunately, his father died when he was 12 years old, but Gary’s siblings and other relatives live in the UK.

He said it took 25 years for them to embrace him after he initially met them in 1999. During the COVID-19 pandemic they wanted to see him again, so he visited and met everyone in 2023.

“It was spiritual, it was another form of homecoming for me, and I felt I was reunited with another part of me that was buried for a very long time.”

Stewart came to Canada from Jamaica in November 1983 at 10 years old. His mother had left him with her mother in Beckford Kraal, Clarendon when he was one year old. He described finally meeting her as a bitter-sweet experience.

With only a few days left before the start of the new school year, the educator said his travels will help him to use his lens of equity, inclusion, justice, and care in interactions with students, parents, and staff.