There are a few reasons why he would have left for Nova Scotia. The first was that his opportunities in River John were very limited. As the youngest son, he would not have inherited the farm when his father died, it would go to his brother Henry. This was not always an issue as there was a second home built on the property for a second family. However, Jack was the fourth child and the second home went to his older brother Alexander Jr. ("Allie"). It may have been possible for him to stay, but a farm can only support so many people and so it made the most sense for him to build a life and a family elsewhere.

In 1926 when Jack was 24, he moved to Worchester. There are a few reasons why he may have chosen Worchester, but the biggest was that he had a cousin already living in the town. It is very common for people to immigrate to a place where they already know someone, as they feel like they won't be alone. This would have been an extra incentive for Jack because his cousin had already found steady work in Worchester, so he would have felt like it was a good place to go. He would also probably have heard that it was a hub of manufacturing and that there were plenty of unskilled jobs.