At the age of 18, Len obtained his Private Pilot's Licence in Hamilton, Ontario. Two years later, he went to British Columbia and took the two year degree in Aviation at Trinity Western University. Over the next few years, he obtained his Commercial Pilot's Licence, Night Rating, Multi-Engine and Float Ratings.

In 1985, Len was accepted to Centennial College in Toronto in the Aircraft Maintenance Technician program, and while at school, took a part-time job at Pearson International Airport with Air Canada as an aircraft cleaner. Air Canada had obtained a contract to service another airline's aircraft. That airline was Air India. On Saturday, June 22, 1985, Len and the crew finished cleaning Air India 182 as part of the normal shift. On it's jouney back to Bombay, the flight exploded over Atlantic Ocean after terroists had planted a bomb in the luggage compartment before it had arrived in Toronto. The Air India tragedy investigation and prosecution took almost 20 years and was the most expensive trial in Canadian history. Following this tragic incident, Len continued working as a Baggage handler for Air Canada until December of that year.

After graduating from Centennial College, Len began as an Aircraft Mechanic at the Welland Airport working on various single and multi-engine aircraft as well as a part-time pilot, which included towing banners on weekends and occasional charter flights. In 1988, Len obtained a job with City Express Airlines at the Toronto Island Airport (now Billy Bishop), working as a mechanic on de Havilland Dash 7 and Dash 8 aircraft.

During these years, Len volunteered at his local church, giving leadership to the youth group. Since he found a great amount of value and satisfaction in leading youth, he jumped at a job offer as Minister of Youth and Children at a church in Hamilton and left the aircraft industry for good.

The year was 1990. Len began a new job in January, married Rebecca in June and in September, began a bachelors degree part time at Heritage College in London, Ontario. It was in an English class that Len's interest in writing came to life. After graduation in 1994, Len continued at the church in Hamilton. After working there for ten years, he took a new position in Parksville, BC as the Minister of Children at a church of about 700 that was situated on Vancouver Island. During his work in Hamilton and Parksville, Len wrote and directed several youth and children's theatre productions. Len has had a variety of his play scripts published and produced in play writing contests in Canada, US (including off-off-Broadway) & Europe. His collection, Reunited Shorts, was published by Dramatic Publishing in 2020.

After four years in BC, Len and his family moved to Ontario. It was while working on staff at a church in London that he created Fridge Door Live Theatre Company for children and youth. In 2006, it began with 25 children over two weeks. The camp now serves over a hundred youth and children with seven weeks of Summer camps.

In January 2010, Len introduced a Monday Night Theatre program in Komoka during the school year. By the fall, a second program was started in Summerside on Tuesday Nights. The program now runs on Saturday Mornings in London and Sunday Afternoons in St. Thoams. In June 2011, Len graduated with a post-degree Certificate in Not-For-Profit Management from the University of Western Ontario. In September 2011, Fridge Door Live officially became a Federally Incorporated Not-for-Profit Organization.

As many people have been influential in his life, Len Cuthbert hopes that the team of Fridge Door Live can also be a positive influence in the lives of youth and children, through the medium of a performing arts learning experience.