Why I Chose Teaching as a New Career: Nicholas Maiese

Key advice in his youth would end up impacting Nicholas Maiese for years to come.

“My mother always told me that my 20s were for figuring things out, so I was trying to find my path,” says Maiese, an English teacher at St. Michael’s College School (SMCS). “I never really knew what I wanted to be. All was possible, but nothing certain. I hadn’t yet found my ‘calling’.”

One thing was certain however.

“I knew that I loved working with words,” he says.

Maiese graduated from Queen’s University and worked in advertising for a decade — for two agencies, working with various clients and helping to launch an award-winning startup. 

“In some ways, I think I always knew that I was going to leave advertising,” Maiese continues. “I knew this despite the fact the people I worked with were amazing, intelligent people many of whom are still friends to this day. I knew this despite the fact the job was fun, energizing, and lucrative. The fact is my parents raised me to believe a job should be more than a job. That we need to do more than earn a paycheck. For them, we must work to do something positive; to make the world just a little bit better in our own way. I came to believe convincing people to buy more beer, burgers, and boots wasn’t enough. I wanted more. So, I ran away in search of more.” 

That pursuit led him to obtain a master’s degree in journalism, followed by a stint as a print reporter covering education, sports, and politics in the U.S. It also rekindled thoughts of positive experiences he had in his previous role.

“In my later years in advertising, I started teaching some guest classes at various schools on advertising and the media,” he says. “First, they became escapes from the 24/7 world of advertising. Then, I fell in love. My time with those students became my favourite part of any week. I loved ‘arming’ them against the very industry I was working in.”

Two careers and nine years later, Maiese decided to dive into yet another new industry.

“Teaching and education became my calling. I’ve come to believe the bedrock of any functioning society is its education system because an educated electorate is vital.”

His biggest challenge in transitioning to this new career direction?

“As a teacher, it is harder to point to tangible accomplishments,” he says. “In advertising, there were the campaigns. In journalism, there were the articles. In teaching, we have our students, but so much goes into shaping a young person it is hard sometimes to find your contribution to the final shape.”

Through each of his career stops, Maiese has amassed additional knowledge that he continues to apply regularly in some way now in his 17th year of teaching and second year at SMCS.

Some of the transferable skills he had accumulated from each industry include: 

1. Advertising 

“How to work with clients who, at times, could be wonderful and positive partners but, at other times, could be emotional, unreasonable, demanding, and insulting.

Moderating focus groups is very similar to teaching. You have to own the room and guide the discussion.

In strategic planning, you are given an objective and you must map a path forward. This is not unlike planning a course in teaching.”

2. Journalism

“How to question ideas and logic. Working in education, this is something I do daily in the class and beyond.

How to interview, which is not unlike leading a class discussion. Probing responses with follow-up questions that push and prod.

Convince with the written word, and how to embrace the three phases of writing (thinking, writing, revising); these traits are now core components of my English classes.”

Some of his challenges as an educator? “Turning off. Work-life balance has always been hard for me,” he says. “I don’t know how teachers leave their work at school. As an English teacher there is so much marking that I feel like I am always marking. Second, when you believe your work is important, it is hard to forget about it.” 

Still, the married father of three children, has no regrets about his multiple-career trajectory. “I think that I get five years younger every time I switch!”   

Nicholas Maiese’s Learnings, Career Tips, and Strategies:

1. “I recognize having choice in what we do is a very privileged position. Given that, I don’t know how people who have a choice stay in jobs that are just jobs. If you are going to devote 40-80 hours of your life each week to something, then that something should matter.”
2. “If your job doesn’t bring you happiness, then you owe it to yourself to change. I don’t think I could be happy if my job didn’t fulfill me in some way.”
3. “If you’re looking to change, then be brave. Do your research. Don’t go in blind or be reckless. Do your homework and then… jump.”
4. “Never use timing as an excuse to not make a change. There are always reasons to not do something. Ignore them and do it anyway. Every time I have changed careers, it has rejuvenated and inspired me.”

This story is part of an ongoing series on the career journeys of St. Michael’s College School staff.

Grade 11 Career Day at St. Michael’s College School takes place on Tuesday, March 2, 2021.