Redefining Retirement: Making Life Better, Meet Randall Postiglione

Redefining Retirement

Randall Postiglione is driven by an old Albert Einstein quote that was more recently adopted by Will Smith: “If you’re not making someone’s life better, then you’re just wasting your time.” He is a former chef, CPS teacher, college math teacher, taught math for the trades at US Steel, and is now a self-described ‘math teacher at-large’ who works ‘on assignment.’

Before his teaching career began, Randall was a chef for Marriott Corporation and owned a restaurant. He entered the Teacher for Chicago Program in 1999 and began teaching shortly after.  He was asked to teach mathematics when he was really more prepared to teach graphic arts. But alas, being a glass is half-full kind of guy; he adapted and brought his innate creativity and positivity to the classrooms in an effort to make a difference in a student’s life.

Fast-forward to 2020, Randall can still be found in a classroom working on short-term assignments. He finds these opportunities through his vast network of teaching colleagues, on websites, and even through former students. He teaches because he “loves to share knowledge, enjoys the challenge of getting kids to learn, and is fulfilled when he sees the confidence on a student’s face when they master a skill.”

Memorable teachers create lessons that are engaging and effective for their students. Randall strives to do this in every classroom that he works in. From placing white boards around a room to get students out of their seats to teaching through games, he feels he is a “contributor to the betterment of the world.” Even during the COVID-19 pandemic, Randall connects with his students by creating entertaining YouTube videos with accompanying original worksheets. His goal is to replicate good classroom instruction remotely.

In his spare time, Randall is writing a digital workbook for junior high and high school students. It is composed of worksheets that he compiled over the years. As a trained chef and former restaurant owner, Randall cooks all of his family’s meals. He exercises regularly and refers to himself as an “indomitable film viewer” and enjoys weaving this passion into his math lessons. Randall describes his career and his life as a “great journey, marked by reinvention.”


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