Tom Diascro ’85

The Fourth Thursday in April and the First Tuesday in November. Perhaps these dates aren’t as recognizable as the Fourth of July or Christmas Day, but if you’re Tom Diascro ’85 those dates are circled on your calendar. Even though he’s lived in Connecticut for almost 20 years now, you may be surprised to learn that on Thursday, April 28, the start of this year’s NFL Draft, Tom wasn’t keeping an eye on the New England Patriots, but rather the Washington Commanders. And even though he’s currently working at an independent day school (and not running for office), Tom NEVER misses watching Election Day results… sometimes into the early morning hours.

How does one live in Connecticut as a Washington, D.C. football fan and how does one become an Election Day enthusiast?  The answer is both simple and complex.

According to Tom his professional journey has been – in one word – “meandering.” While many of us are taught to imagine what we want to be when we grow up, Tom took a different approach. He followed his passions to each next step.

Certainly, as a new Perkiomen School graduate, Tom would not have envisioned a meandering path for himself. How could he? All he knew is, after five full years as a day student at Perkiomen, he was graduating as Valedictorian. Studious and a bit of a perfectionist, Tom reflects he would have performed just fine had he stayed in the public school system. But at Perkiomen, he blossomed as a person! At 5 foot, 4 inches and 120 pounds, he was a tiny eighth grader… who tried out for the football team. He joined the acapella group and was involved both on and behind the stage with the theater program. As a senior, from 8 a.m. chapel to after school soccer in the fall (he was awarded Most Improved Player his senior year!) and lacrosse in the spring, to theater and visiting with friends in the evenings, he rarely went home. He also stayed on campus during the weekends to hang out with friends. Tom can still close his eyes and imagine the sights and smells of the pre-fire Kriebel Hall basement where the yearbook office and day student lounge were located. Old and, at best, shabby chic, especially by today’s standards, he and his friends would not have traded it for any upgraded facility in the world. Bonus: Tom’s mom, Faith, worked upstairs as the Assistant to the Director of Admissions and was part of the Perkiomen fabric for almost 30 years!

Tom went from being a shy eighth grader to a Wesleyan University student and landed his first job as a paralegal, assuming his path would lead to law school. After two years at a Wall Street law firm, he realized it wasn’t for him and changed directions toward George Washington University where he earned his master’s degree in political management. This led him to seven years working on political campaigns in Washington, D.C. and then Pennsylvania! Afterwards, he turned his sights to communications and media relations, skills he pulled from his first set of jobs, including at a Philadelphia law firm where he worked in public relations. After 15 years, ending as a chief marketing officer for a law firm in New York, the itch for change crept up on Tom, and he found himself wondering what was next.

When a close family member suggested he consider a second career in Development (his college alma mater, Wesleyan, did have an opening for a Major Gifts Officer), he felt immediate imposter syndrome. Why would they choose him with no prior, traditional advancement experience? The real question should have been: Why wouldn’t they choose him? Tom was a natural at making connections and ignored algorithms and statistics in favor of building relationships. Before he knew it, Tom realized his meandering path had led to a dream job of directing alumni and parent relations for his alma mater. He thought, this was it! This is where he’d eventually retire… until a headhunter contacted him. Would he consider working at an independent day school in New Haven, CT? Upon further reflection, Tom realized it would be an opportunity to return to his roots: an independent school similar to where he first found his confidence.

“My independent secondary school experience [at Perkiomen] was the most foundational and transformational experience for me, even more so than what I experienced in college or graduate school,” Tom states.

Today, he and his team are raising millions of dollars to help students at Hopkins School in New Haven, CT, the third oldest independent school in the nation (established more than 360 years ago). Thanks to the work of his department, Hopkins students receive an education they may not otherwise have been able to afford or have access to.

“It’s energizing seeing young people on campus every day,” Tom reflects.

He takes tremendous pride knowing his office helps kids receive an education that gives them a leg up on the ladder of success. Many of these students go on to Ivy League schools. Most of the rest attend the other top 50 schools in the country.

“They have the talent and drive to be great humans and world citizens!” Tom says proudly.

Tom’s wife, Stephanie, may have said it best: “You don’t seem to have a plan, but you always seem to land in the right place.”

Following his passions led to exactly where Tom was meant to be. Today, he and Stephanie enjoy traveling and spending time with their kids, Ben, Carly, and Jacob. Being back at an independent school, Tom has had an opportunity to reflect on where life has taken him and is grateful for his faculty advisor Reid Watson; Bill “Toby” Thobaben in the theater department; Wayne Engle, who gave Tom extra help with math, the subject that eluded him; and everyone at Perkiomen who, along with his parents, Faith and Tom Sr. supported him and his brother, Matt, also a Perkiomen alum.

It’s because of this experience that Tom has committed to a multi-year pledge to Perkiomen’s Our Moment to Lead campaign. Tom gives back in recognition for what Perkiomen did for him as a person and what a gift it was to receive a free education as a result of being a “staff brat.” His gift will be matched by Stephanie’s company, the United Health Group, and together, they will help students at Perkiomen have a leg up on that ladder when they are looking toward the next step along their own paths.