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After serving aboard a U.S. Navy aircraft carrier for four years, Michael Phelan, EMBA ’12, took a very important lesson to heart: learning to trust—and be trusted by—his team members.

“That sense of teamwork is really about the person next to you. It’s about accomplishing your mission together,” the proud veteran explains. “You have to trust that other people have your life in their hands, just as you have theirs in yours. It’s the only way it can work.”

After deployment, Phelan sought out similarly collaborative situations at companies like Boeing and EMC. It was not until later in his career, when he joined the MIT Sloan Executive MBA Program’s inaugural class, that the former seaman returned to familiar waters.

“MIT Sloan taught us how to help each other, how to work together as a team,” he says. “Everyone is divided into groups, and by the time the class is almost over, they’re your best friends in the world. You know what everybody’s superpowers are and how to leverage them.”

Nearly a decade later, Phelan is vice president of professional service strategy at VMware, an infrastructure software company that equips businesses with virtual computing power. As extraordinary as his career turned out, enlisting in the military and attending MIT Sloan were not always a part of the plan. While growing up on a veal farm in rural Illinois, all he knew was he wanted to work with computers—big ones.

“I always had an interest in technology, and deep down, I knew I was going to do something with computers,” he recalls.

In elementary school, Phelan was chosen to help demonstrate a then brand-new Apple IIe to the parent-teacher association. Outside of this experience, he was not exposed to computers all too often, but that did not stop him from developing a strong interest in technology.

His fascination with computers and computer logic grew so strong, he only had one request for the Navy recruiter when he enlisted two weeks after his eighteenth birthday.

“I said, ‘I want to work on big computers.’ I didn’t know any more than that. The big ones just seemed more important.”

Based on the results of his aptitude exam, Phelan was enrolled in training to become a data systems technician. He excelled so fast and far, he was officially invited to attend the United States Naval Academy in Annapolis, Maryland. However—and despite protestations from a senior officer—he turned down the offer.

“If I went to the Naval academy for four years and served another six, I wouldn’t have gotten out until I was twenty-eight. I thought my life would be over!” he laughs before turning serious. “Now, as I look back on my life, it’s not the mistakes I’ve made that I regret. It’s the opportunities I didn’t take. I would characterize that moment as my biggest professional regret. It was a rough lesson, and ever since then, whenever a door opens, I walk through it.”

That is precisely what happened when Phelan received an email inviting him to apply to a new executive course at MIT Sloan. “I remember reading it and thinking, ‘I’m going to do that,’ which is absurd,” he recalls, “but I just had this feeling I was going to do it.”

He searched for everything he could find about the school and spoke to MIT Sloan Fellows MBA Program alumni about their experiences. He even found the contact information for Jonathan Lehrich, the EMBA founding director, and called him. Phelan was concerned about his educational history, but Lehrich was so impressed by his professional background—and his tenacity—that he encouraged him to apply. Phelan was accepted without issue.

He filled his knowledge gaps by teaching himself calculus and enrolling in Khan Academy online classes. Though these efforts were necessary, he credits the MIT Sloan curriculum—and the teamwork exemplified by the teachers and students who discussed it regularly—with his continued success.

“I was bringing skills to the table every Monday that I didn’t have on Thursday,” he says. “It was good for the business, and it was good for me personally.”

Phelan also believes what MIT Sloan does is good for the world, especially as the COVID-19 crisis continues to affect the globe. He insists all Sloanies, particularly alumni like him who are “coming towards the end of their careers,” should band together and do everything in their collective power to help—because they’re the right team for the job.

“This pandemic will change the world, period. It’s that next sentence that needs to be written, and we need to play a very active role in writing it. Because if we don’t do it, who else will?” he asks. “I don’t think anyone who went to MIT Sloan is comfortable with that question right now, but I’m happy to be one of the people who can start the conversation.”

To learn more about how you can support the next generation of Sloanie veterans, please email Wendy Connors at

For more info Andrew Husband Senior Writer & Editor, OER (617) 715-5933