As a part-time graduate student at the School of Information Studies, I’m in my ninth semester at the iSchool. That fact means that I’ve enjoyed nearly three full years’ worth of exposure to the many great things that are happening here, and the many exceptional talents who have emerged from, or visited, this learning institution.

I love what I get to take away from the speakers, entrepreneurs, and fellow students who knowingly (or not) have been part of my learning experience as they impart their wisdoms during special events and speaking engagements here.

Among those fascinating personalities—and it turns out, teachers, for me—is Philip Kaplan.



A 1997 graduate of the iSchool, Philip was the keynote speaker for Convocation 2014. It’s one of many connections he’s purposefully made with his alma mater. Philip has been a member of the School’s Board of Advisors for six years and has hosted student groups at the annual Spring Break in Silicon Valley entrepreneurship exploration trips. He came back specifically to speak at one year’s Emerging Talk, and while here, spent time engaging with, and encouraging, young entrepreneurs.

I’ve had the chance to meet and speak with Philip on three separate occasions, and each time, I’ve come away with some important life lessons.

Philip is someone who first went into a traditional career as a project manager at a web design firm. When that work no longer fulfilled him creatively, he pivoted, took risks, started his own firm, grew it, then developed several startups. He’s now a highly successful serial entrepreneur doing leading-edge work in the information field.

What I’ve learned in talking with him comprise some exceptional educational, life, and worklife lessons:

1) Sometimes creative geniuses and successful entrepreneurs are unconventional or mediocre students. Philip told me was the kind of high school student who worried his parents, and even was at risk of being expelled. (He might have been engrossed in the early Internet when no one else was instead.) But that turned around in college, when he found a whole catalogue-full of courses–at the iSchool–that thoroughly engaged him.

2) Be true to what drives you. As Philip relayed at Convocation, the desire to work for himselfeven if the motivation was simply about sleeping in and creating his own work timetableis worth listening to. It’s what drove him, and consequently, led to his ensuing successes.

3) Do work that feels like it is art or hobbies. Philip told the Convocation audience that almost all of his 100 or so products, apps, websites, online services and companies “started out as hobbies.” He advised, “Think about your work as if you were an artist, like a musician, and any job you have or company you start, or trade you learn, it’s like putting out an album…so none of it feels like real work.”

4) It’s perfectly acceptable to fail or to decide to quit. “If you’re working on something and you decide midway through that it sucks, paint over it and start again.”

5) Don’t listen to other peoples’ advice about what you should do. “Everyone in the real world wants to tell you what they think you should do, and why your idea will never work, and how they would do it if they were you. Mentors and experts are important…only listen to their stories [and not their advice].”

6) Go with your gut. “Every regret I have in business is because I took somebody else’s advice. The problem isn’t just that their ideas didn’t work out; it’s that I’ll never know because in most cases, I didn’t do my ideas.”

7) Find work that feeds your soul. In Philip’s words, “For a creative person, happiness isn’t whether you made the right or wrong decisions, it’s that your made your decision, that your realized your vision.”

Here’s the video Philip made accepting the iSchool students’ invitation to be their Convocation speaker.


Has an entrepreneur, speaker, or special guest at the iSchool or elsewhere inspired you with their words? Let us know, and leave your comments here!