IRL with Simon Holstein

One huge benefit of the part-time program is that you can immediately apply the lessons you learn in class to your workplace or “in real life” (affectionately abbreviated as “IRL”). In this column, we will celebrate the lessons students learn in class and how they apply them IRL. Do you have a story that has inspired you? Feel free to write to me – your affectionate writer, known as CFN – at

Have you ever learned that it’s okay to be wrong? That to be right, you may be wrong first?

Catherine Frances Napier, '18

Catherine Frances Napier, '18

Upon Booth admission, Simon Holstein (‘18) had the confidence and the courage to try something new. He quit his job to pursue his entrepreneurial ambitions (even finding an office at 1871), knowing he had the security of a Booth degree and the Booth community. Even though the idea didn’t take off, Simon learned it is okay to be “wrong”. What others may view as failure, Booth students see the right opportunity to learn.

Simon elaborates, “Before I even took a class, I had the confidence to take a risk. And then when I took that risk and I was wrong, I was already in an environment where if I told [Booth friends] about the start-up, they weren’t judgmental or in any way negative. The questions I got from my peers weren’t focused on my failures, they were focused on that experience and why I chose to do that, and why it didn’t work – from a perspective of being interested and not from a perspective of you failed.”

At Booth, students are encouraged to take what Simon calls “smart risks”, as this is the place to try something out of our comfort zone. If Booth students take a risk that doesn’t work out, Booth students humbly embrace a “wrong experience” and turn it into the right learning opportunity.  Perhaps, even more importantly, students like Simon learn to try again.

Simon Holstein, '18

Simon Holstein, '18

Even with a full-time job at Avant and school part-time, Simon is already back on the entrepreneurial scene, with two current entrepreneurial adventures. (Check out R-YA NUTS – where Simon is CFO—and watch him compete in the New Venture Challenge with the Freenters team).

To get involved with this year’s New Venture Challenge, Simon simply registered on the interested-student spreadsheet. “I had the confidence to put my name [there] because I knew that whoever was looking at it already started trusting that I was credible and legit. Being in environment like that unique to Booth. I don’t know other place in the world where you could pick a stranger’s name off the spreadsheet and want them to be a part of your startup or a part of your business.”

In this special community, Booth students like Simon fearlessly learn to try and to try again. Booth students learn to take risks “in real life” and enjoy the learning opportunity along the way.

As he says, “I have more confidence in taking risks. Being at Booth has put into perspective a lot of things, like how much I do know and how much I still have to learn – and being okay being in that position.”

Catherine Napier is a first-year MBA student in the Evening MBA Program at Chicago Booth