What’s Possible w. Ilene Schaffer
Jul 30, 2026 · 44 min · 10 segments
What if failure is not the thing that holds your career back, but one of the things that helps you grow into a stronger leader? In this episode of *What’s Possible*, Ilene Schaffer talks with Stephen…
Stephen SharfGuest
Ilene SchafferHost
If you haven't had any failures, then you haven't tried hard enough, right? But when people come to me and say, you know, I've had an amazing career.
I'm like, well, then you probably only realize half your potential, right? You probably could have done a lot more if you had pushed the envelope a little bit further.
Behind every powerhouse communicator and relationship builder is a strategic thinker who leads with curiosity.
Because of that, we believe that your journey to becoming the best leader starts with you.
Are you someone who strives for success 100% of the time? Do you go for opportunities you know you can nail? What about opportunities where you might fall short? If you avoid failure at all cost, this episode might have you thinking differently.
Today, I'm joined by Stephen Sharf, managing director and chief information security officer of a multinational investment company with more than 25 years of experience in cybersecurity.
In this conversation, Stephen candidly shares stories about the mistakes, high stakes decisions, and leadership lessons that shaped his path all the way to the C-suite.
He also shares why he thinks learning from failure is an essential ingredient for extraordinary success.
We cover everything from well-being to the need to fall down periodically and ultimately how to get back up and maximize your potential.
Let's find out what's possible when we stop fearing failure and start playing on the edge.
Read the full transcript.
Create an account to read the whole episode, search across every transcript, and follow the shows you care about.
If you haven't had any failures, then you haven't tried hard enough, right? But when people come to me and say, you know, I've had an amazing career.
I'm like, well, then you probably only realize half your potential, right? You probably could have done a lot more if you had pushed the envelope a little bit further.
Behind every powerhouse communicator and relationship builder is a strategic thinker who leads with curiosity.
Because of that, we believe that your journey to becoming the best leader starts with you.
Are you someone who strives for success 100% of the time? Do you go for opportunities you know you can nail? What about opportunities where you might fall short? If you avoid failure at all cost, this episode might have you thinking differently.
Today, I'm joined by Stephen Sharf, managing director and chief information security officer of a multinational investment company with more than 25 years of experience in cybersecurity.
In this conversation, Stephen candidly shares stories about the mistakes, high stakes decisions, and leadership lessons that shaped his path all the way to the C-suite.
He also shares why he thinks learning from failure is an essential ingredient for extraordinary success.
We cover everything from well-being to the need to fall down periodically and ultimately how to get back up and maximize your potential.
Let's find out what's possible when we stop fearing failure and start playing on the edge.
