Not Simple

“The more complex work that I’ve tried to do is to really dig into those unwanted identities… and say, ‘Well, is it really true that I’m a burden to others?’”

Rachel Simmons, coach and author, stopped by to explore our oversimplified binary of capable/needy and why it's so hard to ask for help.

“Even that simplifies the process; it’s just a box and a name on a tree and then you pick up the phone and there’s a voice on the other end of it and it alters the landscape just a hair.”

Tom Draffen is a retired Marine Corps air traffic controller and a coach/consultant. He joined Wendy to discuss the complexities of sealed records, discovered siblings, and what it means to have a both/and family.

“What we find is that there are three aspects of life that they are good at nurturing… performance or achievement, personal growth, and well-being.”



Nicolai Tillisch is a colleague at Cultivating Leadership and the co-author of the best-selling book Return On Ambition. Here he introduces us to the seven frenemies, tools for goal-setting, and the many ways we oversimplify ambition.

“The problem with strategic planning in a pandemic is there are so many different elements in there that impact our ability to have student achievement, but we can’t lose sight of that goal.”



Six months after she first spoke to Wendy about the complexities of reopening school during Covid, elementary and middle school principal Aletha Snowberger returns to update us on how things are going.

“I’m trying to say yes to the things that bring me more joy.”

After a long hiatus, Not Simple is back with producer Rebecca Scott, a Leadership Coach and part of the Catalyst team at Cultivating Leadership, joining Wendy to unpack the complexities of setting boundaries.

“Public health is happening in communities, in neighborhoods, where you live, where you work, and there’s not really enough appreciation for that.”

Epidemiologist April Carson joins Wendy to discuss public health and the complexity of getting people to listen to simple messages—especially during COVID.

“There’s something very powerful about the fact that we see ourselves in stories.”

Ann Kowal Smith, CEO of Books@Work, returned to discuss Franz Kafka’s very short story “Poseidon” with Wendy and a few colleagues. Together they discover the leadership lessons and complexities within what is, at first glance, a quite simple story.

“There’s one race, the human race. There are cultural groups. There are differences in skin tones and facial features and body features, but these don’t dictate who we are.”

Amiel Handelsman is an executive coach and writer, as well as a semi-retired podcaster. He joined Wendy to discuss the many ways we oversimplify racial identity in America. 

You can learn more about Amiel and his work on his website.

“This could be the year that Americans find out that their simple assumption that we do elections well or right will be forever destroyed.”

Jerry Mayer is a professor of Political Science at George Mason University and a self-proclaimed obsessive about all things election-related. He joined Wendy ten days before Election Day in the US to discuss everything from the Electoral College to the overlooked implications of high voter turnout.

“The reality is that friendships are infinitely messier and nastier and deeper in all sorts of ways good and bad than just two people who like each other and get along and are nice to each other.”

Susan MacDougall, an anthropologist at Cambridge University, joins Wendy to discuss the complexities of friendship, its history, how it has changed in Covid times, and how its rules vary across cultures.