What happens when a successful corporate career collides with everything else life demands? In this episode of the Business Legacy Podcast, Paul Dio sits down with Zeynep Tolan, a former technology executive who left corporate life and now works as a career counselor at Carnegie Mellon. This conversation is the first in a series exploring what life looks like after corporate careers and what goes through a leader's mind during a major transition.

Zeynep came to the United States from Turkey to study computer science at Duke, then spent six years at Microsoft working on Internet Explorer and early mobile email syncing. After earning her MBA at Carnegie Mellon, she consulted at McKinsey, spent more than a decade at IBM in roles spanning sales, marketing, and cloud customer operations, and later joined Wayfair. Then, during COVID, with two kids at home and her parents' health declining in Istanbul, she reached her breaking point and stepped away from it all.

After time to regroup and care for her family, a conversation with former Carnegie Mellon contacts led to a role in the university's career center, where she has now spent four years helping students refine their stories, prepare for interviews, and launch their careers. Zeynep shares why she remains optimistic about AI and the job market, while warning that offloading all of our thinking to AI is a slippery slope. She also reflects on the one thing she would do differently, building more connection into her off ramp instead of navigating the transition alone.

Paul and Zeynep connect over life in the sandwich generation, the urgency of making the most of the healthy years ahead, and the motto she keeps close: if not now, when? Zeynep also pressure tests her next venture live on the show, a consulting offer that helps companies modernize their hiring and support new graduates through their difficult first year. Her legacy, she says, is helping people navigate the transitions that once made her feel like she was failing.

00:00 Welcome and introduction to Zeynep Tolan

01:00 From Turkey to Duke and Microsoft

02:00 Carnegie Mellon MBA, McKinsey, and IBM

03:00 Joining Wayfair

03:30 COVID, caregiving, and the breaking point

05:00 Saving and the luxury of stepping away

06:00 What Zeynep loved most about corporate life

07:30 The sandwich generation

09:00 Going home to Istanbul and regrouping

09:30 The path into career counseling

11:00 Helping students tell their stories

12:00 Why Zeynep is optimistic about AI

14:00 The danger of offloading your thinking

15:00 Teaching case interviews at home

16:30 The loneliness of the transition

17:30 The power of connection

19:00 Being in the middle and the reframe that helps

20:30 The memory dividend and making the most of experiences

23:00 If not now, when

24:30 What legacy means to Paul

26:30 The work you would not trade for anything else

28:00 Pressure testing Zeynep's new consulting idea

30:00 Hiring for attitude, not aptitude

31:00 Where to connect with Zeynep

Follow Zeynep as she helps job seekers and companies navigate career transitions, smarter hiring, and that challenging first year on the job.

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