You did everything right. The degrees, the titles, the career your family prayed for. So why does it still feel like you are running a script someone else wrote? If you are successful but unhappy, the answer may have little to do with how hard you work.

Craig M. Robinson earned degrees from MIT and Harvard Business School, led national real estate businesses as a division CEO, and ran global development at WeWork. Then his professional identity began to unravel, his marriage came to an end, and he began questioning the beliefs that had shaped his life. On still Ambitious, Bryan B. Sanchez and Divya Brown sit down with Craig to talk about The Happiness Reboot, his new book on the scripts that shape high achievers.

Craig explains why high achievers are unhappy even after every box is checked, and why the weight he carried to MIT only grew with each promotion. Bryan admits that twenty years in real estate private equity trained him to speak with conviction about things no one can predict with certainty. Craig's perspective on curiosity over conviction may change how you approach your next big decision. You will also hear Craig's take on the IRR of happiness, a hard look at the retirement bet most leaders make without question.

If you feel successful but unhappy, or you are facing a career identity crisis or experiencing the early signs of high achiever burnout, this conversation gives you a place to start. Press play for a practical path to finding purpose in your career while your ambition stays intact.

Episode Breakdown:

00:00 Why Bryan and Divya Built still Ambitious

01:43 Craig M. Robinson on Being Successful but Unhappy

06:36 Carrying the Golden Child Script to MIT

10:12 Why Craig Walked Away From Goldman Sachs

14:37 Colliers, WeWork, and the Hidden Cost of Success

20:59 Divorce, a Lost Title, and an Identity Crisis

24:28 Inherited Scripts and the Science of Happiness

32:01 How to Audit the Scripts Running Your Life

40:38 The IRR of Happiness and the Retirement Bet

43:16 Faith, Doubt, and Curiosity Over Conviction

Connect with Craig M. Robinson

Visit Craig's website

Connect with Bryan and Divya:

Visit the still Ambitious website

Connect with Bryan on LinkedIn

Connect with Divya on LinkedIn

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Who are you when the company you built no longer needs you? For most founders, life after selling your business to private equity can take shape long before the deal closes. J.R. Greene started planning while he was still CEO.

J.R. is the vice chair and former CEO of Psychiatric Medical Care, one of the largest behavioral health companies in the country. His father founded it. When it was losing money, J.R. told his dad it was time to shut it down. His dad refused and asked, “Who’s gonna take care of my patients?” J.R. stepped in and spent the next 15 years scaling it. On still Ambitious, Bryan B. Sanchez and Divya Brown talk with him about the turnaround, the growth that followed, and how he knew it was time to step aside.

That meant making some deliberate decisions along the way. J.R. explains why he accepted 10% less money to work with the right private equity partner, how a dropped spoon at dinner helped him rule out another, and why hiring the right people for each stage of growth mattered. He also shares how he knew it was time to replace himself as CEO and why making that decision before Carlyle came along gave him the freedom to leave on his own terms.

Then comes the part most exit stories skip. J.R. is returning to an old ambition: becoming a game show host. He shares the story of selling a game show concept to Merv Griffin, being told he couldn't host it, and why he now considers this chapter his first act. And for founders who keep moving the goalposts, he offers a lesson he wishes he'd learned sooner about ambition, celebrating success, and knowing when enough is enough.

Episode Breakdown:

00:00 Bryan and Divya on the Cost of Striving

01:50 The Night J.R. Led Tennessee Onto the Field

08:36 From Coca-Cola Surge Man to Revlon Executive

11:39 Selling a Game Show to Merv Griffin

18:04 The Revlon Promotion He Lost and Why

20:57 Turning Down a KIND Bars CMO Role to Pursue Entrepreneurship

31:52 Choosing a Private Equity Partner Over Higher Offers

34:17 The Improv, Musical, and Syndication Hiring Framework

39:12 Life After Selling Your Business to Private Equity

47:18 Advice for His Younger Self on Ambition

Connect with J.R. Greene:

Listen to the SuperFan Diaries Podcast

Get a copy of My Magic Tux

Connect with Bryan and Divya:

Visit the still Ambitious website

Connect with Bryan on LinkedIn

Connect with Divya on LinkedIn

Podcast production and show notes provided by HiveCast.fm

You built the title, the reputation, and the results. Then a harder question shows up. Who am I without my job? Most high achievers treat that question as a threat. Jill Nykoliation treated it as a starting point.

Jill founded Juniper Park\TBWA and built it into an award-winning agency with clients including PepsiCo, Nissan, and Apple. In 2015, she was at the height of her professional success, but behind the scenes, her marriage was ending, her business partnership was fracturing, and her health was suffering. She joins Bryan B. Sanchez and Divya Brown on still Ambitious to talk about that season of high achiever burnout and a piece of advice from her coach that has stayed with her for 11 years.

Every leader eventually has to decide how long to wear the armor that helped them climb. Jill explains how letting go of that armor allowed her to lead more authentically and why stepping away from the agency she built actually felt like an exhale. She also shares the story behind the highly successful and deeply meaningful advertising campaign that gave her the peace to know it was time to move on professionally. Divya recognizes her own experience in the masculine language many women leaders learn to speak fluently. Bryan, who stepped away from a career in private equity, opens up about his own executive identity crisis and the archetype he had shelved for 25 years.

For anyone questioning what comes after professional success, Jill offers a different way to think about identity, ambition, and fulfillment. Her story is a reminder that your next chapter may be your most meaningful one yet.

Episode Breakdown:

00:00 Meet Jill Nykoliation and the Still Ambitious Mission

03:41 Kraft, PepsiCo, and Codifying the Lululemon Brand

09:48 The 2015 Lifequake Nobody Saw From Outside

14:57 Taking Off the Armor in a Masculine Industry

22:59 Leading With Kindness Through Divorce and Lockdown

31:45 Wholeheartedness, Authenticity, and the Pull of Attachment

38:00 The Story Behind The Creation of the Universal Sign For Help

45:46 Who Am I Without My Job? Rebuilding Identity

51:11 Jungian Archetypes and the Outlaw Bryan Buried

57:17 What Jill Knows Now About Ambition and Armor

Connect with Jill Nykoliation:

Know more about Jill

Connect with Bryan and Divya:

Visit the still Ambitious website

Connect with Bryan B. Sanchez on LinkedIn

Connect with Divya Brown on LinkedIn

Podcast production and show notes provided by HiveCast.fm