The Anxious Achiever

morra@morraam.com

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"On The Internet, Everyone Looks Rich" with Jenny Blake

July 21, 2026

What happens when the strategies that always worked for you suddenly stop working? How do you keep believing in yourself when success no longer feels certain? In this episode, I sit down with entrepreneur and author Jenny Blake to talk about financial uncertainty, career setbacks, and the emotional toll of building a business. Jenny shares what it was like to lose major clients, question long-held beliefs about success, navigate the "flop era" of entrepreneurship, and find new meaning through...

"Death, Sex, and Money": Talking Smart About Hard Things With Anna Sale

July 16, 2026

Which conversations have you been avoiding at work? In this classic episode, I sit down with Death, Sex & Money host Anna Sale to talk about why conversations about money, mental health, and personal struggles still feel so difficult in many workplaces. We discuss the shame that often shapes our financial decisions, how your upbringing influences the way you negotiate and advocate for yourself, and what to consider before telling your boss you're struggling. Anna also shares advice for settin...

Exploring Liminal Spaces with HBS's DJ DiDonna

July 14, 2026

Would you take four months away from work? Have you ever wondered who you'd be without your job for a while? In this episode, I sit down with Harvard Business School lecturer and The Sabbatical Project founder Dennis “DJ” DiDonna to talk about why many of us keep pushing until burnout forces us to stop, how intentional time away creates space to reflect on what really matters, and why rest isn't about doing nothing. DJ also shares ways to plan a sabbatical, navigate the uncertainty that comes...