Lessons Learned from 50 Years as an Entrepreneur with Steve Bennett
Your Working Life with Caroline Dowd-Higgins
Release Date: 05/05/2025
The Power of No in a World That Demands Yes with Dr. Sunita Sah
Your Working Life with Caroline Dowd-Higgins
is an award-winning professor at Cornell University and an expert in organizational psychology. She leads groundbreaking research on influence, authority, compliance, and defiance. A trained physician, she practiced medicine in the United Kingdom and worked as a management consultant for the pharmaceutical industry. She currently teaches executives, leaders, and students in healthcare and business. Dr. Sah is a sought-after international speaker and consultant, advisor to government agencies, and former Commissioner of the National Commission on Forensic Science. Her multidisciplinary...
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Embracing Uncertainty with Margaret Heffernan
Your Working Life with Caroline Dowd-Higgins
produced programmes for the BBC for 13 years. She then moved to the US where she spearheaded multimedia productions for Intuit, The Learning Company and Standard&Poors. She was Chief Executive of InfoMation Corporation, ZineZone Corporation and then iCast Corporation, was named one of the “Top 25” by Streaming Media magazine and one of the “Top 100 Media Executives” by The Hollywood Reporter. The author of six books, Margaret’s third book, Willful Blindness: Why We Ignore the Obvious at our Peril was named one of the most important business books of the decade by the...
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The Flexibility Paradigm with Manar Morales
Your Working Life with Caroline Dowd-Higgins
is a national thought leader and visionary on building human-centered workplace cultures at the intersection of diversity, flexibility, and well-being. As the Founder & CEO of the , Manar is on a mission to empower organizations to unlock their full potential by creating inclusive environments, implementing effective flexible work strategies, and prioritizing holistic employee well-being. A sought-after speaker, author, and trusted advisor, Manar brings a wealth of expertise from her background as an employment litigator and adjunct faculty member at Georgetown University. She is the...
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The Quiet Burn with Lynn Blades
Your Working Life with Caroline Dowd-Higgins
Lynn Blades episode: Minimal Brain Activity by Unheard Music Concepts (source: Free Music Archive) (CC BY) Lynn Blades, author of , is the founder of Legacy Leadership, an executive leadership consultancy, and a dedicated DEI advocate. She has strived to cultivate a 21st-century leadership workforce that truly reflects the diversity of our society. RECOGNIZING AND PREVENTING BURNOUT Demanding Careers Should Not Overshadow Health And Well-Being Women face numerous challenges in their careers – dealing with sexist and demeaning work environments, juggling work and family...
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How to Succeed in Business without Really Crying with Tom Johnstone
Your Working Life with Caroline Dowd-Higgins
After graduating from Boston’s Emerson College in 1985, Tom headed west to work in the film and television industry. In Hollywood, he honed his writing skills through the trials and tribulations of episodic TV, animated series, screenplay options, and game shows for over two decades. When the feast or famine lifestyle of a Hollywood Writer became too sporadic for his maturing life (He had grown to enjoy eating two to three times a day – every day), he took a job at a call center to make ends meet. After his first day on the phones, his manager asked him to stop. He was terrible at...
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How to Be a Likeable Badass with Alison Fragale
Your Working Life with Caroline Dowd-Higgins
Alison Fragle episode: Distances by Beat Mekanik (source: Free Music Archive) (CC BY) ALISON FRAGALE, PhD Speaker. Professor. Compulsive Organizer. Website Newsletter ALISON FRAGALE is the Mary Farley Ames Lee Distinguished Scholar of Organizational Behavior at the Kenan-Flagler Business School at the University of North Carolina. Her scholarship has been published in the most prestigious academic journals in her field, and featured in prominent media outlets such as The Wall Street Journal, The Washington Post, Financial Times, Boston Globe, and Inc. She is...
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Learn How to Be an Unstoppable Entrepreneur with Lori Rosenkopf
Your Working Life with Caroline Dowd-Higgins
Lori Rosenkopf is the Simon and Midge Palley Professor at the Wharton School of the University of Pennsylvania. As Vice Dean for Entrepreneurship, she serves as Wharton’s faculty director for Venture Lab, Penn’s home for student entrepreneurs, and also their San Francisco campus. In a prior role as Vice Dean of Wharton’s Undergraduate Division, she introduced a new curriculum and developed experiential classwork in the tech sector. For over thirty years, Rosenkopf has taught entrepreneurship and management of technology to more than 20,000 high schoolers, undergraduates, MBAs, and...
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The Roadmap to Money and Love with Abby Davisson
Your Working Life with Caroline Dowd-Higgins
Abby Davisson episode: Quickening by malictusmusic (source: Free Music Archive) (CC BY) Abby Davisson is an author, speaker, and award-winning leader obsessed with holistic decision-making (the kind that takes multiple bottom lines into account). After spending two decades making change from within existing organizations, she launched her own, focused on helping leaders make smart choices for lasting success in work and life. The book she co-wrote with Stanford Professor and labor economist Myra Strober, Money and Love: An Intelligent Roadmap for Life's Biggest Decisions,...
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Finding Meaningful Work with Tamara Myles & Wes Adams
Your Working Life with Caroline Dowd-Higgins
Distances by Beat Mekanik, via Free Music Archive (CC BY) Wes Adams is the CEO of SV Consulting Group. He partners with Fortune 500s and scaling companies to develop high-impact leaders and design operating structures that support high performing teams. He is also a positive psychology researcher at the University of Pennsylvania where he studies the leadership practices and organizational structures that help employees thrive. He lives in Atlanta, GA. Tamara Myles is a speaker, author, professor, and entrepreneur specializing in the science...
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Redefining the Successful Rainmaker with Karen Freeman
Your Working Life with Caroline Dowd-Higgins
Karen Freeman is Chief Product Officer at DCM Insights and one of the authors of the Activator research published in Harvard Business Review, titled "What Today's Rainmakers Do Differently." That article was named one of HBR’s top 10 reads of 2025. At DCMi, she is one of the global faculty and responsible for the company’s training products and diagnostics. She has delivered the Activator research and training programs across the globe to clients in the legal, consulting, accounting, and talent advisory sectors. Before joining DCMi, Karen was head of digital...
info_outlineSteve is a visual artist whose work has been displayed in numerous galleries, juried exhibitions, and prestigious corporate art spaces. He’s planning on transitioning to full-time artist from managing the creative side of a web design firm he founded 25 years ago. Previously, Steve had engaged in numerous careers: media training, tech journalism, book writing (he penned more than 50 solo titles and collaborations, including a million-copy, bestselling parenting book). He was also the founder of a successful ad agency and founder of numerous ill-conceived small businesses that failed miserably. Prior to striking out on his own, Steve had intended to become an academic in the field of ancient Chinese science and technology. But after receiving his masters in East Asian studies from Harvard, he decided that academia was not for him. From the outside, his professional life seems to be a maze of disparate paths; from the inside, it’s all logical stepping stones.
Topics: What I’ve Learned from 50+ years of Making a Living as an Entrepreneur
1. “Accidental” vs “intentional” transitions; riding the currents vs steering the boat.
2. Being receptive to career/entrepreneurial opportunities—even when you’re not looking for one. My train station metaphor.
3. ABN: Always Be Networking! Networking as a “long-tail” activity.
4. Don’t believe that if you do what you love the money will follow. It often doesn’t.
5. Hope and blind optimism are not strategies for success. Get real.
6. Everyone fails along the way. Failure is a great teacher. But it still sucks. If failure will rock your self-esteem, travel a safer path.
7. Retirement is a four-letter word. Wearing out vs rusting out. Think encore career.
8. Choosing visual arts as an “encore” career entails unique challenges. The solution: treat it like any other kind of business in terms of promotion and marketing, tactics, and strategies.
Social media:
LinkedIn: https://www.linkedin.com/in/stevebennettvisualartist/
IG: https://www.instagram.com/sjbennettvisualartist/
X: https://x.com/sjbennettvisual