Lessons Learned from 50 Years as an Entrepreneur with Steve Bennett
Your Working Life with Caroline Dowd-Higgins
Release Date: 05/05/2025
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Lessons Learned from 50 Years as an Entrepreneur with Steve Bennett
Your Working Life with Caroline Dowd-Higgins
Steve 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...
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