Live sessions
Join a live session with Second Act.
Free executive roundtables, workshops, and conversations for experienced professionals figuring out what's next. No pitch, no filler — just real talk and practical tools.
Upcoming Sessions
Wednesday, October 21, 2026
Retell Your Career in Six Words: Executive Roundtable with Larry Smith
Larry Smith, creator of Six-Word Memoirs, leads a roundtable and workshop on telling a shorter, sharper career story for the role you want today.
Tuesday, November 17, 2026
Starting an AI-Powered Company: People First, AI as Your Superpower
Gregg Spiridellis, co-founder of JibJab and StoryBots, on starting a company with AI at the core. Includes a hands-on session sketching your own AI-powered team.
The Second Act Shift
Fourteen weeks, lasting momentum.
A 14-week program that kicks off with a two-week intensive: live sessions, real work, and a small group of peers moving through the same questions you are.
New cohorts run every few weeks — see open dates and application deadlines on the apply page.
Your facilitators
A coach and an AI strategist, in the same room.
You don't need a career coach who pretends to know AI, or an AI guide who pretends to know careers. You get both leading the opening two-week intensive, with support continuing across the full 14-week program.
Dan Rollman, ACC
Executive & Career Coach. Creator of the Second Act Framework.
Twenty-five years at the intersection of creativity, reinvention, and human potential: as a copywriter who wrote two Top 10 Super Bowl ads, a startup founder who raised venture capital and appeared on Late Night with Jimmy Fallon, and now an ICF-certified coach (Co-Active Training Institute) who has guided over 200 clients through the biggest transitions of their working lives. Featured on Shark Tank, CNN, and CBS Sunday Morning. Co-creator of the Global Day of Unplugging, observed annually since 2009.
He knows what it feels like to outgrow a career and build the next one. He knows how to help others do it with clarity and intention.
Kenny White
Founder of Electric Thinking. Three-time entrepreneur.
He's led over 1,000 professionals through their own AI transformation at companies like Disney, ABC, and Visa, with a 9.5/10 average rating. Leadership teams call him when they need to figure AI out without slowing down.
He's also been the strategist behind projects for ESPN, Meta, and OpenAI, and the founder of a company that made the Inc 5000 list of America's fastest-growing companies. He's written about the future of work in Harvard Business Review and Fast Company.
He knows what it feels like to outgrow one chapter and build the next. He knows how to help others do it when AI is rewriting the rules.