The Second Act Sprint
You're too experienced to start over. Too ambitious to stand still.
The Second Act Sprint is a two-week boot camp for experienced professionals ready to clarify their purpose, articulate their value, and build an AI-powered support system for what comes next.
Dan Rollman, ACC
Executive Coach
Kenny White
AI Strategist
Free live session
Learn more at our free webinar.
Friday, May 29 · 9am PT / 12pm ET — one hour with Dan & Kenny on what your second act could look like.
Human-led, AI-augmented.
Led by Dan Rollman, an ICF-certified executive coach, and Kenny White, an AI transformation leader whose work spans Disney, ABC, and Visa, the program gives you the foundations of your second act: a purpose statement, sharper positioning, tailored AI tools, and a peer network built for momentum that extends well beyond the cohort.
We've worked with leaders at
- Apple
- Anthropic
- OpenAI
- YouTube
- ABC
- ESPN
- Disney
- Sundance Institute
This is for you if…
- You're not done. But you may be done with the work identity that got you here.
- You've built judgment, wisdom, perspective, and scar tissue. But no clear vision for what comes next.
- You use AI, but mostly as a smarter Google, and sense an opportunity to unlock a lot more.
- You don't have six months to wander your way into clarity.
- You'd rather build this with peers, tools, and structure than figure it out on your own.
This is not for you if…
- You expect someone else to figure out what lights you up.
- You're not ready to show up authentically and consistently alongside others in your cohort.
- You're not ready to lean into a focused, two-week sprint.
- You need a new job yesterday. We'll help uncover your messaging, credibility, and positioning, but it's not an overnight transformation.
Two weeks.Real commitment.One clear next chapter.
How the two weeks work.
This is a full commitment. Not a workshop you drop into. Carve out 16 - 20 hours per week to show up completely to yourself, your cohort, and the work of figuring out what comes next.
Anchored by the Second Act Framework, a format pressure-tested by over 200 professionals, you'll be given space to clarify your North Star, reflect in nature, and create a to-don't list so you can focus on what actually matters.
You'll receive a custom AI education that ends with you having built real tools, not just learned about them. And you'll walk out with a LinkedIn and resume that reflect who you are today, not who you were at your last job.
Program details
June 15 – 25, 2026
8:00 – 10:00 am Pacific · 11:00 am – 1:00 pm Eastern
Live online · 8 sessions over 2 weeks · 16 hours live, plus 16–20 hours of between-session work
See all 8 session datesHide session dates
- Mon, Jun 15
- Tue, Jun 16
- Wed, Jun 17
- Thu, Jun 18
- Mon, Jun 22
- Tue, Jun 23
- Wed, Jun 24
- Thu, Jun 25
What you walk away with by June 25.
By the end of the program, you won't just have ideas. You'll have direction, tools, and tangible results to show for it.
Clarity
A path ahead that lights you up.
- A clear Second Act Purpose Statement with language aligned with who you want to be, not who you've been in the past.
- A purpose-driven calendar that builds in thoughtfully designed time blocks, so your days stop disappearing into LinkedIn, errands, and chores.
- A To-Don't List that helps you stop scattering energy across half-baked ideas and projects.
Visibility
An overhauled digital presence.
- An updated LinkedIn headline and About section to reflect your new direction.
- An ATS-friendly resume aligned to your second act, not just a polished version of your old one.
- A webpage you can send to people: your story, what you do now, and why you're worth talking to.
AI Operating System
An AI support system built around you.
- A personalized AI Chief of Staff that knows your background, your direction, and the work you're trying to move forward.
- A set of AI tools and agent workflows built around research, outreach, positioning, planning, content, and opportunity development.
- A research practice that gets you conversant in a new field fast, so you walk into calls and interviews with confidence and swagger.
- One concrete thing shipped: a vibe-coded tool, workflow, or asset that makes your second act more real in the world.
Plus, ongoing support
- Four office hours over the following two months with your facilitators and cohort to pressure-test what you're building and keep you moving.
- Access to the Second Act alumni community. People who understand the season you're in, and help you remember you're not doing this alone.
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, in the same room, for two weeks.
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.
Twenty years at the front edge of AI and the future of work — as a strategist behind projects for ESPN, Meta, and OpenAI, the founder of a company that made the Inc 5000 list of America's fastest-growing companies, and now the person who has led over 1,000 through their own AI transformation at companies like Disney, ABC, and Visa, with a 9.5/10 average rating. He has written about the future of work in Harvard Business Review and Fast Company. He's the person Fortune 500 leadership teams call when they need to figure AI out without slowing down.
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 changing the rules underneath them.
A real cohort
Twelve people. Two weeks. One real change.
You're not figuring this out alone. The cohort is the catalyst — and it stays with you long after the two weeks end.
Alumni
What Second Act alumni say.
I came out a different person than when I started.
This program gives you a structured, nurturing space to do some soul searching, articulate the passions you've put on the back burner, and validate them as not just worthwhile but possible.
In a time when I felt particularly lost, it was invaluable to connect with a group of people who understood exactly where I was.
The program rescued me from endless floundering and helped me find direction when I needed clarity. I am thankful for this gift.
Investment
Both, integrated — for one tuition.
Tuition
$2,995
One time. Twelve people. Two weeks.
What's included
- 8 live sessions plus exercises, writing assignments, and structured activities throughout
- Ongoing cohort connection and collaboration between sessions
- Your AI Chief of Staff and agent workflows (yours to keep)
- 4 office hours with Dan and Kenny over the following two months
- Access to the Second Act Alumni Community
- Second Act Guarantee or your money back
How that compares
An 8-session coaching engagement with an ICF-certified executive coach typically runs $3,000 to $6,000. A comparable AI training program adds several thousand more on top. Second Act Sprint gives you both, plus a hand-picked cohort, plus structure, peer accountability, tailored AI tools, and post-program support for $2,995. By most measures, it should cost two to three times as much.
The Guarantee
Our Second Act Guarantee.
If it doesn't work, we refund your tuition.
Show up live for all 8 sessions and complete the exercises. If you don't have all three of these within 48 hours of the final session, email us, and we'll refund every dollar.
- 01A clear Second Act statement you can say out loud
- 02Updated LinkedIn positioning that reflects where you're going
- 03At least one working AI agent or AI-built asset doing real work for you
The alternatives (and their limitations).
Career coaching. Good identity work, minimal AI. You come out clearer but not more credible in an AI-rewritten market.
AI courses and tutorials. Tools without context. The features you learn aren't built around the new path you're embarking on.
Outplacement / LinkedIn Premium. Doesn't harness AI's potential to help you find the right jobs and apply for them efficiently.
Therapy / time off. Vital for the soul, but not designed to propel your career move forward.
Frequently asked questions.
Free live session
Learn more at our free webinar.
Friday, May 29 · 9am PT / 12pm ET — one hour with Dan & Kenny on what your second act could look like.
Apply now
If this sounds like the two weeks you wish you'd had a year ago, that's on purpose.
Only 12 seats. We start on June 15.
Want to feel it out first? Join the free May 29 session →
Not the right time? Join the waitlist for future cohorts