The Second Act Sprint
You're too experienced to start over. Too ambitious to stand still.
The Second Act Sprint is a two-week program 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
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
- Netflix
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 to 20 hours per week, including the live sessions, 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 something you built yourself, running, that didn't exist when you started.
You'll work in Claude and build in Replit, along with a few other tools that make the rest easier. We'll set you up in advance so we don't burn live session time on installs. Everything you build is yours and works anywhere, including after the program ends.
Cohort 3 (Shift) · Next cohort
September 14 – 24, 2026
8:30 – 11:00 am Pacific · 11:30 am – 2:00 pm Eastern
Live online · 8 sessions over 2 weeks, Monday–Thursday · 20 hours live, plus 16–20 hours of between-session work
See all 8 session datesHide session dates
- Mon, Sep 14
- Tue, Sep 15
- Wed, Sep 16
- Thu, Sep 17
- Mon, Sep 21
- Tue, Sep 22
- Wed, Sep 23
- Thu, Sep 24
Cohort 4 (Shift) · Later cohort
October 5 – 15, 2026
8:30 – 11:00 am Pacific · 11:30 am – 2:00 pm Eastern
Live online · 8 sessions over 2 weeks, Monday–Thursday · 20 hours live, plus 16–20 hours of between-session work
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- Mon, Oct 5
- Tue, Oct 6
- Wed, Oct 7
- Thu, Oct 8
- Mon, Oct 12
- Tue, Oct 13
- Wed, Oct 14
- Thu, Oct 15
Cohort 5 (Shift) · Later cohort
November 2 – 12, 2026
8:30 – 11:00 am Pacific · 11:30 am – 2:00 pm Eastern
Live online · 8 sessions over 2 weeks, Monday–Thursday · 20 hours live, plus 16–20 hours of between-session work
See all 8 session datesHide session dates
- Mon, Nov 2
- Tue, Nov 3
- Wed, Nov 4
- Thu, Nov 5
- Mon, Nov 9
- Tue, Nov 10
- Wed, Nov 11
- Thu, Nov 12
What you walk away with by the final session.
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.
- A 30-day action plan where your first commitments are already booked on your calendar. Nothing leaves as a good intention.
Proof
Something you built, not just something you say.
- You scope a prototype for your Second Act and build it live, with an AI agent doing the actual coding. An app, a website, a tool, a simulator.
- You keep the prototype. You also keep the method: scope it, plan it, build it, break it on purpose, iterate.
- A skill that writes in your voice, so you can sharpen your LinkedIn and resume to align with the new personal narrative you're building.
Your AI Team
Agents that know you and work on your behalf.
- A Chief of Staff that knows your background, your strengths, and where you're heading. It keeps its own files, remembers what you told it last week, and connects to your calendar, your email, and your notes.
- Skills you build, not download. One that writes in your voice. One that keeps your network warm and tells you who's gone quiet.
- An Agent that runs without you. A morning brief that lands before you're up. A weekly networking pass that drafts the notes and leaves the sending to you.
- At least one more teammate, hired outright. A real job description, a real job it owns, and a trigger that sets it going.
- A research practice that gets you conversant in a new field fast, so you walk into calls and interviews with confidence and swagger.
Plus, ongoing support
- 30-Day Check-In with your facilitators and cohort to pressure-test what you're building and keep you moving.
- Three months of access to the Shift Network, an alumni group that meets for a live session every Friday to learn, share, and connect.
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.
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.
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.
It's ironic that an online course based around AI is one of the most human experiences I've ever had.
In eight short days, I came away feeling completely different about my direction, my potential, and my ability to realize this next exciting chapter of my career.
The Second Act Shift gave me a ton of confidence in defining and moving towards my next chapter. The AI part of the course opened up a whole new world for me. 10 thumbs up.
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, your skills, and your agents (yours to keep)
- 30-Day Check-In session with your facilitators and cohort to drive post-program momentum
- Three months of access to the Shift Network, including live weekly sessions
- 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.
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 Purpose Statement that lights you up and provides clarity on where you're headed.
- 02A prototype designed to propel your Second Act forward. A vibe-coded app, a website, a tool.
- 03A Chief of Staff that knows your background and your direction, plus at least one skill or agent running real work on a schedule.
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.
Apply now
If this sounds like the two weeks you wish you'd had a year ago, that's on purpose.
Only 12 seats. Registration closes September 11th. We start on September 14.
Not the right time? Join the waitlist for future cohorts