The Second Act Shift
You're too experienced to start over. Too ambitious to stand still.
The Second Act Shift is a 14-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
Two focused weeks.Twelve more of support.One clear next chapter.
How the 14 weeks work.
Weeks 1 to 2: The Second Act Sprint
Eight live sessions, 20 hours total, Monday to Thursday across two weeks. Plan on about 8 to 10 more hours a week for exercises, writing, and building your AI tools. This is where the heavy lifting happens, so protect the time.
Weeks 3 to 14: The Shift Network
Live alumni sessions every Friday to keep learning, reflecting, and connecting with others on a similar path. About a month after the Sprint, your cohort and facilitators will also reconvene for a one-hour check-in to share progress and troubleshoot.
Throughout: Your online hub
A private Circle community where you share progress, message your facilitators and cohort directly, and access the Content Library, including Shift Network session recordings.
What you'll have after the Sprint.
Built on the Second Act Framework and pressure-tested with more than 200 professionals, the two-week Sprint sends you off with direction, tools, and tangible results you can point to.
Clarity
A path ahead that lights you up.
- A Second Act Purpose Statement in language that fits who you're becoming.
- A To-Don't List and a Purpose-Driven Calendar, so your energy goes where it matters.
- A 30-day action plan with your first commitments already on the calendar.
Proof
Something real to show for it.
- A working prototype for your Second Act (an app, a website, a tool), built live with an AI agent doing the coding.
- The method to build the next one: scope it, build it, break it on purpose, iterate.
- An AI skill that writes in your voice, ready to sharpen your LinkedIn and resume.
Your AI Team
Agents that know you and work on your behalf.
- A Chief of Staff that knows your background and goals, remembers your conversations, and connects to your calendar, email, and notes.
- Agents that run without you: a morning brief before you're up, and a weekly networking pass that drafts outreach for you to send.
- A research practice that gets you fluent in a new field fast, before calls and interviews.
From people who stood where you are.
“‘Awakened.’ That's the single word that describes how I felt after the Second Act Sprint. I left feeling genuinely awakened to what's possible."
Larry Smith
Creator, Six-Word Memoirs
10/10
Program
rating
“The program gave me three things I needed at once.”
- 01Clarity about what I wanted
- 02A community that lifted me up
- 03An AI team to move me forward
Scott Lodge
Nine-time Sports Emmy winner
“I use what I learned every day. I now use AI to create prototypes, talk through problems, explore opportunities, and figure out how to show my value. It gave me a new way to think and create.”
Tracy Green
Journalist & Producer (Big Brother, Deadliest Catch)
“It's ironic that an online course based around AI is one of the most human experiences I've ever had.”
Michael C
Operations Director
“Second Act Shift helped me find a North Star for the next 20 or 30 years, then gave me enough practical sailing skills to begin exploring.”
Ken Warun
Creative Director (ex-Amazon)
“The program rescued me from endless floundering and helped me find direction when I needed clarity.”
Margo B
Health Care Manager
“Second Act Shift was valuable in refining and affirming the pivot I've undertaken, and provided an awesome set of powerful AI teammates to support it.”
Jeff Reiser
Strategy & Analytics Director (ex-Moody's, ex-American Express)
“I came away feeling completely different about my direction, my potential, and my ability to realize this next exciting chapter of my career.”
Jay B
Founder/Entrepreneur
Our program alumni have led at
- Visa
- Amazon
- Disney
- Netflix
- American Express
- Apple
- Moody's
This is for you if…
- You've had a successful first act, but you're ready to design the next one.
- You're curious about AI but not sure how it fits into your work or your future.
- You'd rather build what's next with peers, structure, and accountability than figure it out alone.
This is not for you if…
- You expect someone else to figure out what lights you up.
- You can't give the opening two-week Sprint your full attention.
- You need a new job next week. We'll sharpen your story and positioning, but this takes more than a few days.
A real cohort
Twelve people. Fourteen weeks. One real change.
You're not figuring this out alone. The cohort is the catalyst, and it stays with you throughout the 14-week Shift and beyond.
“Once I experienced it, I realized community wasn't just great. It was absolutely necessary. There is too much changing to navigate all of it alone.”
The 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. Every cohort is led by both: a certified coach and an AI strategist, together for the Second Act Sprint and supporting you across the full 14-week Shift.
Program designed and co-led by Dan and Kenny alongside additional trained facilitators.
Dan Rollman, ACC
Career & Executive 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 by thousands annually since 2009.
He's reinvented his professional identity multiple times, and he coaches from that experience.
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 makes AI practical for people who don't think of themselves as technical. Nothing energizes him more than the moment it clicks.
Investment
A coach, an AI strategist, and a cohort. One tuition.
Tuition
$2,995
Twelve seats per cohort.
Payment plans available. Professional development budgets welcome.
How that compares
Up to 33 live hours, less than $100 an hour. One-on-one executive coaching typically runs $300 to $500+ an hour, before any AI training. Second Act Shift gives you both, alongside an intimate cohort, an alumni network, and AI tools built around you.
What's included
The Second Act Sprint
- 20 live hours with a certified coach and a senior AI strategist
- Your AI Chief of Staff, prototypes, and agents, yours to keep
The next 12 weeks
- Live Shift Network sessions every Friday
- A 30-day check-in with your facilitators and cohort
Throughout
- Private community and content library
- Backed by the Second Act Guarantee
Next cohorts
Cohort 4 (Shift) · Next 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 about 8 to 10 hours a week between sessions
See all 8 session datesHide session dates
- 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 about 8 to 10 hours a week between sessions
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
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.
Frequently asked questions.
Apply now
The best time to start was a year ago. The next best is November 2.