The (AI-Powered) Midlife Rethink (INSEAD)

THE MIDLIFE RETHINK

Redesigning Your Next Chapter in a Longer, AI-Enabled Life. A three-part strategic programme for INSEAD alumniLed by Avivah Wittenberg-Cox

WHY MIDLIFE NEEDS A RETHINK

We are living longer, healthier and more complex lives. Careers evolve, identities shift, and opportunities emerge in ways previous generations could not imagine. Yet few of us pause long enough to process the transitions already underway, or to intentionally design what comes next.

The Midlife Rethink offers a highly structured, intellectually rigorous space to step back, assess where you are, and strategically re-shape your trajectory.

A PROGRAMME FOR ALUMNI IN MOTION

The Midlife Rethink draws alumni who are in motion — people sensing their next chapter may look different from their last, even if they cannot yet articulate how. Some seek reinvention, others renewal, others clarity or reinvigorated purpose. What unites them is momentum — and appetite.

I speak from experience. I redesigned my own life and career at 60 — not because I was slowing down, but because I was still building. To kickstart it, I did a year as a Fellow at Harvard’s Advanced Leadership Initiative. The Midlife Rethink is a fast, accessible digest of the key things I learned there – and since. These transition moments can be energising and disorienting. It’s better to do it in good company.

WHAT’S NEW FOR 2026: AI AS A STRATEGIC ACCELERATOR

This edition introduces a practical layer: AI-powered analysis and scenario generation woven into each session. The goal is simple: accelerate your clarity, sharpen your thinking, and equip you with a repeatable tool for future reinvention. AI helps:

• extract strategic patterns from your past.
• produce a gap analysis of your current situation.
• and generate future options and pathways based on your goals.

PROGRAMME STRUCTURE

SESSION 1 — HARVEST THE PAST

Where you’ve been: your trajectory, decisions, successes and strategic patterns.AI acceleration: A targeted prompt extracts your strategic patterns and most leverageable assets.

Takeaways:

• A concise strategic narrative of your career-to-date
• Clarity on the forces that have shaped your journey
• Foundational insights for the next chapter

SESSION 2 — ASSESS THE PRESENT

Where you stand today: commitments, constraints, opportunities and energy allocation.AI acceleration: a rapid diagnostic and prioritised action plan (90 days / 6 months / 3 years).

Takeaways:

• A clear diagnostic of your current state
• A prioritised transition plan
• Precision on what to invest in, reduce or redesign

SESSION 3 — MAP THE FUTURE

Who you want to become: options, possibilities and future pathways. AI acceleration: a synthesis of your data and dreams into future scenarios, opportunity sets and capability maps.

Takeaways:

• Three viable next-chapter paths
• A refined professional narrative and updated bio
• Clear opportunities and the capabilities required to pursue them

WHAT YOU LEAVE WITH

• A structured understanding of your past, present and next chapter
• A strategic roadmap for the next 3 years and next 90 days
• An AI-enabled repeatable method for future reinvention
• A revitalised personal and professional narrative
• A community of like-minded INSEAD alumni navigating similar transitions

FORMAT & LOGISTICS

Three interactive Zoom sessions. Worksheets and AI prompts provided after each session.No technical or AI background required.