Bridging the Generational Gap in Exit Planning

A new report by The Exit Planning Institute, the 2025 State of Owner Readiness: Generational Report, sheds light on how Baby Boomers, Generation X, and Millennials approach exit planning — and the differences are striking. While the importance of planning is broadly recognised, the level of preparation varies dramatically by generation.

Key Findings by Generation

Baby Boomers (Ages 61–79)

• Least prepared for exit despite being closest to retirement.
• Only 13% have a written personal plan, 35% a personal financial plan, and 22% have completed a value enhancement project.
• Strong preference for third-party sales over internal transitions.
• Just 42% have received formal exit planning education — the lowest among generations.
• High risk of regret post-exit, largely due to weak personal planning.
• Many businesses remain overly dependent on the owner’s leadership and relationships, creating cultural and operational risk.

Generation X (Ages 45-60)

• Moderately prepared, with 70% educated in exit planning and 62% holding personal financial plans.
• Value autonomy, adaptability, and balance, but that independence can be a barrier — only 11% have built a formal advisory team.
• 57% list exit planning as a priority, but many lack written transition plans.

Millennials (Ages 29-44)

• Most proactive generation, with 85% educated in exit planning and 68% holding financial plans.
• Embrace the concept of “boomerang exits” — building, selling, and reinvesting in multiple businesses.
• 84% have undertaken value enhancement or due diligence projects, far outpacing older generations.
• Tend to decentralise leadership and foster inclusive, growth-oriented cultures.
• Still, confidence sometimes outweighs documentation — many rate themselves highly but lack formal written proof.

Generational Mindsets & Values

• Baby Boomers: Stability, success, commitment.
• Gen X: Autonomy, adaptability, balance.
• Millennials: Collaboration, growth, purpose.

Emerging Trends

• Generational power shift: In 2013, Baby Boomers dominated business ownership; today, Gen X and Millennials lead.
• Education drives readiness: Owners with formal exit planning education are consistently more prepared.
• Internal transitions on the rise: Younger owners increasingly prefer family transfers, management buyouts, and ESOPs.
• Yet only 13% of all owners have a formal exit plan, and just 5% of Boomers have a full advisory team.

The Three Legs of the Stool™

Exit planning requires balance across:

1. Personal readiness: life goals, estate planning, purpose beyond the business.
2. Financial readiness: wealth gap analysis, documented strategy.
3. Business readiness: valuations, risk assessments, and transition planning.

Recommendations

For Baby Boomers:

• Shift mindset from success to significance.
• Focus on building intangible capital (people, systems, customer relationships)
• Start planning now — waiting for the “right time” risks regret.

For Generation X:

• Use your adaptability to your advantage.
• Build a formal advisory team, ideally led by a CEPA.
• Turn “priority” into action with written plans.

Baby Boomers (Ages 61–79)

• Don’t let confidence replace planning — formalise your strategies.
• Stay disciplined with financial planning.
• Continue using exit planning as a tool to align business, life, and purpose.

One clear message comes through from the report: exit planning isn’t tied to age, it’s about being prepared. Whether you’re close to retirement or still early in your business journey, the sooner you start, the more options you’ll have to protect value, reduce risks, and shape the legacy you want to leave.