People Ops Collective strengthens existing ecosystems by connecting them across generations, industries, and real-life systems

The In-Between

An Intergenerational Roundtable

Meeting in the Middle

A 90-minute monthly virtual roundtable for people navigating real life alongside work.

This is a space for the in-between:

• Where work meets life.
• Where generations meet.
• Where perspectives meet.

A real conversation designed to help you think clearly, make better decisions, and move forward.

Our 3 Pillars - Aging is Living

Everything we do is grounded in:

• Aging & Senior Society

→ learning across generations, preparing for what’s ahead

• Wellbeing (through the lens of aging)

→ energy, mental health, sustainability over time

• Leadership in Real Life

→ decisions, system navigation, and access to the right resources

How it works

Each session is co-led by an industry expert + lived experience voice and designed for active participation and real connection.

Agenda (90 minutes)

1. Perspective (20 min)

A focused lens to reframe the topic

→ expert insight + real-world context

2. Breakout Discussions (40 min)

Small groups

→ guided prompts

→ intergenerational mix

→ honest, grounded dialogue

3. Integration (30 min)

Group share-back

→ clearer thinking

→ practical next steps

What to expect

• A room that reflects the full reality of your life—not just your role
• Thoughtful, structured conversation with diverse perspectives
• Space to process, challenge ideas, and expand your thinking
• Meaningful connections that extend beyond one session

The Model

This is a top-of-funnel ecosystem experience.

Each session stands on its own.

Together, they create a connected system.

• You enter through one conversation.
• You stay for the clarity, relationships, and momentum that build over time.

What you’ll gain

• Clearer thinking in complex situations
• Broader perspective across generations and industries
• Grounded decisions you can act on immediately
• Exposure to new ideas, tools, and resources
• Relationships built with intention—not by chance

You’re in a room with people who are:

• navigating similar pressures
• making real decisions
• open to learning and contributing

Over time, this leads to:

• trusted relationships
• new opportunities
• stronger support systems

Who this is for

C-Suite, leaders, founders, operators, grads, and students navigating multiple realities at once and looking for a space that reflects that.

Learning outcomes

You will:

• strengthen your ability to think clearly under pressure
• build awareness across aging, wellbeing, and leadership
• improve decision-making across work and life expand your perspective through intergenerational dialogue
• develop relationships that support long-term growth

Monthly Topics (2026 Series)

Each one explores a different part of the “in-between”:

May — The Cost of Holding It All Together

Burnout, pressure, invisible load

June — Money, Stability & Real-World Decisions

Finances, housing, long-term thinking

July — Caregiving & the Workforce Reality

Supporting others while leading

August — Brain Health, Energy & Performance Over Time

Sustainable leadership

September — AI, People & The Future of Work

Staying relevant, staying human

October — Transitions, Identity & The In-Between

Navigating change without clear answers

November & December — Group Choice

Topics shaped by the room

See you soon!

A portion of our proceeds will support EyeRide, a registered charity funding programs that strengthen connection, confidence, and well-being for people living with vision loss.

This year, People Ops Collective is supporting the event by managing the volunteers, ensuring that everyone sharing their time and energy feels truly valued and supported.