60 Minutes with...

Oscar Trimboli | Award-Winning Author & Host of Deep Listening Podcast

What if the next chapter starts with better listening? Join us for 60 Minutes With Oscar Trimboli, award-winning author and host of Deep Listening, for a thoughtful online conversation exploring why listening may be one of the most important developmental skills of midlife. Together, we’ll discuss self-awareness, relationships, distraction, leadership, and what becomes possible when we learn to better listen to ourselves and others in the second half of life.
Date:
October 8, 2026
Time:
7:00 PM PT
Location:
Zoom

What if the next chapter starts with better listening?

Join us for 60 Minutes With Oscar Trimboli, award-winning author, keynote speaker, and host of the Apple award-winning podcast Deep Listening, for a thoughtful online conversation exploring why listening may be one of the most important and overlooked developmental opportunities of midlife.

Many people move through the first half of life responding to pressure, expectations, busyness, and momentum. Then midlife arrives and different questions begin to surface. Questions about meaning, relationships, work, identity, health, and what comes next. Yet few of us have ever been taught how to truly listen. Not just to others, but to ourselves.

Together, we’ll explore:
• why listening to ourselves becomes more important in midlife
• what distraction and busyness may be costing us
• how better listening deepens relationships and connection
• why listening shapes leadership, parenting, partnership, and decision-making
• and what becomes possible when we learn to hear ourselves more clearly

Oscar’s work has helped leaders and organizations around the world rethink communication, attention, and presence. Through his books How to Listen and Deep Listening, he has become one of the leading voices helping people move beyond surface conversation and learn how to listen beyond words.

The format is relaxed and conversational. Peter Reek will host a live discussion with Oscar, with audience questions and reflections woven throughout the evening.

Because sometimes the next chapter of life begins by listening differently.

SHIFT Into Life Presents
60 Minutes With Oscar Trimboli
Award-Winning Author & Host of Deep Listening

This day could be for you if ...

The Format: Here's how it unfolds

The Benefits

What you'll walk away with

60 Minutes with...
Oscar Trimboli | Award-Winning Author & Host of Deep Listening Podcast
$
19.95
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Facilitated by

Author • Educator • Podcaster
Oscar Trimboli is an award-winning author, speaker, and host of the Apple award-winning podcast Deep Listening. Considered one of the leading experts on workplace listening, Oscar helps leaders and organizations communicate more effectively by learning to listen beyond words. He is the author of How to Listen and has worked with companies including Google, Salesforce, Cisco, HSBC, and American Express.
Founder and CEO, SHIFT
Peter Reek is the author of SHIFT and the founder of ShiftInto.Life and The SHIFT Sessions. With decades of leadership and coaching experience, his work focuses on helping people navigate midlife as a season of clarity, meaning, and possibility. Through coaching, community, and shared language, he supports individuals in making thoughtful, deliberate choices for the second half of life.
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