What if the traditional markers of success, job titles, team size, and climbing the corporate ladder, aren't actually what matter most? 

In Part 1 of this two-part conversation of the Time Billionaires podcast, career coach and former Chief Product Officer Carlotta Negri Di Sanfront shares why ambitious professionals need to unlearn conventional definitions of success and replace them with values-aligned goals. 

Rebecca and Carlotta explore the gap between what we say we value and how we actually spend our time, the chemical wiring behind risk-taking and bold career moves, and why being satisfied with "good enough" might be the most underrated skill in modern leadership.

What You'll Learn:

If you want to define success on your own terms, align your daily choices with your core values, and make bold career decisions without fear of regret, this episode gives you a simple framework to audit your life and reclaim what matters most.

Timestamps:

02:15 - Why job titles and promotions don't equal success

03:45 - Simple exercise: Do your calendar and values align?

07:10 - Are career choices really irreversible?

08:31 - What "bold decisions" actually look like in practice

09:15 - Leaving corporate security for flexibility and purpose

11:43 - When to take risks versus when to be satisfied with 80%

12:50 - The dopamine-driven brain: Why some people are wired for risk

Get in Touch with Carlotta!

LinkedIn: https://www.linkedin.com/in/carlottanegridisanfront/

For more insight on making the most out of the small moments in your day, follow Rebecca and the Time Billionaires Podcast on LinkedIn!

And if you liked the show, subscribe to follow it.

In this episode of Time Billionaires, Rebecca speaks with Dan MacQueen about the life-altering brain hemorrhage that struck him at twenty-eight, the weeks he spent in a coma, and his long journey through brain injury recovery—learning to walk, talk, and fully re-enter daily life. Dan shares how surviving a traumatic brain injury reshaped his relationship with time, energy, and control.

From the moment he adopted the stoic principle “control the controllables” to the daily commitment to keep moving forward one decision at a time, Dan’s story offers a grounded, honest look at resilience after injury. Rebecca and Dan unpack the practical mental tools that helped him rebuild his life after a brain hemorrhage—and how these same strategies can help anyone navigating recovery, burnout, or major life disruption.

Together, they explore the psychological cost of rumination and regret, how to distinguish between controllable vs. uncontrollable stressors, and share a simple five-minute exercise for reducing anxiety, restoring focus, and conserving mental bandwidth.

Whether you’re recovering from a serious injury, facing an unexpected setback, or simply looking for practical tools to improve focus and productivity, Dan’s journey offers a powerful blueprint for progress over perfection, emotional resilience, and learning when to let go of what you can’t change.

Connect with Dan

Website: https://www.macqueendan.com/

LinkedIn: https://www.linkedin.com/in/macqueendan/

For simple daily mindset tips, follow Rebecca and the Time Billionaires Podcast on LinkedIn. 

And if you enjoy the show, please rate it and subscribe to follow it.

In this episode of Time Billionaires, Rebecca sits down with Jake Kennington, founder of Actively Human, to explore how deep work, intentional breaks, and clearer boundaries can help professionals reclaim their time, and their sense of fulfillment.

Jake, a former licensed structural engineer, husband, father of four, and executive coach, shares how he helps mid-career professionals overcome burnout, break free from society’s default definition of success, and design a life aligned with their values rather than a “full calendar that leads to an empty life.”

Together, Rebecca and Jake unpack:

Toward the end of the conversation, Jake explains why so many high-achieving professionals feel unfulfilled: they’re chasing someone else’s version of success. Drawing on the idea that “no one ever steps in the same river twice,” he walks through the importance of redefining success, realigning daily routines, and reconnecting with the people and work that matter most as life evolves.

Jake closes by revealing the surprising numbers behind his own journey, 25 homes, 14 cities, and 22 jobs, as a reminder that intentional choices around time, focus, and purpose are the real currency of long-term fulfillment.

Timestamps

Connect with Jake Kennington!

Website:https://activelyhuman.com/

LinkedIn: https://www.linkedin.com/in/jakekennington/

For simple daily mindset tips, follow Rebecca and the Time Billionaires Podcast on LinkedIn. 

And if you enjoy the show, please rate it and subscribe to follow it.

Why do capable, experienced people still hesitate to speak up — even when they know what they’re saying is right?

In Part 2 of this conversation on Time Billionaires, Rebecca Shaddix and Groundlings improv alum Holly Mandel explore how real confidence is built not through more preparation, perfection, or credentials, but through learning how to take up space before you feel ready.

Using principles drawn from improv (but not acting for the sake of performance), this episode breaks down why overthinking is often a stress response, how fear of “getting it wrong” quietly erodes confidence at work, and why waiting to feel confident first almost never works. Instead, Rebecca and Holly unpack how confidence grows through action, presence, and small moments of courage that compound over time.

You’ll hear practical, relatable ideas anyone can apply, whether you’re leading a team, contributing in meetings, navigating feedback conversations, or simply trying to trust yourself more in high-pressure moments:

This episode reframes confidence as something you practice, not something you wait for, and shows how everyday micromoments can quietly rewire how you show up, speak up, and lead.

This episode is especially relevant for anyone interested in confidence at work, leadership development, communication skills, and overcoming overthinking.

Timestamps

Connect with Holly 

Website: https://www.hollymandel.com/

LinkedIn: https://www.linkedin.com/in/holly-mandel/

For simple daily mindset tips, follow Rebecca and the Time Billionaires Podcast on LinkedIn. 

And if you enjoy the show, please rate it and subscribe to follow it.

In this episode of Time Billionaires, Rebecca Shaddix explores how improv training builds better leaders, more creative teams, and faster collaboration with Holly Mandel, an improv professor and corporate trainer who has worked with PwC, IBM, and Pfizer to bring improv principles into their team dynamics.

Trained at Los Angeles’s Groundlings Theater, Holly explains why the core improv principle “Yes, And” isn’t about agreement, but about creating momentum and collaboration by acknowledging someone else’s version of reality. Together, Rebecca and Holly unpack how improvisers build trust, interrupt cycles overthinking, and easy ways to unlock creativity, confidence, and adaptability with easy improv warm-ups anyone can do in 5 minutes. 

This conversation goes beyond “being present.” You’ll learn how:

They also dive into the neuroscience behind improv, explaining how shifting out of a fight-or-flight brainwave can reduce stress, spark fresh insights, and rewire your default mindset toward openness and innovation. By the end of this conversation, you’ll understand why improvisers don’t fear not knowing the next step, because they realize they already have all the tools they need to use uncertainty to create something entirely new.  

Timestamps

Connect with Holly 

Website: https://www.hollymandel.com/

LinkedIn: https://www.linkedin.com/in/holly-mandel/

For simple daily mindset tips, follow Rebecca and the Time Billionaires Podcast on LinkedIn. 

And if you enjoy the show, please rate it and subscribe to follow it.

In Part 2 of this Time Billionaires conversation, Rebecca continues her discussion with Naomi Midanik, cancer survivor and Founder at Bright Balance Psychotherapy. This episode dives deeper into the misconceptions around workplace burnout and why it's become the "most socially acceptable way to talk about mental health at work."

Naomi clarifies the true definition of burnout - emotional exhaustion, cynicism about work, and reduced effectiveness - and explains the critical test: if rest from work doesn't help your symptoms, it's likely not burnout. The conversation explores how high-achieving professionals often misdiagnose themselves, missing underlying factors like hormonal changes, unprocessed trauma, or other mental health conditions that require different treatment approaches.

The episode also tackles the trap of overthinking decisions and how our brains try to "outthink" anxiety through endless pros-and-cons lists. Naomi shares the story of Rebecca's coaching breakthrough, where 50 minutes of analysis was solved by 15 seconds of intuitive knowing. She introduces practical grounding techniques, including the proper way to do the 5-4-3-2-1 sensory exercise and simple mindfulness practices that don't require meditation.

Timestamps:

Connect with Naomi: 

Bright Balance Psychotherapy: https://www.brightbalancetherapy.com/

LinkedIn: linkedin.com/in/naomimidanik

For more insights on turning hidden minutes into your greatest asset, connect with Rebecca and the Time Billionaires Podcast on LinkedIn!

And if you love the show, subscribe to follow it.

Shout-out to Graham Duncan from East Rock Capital for the "Time Billionaires" concept that inspired our show name - originally shared on The Tim Ferriss Show.

In this episode of Time Billionaires, Rebecca speaks with Naomi Midanik, a cancer survivor and Founder at Bright Balance Psychotherapy. As a registered psychotherapist practicing in Ontario, Canada, Naomi brings a unique perspective, having spent 17 years in corporate marketing before transitioning to therapy. Her specialty focuses on professionals, entrepreneurs, and working moms navigating career challenges and workplace burnout.

The conversation explores the reality many face: being stuck in a job they hate without the immediate option to quit. Naomi introduces the concept of radical acceptance from dialectical behavior therapy, explaining how to validate your negative feelings about work while simultaneously focusing energy on what you can actually control. She shares practical strategies for making the best of difficult situations, from reframing your commute to managing difficult boss relationships.

Timestamps:

Connect with Naomi: 

Bright Balance Psychotherapy: https://www.brightbalancetherapy.com/

LinkedIn: linkedin.com/in/naomimidanik

For more insights on turning hidden minutes into your greatest asset, connect with Rebecca and the Time Billionaires Podcast on LinkedIn!

And if you love the show, subscribe to follow it.

Shout-out to Graham Duncan from East Rock Capital for the "Time Billionaires" concept that inspired our show name - originally shared on The Tim Ferriss Show.

Have you ever walked away from a discussion—about work, politics, parenting, or even something small—wondering how two reasonable people could hear the same words and leave with completely different conclusions?

After years studying how people interpret ideas, first in public policy, then in marketing, and eventually in her own family, Rebecca noticed a pattern: it’s often not what we’re saying that derails conversations, but the invisible opposite our words quietly introduce.

Whether you’re trying to advocate for something you care about, explain a decision at work, or stay connected with people who see the world differently, this episode offers an easy mental shift that can keep the people you’re interacting with engaged, curious, and willing to keep talking.

What you'll learn:

For more insights on turning small moments into your greatest asset, follow Rebecca and the Time Billionaires Podcast on LinkedIn!

And if you love the show, subscribe to follow it.

In Part 2 of this Time Billionaires episode, Rebecca continues her conversation with Oren Shai, Co-Founder of Feeling School, exploring the deeper connections between nervous system regulation, success, and emotional well-being. Oren explains the difference between parasympathetic (rest and digest) and sympathetic (fight or flight) nervous system states, offering practical techniques like elevating legs above the heart to quickly access parasympathetic responses.

The conversation takes a turn as they discuss how most people misunderstand success, operating from what Oren calls the "coffee and trauma" model, constantly medicating themselves with stimulants while chasing achievements that they believe will finally make them feel complete. Instead, he advocates for redefining success as living authentically, contributing meaningfully, and connecting with others. 

Timestamps:

If you'd like to connect with Oren, you can find Oren on LinkedIn and learn more about Feeling School here.

For more insights on turning hidden minutes into your greatest asset, connect with Rebecca and the Time Billionaires Podcast on LinkedIn!

And if you love the show, subscribe to follow it.

Shout-out to Graham Duncan from East Rock Capital for the "Time Billionaires" concept that inspired our show name - originally shared on The Tim Ferriss Show.

In this episode of Time Billionaires, Rebecca speaks with Oren Shai, an organizational psychologist, neuroscience-based executive coach, and Co-Founder of Feeling School. Oren teaches his signature methodology to high-achieving leaders, integrating cutting-edge neuroscience with depth and humanity to help them step into their most connected, alive expression of leadership at work and in life.

The conversation explores why we fight our natural energy fluctuations instead of working with them. Oren introduces his concept of the "human wave",  the natural cycles of energy that everyone experiences throughout the day, week, and seasons. He explains how fighting these cycles creates tension and shame spirals, while recognizing and supporting ourselves through them leads to better performance and well-being. Oren also shares practical somatic tools for resetting during busy workdays, including visual system resets, pattern interrupting techniques, and the importance of giving our nervous systems intentional breaks from the constant vigilance required in urban environments.

Timestamps:

If you'd like to connect with Oren, you can find Oren on LinkedIn and learn more about Feeling School here.

For more insights on turning hidden minutes into your greatest asset, connect with Rebecca and the Time Billionaires Podcast on LinkedIn!

And if you love the show, subscribe to follow it.

Shout-out to Graham Duncan from East Rock Capital for the "Time Billionaires" concept that inspired our show name - originally shared on The Tim Ferriss Show.