Tag Archives: career empowerment

Do I Need Permission for Career Success?



On What’s Your Work Fit we posed this question: Do I Need Permission for Career Success?

Answering that question and others is our guest, Jillian Reilly.

Jillian has been an Executive Coach helping executives and companies to navigate disruptive and profound change and an aid worker on the frontlines of HIV/AIDS.

She is also an author of two books including her latest, The 10 Permissions: Redefining Rules of Adulting in the 21st Century.

We also discover Jillian’s answer to the question, “What’s Your Work Fit?” Her answer will resonate with many listeners.

This conversation originated as a live show on September 10, 2025. You can watch it on the What’s Your Work Fit? YouTube Channel.

About our guest:

Jillian Reilly is the author of The 10 Permissions: Redefining Rules of Adulting in the 21st Century. She lives and works in Cape Town, South Africa.

EPISODE DATE: September 19, 2025

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How Can I Give Sage Advice to My Direct Reports?



On What’s Your Work Fit we pose this viewer question: How Can I Give Sage Advice to My Direct Reports?

Our guest is Cristina DiGiacomo.

Cristina is an organizational change expert and a practical philosopher who provides CEOs and entrepreneurs guided spaces for deeper thinking. With Cristina’s help, they motivate themselves to achieve greater success with direction and determination.

This week’s lead question was posed by What’s Your Work Fit? viewer Benno:

Benno is a senior team leader for a major insurance company. He freely admits that he was not a great student of philosophy in college and did everything he could to avoid Philosophy 101, one of the handful of elective courses available to him at his state university.

Years later, Benno has done well in his career and currently leads a team of about 20 managers. The work is challenging and the demands on his team (from the C-suite) can be unrelenting. Benno’s run out of his bag of tricks–and sports metaphors–to keep his team inspired, engaged, and happy.

So, in a hat-tip to the philosophy course he avoided in college, Benno asks: how can I give sage advice to my direct reports?

During this information packed episode, Cristina also answers “what’s your work fit?’ Her personal vision surely will resonate with many career professionals.

About our guest:

Cristina DiGiacomo is an organizational change expert and practical philosopher. She lives and works in New York City.

This episode originated as a live show on August 2, 2023. You can watch the show in its entirety on the What’s Your Work Fit YouTube Channel.

EPISODE DATE: August 11, 2023

Cristina’s social media:

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Can I Reinvent Myself for Career Bliss?



On What’s Your Work Fit we pose this viewer question: Can I Reinvent Myself for Career Bliss?

Our guest is Debra Olshan Cooper.

Debra is the founder and president of Your Career Design Lab; by crafting unique stories, she helps professionals at all stages of their careers to excavate their passions and purpose and turn them into a paycheck.

This week’s lead question was posed by What’s Your Work Fit? viewer Jessica:

Jessica is a middle management executive who has performed well in whatever assignment higher ups have placed her. But sometimes, she feels like she is “just going through the motions,” bored and uninspired, and not achieving her own work fit.

Jessica asks: Can I reinvent myself for career bliss?

During this information packed episode, Debra also answers “what’s your work fit?’ Her personal vision surely will resonate with many career professionals.

About our guest:

Debra Olshan Cooper has enjoyed a multi-act executive career journey across fashion, public relations, marketing and serial entrepreneurship. She founded her executive career coaching company, Your Career Design Lab, in 2018. What is more, Debra is the host of The Passionate Professional podcast. She splits her time between New York City and Miami, Florida.

This episode originated as a live show on May 17, 2023. You can watch the show in its entirety on the What’s Your Work Fit YouTube Channel.

EPISODE DATE: May 26, 2023

Debra’s social media:

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