In this special, live episode from the Config conference at the Moscone Center in San Francisco, Jesse James Garrett recounts his significant career co-founding Adaptive Path, pioneering foundational processes in software design, and navigating strange waters as his company was sold to Capital One. Just as he was finding his footing as a design executive coach, he got a cancer diagnosis that reshaped his view on work and life. Now on the other side of cancer, he shares what he learned.

Transcript and show notes: http://reconsidering.org

Being nice is a virtue—until it's not. Compulsively helping and staying positive to the detriment to your sanity and needs can lead to resentment and broken relationships. Dr Aziz Gazipura, author of Not Nice: Stop People Pleasing, Staying Silent, and Feeling Guilty... And Start Speaking Up, Saying No, Asking Boldly, And Unapologetically Being Yourself, wants to help us rethink what it means to be "nice".

In this episode, we talk with Dr Aziz about his personal journey from habitual people pleasing to setting boundaries and learning to communicate honestly. He shares practical guidance about how you can be kind, which is different than being nice, while still being true to yourself and your needs.

Show notes and transcript: http://reconsidering.substack.com

Americans love a hard worker. The employee who toils eighteen-hour days and eats meals on the run between appointments is usually viewed with a combination of respect and awe. But for many, this lifestyle leads to family problems, a decline in work productivity, and, ultimately, physical and mental burnout.

Bryan Robinson, author of Chained to the Desk in a Hybrid World, knows a thing or two about work addiction. He spent years hiding and repressing destructive addition to his work, which took a toll on his relationships. Today, he’s helping other break the chain including Allanis Morriset who has “greatly benefited from his guidance, experience, knowledge and wisdom on the topic of healing from what I consider to be the quietest and most insidious (and often praised) addiction in today’s times.”

Shownotes and transcript: https://reconsidering.substack.com/p/work-addiction-with-bryan-robinson

It's the Thanksgiving holiday break in the US, so we're re-broadcasting one of our favorite episodes about friendship and community, which is very timely as we approach the holiday season.

Living in isolation for two years without the support of community clarified for many of us just how nourishing and essential relationships are to us. Now that we’re starting to re-enter the world, how might we be more intentional about cultivating community?

Tina Roth-Eisenberg—Swissmiss to her hundreds of thousands of followers on the web—has thought about this deeply. She’s the founder of Creative Mornings, a global creative community in 224 cities and 67 countries that welcomes thousands of people each month to inspiring events. She’s also a master at bringing small groups together for support, and as you’ll hear in this episode, pretty clever at building new friendships.

Show notes and transcript: https://reconsidering.org/episodes/15

Katherine May first joined us on Reconsidering in 2020, during the height of the pandemic, to talk about her book Wintering: The Power of Rest and Retreat in Difficult Times. It was a timely topic and a memorable conversation as most of us were confronting one of the most challenging and isolating holidays seasons of our lifetimes.

With that moment now thankfully behind us, Katherine has returned with a new book, Enchantment: Awakening Wonder in an Anxious Age. This time around, she turns our attention to fundamental questions about how else we might live and in particular how might we find a way to reconnect in a quiet and intimate way with the natural and immediate world that surrounds us all.

It’s an important question, a wonderful book, and a rich starting point for our conversation. Thanks for listening.

Show notes and transcript: http://reconsidering.org/episodes/37

It's time to confront one of life's most certain yet most avoided topics: the end of life. While death eventually greets us all, most of us skirt around the topic and what it means for us and our loved ones. In this illuminating conversation, we aim to demystify this phase of life and empower you to approach it with a sense of preparedness and dignity.

Our guest, Shoshana Berger, serves as the Global Editorial Director at Ideo and brings a unique expertise to the table. She's worked on transformative projects with Zen Hospice to improve end-of-life experiences and is also the co-author of the pivotal book 'A Beginner's Guide to the End: Practical Advice for Living Life and Facing Death' with Dr. BJ Miller.

Together, we'll explore why people are so hesitant to talk about facing death, arm caregivers with essential knowledge for this stage, and discuss how to articulate your own wishes for this profound chapter of life.

Show notes and transcript: https://reconsidering.org/episodes/36

In the bestselling book Radical Candor, author Kim Scott laid out a simple framework for how to create, foster, and thrive in a culture that effectively gives and receives feedback—direct, clear, concise, and actionable. However, when you write a book about feedback, well, you get a lot of feedback, and indeed she did. Rather than ignoring or hiding from it, however, Kim decided to do the hard work of internalizing and processing it with the result being her latest book, Just Work. We had the pleasure of talking with Kim about just work, as well as hearing about the personal journey and experiences that motivated her to write it.

Show notes and transcript: https://reconsidering.org/episodes/35

Think your job is stressful? Try being an emergency response physician at the Mayo Clinic, one of the top hospitals in the US that sees some of the most extreme emergencies. Dr Richard Winters has been responding under pressure in chaotic situations for a long time, and it’s taught him valuable lessons about decision making and leadership.

In his book, You're the Leader. Now What?, Richard distills his knowledge into simple frameworks and practical tactics that can help us lead colleagues and communities with confidence and make decisions with clarity.

Show notes and transcript: http://reconsidering.org/episodes/34

An apology can mend old wounds, reunite people, and heal communities. Despite the potential power it can have, a good apology is hard to find. There's a simple structure to a good apology we should all have memorized along with the traits of a bad apology that will only lead us into pain and misery.

In this episode, we're going to the apology experts for guidance, Marjorie Ingall and Susan McCarthy, authors of the book “Sorry Sorry Sorry: The Case for a good apology” and founders of SorryWatch.com. Marjorie and Susan teach us how to make a good apology and give examples of bad ones. Learning this essential skill will help you preserve and strengthen the most consequential relationships in your life. What could be more important?

Like it or not, change is inevitable. Your career, relationships, body, health, mood are all in constant motion. We can fight it but it’s unproductive and leads to suffering.

Our pal Brad Stulberg is back on the show to help us look at change differently. His new book Master of Change: How To Excel When Everything Is Changing - Including You is full of deeply researched wisdom from science and philosophy that will help you become more resilient and adaptable.

Show notes and transcript: https://reconsidering.org/episodes/32