Are you one of those people who thrives off a check-list? It feels satisfying to complete things, but the satisfaction only lasts for a fleeting moment as a cleared check-list invites more tasks. It's an exhausting treadmill that inevitably gives rise to guilt and shame when we can't keep up.

Madeleine Dore, author of “I Didn’t Do the Thing Today; letting go of productivity guilt” joins us to talk about giving yourself permission to let go to focus on what really matters. We’ll talk about the difference between happiness and satisfaction, burnout and how to spot it, and how to create your own user manual so we can live a more energized and rewarding life that’s tailored just for us.

Show notes and links for this episode are at http://reconsidering.org/episodes/29

A few years ago, most of us were still heading into the office five days a week. But the pandemic changed the workplace dramatically. Most of us now work from home or are working in a hybrid environment, which has introduced challanges in our both our personal and professional lives. How do we navigate these changes?

Annie Jarvis, Vice President of Product at Indeed, joins us to talk about the future of remote work, what she’s seen working at Indeed during the pandemic, and her experiences as a leader working in a remote environment.

Show notes and links from this show: http://reconsidering.org/episodes/28

Mentorship can be a powerful force that improves life but it's often hard to come by. Most of us struggle to ask, “will you be my mentor” and may not even know what kind of support or commitment we're asking for.

Felix Lee, founder of a thriving community of mentors and mentees called ADP List, saw a lot of people losing their jobs and looking for guidance and support during the pandemic. He also recognized that the crisis had caused people to raise their hand to support those in need. At just 25 years-old, Felix founded an organization that's connecting mentors and mentees in the design and technology industry around the world and chaning the trajectory of thousands of careers.

In this episode, Felix Lee shares the power of being a mentor, the rewards of receiving mentorship and how people can come together to enrich and improve their lives.

This episode is brought to you by Indeed Design (http://indeed.design), a resource for designers, researchers, and all UX professionals who do design work that matters.

Show notes and links: http://reconsidering.org/episodes/27

High school sucks. It’s socially awkward, culturally confusing, and academically irrelevant. And though the first two might largely be an inescapable part of the teenage experience, the third is of critical concern to both the stability of society and the health of the economy. Which is why we wanted to spend some time learning more about what’s happening in the world of primary education and the ways in which it’s affecting the future of work.

In this episode, we’re joined by Connie Liu, founder of Project Invent – a non-profit who’s stated mission is to “…empower students with the 21st-century skills to succeed individually and make an impact globally, through invention… creating a generation of fearless, compassionate problem solvers.”

A graduate of both MIT and Stanford, as well as a former high-school teacher at the Nueva School in Silicon Valley, Connie has been a part of some of the most innovative educational institutions in the world. That’s given her a unique perspective about both the current state and the future of high school education. Her insights and observations highlight the challenges, opportunities, and promise of where primary education is headed and what that means for us all.

This episode is brought to you by Indeed Design (http://indeed.design), a resource for designers, researchers, and all UX professionals who do design work that matters.

As recently as a decade ago, most of Western culture dismissed meditation as a sort of “touchy-feely” pursuit with no real value.

Thanks in large part to the rise of meditation apps like Headspace however, that attitude has dramatically shifted from one of skepticism to one of curiosity heading towards broad acceptance. And just in time too as the pandemic and lockdown revealed for all of us the perilous state of the mental health system and the importance of emotional self-care.

Our guest today is Leslie Witt, the Chief Product and Designer Officer at Headspace. In this episode we’ll touch on the importance of preventive mental health as well as the challenges of taking care of yourself when you’re also struggling with the demands of being a business executive, a mom, and of course—your own full person.

Show notes and transcript: http://reconsidering.org/episodes/25

This episode is brought to you by Indeed Design, a resource for designers, researchers, and all UX professionals who do design work that matters. Learn more at http://indeed.design

John Maeda would rather be curious than afraid, despite the tectonic shifts in our world. AI—artificial intelligence—is reaching new milestones that foreshadow big changes in many careers. Some ignore what’s on the horizon, others acknowledge what’s to come but are paralyzed by fear. John Maeda takes a different approach: he just keeps reinventing himself.

John jumped from MIT where he was a professor deeply invested in technology to the Rhode Island School of Design where he shook up the traditional notions of creativity. He then went on to Kleiner Perkins Caufield & Byers where he brought design and venture capital closer together.

In this episode, John shares why he’s always starting over and reconsidering his assumptions and he lays out some of his principles for embracing career and life changes.

Show notes and links: http://reconsidering.org/episodes/24

This episode is proudly sponsored by Indeed.design.

Life is hard. We want to think that isn’t the case but again and again, the universe shows us we’re wrong. We face loss, periods of illness and infirmity, and failure. Such is the human condition and there is no escaping these essential truths. Where better to turn for comfort, insight, and wisdom than the great minds of philosophy that came before us?

Our guest, Kieren Setiya, professor of philosophy at MIT, has been on the show before and he's back to share what he's learned writing his most recent book, Life is Hard: How Philosophy Can Help Us Find our Way. Kieren’s writings have appeared in London Review of Books, The New York Times, Aeon, and elsewhere.

Kieren’s unique and thoughtful writings and teaching won’t necessarily make life any less hard but they will give you some tools, frameworks, and perspective to think differently about the challenges of life and in the end, what other kind of comfort is there?

Show notes and links: http://reconsidering.org/episodes/23

“No regrets.” You’ve heard people proclaim it as a philosophy of life. That’s nonsense, even dangerous, says Dan Pink in his latest book The Power of Regret. Everybody has regrets. They’re a fundamental part of our lives. And if we reckon with them in fresh and imaginative ways, we can enlist our regrets to make smarter decisions, perform better at work and school, and deepen our sense of meaning and purpose.

In this episode, NYTimes best selling author Dan Pink shares what he learned from his World Regret Survey that collected data from more than 16,000 people in 105 countries. Four core regrets emerged that most people have, and Dan breaks each one down. He also tells us how we can make better life decisions to avoid the most unforgiving of regrets.

Show notes and resources mentioned in this episode: http://reconsidering.org/episodes/22

Now that season 2 has wrapped, the Reconsidering team is taking a break. Season 3 is already coming together with exciting new interviews that will further illuminate the elements of a satisfying life. Kieran Setiya will be back to talk about his new book, Life is hard, which explores philosophical insights that can set us on the right path. Dan Pink will share the power of regret and how it can actually help us live a more fulfilling life. And we’re working on a special 5 episode series in partnership with our friends at Indeed that will feature inspiring people like Leslie Witt of Headspace and John Maeda.

It’s going to be an epic season and we’re launching September 20.

If you have any feedback that will help us improve the show or you just want to say hi, shoot us a message at http://reconsidering.org/contact.

We’ll be back on September 20 with season 3 of Reconsidering.

In sports, the coach plays the important role of guiding players and delivering the feedback they need to operate at their best. But in our professional lives we almost never have the guidance and support of a coach, which makes it challenging to reach our full potential and at times leaves us trapped in negative behavior cycles.

In our conversation with Ed, he unpacks the self-coaching methodology and how to shift our aggressive, self-interested warrior approach to work to that of a humble, curious sage.

Show notes and a full transcript: https://reconsidering.org/episodes/21