Wise Up with OpenWater

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Nov 2026

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Wisdom provides more than answers, it delivers context and connects the dots. And when you’re a professional with decades of experience, you have lots of wisdom to share. Wise up and gain insights from OpenWater experts on a range of topics each week.

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58 recent

November 3, 2026Episode 6032 min

Putting the Human Back in Hiring – with Connie "Jo" Loh

For experienced professionals, today's job search can be a frustrating and demoralizing experience, even when they have all the right qualifications. After confronting automated rejections, ghosting, and a frustratingly impersonal hiring process herself, Connie Jo Loh decided to do something about it. In this episode of Wise Up with OpenWater, “Jo” shares how her experience inspired two complementary ventures: The Workaround Collective , a community providing support and resources for job seekers, and Personally , a new platform designed to reconnect qualified candidates directly with hiring managers. We explore: The emotional toll of a prolonged job search, particularly for experienced professionals. How human connection, community, and a different approach to technology could make hiring work better for everyone. What experienced job seekers can do, even today, in the face of these realities If you're looking for your next opportunity, supporting someone who is, or responsible for hiring talent, this conversation offers a fresh perspective on a system that urgently needs rethinking. The Wise Up! Podcast is your regular dose of business wisdom, brought to you by the members of OpenWater.

October 28, 2026Episode 5944 min

Level Up: Finding Your Value in the Age of AI — with David Siegel

As artificial intelligence takes on more of the work we've traditionally been paid to do, where does that leave experienced professionals? Technology entrepreneur, author, and AI advisor David Siegel joins Wise Up to explore how AI is reshaping knowledge work, and why the greatest opportunity may lie not in doing our existing jobs faster, but in scaling our experience to become “engineers” of our own specialties. We cover topics including: Understanding what AI can and can't do, why its extraordinary computational capabilities still require human direction, and what that means for our professional value. Moving from doing the work to directing the work, as AI agents take on increasingly complex tasks and experienced professionals learn to orchestrate them toward meaningful outcomes. Becoming an “engineer” of your own expertise, using AI to build new capabilities, experiment with opportunities, and create value beyond the boundaries of your traditional role. David challenges us to think beyond productivity gains and consider what becomes possible when we combine decades of experience with powerful new tools. His message: don't just work faster. Level up. The Wise Up! Podcast is your regular dose of business wisdom, brought to you by the members of OpenWater.

October 12, 2026Episode 5839 min

Question Everything — with Michele Margolin

What if changing direction doesn’t require reinventing yourself at all? Executive and leadership coach Michele Margolin joins Wise Up to challenge some of our assumptions about career change, success, and what it means to keep evolving throughout our adult lives. Drawing on her own nonlinear journey from law to coaching, Michele argues that the goal isn’t to become someone different—it’s to bring more of who you already are into what you do next. We cover topics including: Recognizing when it may be time for a change, from feeling disengaged or simply going through the motions to realizing that an old definition of success no longer fits. Embracing the idea of “multiple adulthoods,” and giving ourselves permission to reconsider the values, priorities, and assumptions that may have guided earlier stages of our lives. Questioning our own thinking, including the inherited ideas and outside advice that can keep us stuck, and learning to define success on our own terms. Michele offers a useful alternative to the pressure to dramatically “reinvent” ourselves: keep paying attention, keep questioning, and allow the next chapter to emerge from more of who you already are. The Wise Up! Podcast is your regular dose of business wisdom, brought to you by the members of OpenWater.

September 28, 2026Episode 5742 min

A Second Act, With Wine — with Carolyn Moore

After nearly 30 years as an HR executive, Carolyn Moore is building a very different next chapter centered on wine and bringing people together. Carolyn joins Wise Up to talk about turning a longtime interest into genuine expertise, launching a new business after 50, and discovering that reinvention doesn’t necessarily require leaving everything you’ve already built behind. We cover topics including: Building a “portfolio career,” and why starting something new doesn’t have to mean making an all-or-nothing leap from your existing career. Turning passion into expertise, including Carolyn’s journey from wine enthusiast to certified sommelier, and how being a beginner again rekindled her curiosity. Taking the intimidation out of wine, from trusting your own palate to finding interesting, affordable bottles and using food, wine, and conversation to bring people together. For Carolyn, the thread connecting her two careers is surprisingly consistent: reading the room, creating connection, and designing experiences people enjoy. Her story is a reminder that your next chapter can build upon what you already know while opening the door to something entirely new. You can find Carolyn at the following links: https://www.mooretopour.com/ https://www.culturefluenceconsult.com/ The Wise Up! Podcast is your regular dose of business wisdom, brought to you by the members of OpenWater.

September 15, 2026Episode 5631 min

When Grief Comes to Work — with Patricia Bravo

Grief shows up at work in more ways than we may realize. It can follow the death of someone we love, but it can also come with divorce, health challenges, organizational change, the departure of a valued colleague, or the accumulation of smaller “micro losses” that change our experience of work. Leadership consultant and author Patricia Bravo joins Wise Up to explore what it means to build greater grief literacy, and how leaders can make a meaningful difference in shaping an empathetic workplace. We cover topics including: How grief can hide inside everyday workplace experiences, and why seemingly small losses can accumulate and affect people in ways leaders may not immediately recognize. Why acknowledgement and accompaniment matter, and how simply asking what someone needs, and showing support over time, can be more valuable than finding the perfect thing to say. How grief literacy can support both people and performance, helping leaders distinguish temporary struggles from performance problems while balancing individual needs with the work that still needs to get done. We rarely know everything someone is carrying when they show up for work. Patricia offers a practical invitation to lead with greater curiosity, acknowledge what may otherwise go unseen, and stay present when it matters. A link to Patricia’s website can be found here: https://bravoforyou.com/in-the-room The Wise Up! Podcast is your regular dose of business wisdom, brought to you by the members of OpenWater. To be a guest, DM Ken Pasternak.

September 1, 2026Episode 5540 min

Beyond the Answer: AI, Judgment and the Value of a Good Lawyer — with Matti Neustadt

AI can answer legal questions, draft contracts and even pass part of the bar exam. But as international legal advisor and tech founder Matti Neustadt explains, good legal counsel starts somewhere else: understanding a client’s business, goals and risks well enough to identify the questions they should be asking, not only answering the ones they bring to the table. In this episode, Matti explores how AI can strengthen that relationship, giving lawyers more time to apply the judgment and experience clients actually need. We cover topics including: Why professional judgment matters more in an AI-enabled world, and how an experienced lawyer can uncover risks, priorities and questions a client may not know enough to identify on their own. How AI can become a relationship accelerator, helping lawyers learn their clients’ businesses faster, maintain that knowledge over time, and focus their attention where their expertise creates the greatest value. How greater efficiency could reshape the business of law, reducing time spent gathering information and producing routine work while putting greater value on strategy, judgment and trusted counsel. AI may dramatically change how professional work gets done. But Matti makes the case that its greatest potential may be helping skilled professionals spend less time producing answers and more time understanding which questions really need to be asked. The Wise Up! Podcast is your regular dose of business wisdom, brought to you by the members of OpenWater.

August 24, 2026Episode 5444 min

Keep Coming of Age: Choosing Purpose Over Approval – with Jeff Jacobs

After 36 years in human resources and decades working with senior leaders, Jeff Jacobs has learned that many of the obstacles holding us back come down to something surprisingly basic: our reluctance to have honest conversations with each other—and ourselves. In this episode, Jeff shares lessons from his corporate career, his own professional setbacks, and a decade working with incarcerated men to explore how we can move beyond seeking approval and build lives around what matters most to us now. We cover topics including: Why fear gets in the way of honest feedback—and how curiosity and self-compassion can help us respond more constructively What it means to “keep coming of age” by moving from external validation toward a more internally defined sense of purpose How Jeff’s work in maximum-security prisons reinforced powerful lessons about compassion, humility, privilege, and our capacity for change If you’ve ever found yourself questioning what success means at a new stage of life, this conversation offers a thoughtful framework for pursuing purpose over approval. The Wise Up! Podcast is your regular dose of business wisdom, brought to you by the members of OpenWater.

July 13, 2026Episode 5345 min

Beyond Financial Planning: A More Meaningful Definition of Wealth – with Carmen Ortiz

What if financial planning isn’t really about money? In this episode, I speak with Certified Financial Planner (CFP), educator, and author Carmen Ortiz about why traditional approaches to wealth often leave people feeling unfulfilled—even when they have more than enough. Drawing on nearly four decades of experience and her own journey beyond conventional financial planning, Carmen introduces her Transcendent Financial Planning System, a framework that connects financial decisions to self-knowledge, purpose, and contribution. We cover topics including: Why our sense of self-worth often becomes entangled with our net worth—and how to break that connection The evolution from traditional financial planning to life-centered planning, and ultimately to a more transcendent approach rooted in purpose and service Why true wealth extends beyond financial capital to include our relationships, knowledge, experience, and ability to contribute to something larger than ourselves If you've ever wondered whether financial success alone is enough, this conversation offers a compelling new perspective on what it means to live a truly wealthy life. The Wise Up! Podcast is your regular dose of business wisdom, brought to you by the members of OpenWater.

June 16, 2026Episode 5233 min

Leading the Loop: How to Use AI Without Losing Your Edge – With Carl Loeb

Artificial intelligence can make us faster, more productive, and more efficient. But what happens when we start outsourcing not just our work—but our judgment? In this episode, I speak with strategist and creative leader Carl Loeb about the growing risk of "cognitive surrender" and how professionals can use AI without losing the uniquely human capabilities that create real value. Drawing on research, practical examples, and his own experience integrating AI into creative work, Carl offers a framework for staying in control while taking advantage of these powerful new tools. We cover topics including: Why deadline pressure, confirmation bias, and AI "sycophancy" can lead people to trust bad answers The difference between being "in the loop" and "leading the loop" when working with AI Why originality, judgment, taste, emotional intelligence, and point of view remain uniquely human advantages If you're trying to figure out how to use AI without becoming dependent on it, this conversation provides a thoughtful and practical roadmap. The Wise Up! Podcast is your regular dose of business wisdom, brought to you by the members of OpenWater.

June 10, 2026Episode 5132 min

The Strength Behind Success – with Denis Champagne

What if the biggest threat to your business performance isn't market conditions, competition, or technology—but the gradual decline of your own capacity? In this episode, I speak with entrepreneur, coach, and former competitive athlete Denis Champagne about the connection between physical strength, mental resilience, personal alignment, and long-term success. Drawing on more than 35 years in business and a lifetime of athletic competition, Denis shares why leaders must treat themselves as their most important asset—and why discipline ultimately matters more than motivation. We cover topics including: Why "refusing decline" begins with making—and sticking to—difficult decisions How physical strength creates the capacity to recover from setbacks, adapt to change, and sustain performance over time Why structure and discipline outperform motivation when it comes to achieving lasting personal and professional growth If you've ever felt overwhelmed, fragmented, or simply less effective than you once were, this conversation offers a practical framework for rebuilding capacity from the inside out. The Wise Up! Podcast is your regular dose of business wisdom, brought to you by the members of OpenWater.