Start with You Podcast

Ben shares a pivotal personal story about losing his job right after buying a house and starting a family, and how a surprising assignment from his friend Sid led him to discover the life-changing power of journaling.   What began as daily reflection turned into clarity, direction, and ultimately the discovery of the work that would shape his career for the next decade. You’ll learn why journaling...

What makes great leaders, CEOs, and top performers stand out? It’s not that they give everyone advice or do all the talking. It’s that they ask the best questions. In this episode, we explore Precision Questioning, a powerful communication framework from Dennis Matthies at the Stanford Center for Teaching and Learning, and how asking better questions can transform your thinking, your conversations...

Where do real opportunities actually come from? In this episode, Ben builds on Lewin’s Force Field (removing restraining forces) and Flow (momentum once you begin) to explore one of the most powerful ideas from The Defining Decade by Meg Jay: Weak Ties. Many of us get stuck because of a hidden barrier: “I don’t know anyone.” But opportunities rarely come from filling out applications alone. They o...

Take your 20s to the next level. Learn how to shift your life into a flow state that can enable exponential growth in a positive direction and connect you to other people. In Episode 1, we introduced critical reflection as a practical skill to slow down, notice what’s actually happening, and realign your actions with what matters. This episode takes that idea into daily life. Instead of asking “Di...

In this short preview, Ben introduces an upcoming episode on Flow -- the state of focused, energized engagement where work and life feel more natural and fulfilling. Using a simple story from everyday life, he explores how our experience of the same activity can shift dramatically depending on our level of engagement. In the full episode, Ben will introduce the Flow Matrix, inspired by psychologis...

Ever swear this is the week you’ll finally change - start working out, apply for jobs, quit a bad habit - only to find yourself right back where you started? Most people blame laziness or lack of motivation. Kurt Lewin would say that’s the wrong diagnosis. This episode explores Lewin’s Force Field Theory, a simple but powerful model from social psychology that explains why change is so hard and wh...

Clear thinking starts with knowing how you learn. If you’ve been listening from the beginning, you know The 20-Something Toolkit is about making better choices through clearer thinking. Up to now, we’ve focused on decisions. In this episode, we shift gears and zoom in on something even more foundational: learning how to learn. Most people ask vague questions like “What is this?” and then wonder wh...

Based on feedback from my 20-something friends, indecision is a HUGE ISSUE! Why do so many smart people so often feel stuck when facing important decisions in their 20s? This bonus episode explores three main forces that conspire to keep you stuck in the world of indecision. Ben introduces a practical tool called The Value Filter, designed to help you overcome decision paralysis caused by the Para...

What does it really mean to feel “lost” in your twenties? In this episode, Ben shares a real coaching conversation (published with permission) with a young adult navigating uncertainty about direction, identity, and next steps. Instead of rushing to pick a path, the conversation explores a different idea: building identity capital. You’ll hear how value-focused decision making shifts the focus fro...

Back when Ben was in his late 20s, he met up with his friend, Brian, at a bar. Brian was a graduate student exploring if and how to become a philosophy professor. So, Ben created a decision tree at the bar on-the-fly. Brian said: "Ben this is amazing - you should just take these decision analysis concepts and work with people in their 20s who are making big decisions about their life direction!" W...

In his book Measure What Matters, John Doerr famously called OKRs (Objectives and Key Results) a “superpower.” He was talking about companies. But what if this superpower could make an even bigger impact when applied to your life, especially in your 20s? OKRs have driven execution inside organizations for nearly 50 years, from Intel to Google to thousands of companies and nonprofits worldwide. At...

How do you know if a decision was actually good BEFORE the outcome happens? In this episode, Ben introduces a powerful framework from decision analysis, The Decision Stool. Most of us judge decisions by how things turn out. But outcomes involve luck and things beyond your control. Good decisions can lead to bad outcomes, and bad decisions can sometimes lead to good outcomes. So, if outcomes don't...

This special bonus episode introduces one of the most important ideas for anyone in their 20s: Identity Capital, a concept from The Defining Decade by Meg Jay. When you’re choosing jobs, majors, or career paths, it’s easy to get stuck in the paradox of choice: too many options, fear of choosing wrong, and hesitation to commit. But here’s the reframe: it’s not the specific job that matters most, it...

This episode tackles one of the most important thinking traps to avoid in your 20s when evaluating your decisions. Decisions and outcomes are not the same. Yet many of us confuse the two, judging the quality of a decision based solely on how things turn out afterward. If the outcome is good, we assume the decision was good. If the outcome is bad, we assume the decision was bad. This pitfall is kno...

This episode puts value-focused decision making into action and shows you how to apply this powerful tool immediately to your own life. I reflect on my own experience in my 20s to show how taking a value-focused approach helped me eliminate a potential job option. You’ll also follow Jim, a 20-something college senior navigating a job search before deciding whether to pursue an MBA, as he applies t...

This episode builds directly on the foundation of critical reflection and introduces a better way to approach decisions. Ben shows how value-focused decision making helps you go beyond the list of options on the menu of life so you can start getting more of what you actually want. Most of us make decisions by reacting to the choices in front of us, like job offers and choosing a major, without eve...

This first episode introduces why Ben created The 20-Something Toolkit to support 20-somethings beyond standard college advising, career centers, and generic life advice. It sets the foundation for the entire series. If you want to make better decisions, learn faster, and feel less stuck as you move through your 20s, this is the place to start. The episode features a real 20-something case study t...