John Kennedy explains the “Arrival Fallacy;" the belief that happiness will come once you reach a milestone like a certain net worth, retirement, or business success, only to find the feeling quickly fades. He breaks down hedonic adaptation (happiness returning to a baseline) and how dopamine is more tied to anticipation and pursuit than achievement, which is why many high achievers and retirees can feel lost after “arriving.” John argues that lasting fulfillment comes from valuing the process, consistent progress, and meaningful pursuits rather than a single outcome.

On this episode of The Above Board podcast, John welcomes back Brandon Hatcher to discuss how to be “retire ready” beyond just finances, building on Brandon’s recent retire-ready checklist event and their earlier “Power of Positive Aging” episode. They explore how retirement can trigger boredom or an identity crisis, why today’s longer, healthier retirements require purpose, routine, and continued growth, and how to use the “what it’s not” exercise to define an ideal retirement (e.g., not endless TV, not doom-scrolling, not wasting time).

They highlight the importance of community, family and grandkids, health, and aligning expectations with a spouse, including trying a sabbatical or “soft retirement” before fully stopping work. They also briefly cover key financial basics: defining desired lifestyle and cash flow, building income sources, using tax-diversified accounts (taxable, IRA, Roth), and keeping taxes low.

"Your Retire Ready Checklist" Webinar: https://youtu.be/aW8zxVFUpM4

We live in a world that pushes shortcuts: quick wins, fast answers, and surface-level thinking. In this episode, John and Rich talk about why that mindset shows up in your finances and lifestyle, how it leads to frustration, and why real progress comes from slowing down and building awareness first. If you’ve ever felt stuck or tempted to skip the basics, this conversation will help you reset and refocus.

In this episode, we sit down with Jess Jensen, founder of Co-Pilot Communications, to talk about building authentic leadership in a digital world. After nearly 20 years inside Fortune 100 companies like Microsoft and Qualcomm, Jess now helps executives and founders find their voice, clarify their message, and show up online in a way that actually reflects who they are. We unpack why differences sell, how vulnerability builds credibility (not weakens it), the real role of AI in content creation, and why LinkedIn and podcasting are powerful tools for modern leaders.

How to Stay Connected with Jess & CO-Pilot Communications:

This April, Jess is launching ALTITUDE—a private LinkedIn branding cohort for small business owners on the rise. Only 8 spots. Registration opens in March.

Most financial mistakes aren’t math problems… they’re mindset problems. In this episode, John unpacks why knowledge alone isn’t what holds most people back. It’s not that you don’t understand budgeting, investing, or saving. It’s the emotions, habits, fears, and stories underneath your decisions that quietly drive the outcome. We talk about behavior vs. strategy, why self-awareness matters more than spreadsheets, and how to start making financial decisions that align with who you want to become, not just what the numbers say.

John sits down with Pia to explore the connection between creativity, conviction, and living with purpose. They talk about what it means to create from a place of clarity, how culture shapes expression, and the courage it takes to live authentically. It’s a thoughtful conversation about identity, purpose, and using your creativity in a way that reflects who you truly are.

Resources from Pia and the Kollectiv Studio:

Learn More about The Kollectiv Studio

Welcome to the Creative Club: Make Life Your Biggest Art Project

Most money stress isn’t about income, it’s about how money flows.

In this episode, John Kennedy, CFP® breaks down the difference between spending up and spending down, why budgeting often feels frustrating, and how small system changes can create real clarity. He shares a simple framework for managing cash flow and building habits that actually stick. If you’ve ever felt like you’re earning enough but still wondering where your money went, this episode will help you reset the way you think about spending.

Resources mentioned:

In this episode, John talks with Mitchell Osmond, founder of Dad Nation and host of The Dad Nation Podcast, about why success at work may not always translate to fulfillment at home. Mitchell shares practical takeaways for high-performing men who feel driven and capable, but disconnected in their relationships. It’s a grounded conversation about emotional presence, intentional leadership at home, and building real connection where it matters most.

Resources mentioned in this episode:

John shares a simple moment that turned into a bigger lesson about growth, patience, and showing up when things don’t go perfectly. Using an everyday experience, he reflects on how frustration, mistakes, and missed expectations are often part of the learning process, and not signs to quit. It’s a reminder that progress is built through consistency, resets, and staying present, even when things feel messy!

In this episode, John sits down with Estate Planning & Probate Attorney, Jennifer Bondy, to talk about the often-overlooked emotional side of money, relationships, and decision-making. Jennifer shares how our past experiences shape the way we show up financially and personally, and why awareness is the first step toward real change. It’s an honest conversation about growth, clarity, and building healthier patterns that actually stick.

Learn more about Jennifer and her work:

Website: www.bondy.law

Areas of Legal Practice: https://bondy.law/areas-of-practice/