The Above Board Podcast

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

• 02:08 Beyond Money Retirement
• 03:13 Identity Crisis After Work
• 07:43 'What It's Not' Game
• 10:04 Build a Daily Routine
• 15:16 Try a Retirement Sabbatical
• 16:26 Family and Grandkids Rhythm
• 19:30 Community Without Isolation
• 21:57 Money Enables Meaning
• 22:45 Financial Therapy Talks
• 27:39 Mindfulness Shelf Method
• 30:20 Learning And Growth Plans
• 34:07 Funding Your Retirement
• 39:06 Health And Partner Alignment
• 40:43 Try It Before Retiring
• 41:25 Closing Quote

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.

• 01:45 Shorts vs Attention Spans
• 05:27 Brain Rot and Dopamine
• 06:17 News Extremes Example
• 11:12 AI Future and Jobs
• 14:52 Human Skills Still Matter
• 17:39 Life Hacks and Shortcuts
• 20:46 Motivation Content Trap
• 24:58 Viral Speed of Trends
• 26:37 Loneliness and Disconnection
• 29:48 Online Connection Paradox
• 32:23 Social Media Engagement Spiral
• 36:45 Shortcuts Versus Scenic Route
• 39:33 Hard Work and Saving Hurts
• 44:57 Dopamine and Steroid Shortcuts
• 46:53 Do More Than Watch!

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.

•  Join the waitlist here: www.copilotcommunications.com/altitude-waitlist
• Or, connect with Jess on LinkedIn here: https://www.linkedin.com/in/jessicakjensen/

 

• 00:00 Guest Intro
• 01:32 Unreasonable Hospitality
• 04:03 Radical Candor and Trust
• 05:14 Digital Presence Funnel
• 11:03 AI and Authentic Content
• 20:21 Client Process and Storytelling
• 25:03 Setting Story Boundaries
• 25:45 Vulnerability Builds Credibility
• 31:23 Authenticity Shapes Team Culture
• 34:46 Dark Social Flywheel
• 37:36 Podcasting and LinkedIn Strategy

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.

• 00:00 “Just Make $273/Day” Money Math Misses the Point
• 01:13 Hard Work Isn’t the Problem: The Real Causes of Money Stress
• 02:35 The 3 Gaps: Discipline, Awareness, and Identity
• 04:00 Gap #1 — The Discipline Gap (Knowing vs. Doing) 04:37
• Gap #2 — The Awareness Gap (Measure Your Burn Rate & Savings Rate)
• 06:34 Gap #3 — The Identity Gap (Your Money Story Shapes Your Behavior)
• 07:58 Practical 4-Step Reset: Track, Automate, Cancel, Money Date
• 10:28 Share This + Get Help at YourMoneyStory.app

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

• 01:20 Redefining Creativity
• 03:53 Pia's Personal Journey and Career Shift
• 06:03 The Impact of Creativity in Life and Work
• 07:46 Rediscovering Intuition and Overcoming Fear
• 14:49 Balancing Productivity and Presence
• 27:30 Embracing Peace and Self-Service
• 33:35 Unleashing Creativity: John's Journey
• 34:21 The Importance of Self-Integrity
• 39:04 The Power of Slowing Down
• 40:29 Creating Space for Creativity
• 42:50 Finding Flow State
• 58:32 'Welcome to The Creative Club'

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:

• Free Financial Online Course: YourMoneyStory.app
• Live Webinar on Feb. 17th - Your Money Flows: Bringing Order to Your Daily Budget 

 

• 00:09 The Real Problem: Money Psychology
• 02:14 Spending Up vs. Spending Down
• 05:21 The Power of Cash Flow Management
• 05:57 Implementing the Three-Account System
• 08:15 Join Our Free Online Course

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:

• Dad Nation Coaching & Resources: www.dadnationco.com
• The Dad Nation Podcast: Available on all major podcast platforms
• Mitchell on Instagram: @dadnationco

 

• 01:20 Early Warning Signs of Misalignment
• 04:36 The Crazy Cycle in Relationships
• 11:47 Practical Tools for Emotional Presence
• 15:08 Active Listening Techniques
• 18:55 Preparing for Presence at Home
• 26:21 Balancing Work and Family Goals
• 28:07 Understanding Masculine and Feminine Dynamics
• 30:40 The Importance of Emotional Connection in Relationships
• 35:45 Modeling Healthy Relationships for Children
• 41:04 Encouraging Emotional Awareness in Men
• 42:06 Final Thoughts and Resources

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!

• 00:08 A Game of Catch: Lessons from Softball Practice
• 01:41 Embracing Imperfection
• 02:37 Steph Curry: Practice and Perseverance
• 04:20 Applying the Lesson
• 05:31 Reflecting on Life's Blessings

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/

• 01:06 Jennifer's Career Journey
• 03:46 Estate Planning Basics
• 11:04 The Role of Trusts in Estate Planning
• 13:15 Understanding Probate
• 16:09 Avoiding Probate and Family Disputes
• 19:32 Disinheriting a Family Member
• 20:11 Will-Based vs. Trust-Based Plans
• 21:35 The Rise of AI in Legal Services
• 24:59 The Role of Financial Advisors in Estate Planning
• 26:44 The Importance of Proper Document Execution
• 29:28 State-Specific Legal Considerations

Before you start setting goals for the year, this episode takes a step back. John talks about why goal-setting often feels exhausting, not because you’re bad at it, but because you’re overloaded, and why creating space matters more than creating a perfect plan. He shares a simple but powerful approach to slowing down, getting clear on what you actually want your days to feel like, and building goals that support your life instead of running it. A great listen if you’re feeling unsure of where exactly to start this year.

• 00:00 Introduction and New Year Reflections
• 00:32 The Struggle with Goal Setting
• 01:34 Creating Space for Clear Thinking
• 03:52 Collaborative Goal Setting
• 05:38 Life Design Before Goal Setting
• 08:39 Upcoming Episodes Preview