Learnings and Missteps

Jesse
  • 5.0 (19)
  • SELF-IMPROVEMENT
  • UPDATED WEEKLY

The Learnings and Missteps Podcast is about unconventional roads to success and the life lessons learned along the way.You will find a library of interviews packed with actionable take aways that you can apply as you progress on your career path.Through these interviews you will learn about the buttons you can push to be a better leader, launch a business, and build your influence. Find yourself in their stories and know that your path is still ahead of you.

  1. 3D AGO

    Stop Living Reactive And Start Choosing What To Optimize For

    What if your calendar isn’t the problem—your priorities are? We walk through the FIRE Box, a clear, practical framework that helps you stop living reactive and start building a week that reflects what you value. Instead of chasing every ping, you’ll learn how to Finish First on the urgent and important, and, more critically, Invest Focus Here on the important and not urgent work that drives real progress. We start by clarifying urgency and importance in plain terms so you can judge tasks without overthinking. Then we tackle the trap everyone knows too well: staying stuck in constant firefighting. From there, we shift to the growth zone—important but not urgent—and name the areas most people neglect until they explode: exercise, sleep, nutrition, and relationships. These aren’t “nice to haves.” They’re the foundation of sustained performance, and treating them like scheduled work is how you protect your energy and momentum. You’ll get simple tactics to design your week with intent: build a shortlist of priorities you want to backfill into new space, set recurring blocks you defend like any critical meeting, and start reducing and extinguishing the noise that hijacks your schedule. Along the way, we share a preview of upcoming strategies to deal with urgent-not-important and not-important-not-urgent tasks, plus tools to help you plan, commit, and execute with less stress and more agency. Ready to decide what you’re optimizing for and make your calendar serve that choice? Listen now, then share one task you’re moving into the Important-Not-Urgent box. If this helped, follow the show, leave a quick review, and send this to a friend who’s tired of being busy without progress. Get all the templates for mastering your time: https://www.depthbuilder.com/time-management-webinar-sign-up-page Download a PDF copy of Becoming the Promise You are Intended to Behttps://www.depthbuilder.com/books

    16 min

  2. JAN 22

    Learn How To Plan, Commit, And Execute Without Burning Out

    Most leaders don’t have a time problem. They have a decision making problem. We break down a self-first framework that turns chaos into clarity by separating planning, commitment, and execution into clean lanes—each with its own tool and purpose—so you can stop spinning and start finishing the work that matters. We begin with long-term planning across three human buckets: business and professional growth, personal growth, and meaningful connections. By writing goals down and scoring them on impact and effort, you’ll surface quick wins and park the heavy lifts for later. Then we build momentum with a simple plank: sequence your top items, block time for each, and commit to starting in order. No perfection required, just deliberate starts that compound. Next, we clear space with the Firebox. Finish what’s urgent and important, invest in the vital non-urgent pillars like sleep, exercise, and learning, reduce by optimizing or delegating tasks others can do, and extinguish the non-essential. We audit real life—calendar items plus unlisted chores—to see how overcommitted we are, then make bold cuts. The guiding question stays front and center: what am I optimizing for? Finally, we move to daily execution with a pre-built board that helps you focus on one day at a time, track distractions, and protect your best energy windows. We pair a planning canvas for ideas, a kanban board for commitments, and the calendar for execution, ensuring each thinking mode has its own home. Along the way, we share templates, simple tactics, and a path to accountability through a live workshop, support calls, and community. Ready to manage yourself, not time? Tap play, grab the templates, and start building momentum today. If this helped, subscribe, share with a teammate, and leave a review with one change you’re making this week. Download a PDF copy of Becoming the Promise You are Intended to Behttps://www.depthbuilder.com/books

    17 min

  3. JAN 16

    From Overbooked To In Control: A Practical Guide To Strategically Selfish Scheduling

    Ever feel like your calendar is packed but your real life lives off to the side? We dig into a simple, no-fluff system to make every commitment visible, merge the hidden to-dos with the scheduled ones, and carve out protected time for sleep, movement, and deep work—without the guilt. The result isn’t more hustle; it’s a calmer, truer plan that helps us deliver for others while finally honoring the projects and habits that matter to us. We start with a quick refresher on guilt-free future planning: capture big goals, weigh them with a practical matrix, and set a clear order. Then we hit the wall most of us face—there’s “no room” to schedule priorities because our calendars only show meetings while errands, caregiving, community roles, and recovery time sit invisible. That’s where strategically selfish scheduling comes in. We do a one-week extraction of every commitment, including the off-calendar certainties like grocery runs, bedtime, workouts, and drive time. Seeing it all at once breaks the mental negotiation that keeps us stressed and behind. From there, we run a joy vs obligation scan to expose energy leaks and choose the right lever: eliminate what no longer serves, delegate to someone better suited, automate with tools or templates, or optimize through batching and tighter boundaries. We also make the case for a single master view—overlaying personal and work—so conflicts stop ambushing the day. Finally, we place self-first blocks on the calendar before meetings, naming them clearly and protecting transitions. It’s not selfish to do this; it’s the maintenance schedule for a life that actually works and a career that compounds. If this hits home, subscribe, share it with a friend who’s stretched thin, and leave a quick review to help more people find the show. Want the time management for construction templates and workshop dates? Drop “double D” in the comments and we’ll send the link. Get the blueprint to Plan, Commit, and Execute your way into optimal performance: https://www.depthbuilder.com/time-management-webinar-sign-up-page Download a PDF copy of Becoming the Promise You are Intended to Behttps://www.depthbuilder.com/books

    23 min

  4. JAN 8

    You Can Plan Forever, But Nothing Changes Until You Commit To One Next Step

    Planning feels great until reality shows up. We’ve all sketched beautiful lists, only to watch them dissolve under meetings, family needs, and the next urgent fire. Today we turn planning into progress by committing to a simple, visual flow that respects your bandwidth and fuels momentum: brain dump, weigh impact vs effort with the DAMN Matrix, then sequence one big rock at a time. We start by pulling every idea out of your head and onto a surface—career moves, skills you want to learn, health goals, neglected projects, and relationship investments. Once the fog becomes visible, we score each item for impact and effort so the real priorities stand out. High impact and low effort rise to the top for fast wins; high impact and high effort follow to channel that momentum into meaningful outcomes. Low impact items get an honest review, so time‑sinks don’t quietly steal your focus. From there, we make the critical shift from options to order. Instead of juggling five priorities and delivering average results, we pick a single next move and “walk the plank” one task at a time. We cap Month One at eight items—two per week—to match real capacity and protect existing commitments. No date‑drama yet: sequence first, schedule later. This self‑first framework isn’t selfish for its own sake; it’s how you refill your energy and show up stronger for your team, your clients, and your family. Progress becomes visible, resentment fades, and your calendar starts reflecting what you value, not just what’s loud. If you want the Daily Domination Board and templates, drop “DD” or scan the QR to grab them. Want a deeper dive? Comment “webinar” and we’ll send the invite. Subscribe, share with a friend who needs a momentum reset, and leave a review with the one high‑impact, low‑effort win you’ll start this week. Get the blueprint to Plan, Commit, and Execute your way into optimal performance: https://www.depthbuilder.com/time-management-webinar-sign-up-page Download a PDF copy of Becoming the Promise You are Intended to Behttps://www.depthbuilder.com/books

    27 min
  5. The Long Game: Stephanie Wood on Culture and Commercial Success

    JAN 1

    The Long Game: Stephanie Wood on Culture and Commercial Success

    In this episode of the Learnings and Missteps podcast, host Jesse Hernandez converses with Stephanie Wood, co-founder and CEO of Coal Build Construction. Stephanie, with a background in organizational leadership and trauma-informed neuroscience, shares her journey from English literature major to a construction industry leader. The discussion covers the challenges and innovations in fostering a collaborative and human-centered approach within construction, debunking the myth of toughness, and promoting grit and resilience. They introduce Builders Grit, an initiative designed to improve workplace culture and performance by addressing trauma and developing leadership skills. Stephanie also highlights the importance of creating environments for flourishing and the transformative impact her company's philosophy has on the industry's future. 00:00 Introduction and Guest Overview 02:45 The Meaning Behind Co Build 04:35 Challenges and Pushback in the Industry 06:33 The Importance of Respect and Collaboration 09:41 Shoutout to LnM Family Member 11:21 Building a Collaborative Construction Business 13:31 Hiring and Leadership Development 24:09 Personal Journey and Neuroscience of Trauma 30:35 Neglect and Abuse in Subcontracting 31:11 Falling into Leadership Roles 32:45 Learning Leadership Skills 33:50 Embracing Leadership and Overcoming Resistance 38:09 The Myth of Toughness in Construction 41:37 Understanding Trauma and Recovery 45:52 Introducing Grit and Resilience Cohorts 53:58 Final Thoughts and Call to Action Get the blueprint to Plan, Commit, and Execute your way into optimal performance: https://www.depthbuilder.com/time-management-webinar-sign-up-page Download a PDF copy of Becoming the Promise You are Intended to Behttps://www.depthbuilder.com/books

    1h 4m
  6. From Broadway to Brand Building: Liberty Cogen on Reinvention

    12/25/2025

    From Broadway to Brand Building: Liberty Cogen on Reinvention

    In this episode of the Learnings and Missteps podcast, host Jesse Hernandez sits down with Liberty Kogen, a construction social media expert with an impressive background in musical theater and business. Liberty shares her journey from performing in Legally Blonde to launching a successful babysitting agency in Atlanta and eventually transitioning into social media marketing for construction companies. Throughout the conversation, they discuss themes of vulnerability, the importance of human connection, and finding fulfillment in one's career and life. Liberty emphasizes the significance of doing what makes you happy, the challenges she faced, and how she rediscovered her passion for theater under different conditions. The episode is filled with insightful and heartfelt advice, making it a must-listen for anyone seeking to navigate their own career and personal growth. Get in touch with Liberty: https://www.linkedin.com/in/libertycogen/ 00:00 Introduction and Guest Introduction 01:29 Getting to Know Liberty Kogen 01:57 The Power of Vulnerability on Social Media 09:00 Liberty's Journey in Theater 17:57 Transitioning from Theater to Business 19:21 Starting a Babysitting Agency 31:40 Advice for Aspiring Entrepreneurs 39:46 Auditioning for Kiss of the Spider Woman 41:52 The Importance of Human Connection 43:09 Returning to Atlanta and Facing an Existential Crisis 44:28 Realistic View of Pursuing Arts 50:27 Transition to Social Media for Concrete Companies 54:01 The Power of Authentic Social Media 58:37 Encouraging Vulnerability and Storytelling 01:11:37 The Promise You Are Intended to Be Get the blueprint to Plan, Commit, and Execute your way into optimal performance: https://www.depthbuilder.com/time-management-webinar-sign-up-page Download a PDF copy of Becoming the Promise You are Intended to Behttps://www.depthbuilder.com/books

    1h 19m

  7. 12/18/2025

    How To Stop Doing More And Start Doing What Matters

    Want a year that actually changes your life? We break down a practical system to stop chasing busywork and start stacking wins that matter. It starts with a guilt-free brain dump to pull every idea, project, and half-finished goal out of your head so you can judge them by outcome, not overwhelm. From there, we introduce the Damn Matrix, a four-quadrant method that ranks your work by impact and effort. High impact, low effort goes first. High impact, high effort gets planned next. Low impact items wait their turn. The real twist: we score by the value of starting, not the fantasy of finishing, so momentum arrives early and fuels the bigger climbs. Curveballs still happen, and we name them: rabid squirrels. Instead of letting emergencies swallow your day, we use the Daily Domination board to label, log, and move them through Done, then review weekly to spot patterns. When the same sources trigger fire drills, you design guardrails—clear expectations, calendar buffers, and ready-made responses. We also get honest about what overcommitment costs: sleep, exercise, and nutrition. The fix is counterintuitive and effective—shrink the number of daily targets so you stay calm, kind, and focused, even when plans shift. All of this lives inside a self-first framework: plan, commit, execute. We plan across a year, then break it into thirds and months to see where impact compounds. We commit on the calendar to protect deep work and life habits. We execute daily with a simple workflow that tracks progress and interruptions without guilt. You’ll leave with a repeatable way to prioritize for impact, start sooner, and sustain energy so results stack without burning you out. If this helps, share it with a friend who’s drowning in to-dos, hit follow for more practical tools, and leave a review telling us one high-impact, low-effort move you’ll start this week. Your next breakthrough begins with what you choose to start today. Set the stage for an amazing new year with the Self First Framework. https://calendly.com/jesse04/self-first-webinar Download a PDF copy of Becoming the Promise You are Intended to Behttps://www.depthbuilder.com/books

    28 min
  8. No More Mediocre Leadership: Wally Adamchick’s Blueprint for Better Teams

    12/11/2025

    No More Mediocre Leadership: Wally Adamchick’s Blueprint for Better Teams

    n this episode, Jesse discusses the critical role of servant leadership in the construction industry with Wally Adamchick. They explore how a servant leadership mindset, which includes being respectful, setting expectations, and supporting employees, can lead to higher employee retention and profitability. Wally also talks about the importance of developing frontline leaders and the distinction between coaching, consulting, and training. The conversation touches on the specific challenges faced by subcontractors, the growing emphasis on mental health, and the new movement in the dirt world spearheaded by leaders like Aaron Witt. Throughout the episode, they emphasize the importance of contributing to others' growth and the personal fulfillment derived from it. 00:00 Introduction and Guest Overview 02:51 The Importance of Servant Leadership 05:16 Challenges and Misconceptions in Leadership 12:26 The Role of Coaching and Consulting 18:06 Expertise and Practical Experience 23:25 Focusing on Construction Leadership 35:37 Impact of Training on Operating Income and Quality of Life 36:14 Balancing Quality of Life and Profitability in Construction 37:28 Creating a Frontline Leadership Program 38:35 The Success Triangle: Technical Competence, Management, and Leadership 40:15 Challenges and Rewards of Leadership Development 42:55 The Importance of Contribution and Service 44:53 The Role of Culture in Employee Retention and Satisfaction 52:59 The Growing Movement in the Dirt World 57:58 People in Construction Report: Insights and Data 01:02:32 Closing Thoughts and Final Message Set the stage for an amazing new year with the Self First Framework. https://calendly.com/jesse04/self-first-webinar Download a PDF copy of Becoming the Promise You are Intended to Behttps://www.depthbuilder.com/books

    1h 8m
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5
out of 5
19 Ratings

About

The Learnings and Missteps Podcast is about unconventional roads to success and the life lessons learned along the way.You will find a library of interviews packed with actionable take aways that you can apply as you progress on your career path.Through these interviews you will learn about the buttons you can push to be a better leader, launch a business, and build your influence. Find yourself in their stories and know that your path is still ahead of you.

Information

  • Creator
    Jesse
  • Years Active
    2020 - 2026
  • Episodes
    217
  • Rating
    Explicit
  • Copyright
    © 2026 Learnings and Missteps
  • Show Website
    Learnings and Missteps