The Uphill Community Podcast

Tim Pecoraro

The Uphill Podcast By Tim Pecoraro Climbing toward your potential isn’t easy, but it’s worth it. The Uphill Podcast is your companion on the journey of growth, leadership, and turning dreams into reality. Inspired by The Uphill Community (TUC), each episode dives into actionable insights, powerful conversations, and transformative strategies to help entrepreneurs, leaders, and dreamers move forward. Join Tim Pecoraro and guests as they explore what it takes to choose the hard best over the easy good. If you value connection, accountability, and personal growth, this podcast will challenge and inspire you to keep climbing—one step at a time. Ready to unlock your potential? Subscribe now, and let’s move forward together!

  1. 6 MAY

    Don’t Quit in the Rut: “I’m Not Stuck Anymore” I PART 4

    Welcome to the final installment of our four-part series, Don’t Quit in the Rut. If you’ve been journeying with me through the last few episodes, thank you for sticking with it. Today, we’re not just talking about the rut—we’re declaring our exit from it. In this episode, I share why being “stuck” is often just a signal, not a sentence. I explain how to reframe your mindset (your posture) even when your circumstances (your path) haven’t changed. You’ll learn how to take back your motivation, even if the feelings aren’t there yet, and how a few intentional shifts in your environment and community can reignite your progress. I’ll also walk you through three reflection questions and offer simple, actionable steps to prove to yourself—and the world—that you’re not staying stuck. Let’s move forward. Faithfully. Episode Timeline & Highlights[1:44] – “The rut is not your identity”—recognizing that you’re not stuck, you’re invited to move forward[6:02] – Why waiting for motivation doesn’t work—and what to do instead[10:18] – “If you can’t change the path, change your posture”: How to shift your mindset in the dip[13:27] – Three powerful lifestyle changes: change your scenery, your schedule, and your circle[18:42] – How isolation whispers lies and why community is essential for lasting change[21:03] – Make your declaration: “I’m not stuck anymore”—claim it before you feel it[23:16] – The three reflection questions to re-engage with your purpose[24:40] – A final challenge: take one visible, tangible action to prove you’re not staying where you are Key Reflection QuestionsAt the end of the episode, I challenge you to dig deep with these three questions: What has this series revealed to you about your patterns or mindset?What step have you been afraid to take, but now feel ready for?Who can you invite into your journey so you don’t slip back into the rut? Sit with these. Journal them. Talk about them with someone who speaks life into your future. Tangible Action Steps to Get Out of the RutIf you’re serious about making a move, here are a few real-world actions I recommend in this episode: Change your scenery – Rearrange your space, step outside, or go somewhere new to reset your mind.Change your schedule – Add life-giving activities and cut out energy-draining habits.Change your circle – Surround yourself with people who speak vision and believe in your future.End something that drains you – Cancel that subscription, drop the bad habit, walk away from what’s stealing your focus.Start something you’ve been avoiding – Write the first page, make the phone call, open the door to progress.Ask for help or say yes (or no) to something important – These are visible signs of growth. Declare it out loud: I am not staying here.Links & ResourcesJoin the Uphill Community: https://www.uphill.communityFollow Tim on Instagram: @timpecoraroConnect on LinkedIn: Tim PecoraroSubscribe to the Newsletter: Find...

    25 min
  2. 29 ABR

    Don’t Quit in the Rut: “What’s Worth Fighting For?” I PART 3

    This week, we ask: “What’s actually worth fighting for?” Not everything deserves your time, energy, or attention. But some things? They’re worth pressing through the hard moments for. In this episode, we explore how to rethink the ruts you’re in—not always as a sign to quit, but sometimes as a sign to adjust your posture. We’ll unpack the idea that: “If you can’t change the path, change your posture.”Your posture—your mindset, your presence, your approach—can change how you experience difficulty and help you keep moving when quitting feels easier What You’ll Learn in This Episode:Why not every rut means it’s time to quitHow adjusting your posture can change your experienceThe power of remembering your ‘why’ when you feel stuckWhy breakthroughs are built in boring, repetitive placesHow to stack small wins that lead to real progress Reflection Questions:What is something you’re still passionate about—even if it’s hard right now?What’s one small thing you can do this week to move forward?Who can you ask for help, feedback, or encouragement? Weekly Challenge:Write down your “why.”Put it somewhere visible—your desk, mirror, or phone lock screen.Let it remind you what’s worth fighting for, especially when your posture needs lifting. Next Week – Final Episode: “Walking Out of the Rut”We’ll wrap up the series with practical steps to build momentum and stay out of the ruts you’ve outgrown. You won’t want to miss it. Remember: You may not control the path, but you always control your posture.Walk tall. Lean in. Keep going.

    24 min
  3. 22 ABR

    Don't Quit In The Rut: The Dip & The Lull - “This Isn’t Working Anymore” I PART 2

    In this powerful second part of our 4-week series, we dig into the experience of feeling stuck—not just in a situation, but in the Dip and the Lull, two invisible traps that can derail your progress if you’re not careful. You’ll hear the real-life story of R.U. Darby and how being “three feet from gold” taught him a lesson that could change how you approach your stuck seasons. Whether you’re thinking, “This just isn’t working anymore,” or wondering if it’s time to quit, this episode will help you pause, discern, and decide your next move. Key Segments & Takeaways:1. What Is “The Dip”?Based on Seth Godin’s book The DipThe Dip is the difficult stretch between starting something and seeing resultsMost people quit here—but the best push through and succeedDon’t confuse difficulty with a dead-end 2. What Is “The Lull”?The emotional flatline: not burnout, not fired-upFeels like silence, disengagement, or going through the motionsThe Lull is often the pause before momentum returns 3. True Story: “Three Feet from Gold”R.U. Darby gave up mining just three feet from one of the richest gold veinsHis mistake? Quitting during the DipBut he turned the lesson into a new career—and found success in insurance 4. How Close Are You?Could you be just one step from the breakthrough?Most people feel the strongest urge to quit right before the shift happens 5. Dip or Dead-End? Use DiscernmentAsk: Did I start this with purpose?Am I fatigued or misaligned?Would quitting bring regret—or peace? Reflection Questions:Where in your life do you feel like you’re in the Dip or the Lull?What is one area you’ve been tempted to walk away from recently?Is there a moment in your past when you may have quit too soon?What if your next step is only “three feet” from the result you’ve been hoping for? Weekly Challenge:Revisit something you’ve considered quitting. Ask yourself honestly: Am I just in the Dip? Or did I misread the Lull? Write down one action you’re willing to take this week instead of walking away. 🔜 Next Week (Teaser):We’re going deeper into how to fight through the right ruts. You’ll learn how to dig deeper, not just harder—and how to reconnect with your “why” when you feel like giving up. You don’t want to miss it.

    21 min
  4. 15 ABR

    Don't Quit In the Rut: "How did I get here" I Part 1

    Have you ever wondered, “How did I end up here?” You’re busy, going through the motions, but deep down, you feel stuck, drained, or disconnected. In today’s episode, I kick off a brand-new series, Don’t Quit in the Rut, and we’re starting with a powerful truth—you can’t change what you don’t recognize. That’s why we’re diving into the five most common ruts we all face, the subtle statements we tell ourselves when we’re stuck, and how to start waking up to the patterns silently limiting our growth. I’ll help you spot your rut, reflect on how long you’ve been in it, and challenge you to get honest about what it’s costing you. This conversation isn’t about shame but awareness, movement, and hope. Because you’re not broken, and you’re definitely not too far gone. Let’s name the rut and start climbing out—together. Timeline Summary[4:15] - Defining a “rut”: what it is—and what it’s not [7:22] - The Career Rut – “You’re stuck in a job that pays the bills but starves your purpose.” [9:45] - The Relationship Rut – “When conversation turns to convenience, connection starts to decay.” [12:33] - The Personal Growth Rut – “Growth doesn’t happen by accident.” [15:09] - The Faith or Purpose Rut – “Even when you’re disconnected, God hasn’t stopped calling you.” [17:42] - The Health and Energy Rut – “Your body and mind aren’t your enemies—they’re trying to alert you.” [21:01] - How we drift into ruts without even realizing it [24:05] - Four reasons we stay stuck (and how to break free) [26:48] - Your 3 questions for reflection: It’s time to write this down. [28:50] - A preview of next week’s episode: The Dip The 5 Main Types of Ruts1. The Career Rut 👉 “You’re stuck in a job that pays the bills but starves your purpose.” You’re good at what you do, but the passion is gone. You’ve “lost that loving feeling,” and it shows. You’re clocking in and out, maybe even succeeding externally—but deep down, you were made for more than a paycheck. 2. The Relationship Rut 👉 “When conversation turns to convenience, connection starts to decay.” Whether it’s a disconnected marriage or a one-sided friendship, the spark is missing. You’re going through the motions, and relationships that once brought joy now feel transactional, hollow, or strained. 3. The Personal Growth Rut 👉 “Growth doesn’t happen by accident—it happens because you pursue it.” You’ve stopped stretching, stopped learning. Life may look “fine,” but inside, you’re stagnant. You’re not thriving, just surviving, and deep down, you’ve lost your hunger for becoming better. 4. The Faith or Purpose Rut 👉 “Even when you’re disconnected, God hasn’t stopped calling you.” You believe in something greater, but it feels distant. You might go through the motions spiritually, but your soul feels dry. Whether it’s a purpose lull or a spiritual drought, it’s time to reconnect. 5. The Health & Energy Rut 👉 “Your body and mind aren’t enemies—they’re trying to alert you.” You’re tired all the time—physically, mentally, and emotionally. Maybe your habits have slipped, or you’re doing all the right things but still feel drained. This rut sneaks in when we ignore the signals and feel depleted. 3 Reflection Questions to Write DownTake a moment to journal or talk through these prompts: What rut or ruts

    30 min
  5. 8 ABR

    DREAMS: Activating Your Dream From Clarity to Commitment I PART 5

    This is the final installment in our five-part series on putting your dream to the test. If you’ve been on this journey with me, you know we’ve been digging deep into what it takes to identify your dream, clarify it, strategize around it, strengthen your support system, and build resilience. But none of that means anything unless we take action. In today’s episode, we cross the line from thinking about your dream to living it. I’m challenging you to reflect on three big ideas that will move your dream from concept to reality. Are you ready to live it? Do you have what it takes to not only chase your dream but carry it when it shows up? This conversation will stretch you, but I believe it will activate something powerful in your life. Let’s go! Main Teaching PointsClarity Without Action = StuckYou can have all the clarity in the world, but without movement, it means nothing. Action is what breaks the cycle of overthinking and hesitation.Fear Behind CommitmentSometimes, it’s not failure we fear—it’s success. Success changes everything and requires more of you. Are you holding back because of what success will require?Take One Bold, Irreversible StepMomentum is a gift—don’t waste it. What’s one action you can take this week that is visible, irreversible, and says, “I’m in”? Timeline Summary[1:40] - Kicking off with March Madness energy and life lessons from the game [4:30] - Why clarity must be backed by movement to matter [7:05] - The gold rush analogy: Don’t stop digging 12 feet from your breakthrough [11:20] - Reflecting on readiness: Would you be ready if your dream came true today? [14:10] - The fear of success and why it keeps us from committing [17:35] - The cost of playing it safe and staying in “prep mode” [20:20] - One courageous, visible step to activate your dream—what’s yours? Links & ResourcesJoin the Uphill Community: https://theuphill.communityFollow me on Instagram: @TimPecoraroConnect with me on LinkedIn: Tim Pecoraro This is your moment. You’ve done the inner work—now it’s time to let your outer life reflect that. Your dream doesn’t need to be perfect. It just needs a yes. So if this episode spoke to you, I’d love for you to follow, rate, and review the show on Apple Podcasts, Spotify, or wherever you’re listening. And, of course, share it with someone ready to activate their dream. Until next time—remember: the best things in life are uphill. Keep climbing.

    25 min
  6. 1 ABR

    Dreams: Are You Ready to Pay the Price? I PART 4

    Part four of our dream series discusses the grit and resilience it takes to keep pushing when things get tough. You’ve clarified your dream, built a strategy, and evaluated your community—but what happens when resistance shows up? That’s what we dig into in this episode. If your dream is starting to feel heavier than expected, or if you’re facing setbacks making you question your journey, this one’s for you. I’m sharing real talk on the cost of pursuing your purpose, the power of resilience, and the mindset you need when your dream demands more than you thought it would. Let’s get real about what it takes to keep going—and why it’s worth it. Timeline Summary[1:35] – A quick recap of the dream series so far: personal ownership, strategy, and community. [4:12] – What happens when your dream feels harder than expected? [7:40] – Two essential questions to ask yourself: Am I willing to pay the price? How do I handle obstacles? [11:26] – Stories of grit: J.K. Rowling, Michael Jordan, and the power of pushing through rejection. [16:50] – Turning your setbacks into fuel and lessons instead of roadblocks. [20:44] – The real cost of a dream—time, energy, discomfort—and why it’s worth it. [24:03] – How to develop a resilient mindset and keep moving, one step at a time. Links & Resources• Book recommendation: Put Your Dream to the Test by John Maxwell • Book recommendation: What Should I Do with My Life? by Po Bronson • Join the Uphill Community: theuphill.community • Follow me on Instagram: @timpecoraro • Sign up for my newsletter: Link in Instagram bio • Learn more about my leadership coaching and team development work: LinkedIn - Tim Pecoraro

    29 min
  7. 23 MAR

    DREAMS: The Company You Keep: Who’s On Your Team? I PART 3

    What if the success of your dreams isn’t just about clarity, plans, or passion — but about people? In this episode of the Uphill Community Podcast, I unpack your relationships' powerful role in pursuing your dreams. Whether building a business, pursuing a calling, or pushing yourself to the next level, one truth holds steady: you can’t do it alone. I reflect on a recent experience at Walmart HQ and how it reminded me that even the “small-town” dreamers can play big in rooms that matter — when they show up, step up, and surround themselves with the right people. We also look back at where we’ve been in this dream-defining journey and dive into the importance of your inner circle, the different roles people play in your growth, and how to honestly evaluate which relationships to hold close… and which to let go of. If you’ve ever felt stuck, unsupported, or unsure about the team around your dream, this one’s for you. Summary[0:00] - Opening thoughts on March Madness, Cinderella stories, and showing up to play at your level [4:45] - A small-town guy in big rooms: My experience at Walmart HQ [9:20] - Reminder to connect on Instagram, LinkedIn, and subscribe to the newsletter [12:08] - Recap of previous episodes in the dream series: Ownership, Clarity, Strategy [15:55] - Why hope isn’t a strategy and passion without a plan won’t cut it [18:50] - Intro to this week’s focus: The people around your dream [20:34] - The power of your inner circle and how they shape your beliefs, energy, and habits [26:10] - Who are your five? Evaluating the people you spend the most time with [28:18] - Identifying the right people: Mentors, Peers, and Supporters [34:45] - Recognizing who you may need to let go of—and why it matters [41:00] - Reflection questions and one simple challenge for this week Links & Resources• Follow me on Instagram: @timpecoraro • Connect on LinkedIn: LinkedIn Profile • Join the Uphill Community Newsletter via my IG bio • Visit: theuphill.community Closing ThoughtsRemember, the people around you can either fuel your dreams or drain them. Choose wisely. And don’t forget to do the inner work too — are you someone who uplifts others? If this episode challenged or inspired you, please take a moment to rate, follow, and review the show. Share it with someone who’s walking their own uphill journey. Your support helps us grow this community of dreamers choosing the hard best over the easy good. Until next time… keep climbing.

    28 min
  8. 15 MAR

    DREAMS: From Dreams to Reality - Your Strategy for Success! I Part 2

    Welcome back to the Uphill Community Podcast! This is Part 2 of our five-part series on proving and testing your dreams. Last week, we focused on personal ownership—defining and truly owning your dream. Today, we shift gears to strategy: Is your dream within reach? Do you have a plan to get there? A dream without a strategy is just wishful thinking. This episode is about moving from passion to execution—breaking your big vision into smaller, tangible steps and creating a roadmap to success. I share real-life examples, including how I built the Uphill Community, to show you exactly how to go from idea to action. Episode Highlights: [2:00] – The difference between a dream and a goal: why strategy is essential. [6:20] – Passion vs. Strategy: Fuel vs. Map – you need both! [10:45] – Four essential questions to assess if your dream is realistic. [14:30] – How I built an online leadership academy—breaking a big vision into small steps. [19:55] – Four steps to creating a winning strategy for your dream. [25:10] – Reflection questions to help you take action today. [27:30] – Next week’s topic: Who’s on your team? Are they pushing you forward or holding you back? Reflection Questions: 1. What skills, knowledge, or connections are missing that will help you achieve your dream? 2. What is one small action you can take today to move forward? 3. Are you willing to adjust your plan but stay committed to your dream? Links & Resources: • Join the Uphill Community: theuphill.community • Follow Tim on Instagram: @TimPecoraro • Connect on LinkedIn: Tim Pecoraro If you found this episode valuable, subscribe, rate, and review the podcast! Please share it with someone who needs a strategy to bring their dream to life. See you next week—keep climbing! 🚀

    29 min

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The Uphill Podcast By Tim Pecoraro Climbing toward your potential isn’t easy, but it’s worth it. The Uphill Podcast is your companion on the journey of growth, leadership, and turning dreams into reality. Inspired by The Uphill Community (TUC), each episode dives into actionable insights, powerful conversations, and transformative strategies to help entrepreneurs, leaders, and dreamers move forward. Join Tim Pecoraro and guests as they explore what it takes to choose the hard best over the easy good. If you value connection, accountability, and personal growth, this podcast will challenge and inspire you to keep climbing—one step at a time. Ready to unlock your potential? Subscribe now, and let’s move forward together!