The Corporate Dropout

Brad Didericksen

Every weekend, former geologist and community host Brad Didericksen, who has discovered millions of barrels of oil and now drills into the deep potential of people, delivers raw perspectives on the ever-evolving, purpose-driven path. Join over 500 professionals who receive his weekly reflections on what’s shifting, what’s calling, and what’s emerging next. Each newsletter combines community-sourced observations with lived experiences that resonate with today’s work-life reality. braddid.substack.com

Episodes

  1. 03/15/2025

    011 | Can I Trust Myself to Keep Going?

    This week, I’m walking and talking about something that caught me off guard. That moment I mentioned briefly last week toward the end of Episode 010 when the fire just went out. You know that feeling?…when the drive, the energy, the passion that carried you for months or years on a project or job suddenly vanishes. And you’re left wondering…what now?   For the last five months, I’ve been all-in on connecting Corporate Dropouts. * hosting 22 weekly WaterCoolerCalls, * releasing 10 episodes of the Corporate Dropout Stories Podcast, * writing in detail, 11 WaterCoolerCall Recaps, * sharing my own thoughts through 11 episodes of The Corporate Dropout audio newsletter, * sending 19 private newsletters for email subscribers, * exploring how to build a passion into a paycheck with the Wayfinders Alliance, * leading a 7-day Breakthrough to Brilliance Challenge, * and posting 75+ short form story and poetry Notes for social media. And then, a couple of weeks ago, something shifted. Like someone flipped a switch inside me, my motivation disappeared, and I was left feeling…stuck and confused.   This didn’t feel like burnout. I’ve been there before. I know what that hole looks like. This was something different. A pattern I’ve seen play out in my professional life over and over again. The highs of creation, the deep engagement, the connection…and then, suddenly, a retreat. A step back. A feeling of being trapped by my own expectations.   What’s fascinating (and frustrating) is that this time, there’s no external pressure. No boss. No financial crisis. No looming deadline. No lack of support. Just me, standing in my own way.   So I’m sitting with that. Looking at it from all angles. And trying to understand…if no one else is holding me back…what is?   If you’ve ever felt this cycle → the build-up, the breakthrough, and then the sudden stall…I think you’ll want to listen to this one.   Onward! Brad 8-) Forwarded this email? Click here to sign up Follow me on Linkedin | Facebook | Substack This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit braddid.substack.com/subscribe

  2. 03/08/2025

    010 | If I'm not my job, then who am I?

    010 | If I'm not my job, then who am I? I found myself staring at an endless stretch of road. Not thinking. Not planning. Just listening... Have you ever had a moment where you were forced to slow down, and suddenly, you didn’t know who you were anymore? That moment hit me somewhere in the middle of the Arizona desert, pedaling across America, pretending I had a grand entrepreneurial plan… …when really, I was just riding away from everything I’d known. * Meetings * Deadlines * Promotions The identity I had built around my job. At first, it felt like freedom. Then it started to feel like unraveling. Because when the noise fades and the distractions are gone, the big question rises… If I’m not my job, then who am I? I wrestled with that question on empty highways, under a vast New Mexico sky, and later, on a trip for my 40th birthday in the Utah desert. I used to think clarity came from figuring things out. But really, it comes from learning to listen * without an agenda * without solving * just… listening This week, I hit that point again. A flame inside me, the one that had been burning so bright for building a Corporate Dropout Community, sputtered and died. And I panicked. What do you do when the thing that once lit you up suddenly doesn’t? What if you’ve built something you care about, only to find yourself questioning it? What happens when the fire dies? That’s what I’m exploring in episode 010 of The Corporate Dropout. Not the resolution. Not the perfect next step. Just the honest truth of sitting with it, making space, and learning to trust myself in the quiet. Onward! Brad 8-) P.S. If you’re in this same space, feeling untethered, wondering what’s next…I’d love for you to join us at our Wednesday WaterCoolerCall. No pressure, just real conversations with people who get it. It might be exactly what you need. Register here DropTheCorporate.com This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit braddid.substack.com/subscribe

  3. 03/01/2025

    009 | When No One’s Left to Watch...

    009 | What Happens When No One’s Left to Watch...the hidden fear no one talks about with nowhere to be The summer before I left my corporate job for good, a question was keeping me up at night: What would I actually do if no one was telling me what to do? Not in a weekend retreat kind of way. I mean really…left to my own devices. Outside the structure, the expectations, the built-in purpose of a career… what would happen? I couldn’t answer that in between meetings and commutes. So, I ran an experiment. I took four weeks off, packed up my wife and kids, and drove 24 hours straight to my brother’s house. No work. No deadlines. No Housework. Just wide-open, unstructured time. At first, it was freeing. But then… something strange started to happen. * By the second week, boredom crept in. * By the third, I found myself searching for something—anything—to latch onto. * By the fourth, the answer I had been looking for hit me square in the face. And that answer? It changed everything. But it also led me straight into the next question. One I didn’t see coming. I break it all down in this week’s audio, issue 009 of The Corporate Dropout. If you’re navigating life after corporate like me, this one’s for you. Onward! Brad 8-) P.S. Ever wonder what you’d do without a title, a team, or a corporate structure to define you? Yeah. Me too. Let’s talk about it. Pop in some earbuds and let’s go on a walk and talk together. Then join me live Wednesdays at DropTheCorporate.com This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit braddid.substack.com/subscribe

    009 | When No One’s Left to Watch...

  4. 02/22/2025

    008 | I left the job… so why do I still feel trapped?

    008 | I left the job… so why do I still feel trapped? Letting go of that job doesn’t mean breaking free from its grip... If you’ve ever been hit with that “oh... so you don’t have a real job?” look from old friends, yeah, me too. And if you’ve ever asked yourself, why am I still measuring success by corporate standards even after leaving?…then you’re going to want to hear this one. Put your earbuds in. Click the play button and go for a walk with me. Listen now and then come meet others like me, figuring it out together, every Wednesday at the WaterCoolerCall. Onward! Brad 8-) DropTheCorporate.com This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit braddid.substack.com/subscribe

    008 | I left the job… so why do I still feel trapped?

  5. 02/15/2025

    007 | The fear of being discarded never left me…

    Even though I left my corporate job on my own terms, the fear of being discarded never left me. It followed me into entrepreneurship. Into consulting. Then one day, my worst fear came true - a client blindsided me by replacing me without warning. That's when I realized: This isn't about job loss. It's about identity loss. The corporate world trains us to tie our worth to our position. When that position vanishes - whether we choose to leave or not - we're left asking: Who am I now? But here's what I've learned: You can reinvent yourself. And you don't have to do it alone. → Join our next WaterCoolerCall at DropTheCorporate.com This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit braddid.substack.com/subscribe

    007 | The fear of being discarded never left me…

  6. 02/08/2025

    006 | Real Breakthroughs Demand Their Own Path...

    Stop Wasting Years on Someone Else's Path, Real Breakthroughs Demand Their Own Path... In issue 006 of The Corporate Dropout, Brad Didericksen discusses the challenge of facing a 'blank page' in life and work. Drawing from personal stories, Brad explores the paralysis that comes with starting anew and the fear of making decisions without a set path. He relates this to his journey as a corporate dropout, where following others' steps has sometimes led him in circles. Brad encourages listeners to venture into uncharted territory despite fears, inviting them to join him in the 'Breakthrough to Brilliance' challenge. This episode is a call to embrace the journey, take risks, and pursue what truly matters. DropTheCorporate.com/challenge 00:00 Introduction and Welcome 00:35 The Blank Page Problem 01:26 Overcoming Creative Blocks 03:04 The Corporate Dropout Journey 06:22 A Personal Story of Struggle 10:38 Facing New Challenges 14:27 The Call to Adventure 20:42 Invitation to Join the Challenge 22:22 Conclusion and Final Thoughts This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit braddid.substack.com/subscribe

  7. 02/01/2025

    005 | Passion or Paycheck? Why You Can't Have One Without the Other...

    In episode 005 of The Corporate Dropout, Brad Didericksen delves into the emotional and practical challenges faced by those who leave the corporate world to pursue their own passions. Brad shares his personal experiences and the internal struggles he's faced, including the conflict between chasing passion and ensuring financial stability. He emphasizes the importance of authenticity and self-discovery, urging listeners to define their own success and not just follow set formulas. Brad also highlights the significance of community support and invites listeners to join the Corporate Dropouts community for mutual inspiration and support. 00:00 Introduction and Weekly Reflection 01:41 The Corporate Dropout Journey 04:19 Balancing Passion and Financial Stability 06:44 The Ephemeral Nature of Happiness and Joy 08:02 Embracing Authenticity and Self-Discovery 15:42 The Power of Community and Support 18:15 Invitation to Join the Community This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit braddid.substack.com/subscribe

    005 | Passion or Paycheck? Why You Can't Have One Without the Other...

  8. 01/25/2025

    004 | Answering the Big Questions That Change Everything...

    This is a free preview of a paid episode. To hear more, visit thecorporateafterlife.substack.com The Community That Sparks Change, Three Types of Magic Between Serendipity and Synchronicity & Asking the Big Questions That Change Everything... In episode 004 of “The Corporate Dropout,” Brad Didericksen reflects on the week’s rich discussions in the Corporate Dropouts Community, highlighting the transformative power of serendipity and synchronicity. He shares personal stories, including life-changing questions from his uncle, his cross-country bike ride, and climbing a mountain due to a chance encounter. Brad emphasizes the importance of embracing these magical moments in pursuing one's dreams. He invites listeners to join the growing community and participate in the newly forming Dream Builders Alliance effort to collaborate on building dreams together from the inside out. DropTheCorporate.com 01:07 The Community That Sparks Change 03:06 Discovering the Magic Between Serendipity and Synchronicity 04:40 Asking the Big Questions That Change Everything 07:27 Serendipity, Synchronicity, and Transformation 08:25 #1 The Swirl: Risk and Chaos as Catalysts 10:53 #2 The Nexus: Dream Meets Opportunity 14:09 #3 The Portal: Stepping Into Expansive Potential 16:24 Building Dreams Together 17:25 Your Invitation to Join the Magic

  9. 01/18/2025

    003 | One Small Intentional Shift to Find the Corporate Exit...

    This is a free preview of a paid episode. To hear more, visit thecorporateafterlife.substack.com Feeling Down, Frustrated, and Flustered, Three Groundhog Day Reflections & One Small Intentional Shift to Find the Exit... In episode 003 of “The Corporate Dropout,” Brad Didericksen reflects on feelings of frustration, isolation, and the challenges of discoverability, sharing personal stories about early client relationships and the importance of social connections as a Corporate Dropout. Brad also explores his transition from pursuing work-life balance to finding a more fluid, stress-free approach to energy management. Additionally, he explains how he reconciled his aversion to being put 'in a box' by viewing boxes as opportunities to pour his unique self into various roles and mediums. The episode concludes with a motivational message inspired by the movie “City Slickers.” DropTheCorporate.com 01:37 When Every Day Feels Like Groundhog Day 03:29 Groundhog Reflection #1: Discoverability 08:20 Groundhog Day Reflection #2: Energy Management 11:59 Groundhog Day Reflection #3: Working in a Box 17:38 One Small Intentional Shift to Find the Corporate Exit 19:33 Your Next Breakthrough Starts with a Conversation

  10. 01/11/2025

    002 | Being Yourself Beyond Corporate in a Reflective Space with Fellow Dropouts...

    This is a free preview of a paid episode. To hear more, visit thecorporateafterlife.substack.com Going Deep at the WaterCoolerCall, Three Reoccurring Themes from Real Lived Experiences & Being Yourself Beyond Corporate in a Reflective Space with Fellow Dropouts... In episode 002 of “The Corporate Dropout,” Brad Didericksen candidly shares his personal journey of leaving the corporate world, highlighting the anxiety and financial instability that often accompany such a significant change. Brad recounts the initial reactions to issue 001 and insights from a recent WaterCoolerCall, emphasizing the importance of a financial cushion (six to 18 months recommended) and the emotional challenges of redefining identity outside corporate confines. He elaborates on his own experiences of selling assets and restructuring his life to gain financial stability. Discussing the persistent fear of failure and the need for personal growth, Brad points out the value of community support and continuous self-improvement. The episode concludes with an invitation to join the Corporate Dropouts Community for collaborative growth and support, aiming to help members transition to a self-sustained, purpose-driven professional life. DropTheCorporate.com TIMESTAMPS: 02:08 The Weekly WaterCoolerCall Check-in 03:18 Theme #1: Stuffing the Financial Cushion 10:19 Theme #2: Addressing Identity Beyond Corporate 13:40 Theme #3: Fear of Failure and Taking Risks 18:07 Corporate Dropouts and Future Plans 20:14 Personal Histories Hold Strength 23:57 Community Rhythm for Dropout Success

  11. 01/04/2025

    001 | Reclaiming Authenticity In Pursuit of Connection with Corporate Dropouts...

    This is a free preview of a paid episode. To hear more, visit thecorporateafterlife.substack.com Welcome to the first issue of The Corporate Dropout! Every weekend, I’m writing a personal, private newsletter* filled with raw, honest perspectives on what’s shifting, what’s calling, and what’s emerging next in the Corporate Dropouts space. Real. Raw. No AI. No Grammarly. 100% written by hand. I’ll explain this in a moment… Every week, I’ll share lessons learned. Mistakes made. Wisdom gained. Real perspective from real lived experience. And you are officially subscribed. *This newsletter is replacing the weekly WaterCoolerCall Recap (as our live calls will no longer be recorded). Important: To ensure you don’t miss any future issues, please add brad@dropthecorporate.com to your email safe senders list and subscribe to “The Corporate Dropout” on Apple Podcast or Spotify. 1 | The Quest for Perfect Content I spent the first six months of last year trying to figure out the perfect content to put out, to attract people to start a community. My project was called "Thoughtful Gents". I had recruited my five friends into this community platform and I just wanted to find the perfect content for them every day. What I ended up doing is, driving them all away from it cause I was driving them nuts. I wanted them to read everything I was putting out. I spent probably two to three hours a day…if not more with ChatGPT… over those six months. Everyday… having conversations about content, how to position it — and then I would find the perfect nucleus for the content, the brand, all that. Then I would put a business model around it and I would start simulating it through with ChatGPT. I would try to simulate it as far down the road, as many years down as I could — to make sure it would work before I even launched it. I did this over and over and over. 2 | Realization #1: The Power of Conversations It wasn't until I just got frustrated with it — let it go — and then started posting on Substack, that I landed on the two words, Corporate Dropouts. And then, I just started showing up to meetings like you see on my Zoom right now, it says “Brad - Corporate Dropout.” Then people started saying, “Hey, I'm a Corporate Dropout!” That taught me an important lesson, that connection over content or conversation over content, always, is my priority. But you know… …you get into Substack land, …and then you start getting subscribers, ….and then you feel like you gotta be on the hamster wheel of putting content out. And so content started winning out again, but I had my Wednesday WaterCooler chats to go have conversations and my podcasts. So I was still doing conversations, but still doing a lot of content. And they were just kind of at odds. I think what I realized again and again in December was that it was the conversations that were driving Corporate Dropouts forward. It was the conversations that people were enjoying, not the content, per se, like the recaps and the podcast write ups and all that stuff I was struggling to write. And people that were showing up to my meeting, I kept trying to do breakout rooms and provide quizzes and all this content, like to try to help them make this transition as a Corporate Dropout. They kept telling me, we don't want to be in breakout rooms, we want to be in a conversation with you. We want you to facilitate, we want you there. They wanted me to be there and be part of the conversation. Where… I was trying to let them go have all the conversations and I was trying to use my time to provide all the content. Long story short, that was my takeaway from 2024. → Always prioritize conversation over content. 3 | Realization #2: Moving Beyond Automation Now going into this next year, I thought, “okay, what do I need to learn to prioritize in 2025?” As you start to get into content creation, running a Substack, and my list of things I've committed to, I start feeling spread too thin. I automatically start going to, okay, “what can I automate?” What can I automate to do some heavy lifting so that I'm not so bogged down and I can get back to having more conversations? I got twisted off on a bunch of automation stuff. There were two podcast episodes where I used Descript to do some automation and heavy lifting with the AI. The sound came out horrible… horrible! It lost a lot of the humanity, the conversational stuff that we as humans do, the AI just took it all out. When I went back to do the podcast this week, I said, "okay, no automation and I'm going to focus on the conversation again. I listened to the podcast episode in its entirety. Then I went through myself and found the pertinent moments, the clips that were resonating with me on a deep level and surfaced those, where I was trying to use ChatGPT and Descript to do all that for me. I kept all the ums and ahs in it and all the laughter and all the awkward moments, all the silent pauses. And I'm really, really happy with the podcast episode today. It feels good to me. I'm very proud of it and I feel like I preserved the conversation over the content in that sense. What emerged from doing less automation was more authenticity. My focus in 2025, and it may take me the whole year, it may take me 10 years, I don't know... ... is to… figure out a way to continually prioritize authenticity over automation. Putting together my content strategy for 2025 and keeping that in mind... …When I first started looking at my content strategy, I started looking at “what can I automate here!?!" What can I have ChatGPT do for me or Descript or some other AI tool do for me in the whole content ecosystem I've got going on with podcasts, notes, weekly recaps, newsletters, I'm posting to LinkedIn, commenting on people's posts... Okay! What can I automate here!?! I started down that road and it just took all the authenticity out of it. So I just threw that away and started again. The last couple of days, it's just been kind of churning in the background and I've been having some ideas about how to do this. The linchpin in this whole thing is... “I'm addicted to ChatGPT “ …and I'm addicted to all these tools that we have. It's just too easy to sit down on my computer and go, "write that for me". There's a nice glowing screen with the words. "How may I help you?" “You may not help me anymore!” My pledge to myself is going to be... My newsletter this year will not be written with ChatGPT, I will not load anything into ChatGPT. The only thing I will use ChatGPT for this year is brainstorming, because it is a great brainstorming tool and partner, and if I need it to interview me to pull something out that I'm having a hard time articulating. I had to start thinking, "okay, what is my source of truth here in what I'm doing?" → My community is my source of truth... not ChatGPT If I want to go get a truth, the pattern interrupt there is, "go to your community, ask them what they think, or start a conversation with somebody in your community." As opposed to go start a conversation with ChatGPT or any other AI tool or even Google. That will maintain my focus on conversations... that's my source of truth. And then I thought, "okay, I feel this urgency to get things out sometimes." I'll have something come from deep inside and it just bubbles up and it's like, okay, it needs to come out. I thought, "well, what is the quickest way to get something from my heart through my brain into somebody else's brain and to their heart?” The quickest way I can do that, that's not sanitized, right? So it's just like me and you having a conversation right now…. I'm not sanitizing anything… I'm just saying it as it's coming along… → And this right here, this conversation is what I want to try to produce as a form of content. 4 | Realization #3: Embracing Voice Memos The quickest way for me to do that — and I had forgotten this — is to just go on a walk and start a voice memo and talk about a topic. I went out and experimented with this yesterday and I riffed for like 40 minutes on a topic and it just recorded wind because it was really windy. I couldn't use it… but that's okay. It was a good confidence builder. For my Substack newsletter, I'm going to change the name from "Corporate Dropouts" to "The Corporate Dropout." It's going to simply be a weekly newsletter of me reflecting on what's going on in the community that week… from the WaterCoolerCalls, from conversations I've had with people in the community. I'm going to let my inner compass and radar surface, the themes from those conversations instead of ChatGPT. I'll just go out on a walk and riff on it for however long. I need to shorten it to probably something more like 10 to 15 minutes. It's so easy now, on an Apple iPhone, I'm sure it's the same on a Google or an Android, you do a voice memo and it transcribes it right there for you. It doesn't have to touch an AI tool. I can go post the audio immediately and the transcription and I'm done. That's my newsletter every week. When I'm feeling that urgency, like, "Oh, the community is talking about this, I'm vibing with the community on this, it's coming up on multiple fronts, I'm seeing this theme." When I feel that urgency, I can just get it out and I can just put it out and it's there. (If you know someone I should be looking at or studying to improve my ability to freely express myself online as a community host - please point me in their direction. I would be VERY grateful) 5| Lastly, An Invitation To Hear More Corporate Dropout Stories from Cubicle Captives, Escape Schemers, Brave Leapsters, and Self-Made Sages While you’re waiting for the next issue, here are three recent Corporate Dropout Stories podcast episodes I think you might enjoy: * S1E7 | Can I Redesign My Career to Fit My Life? | Kate Thompson * S1E8 | How Do I Stop Doubting My Intuition? | Mila Popovic Geoui * S1E9 | Can Creativity Sav

  • 11 Episodes

About

Every weekend, former geologist and community host Brad Didericksen, who has discovered millions of barrels of oil and now drills into the deep potential of people, delivers raw perspectives on the ever-evolving, purpose-driven path. Join over 500 professionals who receive his weekly reflections on what’s shifting, what’s calling, and what’s emerging next. Each newsletter combines community-sourced observations with lived experiences that resonate with today’s work-life reality. braddid.substack.com

Information

  • Creator
    Brad Didericksen
  • Years Active
    2025
  • Episodes
    11
  • Rating
    Explicit
  • Copyright
    © Brad Didericksen
  • Show Website
    The Corporate Dropout