by David Sherry
Learn how your favorite creators are building a brand and community around who they are. This podcast is hosted David Sherry, Founder of Death to Stock and Community organizer of Jacuzzi Club.
Language
🇺🇲
Publishing Since
5/19/2020
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April 17, 2025
<p>People launch businesses for wildly different reasons…</p><ul><li>Escape the corporate life</li><li>Make a lot of money</li><li>Create a meaningful product or service</li><li>Have flexibility in daily life</li><li>Build relationships and be seen</li></ul><p>They’re chasing something that they believe that business, as a vehicle, can give them.</p><p>But once you're in the midst of creating the business or doing the new type of work, you realize it might not always give you what you are looking for.</p><p>For one thing, <strong>you don’t achieve freedom once and check it off the list.</strong> Purpose isn’t something you discover and then never have to think about again. </p><p>Money comes and goes (often). </p><p><strong>Running a business isn’t a static experience—it’s a constantly shifting process.</strong> And the sooner we recognize that, the sooner we can start to see our business for what it actually is: something that evolves alongside of us, and even changes depending on the day, depending on how we feel, or how we’re choosing to show up.</p><p>I remember learning a tough lesson about freedom and business.</p><p>I remember walking down the street on a beautiful sunny Tuesday, heading to get some work done (this was 2018), and then realizing I was feeling completely anxious about the day ahead. </p><p>On paper, I was free. I didn’t have a boss, a fixed schedule, and no one telling me what to do. But internally, I wasn’t free. I was carrying stress, worry, and pressure with me everywhere I went. I couldn’t enjoy the sunshine, and I was feeling a bit terrible walking into the coffee shop to check my email. </p><p>I learned that external freedom—no boss, no set hours—doesn’t mean much if you’re not also free inside. I hadn’t considered that I would need to learn internal freedom as much as I would learn about creating external freedom.</p><p>That’s a tough lesson to learn, and it made me question what I was really after at work in the first place. I had forgotten where I started, or maybe I had evolved and found myself seeking something different. </p><p><strong>What Do You Want from Your Work?</strong></p><p>At different phases, our work can provide us with different things. </p><p>I often find that businesses give you exactly what you need when you need it. </p><p>Sometimes, I see business owners who really need stability in their business because their home life is having a huge crisis, and it somehow supports them through. Othertimes, a business owner is undecided, and the business forces them one way or another. </p><p>What we want and need evolves, and maybe now for you, it’s more about your creativity, your relationships or finding financial security for the first time.</p><p>The best thing you can do is check back in with your current set of needs. </p><p><strong>What do you want, </strong><strong>right now?<br></strong><br></p><p>If you look for it, you’ll find it.</p><p><strong>Instead of waiting for some distant milestone—freedom, success, purpose—</strong><strong>how can you start connecting to those things today?<br></strong><br></p><p>It exists there, however small, and if you recognize where it exists, you can put effort into expanding that part of your work and life to have more of it.</p><p>Right now, I’m really focused on my own creativity and experiencing my own creativity. My work is giving me these beautiful moments of feeling fully creative and fully alive through my work and writing and video creation. I’m seeking this out, I’m recognizing when it’s there and when it’s not. I’m allowing myself to give myself more of what I want. </p><p>You’d be surprised at how much of success (in any area) is about allowing and embracing it instead of pushing it away. </p><p>Can you allow yourself to have the freedom, purpose, or income from your business that you’ve been seeking?</p><p>What if you already have the freedom or meaning you’re after? Look for it in the small ways, or recognize what your work is telling you about what you’re truly after – like a reflection in the mirror….</p><p><strong>Your business isn’t going to </strong><strong>give</strong><strong> you freedom or purpose</strong>—you get to discover it for yourself through your business as the vehicle for your growth and exploration.</p><p>I wish I had been more grateful to have noticed my insecurity and stress in the moment, seeing how my work was telling me what I needed to hear and showing me what I needed to see. It sent me on a path of finding internal freedom after I found it externally. </p><p>I’m on another type of pathway now – one related to creativity, and I believe that I’m more aware of its gift to me now.</p>
April 15, 2025
<p>What opportunities do you have for creating more connection in your life?<br><br></p><p>A big theme of mine this year is exploring connection – how we connect with others, how we open up to connection, and what forms of communication lead to connection.</p><p>I became more seriously interested in this area of my life after spending a week in Costa Rica with a group of people with the highest quality communication skills of anyone I’ve ever spent time with. It led me to not only learn rapidly but also experience more depth and duration of connection that I typically feel day to day. </p><p>As part of this exploration, I’ve been in Art of Accomplishment Connection course with my wife. </p><p>What people really want to experience in community, with friends, and with family is depth of connection. But the number of walls we have up are numerous, and <strong>we often seek connection all of these strange ways that are </strong><strong>indirect.</strong> <br><br></p><p>People sometimes show their care through safety, fear for others, or they create connection through gossip or shared anger/struggle. </p><p><strong>Connection through Fear<br></strong><br></p><p>Instead of connecting, you use fear as a stand-in for vulnerability, and you unconsciously feel “If I worry about you, that’s me caring about you.”<br><br></p><p>This isn’t necessarily bad, but rather that it leaves you less satisfied than having a full connection experience with someone else. Often your pseudo-connection pushes others away, rather than connecting which was the point in the first place.</p><p><strong>Connection through Taking up Attention, or Hiding from it<br></strong><br></p><p>Another common stand-in to connection is allowing others to have attention but not receiving it yourself. I’m guilty of this one. </p><p>When you’re afraid of connection, you feel more comfortable putting attention and caring for others instead of allowing others to care for you. It’s like the spotlight is better on anyone else but you.</p><p><strong>Here…it feels good to give but not to receive.</strong> Connection doesn’t fully happen in this experience because two people need to be both open to giving and receiving, and you’re shut down and playing the part of connection rather than truly participating. </p><p><strong>The Quality of Our Experience<br></strong><br></p><p><strong>What surprises me most about these experiences or courses is how much </strong><strong>connection is not in the actions you take or don’t take, it’s an experience, a quality of attention that you feel.</strong> You might have experiences at holidays or after a long weekend with friends or a long dinner? Or maybe you get this experience at Church or with a local community group you volunteer with? You can attend those same events and have little connection.</p><p>Connection itself is satisfying, significantly more satisfying than many other things we spend our time doing, possibly even more than praise at work or accolades. </p><p>When you truly get deep, prolonged connection time with others it feels like having a glass of water after being very thirsty. You’re nourished, recharged.</p><p>In this way I think connection can be addicting, <a href="https://youtu.be/-Vd3aStbSiQ?si=H-RtWxbWwC41lhdi"><strong>but it’s a good addiction</strong></a>, one that is fun to experience and play in the nuances with. </p><p>Connection is something we can have more or less of every day depending on how we choose to relate to ourselves or others. That’s the big lesson.</p><p>It takes openness with yourself, and some skill re-building for you to find and create more connection in your life. </p><p>It’s worth it.</p>
April 10, 2025
<p>What if your best creative ideas show up when you let go and disappear into your work?<br><br></p><p>I’ve been testing a new approach to writing, thanks to my work with the amazing writing coach and friend Azul Torronez.</p><p>It feels entirely different. I let the writing come through me rather than forcing myself to come up with ideas. I sit down to write with no preconceived plan, and as I write I explore what’s on my mind. When I do it this way, without a specific agenda, but rather for me to discover what it is that I have to say, I’m able to feel what I write more than think it. The key way that I know that I’m writing well is when I feel it.</p><p>Strangely, when you write in this way, you read through what you wrote and think to yourself, “huh, I had no idea I wrote that?”<br><br></p><p>This type of writing feels complete in a whole different manner. The piece itself is complete, even if it needs editing. I know it’s complete because I can’t feel anything else to say.</p><p>And what I end up writing comes as a surprise, even to me!</p><p>In writing, and possibly in many other domains, my best work is when I don’t try so hard. </p><p><strong>When I surrender, It feels like I’m disappearing into the process and allowing it to happen rather than trying to make it happen.<br></strong><br></p><p>This is very difficult for those who believe that they should have a plan or every outcome.</p><p><strong>Creation as Discovery & Vulnerability<br></strong><br></p><p>What Azul taught me is that everyone gets the craft of writing backwards. Many people have an idea for a book or a topic, and then they outline it, and then they try and write their point. At least for me, what I’ve discovered is that I can do the opposite. I get curious about something and then explore it through writing. </p><p>The point of what I write arrives at the end, as does the title and as does me understanding what I have to say. I feel into different ways of communicating as I’m sunk into the writing process without being so directed. I can write something that I *know* I should write without me knowing that I should have written it moments before. It’s like pulling a thread and seeing where it leads and then getting clear signals about what you must say or share. </p><p>In this way, I’m writing as a discovery process – the ideas are ahead of me, not behind me. <strong>My best writing exists in what I discover, not in what I know.<br></strong><br></p><p>The more vulnerable I am to go places in my writing, the more I feel connected to the thread I’m following, and the better the writing feels for me. There’s a time and place for editing and categorization, and that comes after you’ve gotten out what you want to say. </p><p><strong>Going Beyond Your “Self” in Your Work<br></strong><br></p><p>Where do I pull my ideas from if not myself? How do I write things that I don’t already know that I have to say? I believe that this is where artists get it right, that there is some other aspect of consciousness, our own or others, that we can tap into that is more spontaneous. </p><p><strong>When you write from a source beyond yourself, you are able to pull ideas out from beyond your own mind’s limitations.<br></strong><br></p><p>Because I’m pulling from a source that is expanded beyond myself, my ideas themselves are more expansive and whole in their form. </p><p>If I was writing only what I already knew, I would only be writing over well-worn territory. How did Einstein come up with novel ideas in physics? He used his imagination to go beyond his own limitations, he connected to something beyond thinking. He dismissed logic and praised imagination. </p><p>The mind knows the past, and where you’ve been. <strong>As you go beyond your own thinking,</strong> your creative future is in an intuitive synthesis, connecting to a consciousness beyond yourself. When you go beyond your individual self, you connect more with the whole. </p><p>All of this has me wondering and learning more about how and where I can apply this process beyond writing. How can this same process work in speaking, recording, coaching, coding… even making decisions? </p><p>Another interesting area related to this is learning. </p><p>Have you ever just “known” something? </p><p>Or have you ever picked up a new skill set and it just “clicked?” immediately? I felt this way when I picked up a camera.</p><p>Everything about how a camera worked to me was intuitive. I didn’t *technically* understand a camera but I knew intuitively how it functioned so that I could use it well despite not having technical understanding. </p><p>Have you ever said something or seen something or created something genius that didn’t feel like it was yours at the end of it?<br><br></p><p>What if the most innovative ideas, the ones with true creative spark, show up only when I’m willing to loosen my grip and let go?<br><br></p><p>This idea I’m talking about is not new or novel. Artists across history have spoken about the muse, or how they pull from something larger from themselves to create their work. </p><p>The direct experience, however, for me is still and always completely new and novel, because it’s always surprising, spontaneous, and more enjoyable than working with your mind as the planner and control.</p><p><strong>Create Freely, Then Organize.<br></strong><br></p><p>A big takeaway from this process for me is to create first and organize later. When I let go, the raw material emerges in a way that’s more authentic and surprising. </p><p>Afterward, I can refine, categorize, and polish. You want the initial spark to come straight from the source—wherever that mysterious muse might live. Then you can edit and organize, and often it needs it. The material is raw, it’s precious, but needs refinement. </p><p><strong>There is often a need to edit and adjust after the initial spark.<br></strong><br></p><p><strong>Boundaries and constraints help as well</strong>, for example, word counts or lengths of a song. I like to use 1,500 word counts as a basic constraint. Constraints help bottle the creative stream of consciousness and help you pour it into something more structured and concrete. </p><p>You can still do “planning” just enough to create direction and constraint, and then you can let go and allow the experience or work become what it wants to be. </p><p>What I’ve noticed is this work also feels more “complete” than work that I would have otherwise tried to plan to a T. </p><p>I love this sense of completion, it’s satisfying because you feel like you reached into the depths and grabbed something and now that you’ve pulled it out, you’ve done your job and the work was the work it was meant to be at that time.</p><p>I talk a lot about enjoying your work as you do it, and there’s no better enjoyment than getting into a flow state with your work and not forcing any agenda. </p>
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