Grieving The Future Self

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1. 

   12 Mar 2026 · 26 min

   Technicians, Visionaries, and the Myth of Going Solo

   To the uninitiated, "being your own boss" sounds pretty nice. Of course, the moment you go into business for yourself, you realize the wide variety of skills it requires—skills that you yourself do not possess. Skills that you don't want to and have no intention of learning. Being your own boss means balancing a host of functions within one corporate (that is, "body") system. You can address the variety of those functions in a number of ways: learn, hire, minimize, or fight like hell and hope the problem goes away on its own. Today, I'm exploring how we think about who a small business owner…

2. 

   5 Mar 2026 · 29 min

   This Process is a Mess

   I live for people explaining how they approach analysis and critique. I desperately want to know how other people think about things so I can learn to think in new ways. I want a compelling intellectual or journalistic project, but I also want to know how it was conceived and executed. I hope you enjoy hearing that kind of behind-the-scenes, too, because that's exactly what this episode is. It's a case study that I shared with the last cohort of Making Sense, my 8-week program for turning "Wait, what?!" moments into compelling content, explaining how an article I published last year came…

3. 

   19 Feb 2026 · 24 min

   How I Learn a New Skill

   So a couple of weeks ago, I downloaded Final Cut Pro and committed to learning how to use it. Despite logging hundreds, if not thousands, of hours in other video editing software, this is a big challenge. I took some time to reflect on how I make sense of learning a new skill like this—because learning new skills is an essential component of navigating the 21st-century economy. Footnotes : Read the essay version of this episode here. The Adult Learner by Malcolm Knowles " Apple Creator Studio is launching to take on Adobe " on The Verge Registration for Making Sense, an 8-week workshop…

4. 

   12 Feb 2026 · 10 min

   Wait... what?!

   You’re going along, minding your own business, and then it hits you: “Wait, what?! ” Your expectation or assumption bumps against the facts. Things aren’t the way you thought they were. It’s not always a life-altering surprise. It might be something tiny—just enough of a shock to make you rethink what you thought you knew. Today, how we resolve those “Wait, what?!” moments. I’m kicking off my 8-week workshop series, Making Sense , on March 24. This program walks you through the sensemaking process and takes you step by step through applying it to a media-making project. By the end of the 8…

5. 

   5 Feb 2026 · 54 min

   Rethinking Higher Ed for the 21st-Century Economy with Lauren Lassabe Shepherd

   It's no secret that one of my, let's say, special interests is higher education. The reasons for this are at least threefold. First, I have a kid heading off to college next year. Second, I have past regrets and future fantasies about the academy. And third, the world of work and the realm of education overlap in myriad ways. Work and education have always had a close relationship. Access to education influences access to different types of work. New forms of work influence how we organize and deliver education. I've been talking about doing an episode or a series on the intersection of…

6. 

   22 Jan 2026 · 21 min

   Circling Back

   How often do you revisit old work? Do you have systems for circling back to what you've created in the past to see how you could improve upon it or take it in a new direction? In this episode, I consider the practice of circling back through Mckenzie Wark's theory of "hacking." And I explain why my latest project, Blank Slate, is a hack and how it came to be. Footnotes: Read the essay version of this episode. Learn more about rethinking your small business status quo with Blank Slate . " Broken Links " by Tara McMullin on What Works Capital Is Dead: Is This Something Worse? by Mckenzie Wark…

7. 

   15 Jan 2026 · 30 min

   Making Intelligence Masculine Again

   I've had all the various parts of this episode swirling in my head for months—from The Paperclip Maximizer to The Great Feminization to Meta's Masculine Energy to mind-body dualism to the AI industry's role in what I propose is The Great Re-Masculinization. It is absolutely about both the present and the future of work, and whether we accept the inevitability of regressing to an imagined past or forge into a more dynamic, multi-dimensional workplace that values the contribution of all sorts of intelligence. Footnotes: Read the essay version of this episode " The Great Feminization " by Helen…

8. 

   8 Jan 2026 · 23 min

   What Else Must Be True?

   Have a big decision on your mind? Trying to choose between a bunch of good options? Today, I'm talking about decision-making… not so much how to choose, but the context of our choices. No decision gets made in a vacuum. Choices are always framed by circumstances, relationships, emotions, fears, and desires. The good news is that deepening our self-knowledge can be a great way to illuminate the context of our choices and point us in a productive direction. So I'm sharing an exercise from my new guide, Blank Slate , to unlock some of that self-knowledge as you head into the new year. Blank…

9. 

   4 Dec 2025 · 52 min

   Getting My $#*! Together: A Messy Review of 2025

   Here we are at the tail end of 2025. I just "opened" my Spotify Unwrapped... And after 3 years of burnout recovery, I’m finally ready to figure out what getting my shit together in the shadow of everything I’ve learned about myself and my needs in the last five years is going to look like. It’s tempting to assume that getting one’s shit together is a forward-looking pursuit. You know, “Here are all the things I’m going to do.” But, in my opinion, an important part of getting one’s shit together is taking stock of said shit. And so this episode is a step in that direction. I enlisted my…

10. 

    20 Nov 2025 · 30 min

    On Getting Attention, Encoding Messages, and Diving into the Deep End

    How do you get people to care about what you care about? It's a marketing question. A movement-building question. A question at the heart of the attention economy. And in one form or another, it's the question I've probably received more than any other over the last 15+ years. After all, there is no silver-bullet social media plan , no door-knocking strategy, no magical meeting agenda that produces results if the message at its heart doesn’t resonate with those receiving it. This episode is in four chapters. In the first chapter, I assure you that getting attention is actually (relatively)…