How I Learn a New Skill

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 or independent worker is, what mental models have informed that identity, and how that identity plays into economic reality as work in the knowledge and creative sectors becomes increasingly hard to come by.First, we'll talk about a pair of influential books. Then, I'll take a look at recent layoffs at The Washington Post. And finally, I'll propose a different way to think about what "going solo" actually means and how it can help identify the trade-offs on offer. After the main episode, I've got a brief coda about some highly relevant Grammarly drama.P.S. Making Sense starts soon! Join me for a 8-week live workshop series that helps you turn your audience's "Wait, what?!" moments into clear and compelling content. Get all the information & register here!Footnotes:Read the essay version of this episode.Get Tara's new guide Blank Slate, a workbook for rethinking your business assumptions.The E-Myth Revisited by Michael GerberRocket Fuel by Gino Wickman and Michael C. Winters"Washington Post lays off one-third of its newsroom" via NBC News"Washington Post cuts one third of its staff" via CNN"Grammarly is using our identities without permission" by Stevie Bonifield on The Verge"Grammarly will continue using authors' identities unless they opt out" by Sean Hollister on The Verge[ UPDATE ] There have been two developments in the Grammarly story. First, it wasn’t user error (thank goodness). Superhuman did, in fact, disable the feature on Wednesday, March 11. Second, journalist Julia Angwin filed a class-action lawsuit on behalf of all those whose identities were used improperly. Superhuman’s CEO issued a statement that did include an apology. (00:00) - Company of Multiple Personalities (02:38) - Part 1: The Myth of Solo Entrepreneurship (08:21) - Part 2: There's Always the Creator Economy (There Isn't) (16:25) - Part 3: Business Beyond Money-Making (20:21) - A Code ★ Support this podcast ★

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 together. You'll hear just how messy the process (and why working through it is worth it).Footnotes:Read the article version of this episode.Check out Mia Sato's article about dupes for The Verge and her TikTok video explaining how she approached the topic."Drafting Towards the Status Quo" on What Works“Wait, What?!” on What WorksLearn more about Making Sense! ★ Support this podcast ★

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 VergeRegistration for Making Sense, an 8-week workshop series on turning "Wait, what?!" moments into compelling content, is open for registration. Program starts March 24. Learn more: whatworks.fyi/makingsense ★ Support this podcast ★

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 weeks, you’ll have made significant progress on your project and have an effective process you can use over and over again to create more compelling content.Registration for Making Sense is now open. To learn more and enroll go to: whatworks.fyi/making-sense ★ Support this podcast ★

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 higher ed and work for... years now. Today, finally, I have an initial installment in what I hope is an ongoing, if nonsequential, look at how these two pillars of modern life influence each other.Joining me to share both her professional insight and her personal journey is Dr. Lauren Lassabe Shepherd, a historian of education and the host of the American Campus Podcast.Footnotes:Read an edited transcript of this conversation.Learn more about Lauren Lassabe Shepherd.Resistance from the Right by Lauren Lassabe ShepherdThe Old is Dying and the New Cannot Be Born by Nancy Fraser"Adjunct professors deserve professional development" by Anna Conway and Thomas Tobin at Insight Higher Ed"An Army of Temps: AFT Adjunct Faculty Quality of Work/Life Report" "The Secret Lives of Adjunct Professors" by Gila Berryman at ElleJustice Lewis Power Jr. and the Powell Memo on WikipediaMore about futurist Bryan AlexanderMore about Indigenous studies scholar Sandy GrandeCheck out the American Campus Podcast:Mentioned in the Episode:"The peak and decline of US higher ed with Bryan Alexander""How to get a job at Harvard in 1860 with prabhdeep kehal"A few personal favorites:"Christianity, manhood, and college football with Hunter M. Hampton""The college bookstore racket with Katya Schwenk""The history of federal student loans with Elizabeth Tandy Shermer" (00:00) - Rethinking Higher Ed for the 21st-Century Economy with Lauren Lassabe Shepherd (00:03) - Cold Open (00:42) - Intro (53:31) - Outro ★ Support this podcast ★

A brief meditation on grief at the loss of one's future self and how often that loss passes unacknowledged.Footnotes:Read the essay version of this episode.“10:00 am” (Season 1, Episode 4) The Pitt on HBO“Ho’oponopono” on WikipediaUnlearning with Hannah Arendt by Marie Luise KnottThe Human Condition by Hannah ArendtMore from Tara:Blank Slate is a guide to rethinking your business for sustainability.Making Sense is an 8-workshop on creating compelling media through sensemaking. New cohort starts March 24. Registration opens on February 12. Learn more! ★ Support this podcast ★

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 WorksCapital Is Dead: Is This Something Worse? by Mckenzie WarkHow to Do Nothing by Jenny Odell"Make Something Heavy." by Anu AtluruCasey Newton on The Vergecast (31:50) explaining his creative system ★ Support this podcast ★

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 Andrews in Compact Magazine"Did Liberal Feminism Ruin the Workplace?" on Interesting Times with Ross Douthat (gift link)"Why does Mark Zuckerberg want more masculine energy in the corporate world? Patriarchy is still in charge" by Ashley Morgan on The ConversationArtificial Knowing by Alison AdamMark Zuckerberg's comments on free expression"GPT-5 has lost what makes GPT-4 so special... Its ability to feel emotional nuance with users" post by alan1cooldude"Did Women Ruin Everything?" on In Bed With The Right (00:00) - Rage Bait Strikes Again (02:24) - The Great Feminization (05:44) - Exploring the Great Feminization (08:49) - Mark Zuckerberg and Masculine Energy (11:36) - AI & The Great Re-Masculinization (17:02) - Mind-Body Dualism (20:37) - The Backlash (26:17) - Conclusion: Embracing a Balanced Intelligence ★ Support this podcast ★

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 Slate officially launches on January 15, but you can pre-order today at an early bird price! Learn more here.Footnotes:Read the essay version of this episode.Clues By Sam"Delightful Misdirection (Or, How to Rethink Your Options)" at What Works"Honeydew" at What Works (00:00) - Puzzles (02:02) - The Challenge of Making Decisions (05:23) - The Important of Self-Knowledge (07:07) - Needs & Priorities: An Excerpt from Blank Slate (09:11) - Business Strategy Is Like Algebra? (14:21) - Exercise: Needs & Priorities (20:12) - One More Thing ★ Support this podcast ★

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 husband, Sean, to do a bit of a year-end review. This review is in no way comprehensive. It’s a wee bit stilted. And if it sounds a little forced, it is—because getting your shit together takes doing some things that you’re out of practice with.This episode is simply an exercise in remembering. It’s that first awkward practice that you just have to get through at the beginning of a new season. Getting my shit together is very much a work in progress, not a grand announcement of some new project or direction for my work. Maybe that will come. Maybe it won’t. My main objective is to feel like I’m steering the ship again.Heads up: this will be my final new episode of 2025. I'll be back on January 8 with fresh ideas, stories, and ways to rethink work.This episode contains repeated uses of the word "shit," so if that's something you'd prefer not to hear. Skip this one!Footnotes:YellowHouse.Media (the podcast & video production agency that Sean and I run)Waxwing BooksRemnant Population by Elizabeth MoonI Who Have Never Known Men by Jacqueline HarpmanThe Wall by Marlen Haushofer"No Good Art Comes From Greed" by Kelsey McKinney on DefectorAlchemised by SenLinYu (00:00) - 2025 Review (00:35) - Introduction (06:08) - Reflecting on 2025 (08:09) - What was unexpectedly fun or easy for you this year? (14:42) - What did you create this year? (19:06) - What habits or systems supported your well-being? (34:06) - What did you read, watch, or listen to that stuck with you? (45:02) - What was your favorite word this year? (46:51) - What are you looking forward to in 2026? (50:28) - Last Thing ★ Support this podcast ★