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 Gerber
Rocket 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

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