Thinking About a Career Pivot? Let’s Talk Strategy!

From someone who's done it SEVEN times.

Hello, hello, hello!

In Friday’s newsletter, I talked about being the best at the worst—starting at the bottom, spotting weird little opportunities no one else is taking, and exploiting the hell out of them. (Shoutout to the coffee machine at The Daily Show for being my first “in.”)

And speaking of wiggling my way in (seamless transition, right?), today we’re talking about career pivots. Because I have pivoted a lot. Seven times, to be exact. From playwriting to digital PA, to TV, to book writing, to entrepreneurship—it’s been a whole journey. If you had told me back in college that I’d be running my own business, I would have laughed (and then cried).

But here’s what I’ve learned: pivots don’t happen all at once. They’re small, strategic moves. And if you’re thinking about making a change, I’ve got some questions to help you journal through it.

Here’s a video message for you with journal prompts…