#### How do you decide when to take a huge leap in your career? What happens when your therapist thinks leaving your cushy tech job is a terrible idea—but you do it anyway? Googler-turned-comedian Sarah Cooper joins us to talk about writing satire, redefining success, and making men mad along the way.


Sarah’s latest book is called [_How to Be Successful Without Hurting Men’s Feelings: Non-Threatening Leadership Strategies for Women_](http://publishing.andrewsmcmeel.com/books/detail?sku=9781449476076), and it’s out _today_ (we got a preview copy, and it’s _so_ great). She also runs [The Cooper Review](https://thecooperreview.com/), a wildly popular satirical blog about business culture, and in 2016, her first book, [_100 Tricks to Appear Smart in Meetings_](http://publishing.andrewsmcmeel.com/books/detail?sku=9781449476052), was a bestseller.

We love Sarah because she’s funny as hell, and also incredibly open about what it’s like to trade a career in tech for the sometimes lonely—but also wildly satisfying—world of comedy.

> I have so many outlets to discover myself and who I really am, which is something that I think is just really important for a life, you know? To know you left everything on the table and you told every story that you wanted to tell and you let everyone know who you are—and you didn’t leave this world without telling everybody that.

>

> —[Sarah Cooper](http://sarahcpr.com/), comedian and author of _How to Be Successful Without Hurting Men’s Feelings_

She tells us about:

- Leaving a career at Google to perform standup and write satire all day

- What happens when people think your satire is serious

- How being a Jamaican immigrant taught her to observe people so she could fit in

- The pros and cons of being a “people-pleaser”—and how to let go of that when it stops serving you

- How keeping a “best self journal” helps her stay focused while working alone

#### Also in this episode

Sara and Katel talk about the big career choices they’ve made, and how they’ve built structures and support systems to make those careers work for them. Deets:

- Sara celebrates seven whole years without a traditional “jobby-job,” and thinks back on [Cindy Gallop’s advice](http://www.noyougoshow.com/podcast/s3e8) that working for yourself is the least risky thing you can do

- Katel tells us why she took a pay cut to run A Book Apart—and how she handles the lonely parts of working, well, _alone_

- We both definitely wear fancy blazers at all times

> I remember being so excited to work with a much smaller team and fewer people… I was like, “oh my gosh, this is going to be so great, it’s going to be just a few people, it’s going to be really nimble.” And then I realized that most of the time it was really just going to be me working kind of by myself. And it was a lot harder than I expected because there was essentially no structure unless I made it, and it took me at least a good year to kind of figure out how I was going to work, how I was going to be productive, whether I even liked that way of working enough to keep doing it.

>

> — **Katel** on trading corporate life for running an indie publishing company

Plus:

- Our friends at Harvest wan