How to Be a Boss: 16 Tips from Orange Is the New Black

How to Be a Boss: 16 Tips from Orange Is the New Black

 

Photo collage of the cast of Orange Is the New Black. From left to right, characters Blanca Flores (Laura Gómez), Tasha "Taystee" Jefferson (Danielle Brooks), Gloria Mendoza (Selenis Leyva), Alex Vause (Laura Prepon), Piper Chapman (Taylor Schilling), and Galina "Red" Reznikov (Kate Mulgrew).So you wanna be a boss. Netflix and chill will yourself to get off the couch already. How to Be a Boss (According to Your Favorite Shows) is your excuse to binge all the TV you want. It’s career inspiration, right? As for me, chain-watching teen dramas now qualifies as research to bring you this informative series. We all win.


I’ve had day jobs that felt like prison sentences: cells (windowless cubicles), solitary confinement (no perks), wardens (terrible bosses). But I could rage-quit any time I pleased—the trundle bed in my parents’ basement is still a step up from a prison bunk. There’s no quitting in actual prison, though. That’s the point.

It’s no wonder the inmates of Litchfield Prison—the setting of Netflix’s dramedy series, Orange Is the New Black—have to find creative means to get the things they want. The result: a pretty impressive bartering ecosystem. The underground network runs the gamut from contraband cell phones to skimming panties from a sewing production line. Inadvertently, the women are learning valuable leadership skills in spite of the abysmal education program.

What they experience though, as they vie for power and Flamin’ Hot Cheetos, isn’t all that unlike being your own boss on the outside. Resources are limited. Competition is fierce. And the power struggle is real. Here are 16 lessons about being a boss, according to the inmates—and staff—of Litchfield:

1. Find a trustworthy business partner, even if she’s the one who got you into this mess in the first place.
Piper Chapman and Alex Vause hold hands against a tropical mural in an episode of Orange Is the New Black. Nicky Nichols and Lorna Morello look on in the background.
Cara Howe / Netflix
2. ...or the one who sold you out for a reduced sentence.
Taystee Jefferson and Cindy Hayes sit in a jail cell looking at each other in an episode of Orange Is the New Black.
JoJo Whilden / Netflix
3. Your first business attempt may not be your best, but we all have to start somewhere.
A guard confronts Aleida Diaz who is selling drink powder from the trunk of her car in an episode of Orange Is the New Black.
JoJo Whilden / Netflix
4. Test your idea with a focus group. What else do they have going on?
Piper Chapman holds a clipboard and speaks to two other inmates in an episode of Orange Is the New Black.
JoJo Whilden / Netflix
5. Stop working for The Man. Or the two angry women you used to date.
Natalie Figueroa sits and Linda Ferguson stands in an office, both looking off camera in an episode of Orange Is the New Black.
JoJo Whilden / Netflix
6. ...and try out consulting for a while.
Joe Caputo speaks on a prison phone in a visitor booth in an episode of Orange Is the New Black.
JoJo Whilden / Netflix
7. Seek professional advice.
Suzanne Warren sits at a desk raising her hand while a prison guard stands in the background in an episode of Orange Is the New Black.
JoJo Whilden / Netflix
8. Don’t underestimate your competition…and deal with them swiftly.
Madison Murphy speaks to Piper Chapman in an episode of Orange Is the New Black.
JoJo Whilden / Netflix
9. Find a community group of entrepreneur types. Like the mobile phone–peddling gang in C-Block.
Inmates in coats and hats stand in a line against a prison fence in an episode of Orange Is the New Black.
JoJo Whilden / Netflix
10. Get your message out through all channels available (even if the only one is a make-work jailhouse radio station).
Cindy Hayes wears headphones and speaks into a microphone in an episode of Orange Is the New Black.
JoJo Whilden / Netflix
11. …and remember that word of mouth marketing is free (commissary credit is better spent on Kit Kats and instant ramen).
Red Reznikov listens to a receiver on a prison phone in an episode of Orange Is the New Black.
JoJo Whilden / Netflix
12. Find a quiet place to work out your ideas.
Frieda Berlin sits alone in a prison cell in an episode of Orange Is the New Black.
JoJo Whilden / Netflix
13. Celebrate your little wins.
Nicky Nicholson cheers while Lorna Morello holds flowers and cries in the background in an episode of Orange Is the New Black.
Cara Howe / Netflix
14. Dress the part. How will anyone take you seriously in an orange jumpsuit?
Taystee Jefferson, seen through prison bars, wears a blouse and jacket and speaks to someone off camera in an episode of Orange Is the New Black.
JoJo Whilden / Netflix
15. Make an entrance at your next pitch. A cast says, “I mean business.”
Madison “Badison” Murphy enters a common area through prison doors in an episode of Orange Is the New Black. She is wearing an arm cast, and her hands are raised at her sides.
JoJo Whilden / Netflix
16. And finally, embrace failure. You’ve already hit rock bottom—it’s all up from here, sis.
Gloria Mendoza and Maria Ruiz, looking sullen, occupy side-by-side prison cells in an episode of Orange Is the New Black.
Cara Howe / Netflix
Feature image by Niall McClelland

About the Author

Dayna Winter is a Storyteller at Shopify, curious about the humans behind the brands and the moments that motivate them to create. She follows more dogs than humans on Instagram and isn't a real redhead.

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