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What Chelsea Handler and Issa Rae want women to know about getting ahead

Two funny ladies get serious about how women can help each other succeed in the workplace.
Image: Issa Rae and Chelsea Handler
Issa Rae and Chelsea Handler at a LinkedIn panel discussion on March 7, 2018. LinkedIn

As we celebrate Women's History Month, many of us look to honor the achievements of historical trailblazers who have gone before us — or even the various women in our life — but we likely also acknowledge celebrities who have made a difference as well. Ahead of International Women's Day, I made a mental list of acclaimed women I’ve never met who inspire me, ranging from Gilda Radner to Frida Kahlo to Parkland survivor and activist Emma González. Chelsea Handler, the talk show host, actor, comedian and writer wasn’t on the list; nor was the actor, writer, director, producer and "Insecure" creator Issa Rae. Until I heard both women speak in person.

LinkedIn hosted a panel featuring both stars in Los Angeles earlier this month. The setting was casual, intimate and focused on one topic: success. Handler and Rae’s generous, candid and often hilarious advice delivered to a room packed with eager listeners not only landed them on my list of incredible women to learn from, it gave me ideas I could start acting on right away. Here’s a look at some of their most powerful insights that, though aimed at women, can be implemented by anyone at any stage in their career.

Now that the door is open for me, [I’m focused on] making sure that door stays open so that other people can walk through it and tell their stories.

Issa Rae

Don’t Tie Your Plans To Timelines

When setting goals it can be tempting to get very specific about timing, but neither Rae nor Handler find setting end-dates all that useful.

“When I was like 19, I told myself at 21, I’m about to get an Oscar, but I didn’t have a script,” Rae said to a roar of a laughter. “But after that I was like, ‘I’m just setting myself up for disappointment.’ So, I don’t like to specifically plan things and say ‘this will happen in two years or five years’; but I do like to put things out there because once I say it to myself, it’s on my mind.”

Handler added that she’s not a planner in the slightest, and often has no idea what she’s even doing the next day. That may be an exaggeration, but Handler swears that she’s “just not goal-oriented in that way. I’m impulsive. I like that I live my life like that and that I don’t have big plans.”

Image: Chelsea Handler
Chelsea HandlerLinkedIn

Overcome Impostor Syndrome By Dissing Luck and Praising Yourself —Out Loud

Even pioneering women as widely admired as Handler and Rae deal with impostor syndrome. But they’re pretty good at fighting it.

Sometimes you feel like ‘How the [heck] did I fake this that whole time? And conversely you can also feel like, ‘I am proud of myself. I do belong here.’

“Just because you’re successful doesn’t mean you feel like you belong,” Handler poignantly remarked. “Impostor syndrome works both ways: sometimes someone you admire doesn’t want to do a project with you and you take it personally like, ‘oh maybe I’m not part of this club that I thought I was a part of. Sometimes you feel like ‘How the [heck] did I fake this that whole time? What is my talent? What do I have to offer?’ And conversely you can also feel like, ‘I am proud of myself. I do belong here.’ It’s about making that narrative more of the latter than the beginning and saying it to yourself out loud.”

Taking ownership of our achievements rather than attributing our successes to luck is also a powerful tool.

“I know how hard I work,” said Rae. “I have paid certain dues and I know that this is what I want to do, so there is no one that is going to convince me that I don’t belong here, or that I am lucky to be here. I have a lot of conversations with myself, and talk to myself a lot and answer to myself. I try to be as positive as I can in convincing myself that I deserve this.”

Let Fear and Doubt Motivate You

We often look at fear and doubt as obstacles to be overcome. But what if we look at them as platforms to push off of? It works for Rae.

I’m motivated by fear, by [the thought that] I’m never going to have this opportunity again,” Rae said. “Or that people are going to figure that I don’t have [expletive] to say, so I have to say it all now while people are still listening. I love to prove people wrong, for people to doubt me.”

Put Your Dreams Out Into The Universe (Maybe By Making A Vision Board)

Rae was not a believer in the power of vision boards when she made hers “drunk one night” years ago, and notes that she put some “stupid stuff” on hers, including a hair color she hoped to have someday. The board, decorated with magazine pictures Rae cut out “like she was in second grade”, was hidden away for years. But recently Rae pulled it out to find that everything she’d put on the board “had happened.”

“It’s so true,” chimed Handler. “You put it out there, what you want — there’s a powerful energy in that. And I’m not into any of that [stuff] but I know it works. You just have to keep remembering to do it.”

Being Authentic Comes Before Money (Eventually)

Handler noted that when she first moved to Los Angeles as a teenager, her primary goals were to be famous and to have money. “I wanted a cleaning lady!” she cried. Certainly she’s achieved both fame and money (and probably has a housekeeper or three), but her goals have evolved as she’s matured.

“What matters to you changes over time,” she said. “You start to think about bigger things, so I think it’s really about being authentic. [Now], I really try not to do anything ever for the paycheck. I have to care about and be able to get behind it psychologically and that excites me. I feel like for every person it’s unique. For me, it’s about being very truthful to myself and what I care about.”

Treated Badly By Other Women? Vow To Do Better

Handler noted that early in her career, some women in positions of power were less than welcoming.

“That was disenchanting. It was a great lesson though because from that day on I knew ‘I’ll never, ever treat a woman like that,” said Handler. “I don’t ever want a woman to feel like I’m not on [her] side.” Rae agreed, noting that being discouraged by women has made her more resolute to do better.

Image: Issa Rae
Issa RaeLinkedIn

Hold The Door Open For Others To Follow You

Rae added that it is especially important to her to “hold the door open” for others like her, particularly artists of color.

“Now that the door is open for me, [I’m focused on] making sure that door stays open so that other people can walk through it and tell their stories,” says Rae, pointing to her organization, Color Creative , designed to empower emerging young writers of color, and endow them with “experience to go into writers rooms, [and] to get representation, so that nobody can use that excuse, ‘Oh, we couldn’t find anybody [of color who is] qualified!’” Rae stresses the significance of such initiatives if only to ensure that all this conversation around diversity and inclusion “isn’t just a trend,” and as Handler summed up, “there’s room for everybody.”


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