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Luvvie Ajayi Jones On Why Making Good Trouble At Work Benefits Your Organization


What does it take to upend the systems that hold so many people, specifically women and women of color, back in the workplace? Luvvie Ajayi Jones guides readers through how to do exactly that in her New York Times bestselling book, Professional Troublemaker. 

Ajayi Jones cleverly shares the story behind a life-changing TED Talk that almost never happened due to her own imposter syndrome (the video of that talk now boasts 5 million views and counting) in the hopes that others will understand the breadth of missed opportunities when fear is allowed to dictate decisions. She dares readers to be audacious while laying out a very thoughtful framework for decision making for moments where people are faced with a choice to speak up or stay silent. 

It’s telling that the woman who claims she would never be welcome in Corporate America for being too outspoken now commands paid speaking engagements in front of tens of thousands of employees at major global companies such as Facebook, Amazon and Google. In these keynotes, Ajayi Jones is on a mission to convince executives to listen to their employees instead of silencing them. 

I spoke with Ajayi Jones about how important her community has been throughout her journey, why she sees Black women as the moral center of the universe, and how companies can do a better job of celebrating the troublemakers. 

Amy Shoenthal: One of the things I loved most about this book was how much admiration you have for your grandmother and how she’s such a central figure in your life. My grandma is 100 and she’s my absolute favorite person. What is it about women and our grandmothers? 

Luvvie Ajayi Jones: Our grandparents show us a different way of being. They’re older and they’ve gone through all of life’s shenanigans and all the madness and here they are standing — usually pretty tall. We look to them as aspirational because we want to be them one day. 

I wonder though, what if we didn’t wait until we were gray to be audacious. We don’t have to wait until we have grandkids to have that type of energy. As we watch our grandparents take up all this space, we need to understand that they’re actually giving us permission to be these people now. We don’t have to wait 40 years. 

Shoenthal: Speaking of your grandmother and your heritage, let’s talk about oríkìs. Why do you think they’re so impactful – both to write and to read?

Ajayi Jones: The world spends a lot of time telling women that we need to fix ourselves or we need to be different. Either we’re not enough or we’re too much. 

For me, it’s important to have the antithesis of that. The thing that’s saying, you are amazing now in the way that you are. You are significant. We actually need to spend more time gassing ourselves up. People are so worried about sounding arrogant, but you don’t go from under confident to arrogant in a day. Us owning how amazing we are isn’t arrogant. In fact, I think it’s a duty. 

The oríkì is your hype mantra. Have it on hand, especially on the bad days when you don’t feel so confident or so bold. It keeps you moving forward. 

I borrowed the theme from Game of Thrones. Even though it’s tied to my tradition, just think about when Danerys was introduced every single time. I was gassed up on her behalf. We all deserve intros like that.

Shoenthal: You and I are both members of The Li.st which you mention in your book. Can you talk to me about the power of community and how the support of yours been such a part of your journey?

Ajayi Jones: Community has been everything. My community has normalized excellence because everyone in it does amazing work. My community challenges me and they back me up in the moments when I need that. It’s my soft place to land. People who are honest with you will be resources when you win and help you solve things when you don’t. Having a supportive community gives you the freedom to do amazing things, to really show up, take risks, make mistakes and dream big. 

Shoenthal: At one of your launch events you mentioned that you evaluate whether or not to speak up in any given situation by asking the question, “Will I be proud of my silence?” Talk me through that process.

Ajayi Jones: We’re all overthinkers. We’ll leave a room and start replaying the conversation in our heads. We’ll think about what we did, what we said. We wonder afterwards, what if I said this, here’s what I should’ve said, and so on. So I always ask, what if I can leave the room and not have to think about it afterwards? 

Quantifying decisions makes decision-making less stressful. That’s why I have my three question framework, which is: 1 – Do I mean it? 2 – Can I defend it, and, 3 – Can I say it thoughtfully? Running through that framework helps me feel good about those decisions.

 

Shoenthal: You say “Truth telling has to be done in the moments that are really hard. That’s what actually makes the most difference.” Can you tell me about one moment you chose truth even though it was really hard?

Ajayi Jones: The one I can think of is a moment where I really had a lot to lose. I made a choice that meant I might have to face significant financial consequences. In 2017, I was asked to speak at a conference called Next Web, and my team replied to this request with my fee. The conference coordinators replied back and explained that their policy is that they don’t pay speakers but said that it would be good exposure.

When I heard that, I figured people from The Li.st might be able to tell me whether or not that was true. So I asked the entire network, and instantly, the responses came in. I heard stories of friends or husbands who spoke at that exact conference, and were compensated. I started seeing an interesting pattern. It seemed like white men were compensated to speak there, white women had their travel paid for and Black people were expected to pay their way. 

My agents were nervous when I told them I wanted to talk about this publicly. My company’s revenue was 80% speaking. If I went public with this, other conference organizers might see it. I could’ve taken a major financial hit if other conference organizers saw me as problematic. But I had to ask myself in that moment, who do I say I am in public and is that the same person I see myself being in private?

And then I asked myself a second question, which was, who do I expect will do this work, if not me? Is it the person who just started last week? Is it the person who has never been paid to speak? So often, we’re waiting for other people to do the work. 

The worst case scenario was that I would lose all my speaking engagements. I would not be invited to speak at another conference. But weighed against the best case scenario, the choice was obvious, because I knew this conference needed to be held accountable. 

So I aired it all. I went to Twitter. At the same time, my friend Christina Wallace asked if I wanted to go on the record, and she published this piece in Forbes. I know my agents were probably going crazy. And then the conference organizer sent us a crazy email, which Christina later linked at the end of the piece, ultimately proving our theory that this conference organizer was racist and misogynistic. 

There are moments when we are on the hook to speak the truth. In those moments, we have to figure out what we’re afraid of and whether we can deal with it if that thing we’re afraid of does happen. So I had to think through what would happen if I didn’t get one more speaking engagement. How would I live? Would I be homeless? Who suffers more if I speak up or don’t speak up in this moment? A lot of our fears go away if we just run through the scenarios.  

Shoenthal: You say you’d be fired if you ever worked at a place like that marketing firm you started out in, but you wrote a guidebook for professional troublemakers. Do you still think you wouldn’t be welcome in Corporate America?

Ajayi Jones: I don’t know. I still hear stories of people who say they end up getting written up as ‘difficult’ because they spoke up in a meeting. I had a speaking engagement a few weeks ago at an internal company in front of a thousand people (virtually, of course) and I said, however you’re receiving my words right now, think about who the challenger is at your company who did the same thing I’m talking about. Leadership at these companies love to hear what I say, but I’m an outsider. I’m a bestselling author. People receive it differently from me because I’m the Luvvie brand, but how are they receiving this message from their coworkers who look like me? 

I hope that my existence normalizes diversity of thought and diversity of expression in the workplace. I’m hoping companies see that they won’t soar and innovate the way they want to unless they start celebrating — not just tolerating — the troublemakers. They have to create an environment that says I need you here, not just ok, you’re here now be quiet. When I walk out of there, my hope is that the next time leadership hears a message from someone at their organization, they give it more credence. 

Shoenthal: You talk a lot in your book about imposter syndrome. You were a globally recognized speaker before you did that Ted Talk but you share in your book how much fear you had around getting on that stage. Why do you think so many women, even accomplished women, struggle with this?

Ajayi Jones: We just have to unlearn it so hard. It’s deeply embedded in our psyches that we have to do or be different to be worthy. Even for those of us who level up constantly, it doesn’t go away. Imposter syndrome never leaves, it just shape shifts. You psych yourself out, you find excuses to not do the thing. 

I almost didn’t do the TED Talk. People didn’t let me say no even though I tried, and that was such a gift. Imagine me not having done this thing that has been so transformative – not just for me but for a lot of people who watched and listened to it. Imposter syndrome is a bitch because we spend so much time letting it win. We spend so much time letting it make decisions for us, and not even realizing how many things miss out on because of it. 

Shoenthal: In your book you say Black women are the moral center of the universe. Tell me why you think that’s the case.

Ajayi Jones: Black women are the moral center of the universe because the world spends so much time with its foot on our necks. We know what it’s like to constantly be dehumanized. Because of that, we have deep empathy for everyone else. We want to see a solution for a better world. A world where Black women are allowed to be free and to soar is a world where everyone is allowed to soar, just as a matter of consequence. We spend so much time being beat up and abused and traumatized that we’re like damn, we don’t want to do that to anyone else. We don’t want to be the perpetrators of that.

We’re nurturing and caring and wildly smart, and I wish the world would listen to us more and give us more space. But what’s funny is this — in spite of the fact that Black women are not given space, we still take it up. We still soar in spite of everything that stands in our way. 

Shoenthal: I noticed the name Chad comes up several times in your book when you highlight certain scenarios. Do you know Chad? Is he real? 

Ajayi Jones: It’s just a name that makes me laugh every time I hear it. You hear the name Chad and you picture a dude who’s just not thoughtful. It’s like Karen. It’s just these caricature names that we refer to in the moment. Brock is another one. He’s wearing cargo shorts. Everyone knows who I’m talking about.

Shoenthal: Speaking of a certain demographic, we are doing this interview right now because I reached out to you following your experience with a white female journalist who called your team “too much.” First, it’s been a pleasure working with your team to secure this interview. Second, to the extent with which you’re comfortable, can you share what happened and speak to your decision to be so vocal about that experience?

Ajayi Jones: A writer who was representing a major outlet reached out to me because she wanted to interview me, and I responded saying my team will get back to you to set it up. The only people attached to that email were my assistant, my head of publicity at Penguin Random House and my agent. She was only attached to three people. She instantly received the book galley before we scheduled anything. She responded and said she never had to deal with so many people in an email thread to set up an interview. She got on a call with the head of publicity that morning, and they got an interview on the calendar in the next day or two. The very next morning she wrote back to share that she and her editor decided to pull out because, ‘this feels very weird.’ 

She was offended because I dared to be working with a team. She was treated with respect but still felt like she deserved more access to me.

It was important for me to tell this story publicly because people see my name, see my platform and they might think Luvvie has made it. They might think I’ve been successful, whatever that looks like. But I want them to know that despite success, people still see me as a Black woman and I still deal with micro aggressions. People still don’t want to give me my full respect. 

The struggle is real for Black women. No matter how high we go people always want to put us in our place. The work we have to do in order to maintain our confidence when we are constantly tried — it’s wild. 

But that doesn’t mean you should remove those boundaries that you set. It means other people need to adjust to you owning your dopeness, owning your space. You don’t back down or change yourself or internalize any of it based on other people’s projections. 

Shoenthal: Do you know if the journalist is aware that all of this was about her?

Ajayi Jones: She absolutely does because I sent her an email. I said, by the way this conversation that’s blowing up is referring to you. And that publication ended up doing an actual feature on me. The editor apologized. Once I had that new interview set up, I asked them to make sure a Black woman could write the article. 

Shoenthal: What’s the best advice anyone ever gave you?

Jones: If you will not accept somebody’s counsel do not accept their criticism. 

Shoenthal: Best advice you’d give to future authors, entrepreneurs and/or professional troublemakers?

Ajayi Jones: Do it scared. Choose courage in the moments where you are afraid. The other side of courage is truly what you want.



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