7 Boss Women Reflect On Their Biggest Career Lessons Of 2019

Favor ain't always fair, and for these ladies, setbacks gave them the push they needed.


I don't know about you, but 2019 has been one for the books, and not all the stories inside are good. I decided to do a full 360 on my career, and along my journey, I had some wins, cool experiences that brought me out of my comfort zone, and met some amazing people along the way. BUT, because favor ain't always fair, I also had my fair share of setbacks and failures.

Nonetheless, even though 2019 has not been my favorite year, it has taught me a lot, and for that, I can appreciate it. This year, the biggest lesson that I learned was: "You've got to earn it to own it." As a new, full-time entrepreneur, 2019 has taught me that if you want something, you have to literally put in the work. If you don't work, you don't eat, and eating enough boiled eggs, oatmeal, and ramen (not the restaurant-grade kind) this year has taught me how to really work because sis, this boiled-eggs-everyday life ain't for me.

Recently, I had the opportunity to catch up with some other boss women and they candidly shared their biggest lesson of 2019. Keep reading for all the gems!

Annie Jean Baptiste, Head of Product Inclusion, Research, and Activation at Google

Her Lesson: “Intentional living is everything.”

Annie Jean Baptiste, Head of Product Inclusion, Research, and Activation at Google

"My biggest career lesson has been that you need to be intentional about using your voice for causes and projects that matter, but you also need to put yourself in the other person's shoes to create a compelling argument. What works for one person won't necessarily work for the other. But by bringing together data and coupling it with human stories, you can get people to care about the causes you are championing. When you can show people that you can do well and do good, they are more compelled to move. When doing that, I've been able to start speaking up around the power of underrepresented voices and how we should bring these voices to the forefront; not only because it's the right thing to do, but because all people deserve to be seen and represented beautifully and accurately."

Briana Owens, Founder of Spiked Spin

Her Lesson: “I can do anything!”

Briana Owens, Founder of Spiked Spin

"Opening the Spiked Spin flagship location in Bed-Stuy, Brooklyn while also maintaining my full-time job and planning a wedding was one of the craziest decisions that I've ever made, but it was a decision that I believe was divinely timed. This year I have been stretched to capacity in every area of my life and while there were many days of frustration, there were days of complete joy and gained confidence in my purpose. This year has taught me that when I trust God, get out of my own way, move forward in the face of fear, I can literally do anything!"

W.E. Da Cruz, Co-founder of The VGC Group

Her Lesson: “You are defined by what you decline, not what you accept.”

W.E. Da Cruz, Co-founder of The VGC Group

"This year I learned our power is in our 'no', not in our 'yes'. We must learn to anchor people in our value from the start. People get accustomed to devaluing people unintentionally and intentionally when we as the service provider or product deliver cut prices. Additionally, you have to culture people to transact with you in an environment that works best for you as the provider to grow and succeed."

Ericka Perry, CEO & Founder of The Stork Bag

Her Lesson: “Don't let the medals distract you from running the race.”

Ericka Perry, CEO & Founder of The Stork Bag

"My biggest career (and life) lesson of 2019 is accolades can sometimes deter you from your purpose, but stay focused. Now, don't get me wrong, we all love praise, some more than others, but in a world driven by social media and grandiose images, chasing accolades can sometimes result in swaying away from your purpose--your why. As a minority female entrepreneur with a growing brand, I slowly began to allow the accolades distract me from my purpose. While I work darn hard and deserve all the awards presented to me, I recognized that all the smoke and mirrors started to take me away from my purpose, which is serving women and mothers. I found myself slowly becoming busier with the glitz and really started feeling these accolades so much that my 'why' began to fade into the background.

"The entrepreneurial journey can have a lot of twists and turns and sometimes if you allow yourself to forget why you became an entrepreneur, you can lose focus on what's most important. This year really taught me that, I became so busy with everything else that I started to forget why I started The Stork Bag and why I ever wanted to serve this population. Luckily, I realized what was happening and began to pull it back in, but I had to consciously get rid of some of the distractions and learn how to prioritize my time. If I could share a few lessons with aspiring entrepreneurs, mothers, and women in general, I would say this, find your purpose/passion and follow that path, remain focused and remember why you started."

GiGi McDowell, CEO & Founder of Fêtefully

Her Lesson: “Remember your ‘why’ in the face of rejection.”

GiGi McDowell, CEO & Founder of Fêtefully

"In many ways, 2019 was the year of 'no' for me. While building a technology company, there were so many people who told me 'no' this year. From potential customers, to partners, and sometimes the most painful, investors. When you hear a 'no' as an entrepreneur, so many thoughts run through your mind like, 'Is it not good enough?', 'Am I crazy?!', 'Is this even worth it?!' But 2019 has taught me to ask myself 'Why?' when I'm faced with rejection. Why am I doing this? Why does this matter? Why do I want this? After asking myself 'why' when receiving 'no' after 'no', I realized I am not building a company to hear 'yes'.

"I'm building a company to solve problems, to help others, and to transform an industry; not for applause. By remembering why I started, it was easier to remember why I had to keep going. Focusing on my 'why' allowed me to get back to the basics which enabled me to end the year with metrics 5X my initial projections while also developing customer acquisition channels and partnerships for 2020 that I could've never imagined! Rejection is hard and rejection hurts but remembering your 'why' makes it a little bit easier to persevere when things seem tough."

Marty McDonald, Founder of Boss Women Media Group

Her Lesson: “Dream bigger than big.”

Marty McDonald, Founder of Boss Women Media Group

"My biggest career lesson of 2019 has been centered around the idea of dreaming bigger than big. Over this year, I've learned not to take 'no' for an answer, and simply being bold and confident in whatever it is that I am asking for—whether that's pitching to brands for sponsorships or inspiring like-minded women to turn their side hustle into their full-time gig—keep going after your dreams even when you hear the 'no'! I've challenged myself to look at the no's as stepping stones towards that one 'yes', because that is literally all it takes is one 'yes' to keep you on the path of dreaming bigger than big."

Emerald-Jane Hunter, Chief Storyteller at myWHY Agency

Her Lesson: “Take a pause when things aren’t going your way and trust that the universe knows exactly what it’s doing.”

Emerald-Jane Hunter, Chief Storyteller at myWHY Agency

"My new mindset is now 'If it's not moving, it's not meant to be moved.' As PR professionals, we are used to making things happen. It's what we do. We imagine, conceptualize and snap our fingers and poof--magic! (Or so it feels). Not when it comes to entrepreneurship. There were several moments this year where I found myself pushing hard to force past employees to 'get' my vision, to want to work smarter, to crave the need to win for our clients. I went above and beyond to make people happy, thinking that would equal results with work output.

"I found myself pushing so hard to the point of burnout to meet some goals but for how hard I worked (literally), many things didn't pan out how I wanted them to.

"I had to take a step back and the moment I took a deep breath and said 'Let it go! Trust in God. Believe that what's meant to be will be', things shifted. A complete 360-change. I got clarity on so many pain points and I'm ending 2019 stronger than how the first half went. Lesson learned? When you're pushing, pulling, going so hard and things are stalling or not moving, that's a sign it's time to take a pause. Take a step back. Take a breath. It might not be meant to be -- the people, the place, that thing. It'll happen but perhaps not where, when and how you want it. We get so focused on what we want and forget that it's not by our might."

Did you know that xoNecole has a podcast? Subscribe on Apple Podcasts or Spotify to join us for weekly convos over cocktails (without the early morning hangover.)

Featured image courtesy of Ericka Perry

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You may not know her by Elisabeth Ovesen – writer and host of the love, sex and relationships advice podcast Asking for a Friend. But you definitely know her other alter ego, Karrine Steffans, the New York Times best-selling author who lit up the literary and entertainment world when she released what she called a “tell some” memoir, Confessions of a Video Vixen.

Her 2005 barn-burning book gave an inside look at the seemingly glamorous world of being a video vixen in the ‘90s and early 2000s, and exposed the industry’s culture of abuse, intimidation, and misogyny years before the Me Too Movement hit the mainstream. Her follow-up books, The Vixen Diaries (2007) and The Vixen Manual: How To Find, Seduce And Keep The Man You Want (2009) all topped the New York Times best-seller list. After a long social media break, she's back. xoNecole caught up with Ovesen about the impact of her groundbreaking book, what life is like for her now, and why she was never “before her time”– everyone else was just late to the revolution.

xoNecole: Tell me about your new podcast Asking for a Friend with Elisabeth Ovesen and how that came about.

Elisabeth Ovesen: I have a friend who is over [at Blavity] and he just asked me if I wanted to do something with him. And that's just kinda how it happened. It wasn't like some big master plan. Somebody over there was like, “Hey, we need content. We want to do this podcast. Can you do it?” And I was like, “Sure.” And that's that. That was around the holidays and so we started working on it.

xoNecole: Your life and work seem incredibly different from when you first broke out on the scene. Can you talk a bit about the change in your career and how your life is now?

EO: Not that different. I mean my life is very different, of course, but my work isn't really that different. My life is different, of course, because I'm 43. My career started when I was in my 20s, so we're looking at almost 20 years since the beginning of my career. So, naturally life has changed a lot since then.

I don’t think my career has changed a whole lot – not as far as my writing is concerned, and my stream of consciousness with my writing, and my concerns and the subject matter hasn’t changed much. I've always written about interpersonal relationships, sexual shame, male ego fragility, respectability politics – things like that. I always put myself in the center of that to make those points, which I think were greatly missed when I first started writing. I think that society has changed quite a bit. People are more aware. People tell me a lot that I have always been “before my time.” I was writing about things before other people were talking about that; I was concerned about things before my generation seemed to be concerned about things. I wasn't “before my time.” I think it just seems that way to people who are late to the revolution, you know what I mean?

I retired from publishing in 2015, which was always the plan to do 10 years and retire. I was retired from my pen name and just from the business in general in 2015, I could focus on my business, my education and other things, my family. I came back to writing in 2020 over at Medium. The same friend that got me into the podcast, actually as the vice president of content over at Medium and was like, “Hey, we need some content.” I guess I’m his go-to content creator.

xoNecole: Can you expound on why you went back to your birth name versus your stage name?

EO: No, it was nothing to expound upon. I mean, writers have pen names. That’s like asking Diddy, why did he go by Sean? I didn't go back. I've always used that. Nobody was paying attention. I've never not been myself. Karrine Steffans wrote a certain kind of book for a certain kind of audience. She was invented for the urban audience, particularly. She was never meant to live more than 10 years. I have other pen names as well. I write under several names. So, the other ones are just nobody's business right now. Different pen names write different things. And Elisabeth isn’t my real name either. So you'll never know who I really am and you’ll never know what my real name is, because part of being a writer is, for me at least, keeping some sort of anonymity. Anything I do in entertainment is going to amass quite a bit because who I am as a person in my private life isn't the same a lot of times as who I am publicly.

xoNecole: I want to go back to when you published Confessions of a Video Vixen. We are now in this time where people are reevaluating how the media mistreated women in the spotlight in the 2000s, namely women like Britney Spears. So I’d be interested to hear how you feel about that period of your life and how you were treated by the media?

EO: What I said earlier. I think that much of society has evolved quite a bit. When you look back at that time, it was actually shocking how old-fashioned the thinking still was. How women were still treated and how they're still treated now. I mean, it hasn't changed completely. I think that especially for the audience, I think it was shocking for them to see a woman – a woman of color – not be sexually ashamed.

I hate being like other people. I don't want to do what anyone else is doing. I can't conform. I will not conform. I think in 2005 when Confessions was published, that attitude, especially about sex, was very upsetting. Number one, it was upsetting to the men, especially within urban and hip-hop culture, which is built on misogyny and thrives off of it to this day. And the women who protect these men, I think, you know, addressing a demographic that is rooted in trauma that is rooted in sexual shame, trauma, slavery of all kinds, including slavery of the mind – I think it triggered a lot of people to see a Black woman be free in this way.

I think it said a lot about the people who were upset by it. And then there were some in “crossover media,” a lot of white folks were upset too, not gonna lie. But to see it from Black women – Tyra Banks was really upset [when she interviewed me about Confessions in 2005]. Oprah wasn't mad [when she interviewed me]. As long as Oprah wasn’t mad, I was good. I didn't care what anybody else had to say. Oprah was amazing. So, watching Black women defend men, and Black women who had a platform, defend the sexual blackmailing of men: “If you don't do this with me, you won't get this job”; “If you don't do this in my trailer, you're going to have to leave the set”– these are things that I dealt with.

I just happened to be the kind of woman who, because I was a single mother raising my child all by myself and never got any help at all – which I still don't. Like, I'm 24 in college – not a cheap college either – one of the best colleges in the country, and I'm still taking care of him all by myself as a 21-year-old, 20-year-old, young, single mother with no family and no support – I wasn’t about to say no to something that could help me feed my son for a month or two or three.

xoNecole: We are in this post-Me Too climate where women in Hollywood have come forward to talk about the powerful men who have abused them. In the music industry in particular, it seems nearly impossible for any substantive change or movement to take place within music. It's only now after three decades of allegations that R. Kelly has finally been convicted and other men like Russell Simmons continue to roam free despite the multiple allegations against him. Why do you think it's hard for the music industry to face its reckoning?

EO: That's not the music industry, that's urban music. That’s just Black folks who make music and nobody cares about that. That's the thing; nobody cares...Nobody cares. It's not the music industry. It's just an "urban" thing. And when I say "urban," I say that in quotations. Literally, it’s a Black thing, where nobody gives a shit what Black people do to Black people. And Russell didn't go on unchecked, he just had enough money to keep it quiet. But you know, anytime you're dealing with Black women being disrespected, especially by Black men, nobody gives a shit.

And Black people don't police themselves so it doesn't matter. Why should anybody care? And Black women don't care. They'll buy an R. Kelly album right now. They’ll stream that shit right now. They don’t care. So, nobody cares. Nobody cares. And if you're not going to police yourself, then nobody's ever going to care.

xoNecole: Do you have any regrets about anything you wrote or perhaps something you may have omitted?

EO: Absolutely not. No. There's nothing that I wish I would've gone back and said to myself, no. I don’t think at 20-something years old, I'm supposed to understand every little thing. I don't think the 20-something-year-old woman is supposed to understand the world and know exactly what she's doing. I think that one of my biggest regrets, which isn't my regret, but a regret, is that I didn't have better parents. Because a 20-something only knows what she knows based on what she’s seen and what she’s been taught and what she’s told. I had shitty parents and a horrible family. Just terrible. These people had no business having children. None of them. And a lot of our families are like that. And we may pass down those familial curses.

*This interview has been edited and condensed

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Feature image courtesy of Elisabeth Ovesen

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