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7 Powerhouse Women Reveal The Most Difficult Moment Of Their Careers

Seven phenomenal, courageous minority women from a variety of industries to share the toughest moments of their careers.

As much as we’d love for our careers to be simple, straight-forward and blemish-free, it rarely works that way. As much as we’d love for our careers not to blend into our personal lives, our self-identity, and our worth, it so frequently does.

Our careers, just like our lives, can be messy, and are often filled with moments that fuel self-doubt, fear and uncertainty – more times than we’re willing to admit.

But, it’s so much easier to share the exciting parts of our story, the moments of glory and celebration, the promotions, the raises, and the daring career changes. It’s so much harder to reveal that the journey wasn’t easy and that the success carries burdens and sacrifices.

Yet, that’s the part of the story we all need to hear.

So, in honor of Women’s History Month, I gathered seven phenomenal, courageous minority women from a variety of industries to share the toughest moments of their careers. May you see your strength, and find your courage through their stories.


Ukonwa Ojo

Ukonwa Ojo, Senior Vice President at CoverGirl

Ukonwa Ojo: I had just been promoted to my first managerial role as a junior manager and was so excited! When I started, I was responsible for listening to our internal customers, and I found out very quickly that we had quite a lot to fix, and that if we didn’t fix it in a short amount of time, it would create problems for us in the future.

I’m a very direct person; it comes with the Nigerian DNA. But, it was very uncomfortable for me as a junior manager to express that strong point of view, and it was hard for the current team to really listen to that message. So, I really struggled with being assimilated and accepted into that group.

I don’t think my manager knew how to process that or how to help me manage these dynamics. Instead, I was told, “The team’s really struggling with your style,” and that they were going to help me by bringing on a coach. As a junior manager, I went along with it. I met with the coach and the first thing she said was, “You’re really beautiful; I could see why that could be a problem.”

We talked for another hour, and afterwards she stopped and said, “What you don’t realize is that I’ve been filming our conversation, so we’re now going to play the video back and critique all of the things that make your style very difficult for everyone to deal with.”

She went frame by frame, and said things like, “You see when you smile like that, when you look like that, when you put your eyebrows like that…”

She literally started to cut me all the way down, and it was extremely humiliating. What she basically communicated was the way that I was, as I was, was not sufficient to succeed in my role.

So, I had to decide if I was going to change all the things about myself so that I could succeed there, or if I was going to take control of the situation and look for a different place to thrive. I realized that I couldn’t deliver the results they wanted if I couldn’t operate as the person I was created to be, because those things are very intricately linked together.

It was one of the most difficult decisions I ever made in my life, but I decided at that point that I was going to fight for me, as I was created. Beautiful or not. Direct or not, smiling the way I was naturally built to smile. Eyebrows the way they were naturally meant to be arched. And, not too long after that I resigned from the company. I moved to a different organization, with a culture that better suited me.

In fear, I could’ve stayed there and let them cut me down to a common denominator…who knows what could’ve happened to my career. But, I had to find a place and culture where I could walk in confidently as myself, so that my gifts could naturally flow from there.

Lola Snaps Photography

Janaye Ingram

Janaye M. Ingram, Director of National Partnerships at Airbnb, Secretary for the Historic Women’s March

Janaye M. Ingram: In 2013, I was named the National Executive Director of National Action Network. I knew that if I accepted the position, it would require even more than what had been needed for my previous role, and I found out very quickly that I was correct – I learned a lot and developed new skills.

But what I didn’t realize was how many more sacrifices I would be required to make. In taking the position, I missed family events and important milestones like my grandmother’s 80th birthday celebration. I had vacations that I planned and paid for but wasn’t able to take.

My desire to excel in the role caused me to constantly prioritize work over everything else. I kept telling myself that this is what was required of me to make an impact. But, despite what I kept telling myself, I knew that the pace I was working at was untenable. The trouble was, I didn’t know how to stop it.

I lived my days feeling conflicted about leaving or staying. I talked to my inner circle and sought advice; my family told me they were worried about me. I picked up weight due to stress and unhealthy eating habits. But the rewards of the work made me feel like it was worth it.

In 2015, while working on an exciting, yet taxing project, I made the decision to leave. I knew I needed to reset the course I was on. There was always going to be some new thing to conquer or some new task that I would be tackling. But, there was not always going to be an opportunity to relive the moments I missed. I had one life and I needed to focus on the things that were of greater importance.

But even with that realization, it took several weeks to tell my boss that I had made the decision to leave. When I left, I didn’t have another job I was leaving for. I didn’t have a plan, other than to take time and travel. When asked where I would travel, I hadn’t even figured that out, but I knew that I wanted to take some time and refocus my priorities.

While I tried to prepare myself for the reaction of my boss, what I didn’t expect was the reaction of some of my associates and peers. Washington, D.C. is a town obsessed with status and titles and for me to willingly give both up without the security of something more seemed to be questionable to many people.

To make matters worse, I decided to pack up my apartment and return to my parents’ home while I was traveling. For me, it made economical sense to not pay for an apartment that I didn’t need or wouldn’t be using. To others, it seemed like I made a bad decision.

For nine months, I traveled internationally and domestically, I spent quality time with family and friends and I focused on what I wanted out of my life. And after those nine months, I was reborn into someone who makes time for family, friends and the most important things in life. I still have the desire to excel and succeed and sometimes, I even find myself reliving in my old habits, but I now have more tools to help me adjust.

Preston Schlebusch

Dhanusha Sivajee

Dhanusha Sivajee, Chief Marketing Officer at XO Group Inc.

Dhanusha Sivajee: Early on in my career, I took on a new role at a startup marketing agency. Many of my co-workers and clients were very strong-willed and opinionated. Rather than engage in productive debate with them to get to the right answer, I found myself wanting to avoid conflict and going along with their ideas and strategies, even when I knew there were other options that we should have considered and other paths we should have gone down to achieve our goals and drive results.

My mantra had always been “confident on the inside, humble on the outside,” but given the strong personalities involved with this new agency, and given that I was the new kid on the block, who had just taken a big step in her career, I found that I lost my inner confidence for a moment. Rather than trusting my instincts and backing them up with the information and facts that I had, I found myself always looking for more information to formulate the perfect argument, before I spoke up.

Looking back, I realize that I was feeling a form of “imposter syndrome,” where I forgot for a moment that I had earned my seat at the table, just like everyone else, and that I was in this new role because I was good at what I did and people wanted to know what I thought.

Fortunately for me, I had a strong network of peers, mentors and friends who reminded me who I was, what I did best and I was able to get back that inner confidence, chart a new direction and drive the results I knew I could. This experience and similar others, remind me that we shouldn’t let the successes get to our heads, but just as importantly, we should never let failures get to our hearts and our confidence.

Emmelie De La Cruz

Emmelie De La Cruz

Emmelie De La Cruz, Digital Marketing Strategist and Entrepreneur

Emmelie De La Cruz: I went from making pretty decent money to making $40,000 a year as a contractor, with no benefits or insurance. But, people always tell us, “Get your foot in the door.” So, I listened to all that advice, and I set myself up for failure. At the time, I lived in New York City, so in order to afford the cost of living, I worked two other jobs and I was burned out.

In the midst of feeling burned out, naturally, I went back to my comfort zone, which was my ex-boyfriend. We had been dating on and off since I was 17 years old and it wasn’t the healthiest relationship. Remember how I said I didn’t have insurance? Well I had convinced myself I couldn’t afford birth control either, so I ended up pregnant. I was in shock, scared and afraid. After finding out I was having twins, I took it as a double blessing and prepared to be a mother. I let my family, friends, and boss know. Everyone at work and in my life knew I was pregnant.

But, while I was mentally preparing to become a mom, requesting health insurance from my boss, and trying to get everything together professionally, my boyfriend was giving me 675 reasons why having kids was not going to work. I woke up one day and realized that based on my financial situation and my unhealthy relationship, I could not bring two children into this world – not into an abusive relationship, not into poverty, not into any place but love. I decided to get an abortion. I remember getting my friend to schedule the appointment for me.

It was a tragedy, because I was 15 weeks pregnant with twins. It was not only an emotional struggle, but a physical one as well. But, I had to sit down and look at my situation, and realize I didn’t have insurance, I made $40,000, worked two other jobs, and my partner wasn’t supportive.

Had I been in a different situation emotionally, professionally and financially, I would have approached things differently. After I made that tough decision, I left my job and eventually New York City, because I was embarrassed and broken. It woke me up to the reality of my life and poor decisions, and it was what I needed to finally break away from that addictive relationship I had been hooked on for so long.

Until this day, I still carry the shame and the guilt of that decision. It was heartbreaking to go through that, but it is the gasoline that fuels me every day to do better and to be better, to never be in that place again.

Today, I work so hard because I never want money to make decisions for me again. I don’t want my career or finances to dictate how I live my life. I don’t want to have to run away from my problems. I want to be able to tackle them head-on. My life fell apart, but it triggered a series of events that led me to become a successful entrepreneur, a blissful fiancé, a resident of a beautiful new city, and a new woman. I don’t believe it happened on accident and while it is the hardest thing I’ve ever been through, it changed my life.

Kimberly Wilson

Kimberly Wilson

Kimberly Wilson, Vice President of Affiliate Marketing at Disney and ESPN Media Networks

Kimberly Wilson: I had been working for the Walt Disney company for 8 years when I got promoted to Vice President. The position required me to move from Los Angeles to Bristol, Connecticut.

It was during that time that my father became increasingly ill. We used to joke that my father had nine lives. He would get sick and then all of a sudden, he wasn’t sick anymore.

But, around this time when I moved to Connecticut, his health started to decline. I believe the reason I got that job wasn’t for me to become a vice president, or about my career. I believe God put me in that space so that I could get home to my family in Chicago quickly, cheaper and more often, and so that I could be closer if anything happened.

I was really blessed to have a leadership team who values family, they were completely supportive of me working from Chicago and taking vacation time to be with my family.

My father suffered from congestive heart failure and bladder cancer. Two years into living in Connecticut, he continued to get thinner and weaker. I was constantly in Chicago and constantly worried about him. I remember asking my mom, “Should I just quit and move home?” And she said to me, “Why? So you can come home and watch him die? You have to set your life up for when we’re gone. I don’t want you to disrupt that. You have to have a life after this.”

In 2014, my career was going up, and my personal life, because of my dad, was going down. It was an interesting perspective that parts of your life can be really amazing and other parts can feel like the worst.

I came home in August 2014 and I was prepared to stay home for a while. At the time, I had direct reports, I had a big launch coming up at work and it was a lot going on. But, I talked to my boss about it and he was supportive.

I walked in the door and asked my dad how he was doing and he said, “I’ve been better.” I asked him how long he wanted me to stay and he said, “Forever.” I was heartbroken. That’s when I knew, because he never used to say that. I was there until the minute he died and that was forever for him. I stayed home for weeks after that, being there for my mom and preparing his arrangements.

Then, I went back to work. With that, I encountered people who didn’t know what to say or how to approach me and I found myself comforting other people. Then, there were others who were trying to protect me, so they weren’t engaging with me from a professional standpoint as much as I wanted.

But I was like, “Look, I’m back. I’m here. Let’s get to work.” That was hard because you become the comforter, when you’re the one who needs to be comforted. But I understand it’s hard for everyone.

The takeaway that I have from that experience is that when something like that happens, your life and your perspective changes. I changed at work. I wasn’t the same person. There were trivial things that I cared about before that I no longer cared about. My priorities changed. How I dealt with people changed.

But what got me to the other side was my father. He was so proud of me and my sister and what we had accomplished in his lifetime. So, I started thinking about the things he had the opportunity to see, and I try to model myself after that. I carry him with me every day. My drive changed and it’s all because of that experience.

Whitney Gayle BentaWhitney Gayle Benta

Whitney Gayle Benta

Whitney-Gayle Benta, Head of Talent Relations at Spotify

Whitney-Gayle Benta: I had been at the top of my game in the music and talent industry and working at Facebook was new for me, I had to learn things I wasn’t familiar with.

When I worked at MTV, Def Jam and Revolt, music was the primary bread and butter for the company. But when I started working for Facebook, I was at a place where technology and advertising were the bread and butter and music was more like a “nice to have.”

The first six months working at Facebook, everything was so new and I overworked myself and stressed myself out trying to study to make sure that I felt like I was on par and that I could compete. I really struggled with feeling like, “You’re going to be found out that you don’t really know how to do all of this.”

I was feeling incapable, but at the same time, I knew that I had worked so hard in my career and that I was capable. I like to refer to it as the devilish functions that we all have within ourselves, that tells us that we’re not good enough.

It got to the point where I hopped on a flight to go see my mentor, and cried in her house for three days. I got the tough love pep talk that I needed to continue. She put the fuel back in my tank and reminded me that I conquered other things in the past that were difficult and that I’m capable of doing this as well.

It sparked a lot ideas on how to get the support that I needed. I took action immediately after my conversation with her. I felt refreshed and determined and it allowed me to be more successful. In fact, I ended up getting a promotion months later. So for me, having a mentor is super important because you need those people that are going to give you a reality check and tough love when you need it.

Tia WhiteTia White

Tia White

Tia White, Executive Director of Technology at Large Financial Institution

Tia White: I was in a new role at a company, and I was the only woman and person of color on the team. I was leading an engineer function and there needed to be changes related to the design and support of a system. So, I came up with a proposal and plan and every corner I hit, I got pushback: “We’re too busy. We don’t have the money. I don’t think this is the right thing.”

I didn’t get buy-in with the engineering community at the company until I got a technical white male ally that could be my voice of reason in the room, because I wasn’t heard. Even though our technical aptitude was the same level, having his backing and support, opened the ears of the other men in the room to want to listen to me, support me and work with me.

I then had to get an ally in a white female executive, she helped prioritize and get the funding, made sure I had the resources, and got the senior leaders to support the proposal as well.

Then, the plans were implemented. But it took finding allies that were either of a different race or gender. It was an uphill battle. It took three months to implement, but I spent four months before that trying to get the attention of the right people to make progress. I spent more time networking to get buy-in than I probably needed to do, time that could’ve been spent doing something else for the business.

The company hired me because of my differences, my thoughts, my background, and my ability to lead during a difficult time as a transformational technologist. After I delivered and proved myself, I came to a point where I felt if they really appreciate me, then they would accept me for who I am.

I started bringing my whole self to work and I actual was more effective and productive because people no longer judged me and some of the unconscious bias was thrown out the door because of my ability to deliver.

It was hard to make that adjustment though, bringing my authentic self to work every day. It almost felt like I was coming to work with no clothes on every day. I had to be intentional about it and it probably took about 15 to 30 days until I felt comfortable doing it.

I learned to have my authentic voice but to also be mindful of the culture around me so that it could be appreciated and accepted. It allowed me to get more comfortable in my own skin. I was no longer sitting in this room naked, as the odd woman out, I was now a part of the group. But, I had to find the balance between how to be myself and how to work in a way that it could be valued and received.


Originally published at Forbes

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