Charley Woodward from VMware spoke to Alim Kheraj from myGwork about her transitioning journey and the difference that a supportive organisation can make.


Charley Woodward used to think of herself as wearing two hats: the person she was and the person she presented to the world. “I used many different strategies to hide from the world who I truly was,” she shares. “Constantly protecting myself, presenting only the person that I believed would receive maximum acceptance. Acceptance from friends, acceptance from family, and absolutely, acceptance from the working world.”

Charley, now 50, shares how she spent a long time internalising the lack of acceptance she would receive if she was to come out as a trans woman, without actually discussing this with loved ones and instead coming to her conclusions. “Growing up, I got into football, I repaired cars, and generally acted in a way that I knew my parents would recognise as more typical traits of a boy,” she explains over Zoom from her home in Brighton.

From an early age, Charley knew that she was different from other boys. But like many people, she just wanted to fit in. At just 13 she would work weekends in her mother’s hairdressing salon, knowing that this was a career she would love to pursue. Yet, when the time came, under the influence of her father, she chose engineering. “Once again, a decision to fit in. But [in] reality, I never felt like I did fit in.”

Charley stopped working as an engineer fairly early on, pivoting instead to a career in IT sales. A career that has lasted nearly 30 years, always as a top performer. In 2017, she decided to come out as a trans woman to the people she worked with. What she then felt was relief. “I always thought I was wearing two hats. In reality, I was, in fact, wearing many, many different hats.”

Charley’s journey is a familiar one. However, her story is still remarkable. One in which she managed to overcome a heavy weight on her shoulders and find freedom living as her true self. As she says, “I’m a huge believer that everyone is unique, everyone has a story to tell, and actually, if your story empowers other people to feel like they can be themselves, then you’ve done your job.”

For 15 years she has worked at VMware, the world’s fourth largest software company. VMware provides enterprise software that enables organisations to become digital businesses that deliver better experiences to their customers and empower employees. 

Since joining the company, Charley has worked her way to the senior position of EMEA Director Renewals, Channel, where she is responsible for building, implementing, and driving the EMEA renewals channel business. “A large proportion of VMware’s business is sold via our third-party channel of resellers, distributors, OEMs (original equipment manufacturers), and outsourcers,” she explains. “I have a team of people that are focused on making sure those partners are fully enabled, able to articulate clearly our value propositions, and that they understand our process and policies so that they can successfully execute on that business opportunity.”

As someone that “loves being with people”, it’s the sort of job that Charley was made for. And since she transitioned, her performance at work has been enhanced.

The first time Charley realised that she was different was during childhood. At home one day when she was seven years old and eager to dress up as Robin from Batman and Robin, she ventured into her parents’ bedroom and tried on her mother’s tights. She remembers them feeling right. “It was super secret: my parents didn’t know, and my brother didn’t know. But what I felt was excitement,” she recalls.

At school, she tried to fit in with the boys, although she always felt separated from the others. Then, in the 1980s, she saw Boy George performing in Culture Club on Top Of The Pops. “People assumed that [the] gender-bending era was about sex and sexuality,” she says. “I think, to some degree, people still do today, 40 years later. There’s still a lot of confusion about that. Men wearing makeup was unusual. That was me. It became a normal thing for me in the 80s.”

It was during this period when she first met someone who was transgender at the now-demolished Rum Runner club in Birmingham. Incidentally, where Duran Duran was formed. “I remember going to the Rum Runner [and] coming out of the unisex toilets, which at the time was unusual, and washing my hands. There was a great big mirror and I saw a girl come out, she was washing her hands and I said hello. She replied, ‘Hello’ with a deeper voice. I was blown away by that.”

Ultimately, though, she put away that aspect of her life, getting busy with relationships, family, children, paying mortgages and bills. She doesn’t downplay the significance of those middle years: “They defined the person I am today,” she says. “That candle inside me – and I call it a glimmer of light – never died. It just got parked for a while.”

In 2006, Charley found herself with spare time, after the start-up she was working for was acquired. While they said that they wanted to keep her on, they weren’t sure what they wanted her to do. “It’s the classic line: the devil makes work for idle hands,” Charley jokes. “I had a period of my life where the children were growing up, I had time on my hands, and I had time to think about what was important to me.”

She came across dressing services, a world Charley knew nothing about. “I’d describe it as me being a piece of canvas and they were Picasso,” she says. “They covered the mirror up and they chose the makeup, the clothes, and the wig. They chose my look. And, hey presto, an hour later they uncover the mirror and I see a young version of my mother. I cried at the time. I wish I had the photos from back then. I would go to those places to get some release time. But then I would feel hellish guilt like I shouldn’t be doing it.”

For a few years, she was satisfied to keep it at that. The dressing services offering her a safe space. “And then I lost two friends in close succession. One tragically died of cancer and the other got run over,” Charley says. “These are big things, and you realise that life is too short. You have one chance at this and it’s important to live it as yourself and be authentic to yourself.”

She plucked up the courage to go outside as Charley six years later. Although that, too, was done in secret. While she did tell her wife at the time, it placed a strain on their marriage. And while they did find a way to make it work for a while, ultimately their marriage ended. At the same time, Charley’s dad died. “Those two things kind of exploded and I realised that I could be myself without any fear of judgment,” she explains. “That’s the period where I was going out a lot [as Charley] in my personal life, but in my professional life I was still [pretending to be] somebody else.”

In 2016, however, Charley was having dinner with a friend who works in HR at VMware. She told Charley about the company’s recent drive to create a more diverse workplace and how they were now focusing more on diversity and inclusion, including around sexuality and gender identity. “She said to me, ‘For example, in VMware, we only have one transgender person working [for us].’ I was sitting there thinking, ‘Well I know two…’,” Charley laughs. “Obviously she didn’t know that then, but that made me realise that the company really meant what they were saying. It wasn’t just a statement.”

Soon after, she told her boss about her life as Charley. “She wasn’t experienced in people transitioning, but she didn’t cast judgment or jump to conclusions,” Charley says. “She just got the engine of HR involved.”

That’s when the most impactful and surprising thing happened: VMware shared a transitioning guide with Charley. “I just didn’t expect VMware to have that,” she gushes. “That really surprised me. It was a really well-written document that had clearly been written by, or been contributed to by, somebody who has gone through the experience. It wasn’t a document that was thrown together. It was a document that had been given some thought.”

Within the next year, she had told everyone else in the company, sitting down with 22 select colleagues to who she felt she owed more of an explanation than an email. “Other than the birth of my children, it was probably the most humbling experience of my life,” she says.

Charley says that since she came out and transitioned, she has not experienced any negativity and has not lost any loved ones. She has a great relationship with all of her children, as well as her brother, who sees her as a sister now.

VMware’s support and Charley’s willingness to share her story has had a domino effect. She recalls how a fellow member of staff told her that they had joined the company, in part, because of her. She now also acts as VMware’s Diversity & Inclusion Outreach Chair, which involves liaising with third-party companies and sharing their knowledge and approaches to D&I.

“After I made the decision to transition, people at the time were always saying, ‘You’re so brave,’” she says. “That ‘brave’ word is an interesting one. That’s not to say that it isn’t a brave thing to do, but the bravery happened years earlier. I say it’s ‘birth by a thousand cuts’: there’s no one thing that I can say, ‘This arrived me at a place to make that decision.’ It was many, many things.

“And actually, once you step over the line and when you work for a company like VMware, which is so focused and committed to people truly bringing their authentic selves to work, it’s easy. I am a believer in paying it forward. I feel lucky to work for such a great company as VMware that encourages diversity across its workforce and inclusivity of its workforce. I feel humbled by the acceptance I have received from my family and friends. For me, I successfully made the change to become the true authentic me. In the words of Ralf Waldo Emerson, ‘To be yourself in a world that is constantly trying to make you someone else is the greatest accomplishment.’”

VMware is a proud partner of myGwork, the LGBTQ+ business community.

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One thought on “WOMEN ON TOP: “I always thought I was wearing two hats. In reality, I was, in fact, wearing many, many different hats””

  1. Charley is a friend of ours. Her transition has made her a more complete person. Charley is an inspiration.

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