Dev Cleary on self-love, uncovering his pride, and servant leadership

For many of us, the reasons we cover (downplay, hide or filter parts of ourselves) track back to childhood. Fittingly, my recent conversation with Devin Cleary , Head of Global Events at Vimeo , began with his experiences in middle school. A time when our bodies are changing, our identities are becoming more pronounced and we’re forming deeper friendships. Dev said when he first started thinking about covering, “I reverted back to my adolescence.” He saw that it was during his preteen years where covering really started to take place. “It brings feelings of anxiety and stress,” he said.

“I’ve been covering most of my life truthfully.”?

For Dev, covering meant hiding or masking things by trying to wear clothing to blend in with his peers, and not speaking up during class or doing things would put him front and center. It was a mentality of show up, get the A, and then go home and “be my true authentic self with the people I had real relationships with, like my core friends and family,” he shared. This mentality followed him into high-school, where he was an avid hockey player who was also grappling with the fear of acknowledging his identity as a gay man. “Even what my peers were thinking was hindering my performance, it was restricting me from being my best – whether it was in the rink itself or even outside in social settings.” Covering still meant being more timid, trying to blend in, rather than playing a leadership role. Internal questions plagued those years – “Do they know who I am? Do they know my true identity? Are they going to uncover what is going to be this big scandal or will my parents find out? It was all running through my mind,” Dev recounted.?

Later in life, Dev reflected on those experiences, thinking, “I have wasted so much time [covering], when I could have focused on my professional development, on health habits, on living my best life.

In every stage of my upbringing, 50% of my day was consumed by emotions and thoughts of worry and anxiety, not knowing how to navigate, and what my next turn would be.”?

Traumatic events were also part of that journey. A bully during art class who physically assaulted him, forcing Dev to seek medical treatment for injuries. “It was really scary,” he said. “It has never left me.” That experience, and another where a student with mental health issues was planning to bring a gun to school and whose digital diary included a target list of students he planned to shoot. Dev’s name was on the list – based on the assumption that he was gay. That time was both scary and comforting. “As a result, that document had a lot of visibility,” he shared. “My name was associated with a word (gay), and I’ll never forget my parents sitting me down and having a very comfortable, but honest conversation with me. I still covered; I still wasn’t comfortable. That was a moment where two things happened. I was immediately scared, but I was also relieved. It [people’s responses] was a turning point, maybe the world isn’t as scary, negative, toxic, and abusive as I was afraid it was.”?

College provided the space for Dev to begin coming into his own, a place where he could begin uncovering his identity as a gay man. “I drummed up the courage and pledged a fraternity,” he said. “I was selected and went through the whole process. It was surprising how open and supportive the ‘brothers’ were. But, I still didn’t come out until my sophomore year. I had a distinct fear from years and years of hiding and covering, not being comfortable with who I was. It really held me back. But I met someone, for the first time in my life. I was over 21 years old when I had my first date and experienced my first connection” Before then, Dev had gotten to observe other people living life, enjoying their first romantic crushes, coming into their own. “It was really a turning point for me,” he said smiling. “This individual was more experienced, more open and very out themselves, it really inspired me. I came out to my family over the holidays that year, and it was a really beautiful moment.”?

For many of us, college is the time where you really get to start exploring who you are. That was the case for Dev. “My junior year of college is when I started truly uncovering,” he said.

“I was proud, I was out, and really felt like a weight had been lifted… I felt alive, like I had so much life to live and I didn’t want to squander it.”?

But like I’ve shared in previous pieces, covering isn’t usually a one-and-done scenario. It’s something that can take a lifetime to undo, to unlearn, to process through and overcome. And, sometimes we uncover in stages. “It’s like a brick wall, it’s so difficult to climb over and push through. And when finally, you’re able to remove those bricks and walk openly, there is nothing like it,” said Dev. “The minute I was able to come out to my parents, my mother and father looked at me and said, ‘We love you, we’re always going to love you, we are going to support you. We want you to be happy. We know this is who you are, you were born this way. You are exactly the person you were meant to be,’” Dev shared. “We just want to make sure you are happy, healthy, and safe, that’s it.”?

While he was uncovering in his personal life, he was still covering in his professional life. “I worked in a very male-dominated industry (B2B tech),” he shared. “That was a space, especially 10-15 years ago, that was incredibly overpopulated with white cis males that were at all stages of leadership, they were calling the shots and setting the cultural tone for the organizations where I worked.”?

What he can now trace, is a through-line from the hockey team bro culture to the boys club of those organizations. “If you didn’t cooperate and contribute at the water cooler, you were not part of the inner circle,” he said. “As a result, you’d be sacrificing career opportunities, raises, and elevation through new projects. Those things didn’t happen unless you had strong camaraderie, and I would say I 100% got good at mimicking those behaviors. For a portion of my professional career I lost who I was. I felt like when I walked into work I would be one person, and the minute I would leave I’d have a sigh of relief.

I said, ‘I want to work in a place where I can be my authentic self and have a picture on my desk of the person that I love the most in my life.’”?

Covering also included his mannerisms and vocal tone. “I associated that volume and pitch with being more masculine,” he said, describing how he tried to deepen his voice during certain conversations. It reminded me of the recent conversation I’d had about my own experience growing up, and being called “ma’am” on the phone over and over, because people thought I was my mother. That was something that meant that for years, I attempted to speak with a deeper voice – which often meant sounding very monotone. It limited the emotion I demonstrated when I talked and my familiarity with what my vocals can do. A process I’m working to undo to this day.

Dev’s reflections hit on something many of us long for and need - psychological safety. And, after being with the company for a while, Dev started to slowly uncover. “I was more present in meetings, more vocal in presentations - my mannerisms and vocal tone,” he said. “That original company had a workhorse culture, it was 365 days 24/7. As a byproduct of that, emotions were not something celebrated or acknowledged at work.” Thankfully, over the past decade or so, there have been movements across our nation to shift some of that, to recognize and celebrate the human. To see people’s intersectional identities, health and wellbeing, and humanity beyond just someone’s function at a job.?

“A lot of outside macro circumstances have really contributed to helping me find the strength within myself to say, ‘I am exhausted trying to play different parts. I’m exhausted having to act, versus focusing on being happy, on my profession, on growth, and just being who I am,” Dev shared. “If I want to move my hand a certain way or participate in a certain way, I shouldn’t have to think three steps ahead or strategically with a game plan.”?

Those skills, learned from covering, from trying to fit into a mindset and mode of operating that was in conflict with who he was, gave him skills that make him great at his job. “I can scenario plan and forecast and think about different situations and outcomes better than anyone I know,” he said. “So, I’ve gotten a lot of training on that, I wish it wasn’t as the result of covering who I was.”?

Some of those macro influences that supported Dev’s uncovering journeys included news and social media. “I started to see imagery and storylines and to identify with the people I was watching in movies and on television,” he recounted. “That was something that really helped me and made me feel comfortable to start uncovering because I wasn’t alone. Because I didn’t feel like I was the only person that lives in this town or state that is going through this.”?

Having that type of lived experience modeled also became really important at work. “I’ve been very fortunate to have some really empathetic and supportive managers,” Dev said. “Their goal was not to focus only on work, but they understood the importance and need for investing in and supporting the human who was on their team. For me, it was groundbreaking, because every single interaction was slowly rebuilding my confidence in a way that I never felt before.”?

All of these experiences and their impact on Dev became visible to him one morning in his late 20s or early 30s. “There was a part of me that finally achieved self-love when I woke up one day, and it was like a weekend moment, and I'll never forget it,” he recounted. “The sun was shining into my bedroom on my bedspread. I was really living the life that I always dreamed of and never thought could happen. I was dating someone and having a really quality, healthy relationship for the first time. And it was just so eye opening. I just remember like, basking in that moment, waking up on a Saturday morning, and just saying, life is beautiful. Life is amazing. Look how far you've come. It was almost my own TED talk - my own moment of realization. And ever since that moment, which I've never forgotten, I've never looked back.”

Dev described how that moment continued as he walked down the street in Boston. “I saw someone wearing a t-shirt, and I read what was on it, and I almost felt like it was a sign from God,” he said. “It said, ‘You deserve to be loved, without having to hide parts of yourself that you think are unlovable.’ And I never forgot that. It was a turning point for me where I was like, ‘oh my god, I was meant to read that shirt.’ A light bulb went off in my head. And again, with my self-love, accepting myself for all the parts of me - good, bad, whatever. It was a really big milestone in addition to those mentors.”

That intersection of seeing the human in himself, and each of us and having strong mentors who created teams with psychological safety all impacted his leadership today at Vimeo. “Servant leadership is a practice that I’ve always adopted,” Dev said, after I asked how he approaches creating inclusive cultures, especially while building and leading a team. “From my point of view, I work for my team, not the other way around. We spend more time with the people that we work with than sometimes our significant others or our family, so I look at it like another community in my life. A subset of people who I care about, celebrate and support.”?

One way he does that is by asking the same set of 15 questions to everyone he’s in business with. “It really helps me know people on a human level first, before we dive into any project for work,” he said. “I want to understand who they are, where they come from, what makes them tick.” His questions range from more work-related questions like, Are you an early bid or a night owl? to What is the most important thing I can help you with outside of work? “I really like to tailor my working practices individually to everyone,” Dev shared. “The style, cadence and communication I might provide to one person, I do something completely different for another because that’s what they need.” This includes understanding how people like to receive feedback.

“Meeting people where they are is really important to me,” he notes.?

With the deluge of information always coming at us like a firehose with no off valve, and the pressures at work to accomplish our ever-growing To-Do list, Dev uses his 3-1-1 rule to stay grounded and accountable to himself. “I write down three things everyday that I’ll do, so that I’m setting accurate expectations and holding myself accountable,” he said, outlining the three actions. “I do one that each day that brings me self-joy or self-love. So, that could be going for a walk, listening to my favorite album, going to the gym, etc. Second is having a conversation with a friend – calling a loved one and catching up. And finally, I do one that each day that brings someone else joy, a different person each day – so that I’ve impacted 365 lives every single year.”?

As the Head of Global Events at Vimeo, I was interested in hearing Dev’s take on how the platform can support uncovering. What it enables users to do that let’s them tell their story, and have agency when it comes to how they use video to engage with the world. “I think so many people are afraid to record and make a video because it's intimidating,” he shared. They may be asking themselves,“How do I use the tools? How do I edit? What if I make a mistake? Whatever the circumstance or use case might be, our platform is so easy to use, where you can drag and drop. And it's very intuitive based on other core technologies, like your cell phone that you use.” He added, “everyone should leverage the power of video to amplify something they are really passionate about, because you never know who will be on the receiving end of that message and what that level of impact can be on someone else who needs it.

Ultimately, video has the power to make you think differently and open up your eyes to something that you might not have been exposed to.”?

As we closeout Pride month, I hope you’ll consider Dev’s story as you think about how to support LGBTQ+ people of all ages (with a special focus on today’s kids and young people) and whose intersectional identities may mean they need your support now more than ever. Think about how you can use your voice and your platform to combat the hate and anti-LGBTQ+ and specifically anti-trans legislation that is sweeping our nation. And, use your influence and your human connections to help create a world where covering isn’t the payment we make for safety and acceptance, when so many of us want to be loved and celebrated for who we are.??

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