“I’m a happy woman and that is a choice every single day.”

Meet Debra

Hi, I’m Debra Christmas. I am a 60 plus corporate warrior. I’ve been in the high-tech field for 40 years. I’m the mother of four and grandmother to six.

I’ve been in the high-tech space for a very long time. I work for Gartner Canada as an executive partner. For the most part, that means I am an advisor to executives that run the IT organization. There are other executives that have this kind of membership. Sort of what I call a white glove relationship, where they don’t have to waste their precious time trying to sort through a whole bunch of things, and figure out their strategies, and all of that. They have access into Gartner, which is the largest IT research company on the face of the planet. So that’s what we do, we research all things, where things are going, what’s happening with artificial intelligence, and block chain, and augmented realities, and all of that kind of stuff. And then we provide that guidance and advice with the background of what companies are doing around the world. I live in Dundas, Ontario, which is just in the Hamilton area.

What would you say has been the biggest shift in your life since turning 40 (or 50)?

Well, just weeks before I turned 40 my first marriage ended. That was 22 years ago. So that was a big life changing moment. I had a full-blown career in the corporate world with travel attached to it and had made a conscious choice to be a mother and a career professional. In that moment, I had to figure out how I was going to manage my life, take care of my children, and still have my career. How was I going to move forward now that I had a little bit more of a juggling act as a single parent, or even co-parent as a working mother in this new dynamic? The children split their time between their mother and their father. We intentionally lived only five minutes away, so I just had to revisit the work that I was doing, particularly in that first year, to ensure that my children would be fine. I focused on how we could make this transition as seamless as possible for them and how to minimize the damage of separation and divorce. It was important to me to make everything as easy as possible since I realized that the fact that their mom and dad are not living in the same house is big enough. So after 40, there was just a little bit more orchestration of how life is going to play out. 

When do you feel you are most powerful?

We’re either givers or takers in this world. I’m a giver. But that’s all I knew. Growing up, giving to others was in front of me every single day, whether it was to the church, or to friends, or to strangers that were the brother-in-law or the sister-in-law of someone in need. So to me when you really can help somebody, well it’s a fabulous, powerful thing.

We’ve heard that expression, “To whom much is given, much is expected.” My grandmother used to say that a lot and we were raised in that way. Coming out of the black community in Montreal – and that’s a community, I mean it’s a community – we were constantly helping somebody, especially people who were coming from the islands and moving to Canada.

I remember, our house was like a revolving door of people and you were giving up your bedroom, because someone was coming for three weeks or three months. And you just did that without a blink.

So I had very good role models in my parents and my grandparents as givers to the community. 

One of the ways I give to my community is by sharing daily reflections that I have been sending out for over a decade and not a day goes by without someone commenting on how my message touched their heart. These are my musings that come from what I’ve experienced, read, or heard throughout the day. People always ask me, “Where do they come from? And I say, “I don’t go looking for them. I read something, or something crosses my path, and I’m like, “Hm. What do I think about that? And then, out it goes”. It’s been an amazing experience, because I have found that people share their life with you when you share yourself with them.

What are the top three most important things to you right now?

I have a little saying that I’ve put at the end of my emails: “Claim today. Tomorrow’s not yours to own.” I have no idea who said that. I discovered it, I think 10 or 15 years ago, and I thought, “That is so true.” Because you walk out the door every day, and sadly there are people that walk out that door and don’t return home. That’s not a morbid thought, that’s just, stuff happens. The universe had a different plan for them but they didn’t know that. Not returning home is rarely planned. And what was left unsaid, undone, unfulfilled? So I do try to think from that perspective, if tomorrow did not come, what’s this day like? And it helps me keep things in perspective. Time is a very precious commodity to me.

Health is right behind time, if not at the top. It requires a lot of energy to do what I do, and I have a ton of it. So, staying as healthy as I can is important. I am 62 years old and I don’t take a pill for anything, I’d like to keep it that way. That said, I’d like to lose 30 pounds, but I have incredible energy. I need to stay healthy, and I need to take care of myself. When I was younger, people would say, “You take very good care of yourself.” And I said, “Of course I do. Do you see the line of people behind me that are depending on me? If I don’t take care of myself, what happens to all of them?” So that’s how I think of it, I have to come first. It’s not a selfish thing. I have to come first, because I’ve got 45 people standing behind me that need something in some sort of way. So that’s really important. 

The third most important is joy. I’m a happy woman and that is a choice every single day. It doesn’t mean that I don’t see all of the crazy nonsense going on outside there, or people behaving badly, or stupid behaviour, or reckless stuff, or hurtful things that people do and say, because they’re just so “me, me, I, me, me” focused. I see beyond that. I can see it. I try not to take it in. You just have to try not to let it seep in beneath your skin. That doesn’t mean it doesn’t cause a momentary something, but then you have a choice of what do you do with that? And I choose joy. Do the happy dance every day. 

How do you make sure your actions are aligned with what’s most important to you?

I check myself. Self-awareness is a huge, huge thing. And if you live your life thinking, “How can I be my best self?” it means you need to live consciously. You need to think about, “What am I doing? What am I saying?”. Intention is essential. People use to call me Deepak Debra because I’m a very deep, emotional thinker. I’m always thinking about the impact of stuff. If I behave this way, what happens? If I say this, what happens?

I think if the majority of people thought more about the impact of what they said and did, truly,  the world would be a better place. Because the words, “I’m sorry” have lost some of their meaning. People say whatever they want, or do things they shouldn’t and you cannot just say I’m sorry and all is well. With hurtful words in particular – you can’t take them back. Those words can’t be retrieved. They’re out there now. They’ve been said. And the hurt lingers.

People can retrieve those words, and 20 years later start crying all over again. Think about that. They can start crying all over again from something that you said to them 20 years ago.

So we need to be much more conscious of our own behaviour, what we say, and what we do. We all must be accountable for what we say and do. We cannot control others behaviour but we can control our own and how we react to theirs. That is absolutely a choice. To me that is a big part of being an adult and being responsible. That’s living my values.

What seeds are you planting today for the future?

Well, considering that I plan on living another 40 years, the future is long. I’ve told my kids from the time they were young, I plan on living to 100. I could die a few seconds after my 100th birthday and I’ll be happy. And, I plan for that life to be very full. Very, very, full.

So the seeds that I think I plant are, we all have really unique talents and gifts. And I try to help people uncover what those are so they can do that they really love, and know what they’re really good at it. I’m amazed at how many people don’t really have a good sense of, “I’m really good at this.” We’re so quick to beat ourselves up. I mean, quick. We don’t take compliments well. When someone says, “Oh, that’s a lovely dress you have.” And you say, “This old thing? I’ve had it 10 years.” What happened to a simple thank you? Thank you very much. “Color looks fabulous on you.” “Thank you.” Okay. It’s really an interesting thing how we still go to the negative. So for me it’s know yourself really well, and what you’re really good at, and try and find ways to do that.

What advice would you give someone who is interested in redesigning midlife?

I think at midlife, you need to really step back and reflect on what was the first half like? What was fantastic? What worked well for me? Where were the challenges? But more importantly, what do I want the second part to be like? And go design that. Whether that means finding a new job, maybe new friends, maybe changing your circle a little bit, taking classes. My friend at 60 something years old retired from a 37 year career in banking, and took a painting class. She is a gifted artist of massive proportions. And I’m like, “Did you know you could paint?” She had no idea. And I’m like, “You are 60 something years old, and you are just finding out that you can paint, like a painting that I would buy? Good God.” That was amazing to me. Somebody else’s husband gave her a camera as a retirement gift. If I showed you the photographs, you would be, “How did you not know you were a gifted photographer?” She’d never taken a picture with a beautiful camera. And all of sudden, this is a gift. So, to me, these are accidental blessings. So how about if you found them out before you were 65, or in your retirement? Now, maybe there’s a universe destiny thing that lines up for that, that’s possible. But think of designing. Think about what you’d design for your life, instead of potentially living a life that somebody else designed for us. 

How can people connect with you and your work?

Well, I work for corporate America, but I did form a little company, a not-for-profit organization called Stiletto Gladiators. The name seems apropos as I’m known for my beautiful shoes, all hundreds of pairs of them. And it’s really around fiercely going where you want to go.

I started to build a coaching practice focused on helping women in technology, well really helping women period. I added to that my extensive experience with diversity initiatives for the last thirty years because I care about it and I can talk to this very sensitive topic without being militant. As I have said to many people – “I am far more curious than indignant”. I am so very curious as to how someone gets that way. Where do the prejudices and judgments come from?

That said we all have biases, unconscious as they may be. I have a bias towards women, of course, because I’ve succeeded in a field that’s been male-dominated, and I’ve had a fabulous time for 40 years. And I can see where some of our young women are struggling. So I try to help them navigate their corporate world. They can reach me at debra@stilettogladiators.com. They can call me as well. My number is 289-244-5441. That’s that personal company’s phone number, versus my Gartner contact details. And I do a lot of just conversations with people, what they’re trying to do, mostly career-wise and leadership-focused. Because that’s my thing. Leadership interests me. We all know a good one when we see one. I spend a lot of time helping people figure out who they are as a leader and how to they lead the way forward?