Arlene Dickinson Opens Up About Overcoming Her Greatest Obstacle And Finding Her “Rhythm”

Arlene Dickinson, Canada’s favourite venture capitalist, is one of the most recognizable faces in media whose biggest challenge was believing in herself.

By Carolyn Lawrence | Photography by Miguel Jacob |

This South African-born, Calgary raised, Toronto-based woman of influence is a media maven, and she’s taking the entrepreneurial world by storm.

After building herself up off the ground as a divorced 31-year-old mother of four, with a high school education and bills she couldn’t pay, Dickinson took a big bet on herself and worked her way to be Chief Executive Officer of Venture Communications, Arlene Dickinson Enterprises and now YouInc, in addition to being an author, business champion for ScotiaBank and beloved face on CBC’s Dragons’ Den.

She may be known as the ‘Soft Dragon’ but Arlene Dickinson is anything but; she’s full of fire, blazing trails, shattering glass ceilings – even lifetimes – as she discovers her rhythm for success as a Mom, Grandma, Canadian, Entrepreneur and Dragon.

CAROLYN LAWRENCE: WHAT IS YOUR FAVOURITE OCCUPATION?
ARLENE DICKINSON: I don’t think about career and occupation that way. My favourite thing is life; I am in love [with life]. My favourite occupation is, frankly, living it fully.

CL: WHAT DOES THAT MEAN TO YOU?
AD: Not being afraid to do things that put me out of my comfort zone – putting myself into places I never thought I would be. I find that so exciting. I think living life is being in your own, being self-aware. Understanding and appreciating the moment, instead of just getting through [it].

CL: WHAT HAS BEEN YOUR GREATEST OBSTACLE IN LIFE?
AD: My greatest obstacle is myself. It took me a long time and I still struggle with it. I don’t know if this is a female thing or just a truth in general about human nature, but I still struggle with believing “I can.” I tend to overstate resistance, and exaggerate things in my mind [from] what they really are. I think that is because I’m pretty intuitive and I pay a lot of attention to other people’s perspectives, as a marketer. Sometimes I misinterpret that and turn it into a negative as opposed to a positive.

CL: HOW HAVE YOU WORKED THROUGH THAT?
AD: My dad used to always say, “Arlene, you would worry a lot less about what people thought about you if you knew how little they did.” That’s struck me as one of the best truths of life. In a world where we are inundated with news and facts, people don’t dwell on it; they are too busy living their own [lives]. So maybe you make a mistake and make a fool of yourself, but people will roll past it and move on to the next thing. You can’t be devastated by that. It has taken me years of seeing that the world didn’t end when I failed, and worrying more about what I think and less about what other people think about myself. That took a very long time. It wasn’t until my late 40s that I really started to feel more confident. And even today in my 50s I just started to figure out that it matters far less what anyone else thinks. It takes time. It takes feeling centered. I watch my kids, I feel like they are more grounded about who they are than I was [then].

My greatest obstacle is myself. I still struggle with believing “I Can.” I tend to overstate resistance, and exaggerate things in my mind from what they really are.

CL: GROUNDED MEANING CONFIDENT?
AD: Meaning sure of who they are, which makes me happy.

CL: WHAT DO YOU PERCEIVE TO BE YOUR BIGGEST FAILURE?
AD: You know, I have been asked that question a few times and I have probably given a different answer every time. It changes depending on where I am [with] myself, not because I keep making mistakes. I would say my greatest failure – it’s two parts – has been not understanding the value of time. You can’t buy it; you can’t make it. The other failure was lack of confidence in myself. Those two things combined are actually a very fatal combination. Luckily for me, I had people who believed in me when I didn’t believe in myself. However, I wouldn’t classify them as failures; I would just classify them as learnings.

CL: HOW DID THE LEARNING OF HAVING YOUR LIFE DRAMATICALLY CHANGE AFTER YOUR DIVORCE PROPEL YOU IN BUSINESS, TO FIGURE OUT WHAT YOU WERE CAPABLE OF, AND TURN YOU INTO THE ARLENE DICKINSON YOU ARE TODAY?
AD: Necessity is a funny thing. It drives us to do things. I was taught, very young, to have a big work ethic. My parents were immigrants so I was taught work was really important,you worked hard and you had to rely on your own to hands and your mind if you want to put food on your table. When I didn’t have anything, I didn’t think I had anywhere to turn but myself. My parents came here with nothing. That’s a definer. It helps you learn values and helps you understand whose job it is. My mom and dad used to say, “Society owes you nothing.” You don’t turn to the world to take care of you, you turn to yourself. And I think that’s what did it. I always say I have nine lives. Who I am today is not who I was five years ago, and is not who I was 10 years ago. This notion that people don’t change, that’s not true. I have changed enormously and I am going to change again.

CL: ON YOUR WEBSITE, YOU TALK ABOUT “THE RHYTHM OF ME.” HOW DID YOU FIND THE RHYTHM OF YOU?
AD: The rhythm notion came to me actually through business. Because I could actually walk into my company and feel if we were busy or people were not happy. I started to really pay attention to that – this rhythm of the business, and be less afraid of the highs and lows of it. It’s been a true self-discipline to think about when am I happiest; what am I doing when I feel best. I gained some weight last year and I would wake up in the morning feeling lousy. It was self-fulfilling because then you start to believe you don’t deserve any better. I don’t know how many other women feel the same way, but for me, this is what I thought I deserved. So you start gaining more weight, you start feeling worse about yourself. In the meantime, since I am a public personality, I’m expected to show up differently, right? Showing up one way but feeling another. And that’s when I thought I’m not listening to the rhythm of myself.

CL: SO IS THAT WHEN YOU STARTED RUNNING AGAIN?
AD: Four times a week right now. I am training for the Toronto half-marathon. I don’t know if I will be able to do it, but I’m trying. The truth is – and we all know it – when you are well physically, your business is also healthier because you have more energy, you have more drive, you feel better, you feel stronger. And that plays out in your business.

CL: YOU’VE BEEN CALLED THE “SOFT DRAGON.” DO YOU THINK YOU ARE SOFT?
AD: No, I don’t think I’m soft at all. It’s very stereotypical, frankly, for that to be said, and I think it’s also men trying to understand my role without giving me any business cred. I’ve done some really good deals on Dragons’ Den.

I always say I have nine lives. Who I am today is not who I was five years ago, and is not who I was 10 years ago. This notion that people don’t change, that’s not true. I have changed enormously and I am going to change again.

My success rate is high and I feel very good about what I have built as a result of being on that show. I built a business out of that show. That’s [something] I don’t think the other guys have. They have built their business more strongly, but out of what I have learned, I saw the opportunity and the need in the marketplace and I am really proud of that. That’s not soft; that’s smart. And I don’t really care if they call me soft. They can call me whatever they want; I know what I have done.

CL: WHAT HAS BEEN YOUR BIGGEST INVESTMENT RISK?
AD: Putting all my time, money and energy into my business, that was the biggest risk – and the biggest upside was that. I would say this to every women who is reading this publication: it’s wonderful to bet on someone else, but it is never going to be as good as betting on yourself, in terms of what you can do and making the most of your life. In addition to my role at Venture Communications, I am investing in Arlene Dickinson Enterprises and YouInc.

CL: TELL ME ABOUT ARLENE DICKINSON ENTERPRISES AND YOUINC. WHAT ARE YOU EXCITED ABOUT AND WHERE IS IT GOING?
AD: Arlene Dickinson Enterprises was set up to help, in a unique way, what entrepreneurs are all about. Nobody thinks about entrepreneurs and their lifestyle. You see a lot of organizations talking to the professional side of an entrepreneur, and you see some talking to the personal side, but nobody thinks about it as a lifestyle. And it is a lifestyle choice; it’s not a career. It’s who you are. You either are or you aren’t an entrepreneur. You need to embrace the messiness. Nora Ephram said that; life is messy and embrace that messiness. This notion of balance makes me laugh. What does that mean? You stop thinking about work when you go home? Sometimes I would wake up and think about my business before I thought about my family. That’s what an entrepreneur sometimes does. I wanted to build a brand that embraced that, took the shame away from that and said this is who we are. If we can celebrate, collaborate, connect and share with each other, we will feel less like we are somehow lacking because we are not on the soccer field all the time, or we are not the perfect wife [or husband] at home. [I want to] help people feel more special and whole and elevated as an entrepreneur, and embrace the contribution they are making to our economy. I want to be the company and the brand that helps entrepreneurs through that journey. It’s exciting; I am very excited about it.

CL: SHOULD OTHER ENTREPRENEURS PUT THEMSELVES OUT THERE IN THE MEDIA – TO CONNECT AND SHARE STORIES – THE WAY YOU HAVE DONE?
AD: Fame – and I say that in a very small “f” way – for me is only good for the good it can do. Has it helped my business? You could argue that, if you are seen as an extremely successful business woman, then that works against you. In some ways what that means is you don’t need the help, you don’t need the support. So it’s a good and bad; it comes with a mixed bag. It certainly has given me a warm introduction in Canada. People love Dragons’ Den and I am so grateful for that. I would have never gone to Afghanistan twice, [received] the Queen’s Diamond Jubilee medal, had the chance to be the spokesperson for the Breakfast Clubs. How lucky am I that I get to talk publicly about the things that matter to me because [I’m on] a TV show? If [getting in the media] is going to give you the opportunity to do the things that you love, [you should do it]. If you are just looking for the fame; no. Fame is a double-edged sword. You have to be careful not to ever believe in your own publicity. You have to be grounded.

CL: WHAT OTHER TRAITS WOULD YOU LIKE TO SEE MORE IN WOMEN WHO ARE AMBITIOUS ABOUT BUSINESS?
AD: I would like to see less women comparing themselves to their male counterparts and more confidence in the path they are charting. I think we spend too much time and energy playing in [men’s] playground and wondering why they don’t want to play with us. Women need to continue to push for more senior roles and for their voices to be heard and understood across all aspects of business. We need to continue to challenge the status quo, especially as it relates to women in positions of senior leadership and boards. I think incremental change is going to happen at an exponential rate, for women. We haven’t been in business that long; men have been in business for thousands of years. They built the financial market, they built business markets, they created commerce. Women have been doing it for, what, 50 years? And we expect exactly the same [results]. I think we are catching up pretty quickly. We have a long way to go, but we’ve got to put ourselves in perspective and build our own future. Don’t sit there and expect to be rewarded by somebody else, because I got news for you, life isn’t like that. So play your role, do your thing, be as strong as you can be. If it’s not working for you, find another option. Find your path and find your rhythm.