Reinventing Your Self, Your Life and Your Business with Arlene Dickinson

June 3 | On the Elevate Main Stage

At the age of 30, Arlene was unemployed with a high school diploma. Today she’s a CBC Dragon and CEO, and she’s here to teach you how to reinvent yourself.

Throughout the pandemic, Canadians and people around the globe experienced a lack of agency. Entire industries were transformed, others near-folded. Our economy and public health have been upended. Many of us have landed in 600 square-foot spaces, hunched over laptops at kitchen tables, desperately praying for the sweet relief of our children’s in-person school schedules to be announced. No matter how much money we saved by eating at home, or how many new pairs of lounge pants we ordered (sorry jeans, not today), we couldn’t quite convince ourselves this lifestyle offered us any semblance of balance. 

The biggest hurdle today is no different than yesterday’s, we don’t know how the future will look. We are at the whim of science, nature, government, and slackliners that insist on gathering in public spaces on sunny days. 

All we know is this: we don’t want the future to look like the present. And we don’t want it to look like the past. We are at a critical point in designing our future. It’s time to take back our agency. Today is the day for thoughtful, courageous, and intentional reinvention. Of ourselves, our businesses, and our world. 

So…how do we do that?

At Elevate Live, we welcomed icon and reinvention queen, Arlene Dickinson, to the digital stage. In her 30s, Arlene found herself in a terrible situation: unemployed with a high school diploma, recently divorced, and without sole custody of her four children. Within a decade of that, she reinvented her life. Today, a best-selling author, speaker, CBC Dragon, and CEO of District Ventures, Arlene revealed, in an illuminating and uplifting talk, precisely what it takes to design your future.

Take Time to Course Correct

You’re driving to a well-known destination (maybe one of the familiar summer locations from the list up top). You’ve traveled the road innumerable times, and your phone is on straight DJ duty — no GPS necessary. Halfway through the ride you approach a sign you haven’t seen before: 


You’re faced with a choice. You can turn back, find a detour, or pick another destination. 

One thing you’re not going to do? Drive into the flood and pray the dealership forgot to tell you about your Hyundai’s amphibious qualities.

When we’ve succeeded before, it can be tempting to think the same strategies that got us to our destination last time will take us to the next one. It’s a fallacy, and it just doesn’t work like that. 

Fortunately, in Arlene’s mind, facing a hurdle that forces you to re-examine your options and strategies can be the best thing that happens to you. When Calgary suffered unprecedented flooding in 2013, Arlene’s growing company was in a precarious position. Like many businesses today, Arlene faced a choice: to close up shop or reimagine her company.

“That was a time in my life where I had to dig deep and figure out what I was I was capable of.”

In her opinion, there are moments in life that create the need for us to reinvent ourselves or to change. Necessity is what drives us.

“It was the best thing at the end of the day that could have happened to us because it made us rethink everything. Like literally everything. We had to rethink who we were, what we wanted to be, and how we were going to become a different type of agency moving forward.” 

Some situations force you into reinvention. Arlene says we’re inclined to think there will be a time in our lives when we can take our foot off the gas. That with enough experience and reliability, we’ll be able to relax. Unfortunately, it’s just not the case. But those moments that force us to accelerate again will be the ones that get us to our next destination, as long as we dare to take a new route.

The 4 Cs of Reinvention

In Arlene’s book, Reinvention, she outlines four of the critical principles of pivoting successfully. 

#1: Counterintuitive

The first step in Arlene’s blueprint for building a future is the exact opposite of what you’d expect when making a path forward: look behind you. 

“In business and life, we tend to want to move forward all the time. We want to keep going. We’re always thinking about the future. And what we have to do is re-examine what got us where we are what are; the things that led us to the place we are,” offers Arlene. 

Arlene acknowledges that reflection and introspection are rarely a fun activity. Who wants to think back to all the mistakes we made or the bad days we had? But Arlene is confident that taking the time and care to revisit those moments are what will help us build a better road forward.

#2: Currency

The next step is to take a good hard look in the mirror and identify where your value lies. What is it you’re good at? What’s the thing you have that nobody else has? What’s the perspective you have that other people don’t? 

Having self-awareness and a grasp on the things that make you unique will set you apart. Investing effort into something that comes naturally to you will yield extraordinary results. Grit is essential, but if you focus it on something you have talent in, it’s a game-changer. 

#3: Core purpose

“I believe when you find your purpose, your ‘why’, the reason you get out of bed every day; you can figure out how you want to reinvent yourself to serve that purpose.”

To Arlene, finding your purpose is fundamental. It is at the core of having the courage to make giant leaps of faith in yourself and, in times of crisis, will serve as your guidepost and inspiration in difficult decision-making. 

For Arlene, keeping her purpose top of mine was a key component of her reinvention.

“I decided if I wanted to reinvent myself, I had to take a bigger risk; to dream in a way that didn’t temper myself. I had started to marginalize my expectations and I wasn’t pushing boundaries and barriers – that’s not true entrepreneurialism,”

For Arlene, true entrepreneurialism is seeing something that no one else sees and having the courage to push through for it.

“So I set out to start a fund. At the moment, I said I was going to do that is when I realized that’s what entrepreneurialism is: a leap you take when you believe so strongly in something.”

Part of the reason a clear sense of purpose is so vital is that, as any entrepreneur knows, there is a lot of exhaustion, frustration, and rejection in that process. It will take hearing “no” a hundred times before hearing “yes” once, and having a clear purpose is essential for remaining resilient through all of that dismissal.

#4: Context

It doesn’t matter how successfully you accomplish the first three Cs unless you learn how to position them in the current climate. You can’t reinvent yourself in a silo. 

“You have to reinvent yourself in the context of everything that’s happening in the world. What does the world need, and what can you give the world back?” 

Know what people need right now

Once you’ve landed on your key learnings from the past, identified your currency, and established a purpose, you need to find a way to make your idea relevant to other people. Decide whether or not you’re creating something with which people will want to interact. 

To do that, you need a clear understanding of what people need and want right now. Humans have fundamental needs, desires, and beliefs. Arlene believes that, by applying those things, you can help people live happier lives. That’s where your success will come from. 

“Help people get out of the mindset of negativity that’s out there. It’s about not thinking about monetization, but thinking about doing the right thing. That’s the change that we all need to see. Indeed, we’re all in businesses, and we all need to make money. Still, at the end of the day, if we start from a place of trying to help others and build an organization that people will want to be associated with, then everybody will win.” 

Know Where Your Assets Are Today

“I encourage everybody to take this time to think about the assets you have to relaunch yourself to work on wanting people to be able to do business with you.”    

Assets change depending on the environment in which they exist. For example, you may have a product in mind that’s miraculous; it could hold the potential to bring happiness to consumers everywhere. But right now, if you can’t bring it to customers digitally, you’re sunk. So in this climate, focus on your digital strategy. 

“Focus on your ability to be seen located and heard from digitally so people can find you. People have ignored that digital presence for years, and now is the time to focus on it.” 

Verbalize Your Goals

Another great time from Arlene is that it’s important to say your goals out loud. It sounds simple, but so much of the time, we let our highest aspirations sit quietly in the back of our minds. We don’t want to hear that that’s silly, or that we’re out of touch. And we don’t want to hear that we might not be capable. 

But according to Arlene, verbalizing intentions is essential.

“It doesn’t matter if people think we’re crazy. It doesn’t matter what anyone else thinks of your aspirations, but when you start to say it out loud and let people hear you, and you repeat it to yourself. You say it out loud to your friends and family and anyone who will listen, it starts to cement the path that you need to move forward. It starts to define the goal that you have, not just in your head, but everyone else starts to understand it and support it as well.”         

Work With Your Brain

The process of pivoting, as a person or as a business, is demanding. It’s not enough to be willing to do the work. Arlene reminds us that we also have to be able to be strong enough to withstand it. Here are a few of the things she recommends to give yourself the mental space and fortitude to embark on reinvention. 

Leave Room for Creativity

“Creativity is fundamental to us getting through this. Whether it’s intellectual stimulation or helping people get into a new mindset; not thinking about monetization but working to help people; that’s what we need as a society.”

Have a Morning Routine

 “It can be overwhelming. Find time in the morning to focus on things that help your brain disconnect from negativity. Do anything that has nothing to do with what’s happening in the world. 

Limit Your News Intake

“Take your time away from that so your brain can reconnect and think differently. Don’t spend so much time focusing on the news that you get inertia as a result of it. If you get too much negativity, if you get too focused on all of the things people or other people are saying, then you don’t know how to act for yourself. Try not to focus so much on the news, and your Twitter feeds on your Instagram feeds. Just really censor for yourself.”       

Treat Your Body Well

“Physical activity and eating well has helped me a lot – think about are you treating yourself well. Self-care, meditation, and mindfulness are important. Anything to disconnect is critical.” 

Let Yourself Wallow. Then Get Up

“Let yourself think, occasionally, that this is pretty shitty. But then try to get up and refocus and re-energize.”

Engage with Your Life

“Go back to playing with your kids and go back to listening to what your kids are saying; to thinking about what matters to you and go back to the fundamentals. Go back to caring about what people are experiencing and help them.” 

Seek Out Stories

“Listen to podcasts where you’re hearing from people who have experienced recessions and challenges. Learn from them. But use your brain to think about a path forward that’s going to work for you.”

Final Thoughts

At the end of the day, who you are, what you believe, and what you aspire to belong to you. Make sure you treat yourself well and continue to dream big. Continue to think that you can do what it is you need to do. 

I would start with have faith in yourself and encourage yourself and believe in you and play that tape in your head over and over again that you’re good enough. You’re strong enough. You can get through this.

Watch the full session here

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