Reinvention With The Remarkable Arlene Dickinson

SOLO 93 | Reinvention


This week’s episode features a remarkable solo and cast member of Dragons’ Den, the Canadian version of Shark Tank. Arlene Dickinson joins Peter McGraw and Darlene Savoy to talk about reinvention and single living.

Listen to Episode #93 here:

Reinvention With The Remarkable Arlene Dickinson

Welcome back. This episode features a remarkable solo and cast member of Dragons’ Den, the Canadian version of Shark Tank. Arlene Dickinson joins us to talk about reinvention and single living. One brief announcement before we begin, I’ve moved the show to a biweekly schedule in order to give myself a little extra time to plan a reboot. I’m going to make some improvements to the show. In the meantime, please go to to join our Slack channel and let me know how I should improve the show. New versions are coming. I hope you enjoy this episode. Let’s get started.

Our guest is Arlene Dickinson. She is the General Partner of District Ventures Capital, a venture capital fund focused on helping market fund and grow entrepreneurs and their companies in the food and health space. She’s a three-time bestselling author. You may know her from her role as a Dragon/Venture Capitalist for over twelve seasons on the television series Dragons’ Den. Think Shark Tank for Canada. As further evidence that she is living a remarkable life, she has served for many years as an Honorary Captain in the Royal Canadian Navy. Welcome, Arlene.

Peter and Darlene, it’s so nice to see you both.

It’s a pleasure. We are joined by a special co-host, Darlene Savoy. She is a follower of this show, originally from the East Coast of Canada and has returned to live there after living in various other cities for over twenty years. She is a self-described late bloomer who’s always dear to my heart. She is in the midst of yet another reinvention and she aspires to create solo-friendly co-housing developments. Welcome, Darlene.

Thank you.

Darlene was kind enough to introduce me to Arlene. We are here to talk about reinvention, solo living, and then the opportunities that solos have for reinvention. We should start with your book, Arlene, which is not surprisingly titled, Reinvention: Changing Your Life, Your Career, Your Future. In that book, you used your own process for turning around underperforming companies and apply it more broadly. Is that a fair summary?

I use the idea of the strategy that’s been applied to businesses of all sizes, shapes, and forms that are going through strategic reinventions. It’s not so much underperforming. It could be a pivot, a shift in leadership, and many things that are happening. Using the same strategies that we apply there as a consultant in the marketing space to businesses that we work with to thinking about how I could use that for my own business and, in fact, for myself.

You’ve had your own amazing professional and personal reinvention. We need to start with the flood, don’t we?

That’s probably the best place to start. The thing about reinvention is most people wait for something catastrophic or something that has happened in their life to reevaluate themselves. Whether it’s a divorce, death, loss of a job, career change, or whatever it is, we usually wait for these things to happen where we go, “I can reassess my life here.” For me, that moment in time that was a catastrophe was a natural catastrophe that had happened in Southern Alberta, which is where my head office was and is for my marketing company, Venturepark.

At the time, it continued to be the worst natural disaster in the history of Canada. The water flooded right by my office and took out my office with water. We had to move all our people to remote locations. When my office shut down and when the flood hit my office, it was an absolute nightmare because back then, technology wasn’t what it is now. People weren’t on Zoom calls. There was no accessibility and the real ability for people to work remotely.

We are in a creative industry. We’re marketers and we require a lot of cooperation. I had people all over the city at different offices. We were trying to pitch these businesses that were existing businesses. I had people quitting and leaving. I had the office underwater. We didn’t win any of the business. It was a mess. That’s painting the picture of what was happening after many years in business. I’m looking at it going, “How does this even happen? I’m not prepared for it. I don’t know what to do with this.” It was exactly that moment that created the need to reinvent.

What was happening with you, Darlene, at this time?

When I was reading your book, Arlene, I could relate to your state of denial leading up to that because I was right down by the stampede grounds in a tower there on the 24th floor and I woke up the next day and went, “They were serious. There could be a flood all the way up.”

I was there, too.

Were you in the same building? No way. That’s hilarious.

I thought, “There’s no way this is going to happen. Right here, how could this be?”

It was unbelievable.

We have a video going. Arlene and Darlene are smiling right now, but there weren’t smiles at this time. This is a true tragedy. Talk us through the days, weeks, and months that followed as your business faltered and how you got about starting to make these changes.

In any time in life where we’re faced with something that is either tragic or different and difficult for us, I was struck by what to do. What do you do now? How do you manage this? The business was in disarray, but I was busy doing so many other things, Peter, Darlene. I had many business interests by then. This business was self-running. I had a management team in place. I wasn’t doing the day-to-day. I went home and thought about it. My first instinct was, “I should probably shut the business down because it felt too hard to try and rebuild it.”

I went and faxed my banker and he said, “Shut it down. What are you doing? You don’t need this business. It’s just going to drain capital.” I went home and I was depressed because I have all these people working for me. I had clients who relied on me. If I shut it down, I was impacting many lives. I felt horrible. I went to bed and pulled the covers over my head. If I’m being frank, it was one of those I didn’t know what to do. I knew financially what to do, but emotionally, I didn’t know what to do. It was so hard.

Over time, I kept thinking about this team and what I could do in this business that had been in business for 30 years, the legacy of that business, and how I wanted it to carry on between the tears and the fear. I will add something because this is an important point. I’m a public person, so any kind of failure is public. It doesn’t matter that this business wasn’t my core living anymore. It was the businesspeople attached to me and understood me for. If it shut down, that was not going to be good.

Does this business make you? Is this the thing that catapulted you into these other opportunities?

Yes. This was my first foray into entrepreneurialism, building a business, and growing and learning. I felt an obligation. I’m a big believer in your dance with the one that brought you. That business had brought me to where I was. It was difficult. I started to think about it and put pieces together and think, “What is it about this business that I care about?” I realized that what I cared about was helping entrepreneurs and my team. I started to use the strategy that I deployed with all of my clients and myself. We never do the work ourselves but I decided that I needed to, and that’s what we turned around and did.

You said you went home and you pulled the covers over your head. This was an emotional time. At that time, who was at home? Who were those people?

At that time, I was seeing somebody, but I was home by myself. That makes it even harder. I want to liken it to divorce because I’ve been through two of them. If you go through this, you’re alone and you feel lonely. Whether there are people around or not, these are lonely choices and decisions. When you’re running your own business, it doesn’t matter how many people are around you. These are decisions that weigh on you. Especially as an entrepreneur, it’s an incredible burden, which is why that whole it’s lonely at the top is incredibly true. I had lots of people around me, but I was alone.

Also, the choice sits with you. You get the credit or not if you decide to rebuild this business or to shatter it. You decided to start cobbling together your shoes rather than making them for other people. What are those first steps? I want to start to give people this broad understanding. This is a time where people are thinking about reinventing themselves. Coming out of this pandemic, they’re recognizing that there are other possibilities, opportunities, and things that they want to do. They realize life is short and so on. I’m curious, what are those starting points in order to do this? Did you follow it as you talked about in the book?

Yes. Probably, for me, it was more intuitive because I’d been practicing the process for years. I didn’t have to sit down and do it exactly as I outline in the book, but it is exactly what happened. There are four steps to reinvention that anybody can go through, whether it’s a personal reinvention or a professional one. It’s hard heavy lifting work that is not always easy to do, especially when it’s personal because you have to take a hard look at your life and yourself. That’s step one.

It’s four Cs, so we’ll start with it. The first step is Counterintuitive. When you want to reinvent yourself, your first instinct is to think about what you want to do, where you want to be, and where you’re headed. The counterintuitive part is the place where you have to be retrospective and you have to go backwards. You have to spend some time thinking about who you are, what you’ve done in your life that you’re most proud of, the things that have happened to you that you hold dear to yourself, the values that you’ve had, and the people that have helped you along the way. The things that you go, “When I was doing that, I was the happiest.”

At the same time, you’re doing that, you’re thinking about all the things that you did that were wrong. You’re thinking about all the challenges of the people that you met. You’re thinking about the things that you don’t like about yourself. This is hard work. Taking a hard look at ourselves is something people don’t want to do. Businesses are used to doing it, but people aren’t. We don’t want to look in the rearview mirror. We’re trained to look forward and think about what’s now, not what’s been. The first step is to think about what’s good, what you love about yourself, what you loved about what you did, the things that you’re proud of, and bring that stuff forward with you. You don’t want to get rid of everything in the past. You often hear people say, “I got rid of it, my husband, my weight, and my house.”

“I burned it to the ground.”

“I burned his clothes. I did all these things.” That’s okay, but you can’t leave everything behind. What happens is when you see people who have good relationships after they split up, generally that’s because they could hold on to what was good about the relationship. They didn’t just wipe it all out. Step one is counterintuitive. Step two is to think about your Core purpose. What’s your why? We talk a lot about your passion, like, “What’s your passion? Do what you’re passionate about.”

I like to think about your core purpose. What gets you out of bed every day? Why did you get out of bed today? What is it that you are trying to do with your life that is going to give meaning to it? Finding your why also takes some thinking and focus. Once you have your why, you can start to see the things that you were doing that weren’t contributing to your why. You can start to see that maybe you’re on a gerbil wheel or hamster wheel. You’re going around and you’re busy, but you’re not doing things that are contributing to your why. You think about your core purpose.

Can I ask about this process? Number one is looking back and assessing strengths and weaknesses kind of thing, what you’re proud of, and what are your mistakes. This next part is about your why. Do you suggest people to journal? Is there any technique that helps with this? Should they be going out and walking in nature? They’re weak in the woods. Is there some process associated with answering these questions you would suggest?

We’re talking about personal reinvention here. On the first step in terms of looking backwards, it’s found in pictures, letters, cards, music, listening to and thinking people that you met, conversations, and memories. In our day, it was scrapbooks. It is going back through your phone and thinking and seeing the stuff that you go, “I remember I was happy in that picture. Why was I happy in that picture? What was going on in my life then?”

In terms of your why, this is looking at what’s fulfilling you and saying, “What is it that I want to do with this one life I have?” This is a personal journey. There’s no exercise other than contemplating whether what you’re doing is fulfilling the purpose you feel you have in life. If you don’t feel you have purpose, if you’re thinking about it and you’re like, “I don’t know what my why is,” that’s okay, too. You have to, at that point, spend some time understanding what your values are. What you won’t do is as important as what you will do. That helps you narrow it down.

The third C is to think about your Currency. When I say that, people will say, “Money? What do you mean money?” What is it that you’re good at? We’re all good at something. Every single one of us has a skill or a talent. I often use the example of Mrs. Fields, who made cookies. There are people who make great sandwiches. There are people who do whatever they do. We’re all good at something. Is that something that you do? Is that something that’s helping drive your core purpose? Is it something that is reflective of what you’re proud of in your life?

I’ve talked to too many people who say, “I’m not good at anything.” It’s so discouraging because you are good at something. If I have any message for the readers, you are good at something. The way to find that you’re good at something is to stop comparing yourself to somebody else. There might be 1,000 people or 10 million people that are good at making cookies, but you might make the best cookie. You might create Mrs. Fields cookies as a result of that. It’s probably a corny example, but it’s one that’s on the top of my head right now.

The final C is Context. Once you understand your past, what you like about yourself, and what you have done well, and you think about your why and what you’re good at, then you can turn your attention to what’s going on in the world? Can I take who I am, what I care about, and what I’m good at? Can I apply it in the context of today’s world? The answer is always going to be yes.

We can say, “I’m older. What do I know? The things I have are old fashioned and people don’t need that today.” They need your skill and your talent. You just need to think about how you can make what you do relevant in the context of today’s world. Those are the four steps that are outlined in the book. It is a little bit of heavy lifting. I’m not going to lie. This is not work you do on a weekend while you’re out for a stroll. Pay attention to your life work. This is heavy lifting of your life. It requires time, attention, and thought.

How did you then do this on your own? You have this flood and you’re getting advice, “Shut it down, Arlene. It makes a good financial decision.” You have this team and legacy. You decide, “No, I’m not going to do that.” How did you create this reinvention for this company?

I gathered my team around me that was left who were the most loyal people in the world and we started talking about what was possible. We talked about what we like and what we didn’t like about the business. We started to draw out on whiteboards all of these different paths that we are on and all the things. I will tell this to anybody, the good thing when you’re going through this process is, writing it down does help. I don’t think you have to journal, but it does help to draw diagrams. You’d be surprised when you start drawing a few things on a scrap of paper.

When we did that, what we found is there was the central idea of entrepreneurialism that we’d focused on, but we hadn’t really focused on. We started to take all of the things about my life because I was so tied to the business. My brand personality on the marketplace, my time on the show and what that meant for entrepreneurs, the things I stood for in the marketplace, and the things I ventured in in terms of helping entrepreneurs. We had a website at the time that was aimed at entrepreneurs. We put all that on a piece of paper and I said, “Now it’s obvious that it was all linked through that,” but it wasn’t obvious at the time.

We were writing all of these different things. I was off doing my stuff for my brand, the company was doing its marketing thing, and the website was doing its thing. Everybody was off building their thing, but we didn’t connect at all. With my team, we were able to find that connection. When that happened, I started thinking about what it was that I loved about the show and what my why was more. I know this is an American show but it applies anywhere.

We’re big in Canada, Arlene.

I’d seen on the show all these entrepreneurs pitching food ideas and health ideas. They’d come on and they’d be told, “You’re never going to make it. The big companies like Procter & Gamble and Unilever are going to squash you.” That hit me. Here we are as a nation with incredible natural resources and commodities. We ship them everywhere in the world for other people to turn them into products so that we can, in turn, buy them back. That last mile of innovation and added value is where all the money is. It’s where all the true margin is.

I started thinking, “People should care more about their health and we should care more about the food we’re eating.” It was at this time of my life, I was caring more about my health and the food I was eating because as I was going through this reinvention, I was overweight and under a lot of stress. I was not taking care of myself and I was so focused on fixing the business. I was personally broken. All of these things were going through my head about what we could do and I realized I needed to focus on myself where I was going to not be here for the future.

I’d never in my life not worked out and taken care of myself. I probably gained 30 pounds, maybe more. I was a mess. It was because I was so stressed. Thinking about food and health and its relevancy to what it meant to me and I knew to other entrepreneurs, to people in general thinking about Canada’s skills and natural resources. Thinking about all that, I decided to go and raise a fund to invest in the space and to build this brand new ecosystem that had never been done before.

All of this stuff, it sounds like, “You just got up and decided?” No, these are things that evolve. As you start putting the pieces in place, you see a picture much more clearly. I started to see that there was no one in Canada that was investing in these spaces, yet in terms of employment in Canada, food and health, agriculture and health, 2 in 3. We have so much skill in these areas, so I thought, “We’ve got the skill, resources, commodities, and all these things. I’m going to invest some money in a fund that could do this,” and then I couldn’t find the fund that I’ll invest in and I thought, “Maybe I should start the fund.” I had never run a fund before, but I’ve done a lot of investing.

I decided to start a fund and then I thought, “If I start a fund, where are these companies going to go to get scale? How are they going to grow their early-stage companies? Maybe I need to start an accelerator to help these companies along the way.” I opened a not-for-profit accelerator. I started to raise a fund, which was one of the hardest things I’ve ever done. I raised a $100 million fund and opened the accelerator. I created a marketing firm attached directly to the fund because what makes consumer goods brands big? Marketing.

I took all my marketing expertise, took the fund and the accelerator, got a commercial kitchen and a media company attached to it. Now we have one of the most unique ecosystems in North America that focuses on putting capital to work but provides resources to these entrepreneurs through the accelerator program and commercial kitchen. Also, what we do with the media company and marketing.

In 2020 alone, we probably put close to $300 million in revenue into the Canadian economy and employed thousands of people as a result of this idea that came from a company that was underwater to five years later, had helped over 100 companies and created thousands of jobs. Every year, those companies are driving hundreds of millions of dollars in revenue. It started with, “I don’t know what to do,” and me pulling the covers over my head. I’m a testament to the fact that this hard work is worth it, but I’m also a testament to the fact that it can be difficult for you and harmful to you if you don’t pay attention to yourself.

Inspirational story. I’ve read your book and it’s great. Having gone through a few hiccups, I can relate to the divorce one. I can relate to the flood one, although the stakes are different in our situation. I didn’t own property or a business. I feel like as I get older, I become more conscious about these reinventions. I don’t think I could have read this book when I was 21. You have to live through some of it yourself, and then learn from it.

It’s too bad that we, as humans, wait until something bad happens to us for us to think about who we want to be with our lives. I’m only grateful that it happened to me before it was too late. I got a chance to reinvent myself, as do we all have a chance to reinvent ourselves. When I say too late, I don’t mean that about my age. I mean still alive.

Arlene, you were talking about Mrs. Fields. I’m a business school professor by trade, so I talk about the need for a good product but then also the need for a good promotion. What happens sometimes is there’s someone who is good at making pies, cookies, or smoothies, or good at personal training or whatever this thing maybe, but they’re not a businessperson. I want to compliment you on the brilliance of building an ecosystem that not only gives these folks capital in order to develop and scale but then also supports that development and helps them with the scale. They may be good at this one thing, but they may not be good at all those other things.

Thanks, Peter. That’s the future of venture capital and private equity. Venture capital, for too long, has focused on the financial inputs that they give to companies and they might have some people that they bring in to support the businesses that they invest in. These ecosystems that can be constructed are the future. I operate six different businesses, two marketing companies, a kitchen, an accelerator, a fund, and a media company. Those companies, not only are they different in terms of what they do day-to-day, the actual delivery of what they do, but they’re also different in terms of their financial reward for what they do because some of those organizations are not-for-profits.

What they have in common is a common purpose. Each one of them gets out of bed every day to help a consumer goods company in the food and health space succeed. They all do it differently, but that’s what they do. They share a common purpose. They have a different business model. They run different types of businesses, but they get out of bed every day to do the same thing. This is what an ecosystem needs to be. It needs to allow for different business models, common purpose, and different rewards in terms of how people are compensated.

Let’s talk about this because not everybody who’s reading is interested in professional reinvention. A lot of folks are interested in a personal one. This idea of having an ecosystem matter too, for personal reinvention. I’ll kick it off if I can. One of the things that I often talk about is how people, especially singles, need a team, a group of personal friends and family connections, and then also professionals to help support them in living their remarkable life. It strikes me, if you’re going to make a personal change, a reinvention, that you’re going to need to create that ecosystem for yourself also. I’m curious about your reaction to that idea. Have you given this some thought? What’s your reaction to that notion?

It depends on the person you are. As you said that, I thought, “I’m an introvert.” There are people who don’t have big groups of people around them who they can rely on or talk to. I don’t want anybody reading to think that they have to have an ecosystem of friends because not everybody has it. Maybe you do need to develop that. I talk a lot in my book about the notion of frenemies. Your friends can be equally as bad for you as they can be good for you. The people who say, “Why would you want to do that? You don’t want to do that. That’s not what you’re good at. You should do this,” aren’t friends. Those are frenemies. They push you down by telling you shouldn’t or you can’t. You have to be careful who you surround yourself with.

Your point is also true. It’s helpful to have somebody to talk to, for sure. It’s helpful to have resources and a team around you that will support you. The point I’m trying to make is that this team might be completely a new team to you. It may not be your existing friends because you may find that those existing friends are the reason you are where you are.

If someone’s an addict, one of the best ways to stop smoking, drinking, or whatever is you have to get rid of friends who smoke, drink, or who do those whatevers. The recreation might end up happening on the team side of things.

Hiring a therapist.

Let’s talk a little bit about your personal experience in your development as a solo, Arlene. You were married young. There’s a reason you’re on this show beyond the fact that you are great at reinvention. You have become an advocate for single living.

I started a video series on the single life, which I need to do another. You reminded me. I haven’t done one for quite a while. I had so much good feedback on it. It’s been busyness. I haven’t had a chance to, but I will do one. I was married at 19, had four kids by the time I was 27, divorced at 30. That was my first marriage. I went right into another relationship. All my relationships were fairly long-term. I got married again and divorced after seven years, and then I got engaged to somebody after that. From the time I was 19 to the time I was in my 50s, I was in relationships.

We call this the relationship escalator. You were writing the relationship escalator in some way, shape, or form for much of your adult life, it sounds like.

In my generation, when I was young, you were told if you weren’t married by a young age, there was probably something wrong with you. You were supposed to get married and be a good wife. I tried and miserably failed at it. Let me take that back. I don’t know if I failed at it. Sometimes we’ve just chosen the wrong partners and that’s okay, too. It can’t always be that there’s something wrong with me. Maybe there was something wrong with them and with both of us together.

The connection is not right.

I was engaged for several years, and then I broke that off. That would have been in my 50s at the time. I’m bad with time.

I’m getting hooked on figuring that out.

This has been true for me for my whole life. I have no concept of time. It drives everybody crazy because I’ll say, “I just talked to you.” They’ll say, “That was six weeks ago.” I go, “It just happened.” It’s not new to me because of my age. It’s who I am. It’s been about eight years or so since I’ve been single. Even though it was my choice, I didn’t know what to do. I thought I had to get into another relationship. I needed to go and date somebody. I did a little bit of that, and then I realized, “No, that’s not what I need or want.”

Because of my age, I’m a female and a fairly successful female, it’s hard to date. It becomes more and more challenging. I found myself thinking, “What is it I want out of a relationship?” Maybe this is just me, but I found myself becoming increasingly more happy once I let myself be okay with being alone. I was wanting to be in a relationship for everybody else, not for me. I was quite happy.

When I focused on my health, my family, my fund, and everything else, now I say to people, “I’m 98% whole.” When I give up any percent of that 98% to try and make it 100% and find somebody that didn’t make it work and take me down back to 80% or 70% years, no, I wouldn’t do it. I’ve reconciled that I have such an amazing life and I’ve been given such amazing opportunities. I feel so lucky. How wrong is it to feel like somehow, I’m less than or not good enough because I don’t have a partner? It’s such a ridiculous thought. That took me a long time to get there though.

I can relate to that, if you don’t know another way. I sound silly to say that I wasn’t aware of another way. In our generation, that was the way. Where I’m from, the East Coast in a small town, that’s what you do. We were together in high school, sweethearts. We married at 25 and divorced at 30, so similar in that respect. Looking, seeking, and then realizing, “What am I doing?” Speaking of the why, I had to ask myself, “Why am I looking?” I realized, “It’s for this, this, and this. I can find these other things elsewhere. I don’t need to be in a traditional partnership to find those things and make me happy.”

What’s interesting about that, Darlene, and I bet you get this all the time because you’re beautiful. What I hate most is when people say, “You’ll find somebody.”

“Why are you single, Arlene?”

“You’re so good-looking. You’re this and that.” You go, “What on Earth has that got to do with anything?”

It’s the wrong question.

When people say, “You’ll find somebody,” I go, “Is there a yard sale somewhere that I go on the desk? There’s the guy. That’s the one I love. I’ll take him.” It’s so ridiculous. People in their well-meaningness can be unhelpful.

I don’t have the same experience because I’ve never married, but there seem to be two commonalities that both of you have identified. I have it myself and a lot of the readers can identify it. One is you start to realize that there’s a lot of pressure from others about how you should behave. Arlene, you said as well-meaning and I do believe it is well-meaning. That’s unfortunate pressure because it knocks people off. “That’s right for them.”

The second realization is a personal one, which is a realization that you like your life, you enjoy your life, and you’re happy with your life as is. That removes some of the pressure to find someone else to make it better and to also recognize the risks of that other person. They may make it better, but unfortunately, they may also make it worse.

For the readers who recognize the pressure and realize that there’s a lot of good in their life, it may even be a great life or a remarkable life, how do you take that next step and transform yourself from being single to being solo, from viewing yourself as incomplete to viewing yourself as complete? Do they need to do those walks in the woods? Do you need to go through that same foresees process, do you think, Arlene, for that reinvention?

I would certainly encourage everybody to go through the process. The book is self-explanatory and it’s not complex. It’s more hard work emotionally. If you feel like you’re satisfied with your life but still feel these societal pressures, the one thing you have to ask yourself is, “Are you hanging around the right people?” If people don’t want to invite you over for dinner because they insist on having an even number of people at the table, God forbid that they have Darlene there because she’s good-looking.

Some husband.

I’m going to give you, Arlene.

All of these things, you need to ask yourself if you are hanging out with people that are going to encourage your life versus trying to persuade you to be more like them. The normalcy of being married and having kids have got to go away. Equality has to stay. The normalcy of saying, “This is what a perfect woman is. She’s got a man or a partner.” Whether you’re LGBTQ, too, or however you identify, a partnership isn’t going to change who you are and your happiness. You have to be prepared to say, “I’m happy.” You have to start there.

You’re still going to have moments of loneliness and where you wish you could share a moment with somebody and you’re sharing it on your own. At some point, it becomes, “I’m okay sitting at a restaurant by myself, having a great dinner and a great glass of wine, and not being with somebody.” People think that’s weird. I feel like I’ve got such great self-awareness about myself that way. I’m quite happy doing it, so why shouldn’t I do it, because other people think I shouldn’t?

By the way, when you’re at that restaurant eating alone and enjoying that, you should look around at the other couples there. There are a lot of bored couples sitting in silence eating their meals. It’s not always as delightful as you might imagine.

I know that. I have observed them. I’ve been at those tables for 40 years of my life. I’ve been more lonely lying in bed next to somebody I didn’t love than I’ve ever been lying in bed alone ever. There’s a big difference between lonely and alone. This is something that you also have to come to grips with.

You said you do this video series, is there one of them that stands out to you that you’re proud that you share that with the world?

Those videos are what brought me to bring you to Peter. I’d always been following you as far as Dragons’ Den or whatnot, but I didn’t realize that you were an advocate for solos and then I saw one of the videos.

Which one, Darlene?

I can’t remember. I just remember it was the perfect solo rant.

I’ve ranted a few times. I’ve had such great feedback. I’ve had well over 1,000 comments. The feedback I’ve had is crazy. One of them came out and said, “I’m not wearing a bra anymore. It’s uncomfortable. I hate it.” The whole internet blew up and said, “Somebody finally said it. Somebody who’s got a profile is talking about this.” For me, I had enough of a profile that I was prepared to stand up and say, “I’m fine being single. I am happy.” There isn’t one that stands out. I’ve enjoyed doing all of them. Honestly, I do them at the last spur of the moment. I’ll sit there and go, “That bothered me. This is happening and why did that happen,” then I’ll talk about whatever that is.

Darlene, was there one in general that has stood out for you or did you just enjoy the general emotion?

She hit all the nails on the head. People are asking me why I’m single. People are asking me who I’m seeing now. All the annoyances that one experiences, she was bringing them up and ranting. It’s cathartic to listen to.

I’m seeing this time and time again in terms of people. They react because there’s so much pressure. There’s so much conversation about coupling up and riding the relationship escalator. If you give people any alternative to it and you tell them, “It’s okay to feel the way you do. It’s okay to not want this,” they go, “Thank you.” I had a previous guest who said, “I feel seen when I read this.”

I go back and look at the series. I did one called Why am I single? And why does everyone else have the answer?. I’m single because I choose to be, but everyone else has to tell me it’s because I’m too intimidating. I’m not looking enough. I’m too this and that. It’s not the answer. The answer is because I choose to be. That was one of them. I also did one on Do you sleep in all the bed or one side of it?. I did one about Cooking For One?. What that means and how you manage to cook for one. Why are single men treated differently than single women are? Why is it okay to be a single man when you’re older and you’re seen as a catch, but a single woman is seen as a spinster and not desirable? It’s crazy.

This is something that comes up a lot. I’ve noticed a lot of differences with regard to gender and the challenges with it. Some of the challenges for men on the young side, these incels of the world, and then for older women, especially the stereotyping and the prejudice.

If you’re an older woman dating a younger man, it’s taboo. If you’re an older man dating a younger woman, you’re lucky. It’s ridiculous.

One of the themes that I talk about with solo living is what economists call optionality because you are often more mobile, you might be less tethered, and so on. You have more freedom in some ways. You may also have a different set of challenges. I’m wondering if we could, as we start to bring this to a close, talk about that. If you’re reinventing yourself as a married person versus you’re reinventing yourself as a solo person, what are the differences there?

I often think that we find ourselves as solos living by the rules of married people and not even recognizing how much we have that we can deviate from 9:00 to 5:00, how we can take risks and start businesses, and how we could become digital nomads. Do you have any thoughts about the solos who are reading this as they contemplate reinvention or either around opportunity or how they may want to think differently than their counterparts?

What do you think, Darlene? I would love to know your thoughts first.

It’s funny, I’m going through a strange reinvention where I moved back to the East Coast right before the pandemic hit. If it were ten years ago or so, I would look at my life now and say, “You’re going backwards.” Going back to the don’t compare yourself to others syndrome, I realized, “It’s progress. I need to be here now.” I’m in my parents’ home and I’ve been here for the entire pandemic, but I couldn’t have done this years ago.

Certainly, when I was trying to couple, there were certain checkmarks. “You have to be in a couple. You have to be in a house,” whatever the checklist is, but now I feel like I have an open set of checkmarks. It’s for the goal that I have in my mind. Some of the steps may seem like I’m going backwards if I were using my old checklist. It’s a different set of success criteria.

It doesn’t involve a house in a white picket fence and so on.

My solo checklist, path, and criteria for success are different because I can open it up.

There’s more available to you. To the point of optionality, everything’s available to you. If you decide to go back and be a couple again, go back and be a couple again. If you decide you want to stay single forever, stay single forever. If you decide you want to switch sides, do that. This is the thing we all miss in life. This is the most poignant point we can make about life. It is your life and the optionality is yours. You get to decide what you need. Nobody else. Don’t ever give up that choice. Don’t ever give up your agency to somebody else to determine what happiness looks like for you. You’ve got lots of options. You’ve got every option you want as long as it’s the one that’s going to make you the most happy.

Arlene, Darlene and I had a conversation and I was like, “What kind of dragon is Arlene? Is she one of the cutthroat ones or is she one of the supportive ones?” Darlene said, “She’s a businesswoman and she’s good at what she does. She’s sharp, but she’s one of the more supportive ones.” What you said and the way you said it encapsulates those two sides of your life, as someone who has been tremendously successful in the world of business but then is also someone who cares about other people and herself.

I am thrilled that you’re contributing your voice and your energy to making Canada better, but also to making the lives of single people better. I hope you keep making your rants. I hope you keep lending your voice and your experience to this dialogue because you’re doing incredibly important work for folks to license them to recognize, “Other people don’t know what’s right for me. This solo path for now or forever is the right path for me.” I want to thank you for doing that generally and specifically for joining us on this show and doing this.

Thanks, Peter and Darlene. It was my pleasure. This is a topic I do care deeply about. We can’t change the world unless we give each other the opportunity to be okay with who we are and not try and tell people how to live their lives. I appreciate the show, what you’re doing, and how you’re encouraging people to be single if they want to be. Single, solo, and labels need to go away. Whatever it is you want to be, just be that. My mom made a comment, “Getting old is not worth the pain for what you get.” People better remember that old age is coming out of all of us and we want to make sure that we have lived our life, not somebody else’s.

I also want to give a special thanks to Darlene. Darlene is a follower turned participant of the show. One of the things that is going to be important for this is to build a community and connections among like-minded people. You might need to call some friends and I want to provide a place to add some new friends, some people who are going to invite you over, whether you’re going to bring a date or not, no matter how good you look or not. I want to thank Darlene for being a valued member of the community and for contributing and helping make this show better.

Thank you, Peter, for giving me this opportunity. What a special day to meet you, Arlene.

It’s lovely to meet you, Darlene. Good luck whatever your path is.

Thank you.

I love the idea of co-housing for people who want to still have somebody around but don’t want to be in a relationship, so good luck with that. It’s a great idea.

A little preview, I’m taping an episode on the Golden Girls. That will be forthcoming.

I’m older than the oldest Golden Girl that was on the show at this point. That shows you how TV is. We thought they were 100 years old, but they weren’t that old.


Thanks, guys.


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About Arlene Dickinson

SOLO 93 | ReinventionArlene Dickinson is the General Partner of District Ventures Capital, a venture capital fund focused on helping market, fund and grow entrepreneurs and their companies, in the food and health space. She is a three-time best-selling author—and you may know her role as a Dragon/Venture Capitalist for over 12 seasons on the television series, Dragons Den. Think Shark Tank for Canada. As further evidence that she is living a remarkable life: she served for many years as an Honourary Captain in the Royal Canadian Navy.


About Darlene Savoy

SOLO 93 | Reinvention
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Darlene Savoy is a solo podcast listener originally from the east coast of Canada, and has returned to live there after living in various other cities for the past 20+ years. She’s a self-described late bloomer in the midst of yet another reinvention, and she aspires to create a solo-friendly co-housing development.





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