Women Who Lead – Finding Your Edge As A Millenial Leader

My daughter, Terralynn Trask, is a member of the Millennial Generation. At 26, she is actively exploring her career options. Having been raised by two entrepreneurial parents, armed with a degree in Management and an innate set of skills in Marketing, well her appetite is really quite large. Her dilemma however, is what is she going to do with her life. In a recent conversation with her, I was struck by her comment that she wished she had been born with a profession in mind. Her friends were following in the footsteps of parents who were doctors, lawyers, nurses, accountants, business executives, all seem to know at an early age what they were on the path to become. But how does this generation discover where they are going once the studies parrying and traveling have served their purpose in its feeling like the time has come to get serious about making a career choice. I wanted to find out more about what goes on in the mind of our next generation of women leaders, as they make the transition from having fan to getting real. My guest this week is one such individual. Molly Connor, 26, is six months to her professional career as an Account Executive for the Greater Halifax Partnership. This is an organization that brings together public, private and not-for-profit enterprises in a collaborative effort to grow the economy through successful business activity. Molly is both an ambassador and feet-on-the-ground business development advocate for small businesses throughout Rural Nova Scotia. I was curious to find out how Molly had gone from being a global wanderer, having completed her university studies to assisting small business entrepreneurs. I wanted to find out more how a young woman raised in Rural Cape Breton as the daughter of entrepreneurial parents running a bed and breakfast, went from studying Philosophy and Gender Studies to becoming one of 50 fellows of Venture for Canada which recruits, trains and supports young professionals to work for top Canadian startups and growth companies with the mission of fostering entrepreneurship in Canada. Now even with a simple introduction, you may assume that Molly’s career path has been quite straightforward from her childhood upbringing to her new career. But as both she and my daughter remind me, no one really knows nor do they understand the turmoil, uncertainty, anxiety and fear that underlies each step along the way. The Millennial Generation talks a good game but do not be misled, each of them is taking this leap into the unknown. They are new comers in a highly-complex job market, one in which the majority have no idea what’s next. They simply have to get into the game. What is really going on under the surface of what we think as a fairly provado posterior confidence of this generation? What’s going on underneath? Let’s find out from one such new entrant, finding her way as a woman aspiring to lead.

Tune In - Women Who Lead


Lesley:  So, welcome, Molly Connor, and I want to start with this question. How would you describe where you are in your life right now?


Molly:  Ooh, Chaos?


Lesley:  In what way? What’s the part that’s chaos because the audience already knows that you’re accomplishing many, many different things on many, many streams? And so, what’s the notion of chaos?


Molly:  Well chaos has a negative fall away to it, I think it’s really more exploration than anything. I would say that I’ve got my fingers in ten different pies and then kind of seeing where the successes are, and what really pushes me forward, and where I really find that passion for life and what not. So, it’s really interesting to just be in an exploratory phase and looking at, you know, let’s talk about six months. Let’s not talk about two years or five years and finding how do I get with the next six months with the overall goal of being a happy well-rounded individual.


Lesley:  So when you think of happy well-rounded—as you would describe it this point in your life—what would the characteristics that be?


Molly:  Well that’s an interesting one actually because I was having this conversation of that long ago with them, a similar group of female young professionals, and we were all talking about how happiness somehow for us comes from being stressed and on-the-go and constantly being on the edge of uncomfortable, which is not I would’ve said three years ago. Three years ago, it would’ve been, “How can I watch Netflix for them during my day?”


Lesley:  So there’s something about being on the edge that’s important to feeling fulfilled.


Molly:  Oh yeah. And I think it’s really interesting because I’ve kind of hit that limit of… six months ago, I may have actually been overly stressed and on the way to burnout which is terrifying to think that I was six months into my career and looking at that. And then I kind of found a way to pull back and say, “Okay right, I need to figure out what my edges are.” And I need to understand how I can kind of push against them but no one to pull back. And well-rounded is knowing that I can hit those edges, and then knowing when I have to take care of myself and when I have to decompress, and when I have to really focus on spending time building myself.


Lesley:  Because I think most of us are in that world of trying to figure out how to get at the edge because the edge is adrenaline oriented. But going past that edge on too much of a basis is where we go in terms of burning out, and if we’re too far away from the edge which is not motivated enough. So how did you go about figuring out where your edges were?


Molly:  Well I was actually from a really interesting conversation. So back in January, I think it would’ve been, I was at a networking event and Eleanor Beaton was speaking at the event. And she set have got five one hour slots that I’m going to hand out. “Here’s the form, fill it out.” And I got the call that I was going to be given one of these slots which is amazing, because here’s this strong leadership female coach kind of giving me the opportunity to sit down with there. And so we have this conversation, and I said, “You know, I always have to be moving forward, I’m never doing enough. I don’t feel like I am enough.” And it was a very intense, stressful, chaotic time in my life. And she sat me down and she said, “Okay but why aren’t you doing enough? Why isn’t where you are right now?” And she had me kind of list out all of the things that I was doing on a day-to-day basis. So I’ve got fulltime job, I’m managing rental properties. I’m helping my parents with their business and all these kind of stuff. And laughed and I said, “Well I’m doing pretty well.” And she said, “Yeah you are. You are 26, right?” And then we kind of drilled down, and we realized that there’s a huge fear, a personal fear, a vulnerability that I had about going back to the person that I was when I was 21.


Lesley:  Describe me that person at 21.


Molly:  Oh a total disaster. She dragged too much. She didn’t pay her bills on time. She pissed of her friends and family all of the time and really didn’t take care of herself. And was with a hard person to be, and I was her for probably three of four years in my university career. And coming into my professional career I have found financial stability, and I bought a car, and I’ve rent my own bachelor apartment, and I pay all the bills myself, and I really like being that person.


Lesley:  So would you say you’ve grew into it, or did you wake up one day and decided this is what you were going to become?


Molly:  Well that’s an interesting question because it took a couple of very key things in life to kind of guide me there, and I don’t think it was a one day wake up. It was a year and a half of being shaken up and really kind of thrown off the platform that I was on, having to rebuild the platform from absolute scratch with no tools type of thing. And that came from a bad breakup and then feeling really stuck in life and very uninspired, and sleeping too much, and drinking too much, and all that kind of stuff, and then deciding to go on this trip that I went on last winter.


Lesley:  Right. So describe the trip that you did and what it did for you at that time.


Molly:  Oh it was amazing. I always had it in my head that I was going to do Central America and what not. And pretty much I think it was three weeks before I decided “I’m not happy where I am, I need to do something about it. I need to shake things up.” So I booked a flight, drove to Florida with my parents. Flew from Florida to Costa Rica and worked on the Caribbean side of Costa Rica in a little yoga hostel right on the beach for about a month and a half. And then I traveled Central America by myself, and came back to Florida and hung out with my parents. And so I hung out with my mom and dad for about six weeks and then drove back home. And while I was living at this yoga hostel in Costa Rica, that I realized something that I’d always thought was the dream is to go and live on a beach in Costa Rica, and then I did it and I realized I didn’t enjoy it. That was not the dream I signed out for. And you know, it really came from the realization that I’m much happier when I’m productive, and when I’m contributing to society, and when I’m doing things that I’m proud of. And it took sitting on a beach for a month and a half to realize that that was no longer the life for me. When I got to Florida I had this like fire within me that I was applying to jobs for three hours a day for six weeks, because I couldn’t stand not looking for that next step in my life.


Lesley:  So when you were looking for those jobs, what did you have in your mind’s eye as to the job that would start to do this for you?


Molly:  Well understand your limitations when you’re applying for jobs. I mean entry level, those key terms coordinator kind of thing, I had it in my mind that I was going to go into marketing or something like that. And that was probably because it was one of the only things that really appealed to me, but I had no real industry knowledge about what working in marketing is going to be like. But I pretty applied to anything and everything that kind of came up and held my interest. And so I think I have it somewhere a list of how I applied to 110 jobs or 115 jobs. I got two interviews and I was given one job offer, and that’s the position I’m at right now.


Lesley:  So, let’s just think about that that’s the ratio of odds that you have to play. And what sustained you as you were going through that process in getting sort of shrieking number down from a hundred plus, down to the two, down to the one? What kept you going in feeling that this could work?


Molly:  I guess blind faith. I mean that something had to work out, that there was someone on my side and would hopefully realize that I had something to offer. It’s really hard to keep motivated but I also knew that when I came back to Halifax after being around this trip that I didn’t want to go back into this service industry, I was over it and I needed to find something more fulfilling.


Lesley:  So describe the job that you have right now in about one sense, what would be the way you would describe it?


Molly:  So I worked with businesses one on one during economic development in Rural Halifax.


Lesley:  So, what was it about your background and about your experience that led you into the ability to give economic development advice to rural businesses?


Molly:  Well I was born and raised in a rural tourism-based business in Rural Nova Scotia, so I think that the knowledge that I understood how things worked in a rural location.


Lesley:  Very different. So tell me one of the main differences that happen in a rural location that strikes out for you.


Molly:  Well you just have to be able to have that conversation, and let people know that you understand where they’re coming from which you can’t do if you’ve been in a glass castle for your career. And you can’t do if you’ve just been looking at data entry and numbers, and I know that they interviewed some master’s students that were big into data and economics and what not. And I think a big thing was that I was able to balance both that corporate lifestyle. I can wear the skirts and the blazers and go to the 21st floor, but then I can put on my wiles and rain jacket and go hangout on a boat on the eastern shore which not a lot of people can do.


Lesley:  And build the trust and confidence that’s totally necessary, because I think rural anywhere is similar in the sense that unless you have that relationship where they feel that: A) you understand where they’re coming from, and B) you’re not there to tell them what to do. You’re there to be some kind of buffer that can help them figure out where they want to go and provide them the networks and the connections that they need.


Molly:  Yeah and it’s all about relationship building. I mean you look at these communities, there are hundreds of people dig and they’ve known each other since they were kids. And you’re really going to work on building relationships first and looking to support them, and also a lot of the times they just needed cheerleader. So I’m coming in and I’m saying, “This is a great idea we want to help support you succeed.” I mean it’s so interesting to me because I can go from a multimillion dollar luxury distributor to a convenient store, and a campground and everything in between in the spin of the day. So it’s always exciting and different. And I think it’s the soft skills that I hold and personality that has enabled me to work in all of these different industries with tons of different types of people.


Lesley:  So you’ve been specializing all along in entrepreneurship startups and innovation of those natures. So describe for me what you see as entrepreneurship in the world as we know it right now.


Molly:  I think entrepreneurship is looking to create something meaningful in whatever nature industry that you’re in. So, you know, I talk to people and they’re tired of working for someone else. They want to be their own bosses. They understand that they’re contributing to the economy by opening their own business is a good thing, and they want to create something, and they want to have a legacy that’s more than just pushing papers or what not.


Lesley:  And this is because for others may not know this economy as well is a very governmental economy. And so it’s been very, very much supported by people having government jobs all throughout the province and that’s been their way of well-being. But we absolutely as downsizing has happened but also just as the economy’s been shifting have depended more and more on these startups. So, what’s the biggest formative advice that you give somebody who’s just starting to think about the fact that a startup for them might be possible?


Molly:  I would say just start talking to people building your network, building those relationships. It’s everyone is so intertwined in whatever type of community you have that the best thing you can do is build a support system.


Lesley:  And I think what that says to me is that the community in which you’re operating in the physicality of where you are, is often overlooked as people move into thinking that their community is really a virtual community and they can market online. But the reality is, is that a business is located in physical space, and the people who you need to support you and to really get you up off your feet are often the people that are right around you. And if you can build that then the virtual side of it is just an extension of what that is.


Molly:  Yeah. You’ve got to start somewhere, and I think that building your network where you are is the first step to that success.


Lesley:  So describe for me what Venture for Canada is and that you’ve become a fellow of this organization.


Molly:  So Venture for Canada is a non-profit that recruits, trains and connects young professionals or recent graduates to the startup community in Canada. So I was asked to join the 2016 cohort as a fellow, which means that I am connected with the program for two years. They bring us to a training camp at Queen’s University in Kingston, Ontario for five weeks. And you get to build that community once again going back to that, as well as learning everything from pitching yourself in public speaking to marketing, and sales, and designing, and executing a product. And then the eventual goal is to then connect to with a startup for a position. But it’s an interesting model because it’s really just about building that network, and about building that community, and making those introductions for you, and then everything from there on is on yourself.


Lesley:  So how long would a startup have been in business by the time that you would join them and start bringing your skillset?


Molly:  That is totally dependent on startup, everything from six months to five, six years.


Lesley:  So this maturity level of startup is something I think that’s really important. Most people think that a startup is something that happens—as you say—in a six month period, but what really means is the maturing line of that business to say that it’s now a solvent entity that’s to continue to grow and be up to five or six years. So the type of organization that you’re looking for, what would be the characteristics of it?


Molly:  I really keep looking for an opportunity to grow, an opportunity to throw into a project at the point of my life where I want to live, and breathe, and create something. And I think it really just once again going back to building those relationships with the people around me and learning as much as physically possible. Because I’ve realized in the last year that I’ve been with this position, I have learned so much and expanded so much as an individual. You know, leaps and bounds beyond my university experience that’s almost seem pointless now.


Lesley:  But you know what, I think I just want to stop you there because I do think that we can see those stepping stones in relation to what we thought we were going to be doing during that time. And what we end up doing quite different but we couldn’t be where we’re at today if it hadn’t been for that.


Molly:  No, no, no. When I first entered university, I was 18, a huge English nerd. I went into Gender, Women’s Studies and Philosophy for my first year of university.


Lesley:  Gender studies and Philosophy. Well that was been a really be very close to what you’re doing today.


Molly:  And then I think within six months, I said, “This isn’t practical for me, I love it.” I love the discussion and then the intellectual piece but it wasn’t practical for me, so then I switched into Management and then I went into Entrepreneurship. And then I found my ability to sell, and create that personal experience, and build those relationships which is something that I’m continuously working on. And then I got this job, and then I got into Venture for Canada, and every single thing has been a stepping stone to where I am now.


Lesley:  And so that’s why so very often as a millennial generation has been tagged, there’s this kind of notion that you’re a free-spirited. You are high energy to yourself on this and you do junk to things because you need that type of rush to keep interested. But what is it about this particular culture that you’re in right now that actually doesn’t degrade that? It actually says “We understand that and we want to have that as part of who you are.”


Molly:  Oh yeah. Well, I think the best example I could give would be at this training camp for Venture for Canada, we were in a group of 55 young professionals from across Canada. I was absolutely not the smartest person in the room and we were surrounded by some incredible people, and the entire environment was incredibly respectful, incredibly supportive. I mean we’re coming from different industries, and different backgrounds, and going different places in our lives.


Lesley:  And from all over Canada which is a very diverse nation for those who may not understand.


Molly:  Absolutely. And a lot of them came from other countries across the world.


Lesley:  Okay so it’s an international. Okay, even more exciting.


Molly:  So I mean, every tons of international young professionals and the entire energy of the training camp was “What can I teach you and what can I learn from you? How can I support you to succeed?” So, you know, I love my group of girlfriends there, the absolute biggest cheerleaders that I have. But they’re not really going to want to spend their Saturday night discussing business strategy and how you get your first costumer and that kind of thing. And here I am like finally surrounded by 50 people who live and breathe that, and it’s so inspiring to think that these people are going to be in my network for the rest of my life.


Lesley:  Yes and you feel that.


Molly:  I really do feel that and that’s why it’s so unique, and that’s why it’s really quite special.


Lesley:  So I have this other question which is, you have the luxury of going down to a Costa Rican beach and discovering that’s not where you really wanted to end up. But as you’ve done speaking engagements to high schools to help people understand that we’re not limited to standard career paths, or just looking down the road to want to retirement. What’s your advice to people who are sort of where you were back few years ago, not sure about where you’re going and don’t have the luxury of going to a beach to find that out? What have you learned about what you can do from this moment in your life to start opening those stores up?


Molly:  Well, I mean the internet is a great tool for that. But really I would say that keeping an open mind about where you see your path going, understanding that the career paths that have made in front of you by your parents are no longer as relevant as they once were. I mean the sheer amount of different ways that your career path can go where the directions lead you into is incredibly intimidating for some people. But you really just have to look at what gets you out of bed every morning, where does your passion lie, and just start talking to people. That’s what I would say is find industry professionals, use programs like the connector program with the Halifax Partnership.


Lesley:  And other cities would have the same kind and the connector program is…


Molly:  So, the connector program is a program that looks to connect underrepresented groups such as new graduates, recent immigrants or foreign students with industry professionals for a very casual coffee conversation but it really looks to build that network. And that’s what I did I just realized that I wasn’t ready for Gender, Women’s Studies and Philosophy. So I started talking to people and then I started talking to people within the industry, and then realized that, “Hey, I kind of like this business side of things and I grew up in entrepreneurship so I understand it, and I see the value in it, and I find it really exciting.” And looking to expose yourself to as many things as possible. And if you find that there is a wall between you and the professional industry which I really did when I graduated university, I knew the things were out there but you don’t know where they are. Just start googling and just start calling people because everyone is happy and looking for opportunities to connect. You know, these people that are trying to get in the industry to industry professionals to have conversations. People love to talk about themselves, so the second you say, “Hey I really like to learn about what you do.” People are probably going to fall all over themselves to have coffee with you. You know, these great opportunities for online learning free courses online, there’s websites out there that talk about different careers, the career path you need to do with the education you need in order to get there. All of these opportunities and resources are available.


Lesley:  So we’re going to put some of those links up over the course of the week that this show is airing. And I guess the question that I’m left with is entrepreneurship was in your blood. You grew up in it, you understood it, you walked away from it as you went through your studies and did your serving industry experience. Do you believe that there’s something inside each of us that we have embedded in us in an early stage, and that it’s somehow gets nurtured at different stages of our life? We’re not sure when but it will happen?


Molly:  Yeah, entrepreneurship specifically or anything?


Lesley:  Or any of those things where we start to evolve ourselves.


Molly:  Yeah, I think it’s really interesting to look at what you’re exposed to as a child, and the people that you surround yourself with as you go through these really important developmental stages. And I think exploring those things and having an open mind to the possibilities that are out there, and understanding that the path that was followed by your mom and your dad or your grandparents is no longer the path that is available to you. And things are so much more exciting these days, because if there’s so many opportunities and it’s totally terrifying but for someone like me I really, really enjoy it.


Lesley: And when you left that coaching session that you had that one hour special coaching session that caused you to look at the fact that this notion that “I’m not doing enough” is actually a self-talk program that’s disabling you and not enabling you. What was the first thing you did that you walked out of that coaching session in terms of an action that you took as a result?


Molly:  I remember going home and sitting on my bed and going “Okay maybe I am doing enough. Maybe I can actually have a goodnight sleep tonight and not worrying about the fact that I feel inadequate in a lot of different ways.” And I don’t know whether it was that I needed someone that I respected and admired to saying, “You know, Molly, you’re doing great.” Or whether I needed to walk to that process come with a realization on my own. I don’t think that it’s something that I could’ve been told by my mother, because I would say, “Yeah okay mom. Yeah I know I’m doing great.” So, you know, it kind of loss it’s meaning. And I remember calling one of my best friends, and he’s describing this conversation with her, and her going, “Duh, Molly, I’ve been telling you that for years.” It’s like, “Right, but I needed to get there on my own.” And I needed to have that conversation and walk through that mental process. And I’ve never asked myself that I’d never said why do I feel like I’m not doing enough? Why do I feel like working 14 hours a day and then working on my own projects, sacrificing sleep, and my health, and uneating correctly in order to feel like I was doing something productive?  Why did I feel like that was necessary? And then coming to that realization that it wasn’t, and I was enough, and I was happy to be doing exactly what I’m doing right now. And then I was able to kind of sit back and really relax and enjoy life, and it’s totally enabled me to be a more chilled out cool person.


Lesley:  Well, I think that’s probably the best advice to end on, because I think one of the things you’ve said because there are so many opportunities. But at the same time that there’s all those opportunities, we do keep competing in ourselves about “Am I out there enough? Am I doing enough? Am I responding quickly enough?” I mean, we put these huge expectations on our shoulders without having some of that validation about we need to have. So, any one last piece of advice that you’re giving women who are looking to leadership positions and are already doing so that you’d like to offer them before we leave?


Molly:  I would say, just remember when to take care of yourself and remembering that sometimes it’s okay to say no and sometimes it’s okay to walk away, and really understanding that failure is so important because everything that we do is a test. And understanding that if you fail it’s always wanting opportunity and just really building that support of network around you so that you’ve got those people to fall back on.


Lesley:  Thanks Molly!


Molly:  Thank you, Lesley.


Well I do really appreciate Molly’s candor. You know, as a 30-year-old veteran of the entrepreneurial game, I would never have imagined that burnout would be a factor for such a new player. But then again I didn’t enter the market place with so many options. This in itself is a double-edged sword however. Sure there are many, many paths that you can follow, but just for a moment see yourself standing and a fork in the road where there are three or four potential directions but hundreds. Which one of them is a false start going nowhere? Which one is circular, those that take you out and then put you back where you started? Which ones are literally illusions and paved for false hope? As Molly shows us, one doesn’t really know. The key is to take one, and then another, and then another. “All the while knowing where your edges are.” I love that phrase that she used. These are the boundaries that begin a simply quick hit in the gut. And yet when you listen to them, they become powerful guide posts as to where your evolution is taking you. All the while, these guide posts are helping you discern what good pain is and what is not. There is no question that this is a time and memorial reality of professional and career growth, these edges, these stresses, these choices, but the difference for me is that it’s happening now on the lives of 20-year-olds rather than waiting until we’re 40. To find out more about Molly, check her out on LinkedIn Molly Connor M-O-L-L-Y C-O-N –N-O-R. Or on the website For the Greater Halifax Partnership, that’s www.halifaxpartnership.com. There, also take a look at the programs that Molly mentioned such as the Connector Program. I urge you to take a look at similar programs in your neck of the woods, whether you’re a new graduate or an experienced business leader. There is so much potential in the sharing of our various degrees of development where we are and what we can learn from each other. For those of you that got interested in Venture for Canada, you can check them out at ventureforcanada.ca. Well, you know where to find me, lesleysouthwicktrask.com and at womenwholead.co, Facebook Women Who Lead Radio Show, LinedIn Lesley Southwick Trask. As always, this is your program, I am your host Lesley Southwick-Trask. Thanks for listening, see you next time.


1 Comment

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