Women Who Lead – Successful Career Fast Tracking As a Millennial Leader

Last week, I spoke with Molly Connor, a millennial, who is six months into her career. This week, I wanted to spend some time with the member of this new generation of female leaders, who is a tad bit further along in her career path. Rebecca Penty is an award-winning reporter, currently working for Bloomberg, a major global provider of 24-hour financial news and information headquarter out of New York. For the past five years, Rebecca has covered the energy sector, out of Canada’s oil and gas capital Calgary, Alberta. As a business reporter for the Calgary herald, and now the Energy Reporter for Bloomberg, Rebecca’s reporting has gone from covering global energy triumphs during the heyday of top oil and gas pricing to the catastrophic collapse of the energy market around the world. At 31, Rebecca is indeed a powerful and influential player in the world of business journalism. Her career path is about to take another lead forward as she heads for London, England, to become Bloomberg’s European Media Reporter. I wanted to chat with Rebecca because I see her as a shining example of women who are making their mark as leaders in their field. Without a doubt in a world overrun with information, opinion and hearsay, the role of professional journalism has never been more significant nor required in getting real facts, and dare I say the truth out into the public form. In Rebecca’s case, I was in learning about how she’s building her career to a rapid movement of job jumping. My research into millennial career development has suggested a number of underlying factors that support their pace and direction in fulfilling their ambitions. I’ve decided to pursue three themes that are interwoven throughout this interview, they are: risk taking, networking and transitioning. Each of these appears to play a fundamental role in how professionals mobilize and shape their opportunities into career paths that will fulfill their aspirations and desires. Let’s have a listen to find out how this go-getter is quickly becoming a global leader in her field.

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Lesley:  So welcome to the program this week, Rebecca Penty, I’m so glad you’re joining me.


Rebecca: Thank you for having me.


Lesley:  Now, you’re about to have seven jobs in nine years.


Rebecca:  I’m so impressed you did the math. I couldn’t have come out like that.


Lesley:  Well, you know, it’s interesting because for many, many years when I was doing future strategy discussions, I would say to people, “The norm is going to be, that people will change their careers as many times in their lifetime and their job turnover is going to be this high.” And everybody would look at me as if I had ten heads, and said, “That is absolutely impossible for that type of pattern to exist.” And as I started to read more and more about you, I did my calculation and you started in September 2007, and this September 2016 you will be in your seventh job. So I want to know, what is your definition of loyalty?


Rebecca:  That’s a really tough question…


Lesley:  Maybe to whom the loyalty is or for whom it’s based.


Rebecca:  So, I think loyalty is about being loyal to your values, and that will carry you to whatever situation you’re in, whatever you’re with, whatever manager you’re working with. So one of the big ones for me especially as journalist is honesty, I want to be honest every situation. Whether or not I feel like I’m in over my head at work, whether or not I’m frustrated with an employee, whether or not I’m feeling particularly successful and proud of what I’m doing, I’m going to be honest with my professional contracts I’m dealing with.


Lesley:  So then let’s just talk about that because as a journalist there are a lot of different perspectives on how honesty is described by a journalist. I mean honest, based on what? So when you say as a journalist you’re honest, how do you describe that characteristic?


Rebecca: In my story telling, I’m trying to present the truest representation of whatever situation I’m reporting on. It may have many layers, and many angles, and many parties involved to different perspectives in different points of view, but I’m trying to be the representative of the reader in this situation, saying “What do they need to know and trying to decide whether so and so is telling the truth? Am I going to take every piece of what they said, or am I going to recognize when they’re trying to sort of spin me a little bit, and trying to put it altogether into true representation of a situation for the reader?”


Lesley:  So when you started out in your path towards journalism, did you know at that time that you wanted to be a truth-based storyteller?


Rebecca:  I didn’t know, I have thought I was going to be a political reporter. And I didn’t quite really have a concept of exactly what the truth function of a journalist in society. I thought this is going to be a fun career because I’m going to get to look at different topics every day and talk to different people. And I don’t think I was really a huge consumer of journalism at the time, I know I like to write, I know I like to ask questions, I know I’m curious. And as I’ve gotten into my career, I become more and more proud of the work of the journalist do globally. And the function they play in society in terms of lifting the lid on big stories whether it’s in politics, or business, or sports, or whatever, getting to the meat of a situation in a revealing things that are not out there. 


Lesley:  So what’s your opinion about the types of journalism that’s going on in the states right now, where it seems to be very point of views that are extremely held by party politic as supposed to the truth-telling that you’re talking about? I mean, what’s your observation of what’s going on in the run-up to the election of the states?


Rebecca: I think you’re seeing that a lot especially in broadcast, a lot of the different hosts and interviewers who are covering the new debates and elections of having political to talk. I mean you really see it more in broadcast, I find where the story often becomes guided by the opinions of the host and the opinions of the news organization. You know, not into really get into names of different organizations, but it’s definitely a lot different down there than I would say it is up here. I wouldn’t say that there’s a huge difference between the CBC versus Global TV, versus CTV up here when it comes to examining political situations and holding different people to account on TV. And I find in the US it’s much more of an opinion-based.


Lesley:  Partisan-based in many, many ways. So, just how do you assess your degree of unbiasedness?  So you’re a truth-teller, you’re cutting into the story to find underneath from multiple sources what really underneath all of these points of view. How do you assess the degree of how you’re doing in that department?


Rebecca:  That’s a really good question. I think it’s tricky because in certain scenarios you want to talk about what are the big themes that are getting people talking. You know, right now I’m covering business and I’m writing about oil and gas. And so, I’m writing about what is important to the companies, investors, political leaders what is the discussion of the day. That’s going to be colored based on the issue at hand, and I think it’s difficult. I think you always want to make sure you got to balance story. For example, I’ve been reading in the last couple of days about a big debate between regulators and banks basically with regards to liabilities. Anyway it’s a complicated debate.


Lesley:  We’re going to post some of the most recent post that you put up. And that one is really about whose liable for all of the environmental mess and other leftovers of an organization once they’ve been purchased.


Rebecca: Exactly. And I think the companies are going to have one perspective, regulators are going to have another, the land owners are going to have another, the banks who own these assets are going to have another. And trying to cream all those voices into one story, in talking about the controversy at hand, is challenging but I do have to check myself for sure. You will have executives, or investors, or what not, kind of trying to influence you to cover certain topics, and you have to step back and sort of say, “What’s in it for them?” I think that’s the big question that I was had to ask myself with this person who wants me to look into this topic, what’s in it for them, what’s at stake.


Lesley:  That’s a great question. You should keep that on the straight. So, here we are, you are about to make the leap across the ocean to a new job in London, England. Can you tell us a little bit about that job?


Rebecca:  Sure. I’m going to be covering media. So I want to be covering what I do every day the business of media, covering newspapers, magazines, cable TV, the BBC. We all know the BBC and the controversy around that state-funded organization.  And so, I’m going to be looking at where’s the money going, kind of like I do right now with oil and gas, but in that sense it’s going to be the business of media.


Lesley:  Alright. So seven jobs in nine years, you moved from where you sort of went to university in Ontario, and then you bounced over to New Brunswick, and then you bounced out to Calgary, now you’re bouncing over to London. Was this a plan? Did you have a plan that you’re going to do this type of movement so that your career would get you to where you’re going in September?


Rebecca: It definitely wasn’t a firm plan. As soon as I graduated university, I knew I wanted to get out of Toronto. I love Toronto but I wanted to… One of my big goals is always been topical with perspective. It’s a huge value for me. I got to taste of it when I was in university and then an exchange program in Denmark, and got a taste of consuming news from all over the world, meeting indigenous people in the Arctic, in Finland, in Norway, to hanging out in the south of France, cycling through vineyards. And getting that flow of perspective has been really important to me and going into journalism is part of that because I knew that journalist work all over, it tells stories all over the world.


Lesley:  So living both in Europe and in Canada, I clearly understand what you’re saying in terms of a global perspective. What would be one thing that would be different about a global perspective? I’m looking at it from a local or national perspective.


Rebecca:  It’s a good question. You know, I think in what I do in covering business. You know, I encounter people from all over the world, so I understand that there are different ways at doing things or different cultural norms. And when you have a global perspective, when you come across that, you’re not immediately judgmental. You’re not immediately thinking the way I do something is the right way, and the way we do it in Canada is the right way. And so when you look at different healthcare systems, different taxation models, even when you look at oil and gas for example, and the way different governments tax the industry and you look at models around the world. If you have a local perspective, you’re less likely to sort of be reminded, I guess.


Lesley:  So I think that’s what’s really fascinating. I love the way you just described that is that one of your values is a global perspective, which some people might say, “Well how is that in value?” But what you’re really saying is that the perspective is one that holds you with a judgment. And I think that’s really the true art of being a reporter, is that you provide the information from an unbiased, non-partisan view so that the reader can make up their mind about what this means to them. I think that that’s a very challenging skillset and value system to have. Have you ever found yourself where you’ve misled yourself and found yourself scurrying down a path where you might have held, something in a more personal perspective?


Rebecca: That’s an interesting question. I think, on that point, we also can’t be afraid to tell what the real truth is, whether there are multiple opinions about a topic. If it is pretty clear what’s going on and everyone else is trying to spin you and you know, know this is the real truth. I did have a situation that I’ll touch on, and it was a story that I wrote about the situation out here in Western Canada with the caribou. You know, the populations are declining, there’s a federal government mandate for provinces to come up with a plan to save these caribou and bring them back, and yet we have all sorts of human interruptions across the landscape, oil and gas, forestry. And at this point in time, the governments are hunting wolves—the predators of the caribou—in order to save the caribou. And yet, there is a lot of presence in both their efforts to contain industrial expansion, and deal with the expansion that is already taking place. And I’ve heard about this topic and it was a very pointed article, and I got a lot of flak from the industry that I normally cover. But I stood by it because I said, “You know what, this isn’t opinion, these are true facts. And I’m framing it in a way that unfortunately it doesn’t make the industry look good. I’m sorry.”


Lesley:  And that’s where the risk factor comes in. So, how would you describe yourself as a risk-taker?


Rebecca:  I like risk.


Lesley:  What do like about it?


Rebecca: There is a sense of mystery as to what’s going to come, which is exciting. So in the couple of months I’m going to be moving to London, I have no idea where we’re going to live. I know it’s going to be stressful but I’m not letting that get to me. I left New Brunswick and moved to Calgary with no job in the other end, and it was exciting for me.


Lesley:  Well let’s actually give a little more background to that. You left after dating a guy for two and a half months, and decided to cross the country with him and establish yourself here in Calgary with him.


Rebecca:  That’s right.


Lesley:  So, that’s a pretty serious risk-taker.


Rebecca: It was.


Lesley:  So what are you guided by in those moments where your gut is telling you “Just do it.” What goes on inside of you when that kind of decision-making is going on?


Rebecca:  I think it’s great to listen to your intuition, look at your values and whether you’re being true to your values. And when you have those fears, ask yourself, “What I’m I afraid of really? And what’s the worst that could happen?” And usually, there are so much opportunity in change than there is in status quo is what I found, and I usually get restless after a few years of doing the same thing.  


Lesley:  That’s pretty obvious given your track record. Wait for a second, how do you know you’re getting restless? What’s the telltale that Rebecca is starting to get restless?


Rebecca: I find that I may overlook opportunities in my current role because I stopped being as interested. And so in the case of journalism, I may have a story present itself, and I may think “Been there, done that, heard that one before.” And if I was looking at it with a fresh pair of eyes, new in the situation, I might be more likely to be creative to jump at an opportunity and think, “You know what, let’s just go there and check it out and see what I can learn from this.” And as soon as I noticed that I’m starting to have to convince myself to look into things or what not, I’m getting a little restless.


Lesley:  I know that you’re good at comforting that, did you know that at the beginning or you’re just getting better?


Rebecca:  I think I’m getting better at noticing that.


Lesley:  At noticing that and feeling it’s time. Well, I mean, it happens to see you spend all four years in this current job which is long term for you.


Rebecca: Yeah that’s right.


Lesley:  So, you were ready to make this plunge across the ocean. You know what, I’ve been reading your posts on Bloomberg. I’m totally impressed with what you’ve described already which is that you sourced your stories from number of points of view, and a really conglomerative opinion as supposed to one or two views about the situation. And you’ve put it together in a way that I can digest it, and understand what I’m thinking about it. My question to you is, how do you go about building the network that you have had to build so that you know who to reach to, how to reach to on such complex issues as the energy sector, the oil & gas industry which as we know it is in chaos. And then in the economy that so unpredictable, have you been building that network?


Rebecca:  Yeah. Um, day by day, sometimes with foresight and sometimes.… So, I’ve learned a lot through journalism about building a network that I think is applicable to many different careers, many different walks of life and just being a citizen of the world. With journalism and with covering a certain beat, you need to know all the power brokers. You need to know who’s doing what. You need to know their backstory. You need to know “Who are the people I could go to lower down in the food chain, who have access to these people and have access information who might be able to share with me? And what am I going to do in return for them?” That’s a big tough one. And often times, it’s sharing information, sharing insights those of the big trades.


Lesley:  Well I find this very interesting because I think very often when I talk to people about what is networking, and they think about, “Who’s out there that can do something for me?” And what you’re saying is, is that, as you go about building your network it’s not only what’s “What do I need?” but it’s “What can I have to offer them that they will see of equal or better exchange, where there’s a feeling like we have some type of relationship that’s of equal value?”


Rebecca: Yeah. And in my case, it’s typically trading information. In a different career it might be a different exchange, it might be two entrepreneurs who are looking for what’s the best way to get crowdfunding and what’s the investor I need to know and introduce me. In my case, it’s option, information or it might be “Introduce me to someone else.”  Usually, I was on the phone for source recently who gave me a tip about something really interesting, and then I was on deadline and I sort of said, “Okay I got to go.” And he said, “Wait, wait, wait, it goes both ways. What have you got for me?” And it was hilarious because I thought “Wow it’s very true,” and I kind of think to myself “What do I know that he’d be interested in knowing?” And of course in journalism, you always have to be careful at telling people things that are going inside….


Lesley:  Right. You have to have this constant kind of assessment going on in your mind about “What am I free to offer and what am I not free to offer.”


Rebecca:  Exactly. So, you don’t want to suggest anything that’s not allowed, but it’s in exchange and it’s also keeping in touch with this people. You have to be focused on that. So I tend to think I’m definitely going to the same people at least four times a year in my network probably more often, probably every month or two depending on the person. And another thing I found networking is that, “I’ll go for ten coffees and one of them will pay-off.” And that one pay’s off might pay-off really big, might pay-off ten times more than the others because they might introduce me to whole whack of people. Or they might have an ordinate amount of information, or might be willing to develop such a close relationship over the years that they become this really important person in my network, much more important than all of the other misses and that’s just something you’ve got to do.


Lesley:  And just as you said as you walk out of that coffee shop, you have no idea what that’s last exchange is going to be. You know, you might have an immediate feeling of “Well that was worth my time” or “It really didn’t get me where I wanted” but you don’t know because it’s a number’s game. It’s like Molly said when we were interviewing her about her job. She made 110 applications and got two interviews. I mean it’s the same thing. I don’t know how many copies you’ve had but it’s putting yourself out there, and having faith that whatever is down the line may not at all be immediately available to you.


Rebecca: Absolutely. And I found that to being in Calgary, I’ve been here for five years now, and I still reach out to people that I knew on the East Coast and New Brunswick. And I only lived there for two and a half years, and some of those sources in context have been keyed to me in my current role and they’ll reach out to me. You know, I have a former colleague coming into town, he was reaching out to me last week, asking for all sorts of advice about Calgary and just maintaining that network.


Lesley:  Wait till you’re in London, baby, you’re going to have a lot of phone calls I would suggest. So just on that, I’m curious, what are going to be the first two things you’re going to do? Of course, besides finding a house and getting yourself settled but in getting yourself into this new job, what would be the first two things that you’re going to do to get yourself moving?


Rebecca:  Number one is sort of a multitude of things but a ton of reading about the companies that I’m going to be following and the people I’m going to be following to get up speed. And then number two, hopefully going to have a little bit of shortcut, well see, but talking to my colleagues in London and seeing who I need to know. They kind of introduce me to a couple of people, and it’s something that I’m doing right now as I prepare to leave Calgary with the people who are going to be taking over what I do. I’m introducing to really influential people in trying to save them months of time potentially by getting them right to those important people. So, those were the two things that I would do since I get over.


Lesley:  Makes perfect sense. It’s kind of like paying it forward though if you do it well. I mean, I think that there’s a great video out, and the final thing is that is “How do you craft your axit” as supposed to “How do you craft your entry.” And, you know, we think about the exit as something that we’re leaving, and then therefore we put a lot of effort into the entry. But it suggested that the more that we really gracefully, and competently and purposefully create and craft our exit, the much more capable we are of creating the entry into the next phase.


Rebecca: That’s really insightful.


Lesley:  Yeah. I do think that I’ve just known that from my own career. You know, often when you’re finishing a contract, you’re sort of wrapping it up and you’re really getting excited about the next one you’re doing. And all of a sudden catch yourself and say, “I need to exit this contract with the same amount of creativity” and goes back to your restlessness, right?” With the same amount of creativity and intent as I did when I entered it. And if I’m not doing that, I have to do something about making myself insured at.”


Rebecca:  That’s an excellent point. And finding that I’m doing that without having thought of it that way, so I’m reaching out to all of my best sources in having meetings that’ve been doing that for the last few weeks and I’m going to continue to do that. And I’m telling all of them about my move, and they are all really excited and now they know someone in London. And we’re able to have that space time to move on to that next connection where “I’m now someone for them in London” and yet we’re still connected. I’m not running away with just an email.


Lesley:  No. Isn’t that interesting because that setting is creating the brilliance of your entry, or you’re going to have to start that network with a much better ability to leapfrog then just sort of setting yourself in the office in London, and going “Well where is that database of names that I got to have to start calling?”


Rebecca: Exactly.


Lesley:  That’s amazing. Now my last question is, how autonomous do you think you are in your career?


Rebecca:  I think I’m mostly autonomous, and I think part of that is because of the role that I have as a journalist, on the ground as a reporter. So in journalism, the reporters beyond the ground person and then you have all these editors of the food chain, you know, different dotted lines everywhere. Ultimately, they know you’re the one that the information and the sources, and the context, the knowledge, all of that. And so, I always get the question, “Do you come up with your story ideas, or do you get them assigned?” I always laugh because I think what my editors would assign me, they wouldn’t know because I’m on the ground. Often times, there’s a conversation, a back and forth about what I’m going to be doing with my time and how am I going to be focusing on it. But the question I ask them has usually turned back to me, “Well what do you think?” And so, even in an organization with multiple layers, you know, it’s global. You have people in every major city and headquarters that are in New York.  Even in the organization like that where you would expect that it would be top down, I still feel like huge sense of autonomy because at the end of the day I’m in control of my own time, and my own productivity, and my own context and my own story.


Lesley:  Which I think in today’s world is not understood, just how much you, as a professional, with professional standards, and professional training, and professional experience have that level of decision-making around what you do and what you report.


Rebecca: Especially in this date age where you’re moving from job to job, company to company, you really have to be the master of your own destiny. And it’s not an industrial landscape where the path is presented to you.


Lesley:  Well, you know what, I can’t imagine a better conclusion. You are the master of your destiny, and I am so excited about where your destiny is about to take you. And I can’t wish you more luck, and I’m going to talk to you when you’re in London.


Rebecca:  Absolutely.


Lesley:  And find out how it went as you made that brilliant entry into the new world.


Rebecca: I sure I’ll see you in London and maybe Portugal.


Lesley:  Let’s do it. Thanks so much, Rebecca.


Rebecca:  Thanks, Lesley.


So let’s take a quick look at the themes I was curious to explore with Rebecca. When it comes to taking risk, this means being true to her values. In Rebecca’s case honesty, transparency, a global perspective and remaining autonomous have emerged as important principles that she uses to guide her actions and her career decision-making. When it comes to networking, this is about creating relationships built on fair exchange and perceived as such. Rebecca sees this as a fundamental function, not only in each and every job, but as part of the masterplan underscoring her career. She networks for both the short and the long term. She believes in the odds game “You never know where each coffee is going to take you. You simply have to get out there and have them.” And then there is transitioning, rather than seeing a job as a job or a rung in a ladder, so to speak, she used each employment contract as a series of relationships and experiences that will continue to underscore her career. Rather than job hopping, Rebecca is carefully constructing a portfolio of experiences and relationships, as she transitions from one opportunity to another with grace, transparency and goodwill. Like the field she is covering as a reporter, Rebecca is constantly investing, in her case it’s in people. I feel I would be remiss if I did not leave this interview with one other pearl of wisdom that Rebeca offered, and that is “There is more opportunity in change than in the status quo.” I encourage you to take a better look at this emerging leader. You can check her out and her brilliant journalistic talent at Bloomberg.com B-L-O-O-M-B-E-R-G-dot-com. To find out more about her, check her out on LinkedIn Rebecca Penty R-E-B-E-C-C-A-P-E-N-T-Y, and on Twitter Rebeccapenty@rpenty. Well, you know where to find me at lesleysouthwicktrask.com, on Facebook at Women Who Lead Radio Show, our website womenwholead.co. Now you know this is your show; I am your host Lesley Southwick-Trask. See you next time.



  1. I’m not that much of a online reader to be honest but your blogs really nice, keep it up!
    I’ll go ahead and bookmark your website to come back down the road.
    All the best

    • Thanks! I am so sorry you haven’t had any new ones to listen to – I will be rectifying this very soon. Keep me bookmarked 🙂


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