A vision for your business with Jennifer Barrett

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Do you have a vision for your business?

What about for your life?

And what about the people you work with – your clients? Can you tell when they have a vision for their business?

I think you can – that’s when you feel connected and a part of that vision, rather than like an order-taker. You probably also feel empowered to make suggestions, to share ideas, to be part of the team – even when you’re officially independent.

Having a vision is one aspect of leadership and just one of the many aspects of leadership I talked about with Jennifer Barrett, author of Think Like a Breadwinner, former freelance writer and financial journalist and now head of content at fidelity investments.

So listen here and below…

And if you like what you hear, we’d love it if you write a review, subscribe here and sign up for Quick Tips from Marketing Mentor.

Read the complete transcript for Episode #481 here: 

ilise benun

Hi there. This is ilise benun, your Marketing Mentor. And this is the podcast for you if, and only if, you are ready to leave the feast or famine syndrome behind, and I mean for good.

Do you have a vision for your business? And what about for your life? And what about the people you work with, your clients? Can you tell when they have a vision for their business? I think you can because that's when you feel connected and a part of that vision rather than like an order taker.

And you probably also feel empowered to make suggestions, to share ideas, to be part of the team, even when you're officially independent. Having a vision is one aspect of leadership and just one of the many aspects of leadership that I talked about with Jennifer Barrett, who is the author of “Think Like a Breadwinner,” former freelance writer and financial journalist, and now head of content at Fidelity Investments. So, listen and learn.

Hello, Jen, welcome back to the podcast.

Jennifer Barrett

Thanks so much for having me. It's good to be back.

ilise benun

Of course, yes. So you and I were in Nashville together in June at the HOW Design Live conference and for especially how women lead, a new one-day event that they have. And we started talking, if I remember correctly, on the lunch line with food in between us—we were both piling our plates a little bit—about what it means to be a leader and the differences between being a leader and a manager and all of that. So before we get too far, of course, I want you to introduce yourself, but then I'm going to start asking you some of those questions. So tell us who you are.

Jennifer Barrett

Sure. I'm Jennifer Barrett. I'm the head of content at Fidelity Investments, and I think we actually met before I took this role and after I had written a book called “Think Like a Breadwinner,” which is a wealth-building manifesto for women who want to earn more and worry less—and who doesn't? So I think that's actually how we initially met when I was working at Acorns, the startup, as the chief education officer. So a lot of change in the last few years.

ilise benun

Sounds like it, and we've done a couple of podcasts already on the topics of the book, how to think like a breadwinner, and what that means. And so I think we can connect this idea to maybe how to think like a leader or how to evolve into a leader. But maybe the first question is: What exactly is a leader and how is it different from being a manager? Or even someone recently said to me: "I'm the creative director, does that mean I'm a leader?" So how do you think about this?

Jennifer Barrett

Hmm. I think that's an interesting question you posed there at the end because I do think there's a lot of overlap. This is something that I've been reflecting on a lot because I've been in management now more than a dozen years. And yet in this role that I'm in right now, I have a team of about 150 people, and I found that the role was really more of a leadership role than a management role, which is not surprising given the size and the scope.

And what I discovered over the last couple of years in this role is that I had never really thought about what kind of leader I want to be. I had always, in my career, been very focused on achieving business outcomes. Right? Setting a strategy, setting the key performance indicators or specific outcomes, and then working really hard to execute that strategy with my team.

And in this role, it has stretched me in different ways. And the kinds of questions I get from people sort of looking for direction on different things really had me pause and say to myself, "Wait. What does it mean to be a good leader? Am I a good leader? What kind of leader do I want to be?" Which may be surprising because I know a lot of people think about this a lot and ask themselves those questions, but I have had so many different models for leaders that I really had to stop and think about what made certain people good leaders in my mind, and what kind of leader did I want to be.

ilise benun

Pray tell?

Jennifer Barrett

Yes. Well, I think that's still a work in progress. You know, I have come to the conclusion when I've thought about how leadership really is different than management, because it is like a Venn diagram, there is some overlap there. Right? Whether you are a first-time manager or the leader of a company, you're working to achieve certain business outcomes. You're accountable for specific goals, maybe to different people, you're reporting to different people, but you share those certain attributes.

And so I think in both those roles, you need to be strategic. You need to have a good understanding of the business. You need to be responsible and disciplined, and to be a critical thinker.

But I think where I really started to see the difference between leadership and management is that the leader really sets the vision and the direction and the overall strategy. He or she or they communicates the what and the why. And then the managers explain the how—how will we execute or deliver on that.

And so leadership is really centered around a vision, to create change, to have impact, and then to inspire and organize and rally the team around that vision and give them a sense of purpose so that they are driven to move in that direction and achieve that outcome.

I think that's where you differ a little bit from management because managers are really set out to achieve those organizational goals, and that's through implementing processes and deliverables and milestones and all those things. Really to be a good manager, you need to be able to inspire people, as well, and get them to rally around those goals. But I think it's sort of the weighted importance of some of these attributes shifts for leadership. With leadership, you're really inspiring other people. You are empowering them. You are enabling them to help bring this whole vision forward.

And one of the mistakes that I made when I first moved into this role was getting in the weeds a little bit. Your job is not to fix things for people below you, or necessarily to execute on things. Your job is to empower the people on your team to be able to fix things, to be able to help you achieve the vision.

And so everything that you are working toward centers around this vision and your ability to bring this team along with you, and help them to grow along the way, grow and develop.

And that is very different, I think, than management in terms of the focus. The focus is on your team always. And helping them succeed, helping them grow and develop, helping them connect with the vision, understand how their work has meaning, understand the value of what they do and how it's connected to that larger vision. And that is really the core of what you do as a leader.

ilise benun

So two thoughts at once. One is, I imagine you would have to spend some time thinking about that too then on an ongoing basis and need to carve out the time to make that possible.

And at the same time, because most of my listeners are either self-employed people, solopreneurs running their own business, so it's really just them. But the thing about marketing is that it works. So when it works and you do it, then that means there's a potential for growth. And more and more of my clients are building teams—not necessarily hiring employees like at Fidelity that you have, but freelancers and contractors and collaborators and partners.

And so I wonder maybe whether you have experience with this or just even thoughts about how to translate this idea of a vision as a leader for someone who is self-employed—which I was interested, especially, because as my business grows, I'm finding that I need to do that too. As people are helping me, they're really good at what they do, but if they don't understand what's behind it or what's underneath it, it's clear to me that they're just going to do what they do.

Jennifer Barrett

Right. It's almost the difference between a tactical approach and a strategic approach. You could hire someone for one particular job and they could do a great job. But if they don't have the broader context of what you're using that work toward or what your grander vision is, you're leaving them a little bit in the dark and you're maybe not getting the best from them, right? Because they're only seeing one piece of the puzzle.

And as the leader, what you're doing is zooming out and showing them the full picture and how the work that they're doing plays a part in that and why it's so valuable.

Yeah, I agree. I think even if you own your own business, if you're self-employed, whether or not you have other people working for you, it's an important exercise to stop and think: what is my vision for this company and what is the direction I want to go?

What's my one-year vision, my two-year vision, my five-year vision? And then backing into that with what is the strategy I need to get there and who do I need to bring along with me? Because maybe the first year you can do it on your own, right, but then very quickly you're going to want to bring other people in.

I would assume most people who are starting their own business have ambitions to grow and scale it to some degree. And so that really is part of the process, is one, being able to articulate the vision for yourself and your overall strategy, and then two, being able to not just articulate your vision and strategy to other people, but enroll them in it—which is really the key distinction there, right? Is that it has to be articulated clearly and passionately and authentically enough that other people want to be a part of that and want to help you move it forward.

And that's when you really see the magic, because that's when people will push past the, “Okay, I'll get this done for her. Oh, okay, I think I could do this one thing just to ...” They'll look very tactically and say, “Okay, I can finish this in this amount of time, here you go.” But rather you'll get them saying, “Oh, wow, I have an idea for how you could actually move that forward. I mean, I could do this, but I could also do that.”

And that's the magic in it because then it's not all just you. You've enrolled other people in your vision and they want to contribute to it. That dynamic, I think, is really key for having success over the long term, is that you have created something that other people want to be a part of and want to see you succeed.

ilise benun

So now I'm thinking about it from another angle, which is, yes, we need to do this for ourselves as we grow, but what if I'm a freelance writer, for example, or a freelance designer, and I have a client who is not enrolling me in their vision and maybe they don't even know what their vision is. And then I end up maybe just being an order taker or not having enough information to suggest some ideas or to be strategic with them.

Jennifer Barrett

Yes. I mean, first, I would ask the questions you need to ask in order to feel like you have enough information to deliver your best work—and that's part of the process. Sometimes it's a decision ... not every project needs to be the greatest project in the world. But I do think you want to work towards ... If you're a freelancer, I was a freelancer. I mean, the work that had me most excited was work that mattered to me, that I felt like was making a difference and having an impact, and that I could feel connected to in that way.

This would've been 2007 or 2008, I freelanced for about a year and a half while I was working on a book. And over time, I found that I gravitated increasingly toward certain publications or certain companies because I believed in what they were doing and I enjoyed working with them. And I felt like the work I was doing really mattered and I understood how it fit into their larger strategy, vision, business.

And so I think that's important, and I think it's important to ask questions, especially because you can bring so much more to the table sometimes than an employer or a company that hires you as a freelancer is aware of. Or on the flip side, we can hire someone and not even realize the full breadth of value that they're bringing. And by putting them in a box and saying: “I just need this from you and nothing else, and I need it by this time.” Sure, they can deliver that, but you may be missing out on more of the value you can get from that person if you are not giving them more context and giving them the opportunity to give you input too and share their ideas. And I think that goes both ways. As a freelancer, you want to look for those opportunities where you can have more input and build those longer-term relationships, and have more influence.

ilise benun

So I am going to ask you this at the end, but I have an idea for a baby step that might be interesting from this point of view that we're talking about. As a freelancer looking to be more involved and connected to the projects of the clients that they work with, you could just simply ask as part of your discovery conversation: “What is your vision for the business and how does this project fit into it?” My only concern would be, what if they don't know? What if they don't have a vision? Is that embarrassing or would you be putting them on the spot? What do you think?

Jennifer Barrett

Perhaps. I mean, I think there's a way to ask that where you're not necessarily putting them on the spot. You could just say, “This sounds like such an interesting project, how does this fit into the larger work that you're doing as a company, agency, whatever,” and just open the door to that conversation. But I think working at Fidelity, we have worked with agencies in the past. We worked with freelancers. We're usually pretty clear on the brief. We're pretty clear on the problem we're solving for that work: why it's important, how it's connected to larger efforts, and all that.

I mean, Fidelity is probably a little more organized than some companies, but I think before you want to assign work to someone, you should be pretty clear on why that work’s important, how it fits into the broader strategy or the broader vision that you have. And if you start prodding a little bit, and it doesn't sound like they know that, that could be a little bit of a red flag there too on whether you want to continue to work with them for the long term.

ilise benun

Exactly. I love that. So then going back to what it takes to be a leader and what the qualities are and maybe even the difference between how men and women lead, what has your experience been?

Jennifer Barrett

You know, I have had the great fortune to be exposed to several female leaders throughout my career, and I actually didn't realize how unusual that was until I was in management myself. But some of my earliest bosses were women and were sponsors for me, and I'm very grateful.

So when I first was confronted with stories from other women about how competitive it was and how they didn't have anyone supporting them, that hadn't necessarily been my experience. But I think I was an anomaly, to be honest, in journalism just because I happened to have female bosses in whatever departments I was in or when I worked at Newsweek and other companies. At Hearst, I had a male boss, but I worked with four editors-in-chief. I was the GM over the digital side, and they were all women. So I've had the opportunity to see a lot of different female leaders and wow, at Fidelity, I work for a CMO who's a woman, the president of our division, her boss is a woman, and our CEO is a woman.

Yeah, so it's been really interesting and I pay much closer attention to it now than I used to. But I will also say that I have had also those stereotypical male bosses in my life, or at least been exposed to them. So I have gotten a taste of that in my career, as well. And I think through that experience, I would say, I don't know that we're innately different in our leadership styles, but I do think that our environment and the cultural conditioning that we get influences how we lead. So what I have observed is that there is a sense of confidence that a lot of male leaders possess, and I should say white male leaders because that has been what I've been exposed to.

ilise benun

And actually, let me just ask you a question there. You said “a certain sense of confidence they possess.” Is it possessing or demonstrating? Because I think there's a difference.

Jennifer Barrett

I think there's a difference too. And I think it's more than demonstrating. I think that they've been sort of culturally conditioned in a lot of ways to show up with that kind of confidence, so I do think that that's a part of it.

But I also think that there's more of a level of comfort that I have observed in that leadership role, which I think comes from an underlying assumption or belief that they were sort of destined for this path. And I say that because throughout my career, I have seen that male pipeline in motion where male leaders ... and what I've seen is really white male leaders identifying younger male employees that they thought had potential and then grooming them for leadership, so that by the time they moved into those roles, they were very comfortable in them and they felt they deserved to be there.

And I think that is a little bit different. And I've been very fortunate. I've had male bosses who've been incredibly supportive and have helped me throughout my career too. So I haven't had the experience that I know some women have where they feel like they just can't get a leg up sometimes and get that support.

But I do think we are newer to the table and we have often had to fight to be heard, to be taken seriously, to demonstrate our professional dedication, certainly if we had children, and to prove that we deserve to be there or at least we perceive that we have had to prove that, because we are so often still the “onlys” in leadership. And so I think that will affect the way that we show up, certainly early on in our roles. I see that more in women, this kind of sense still that we need to prove ourselves. And again, this is a real generalization.

The other thing that I've observed though in my career is I did see when I was younger, there were so few women in leadership. I mean, I really was an anomaly in that I had female editors and bosses. But if you looked at that senior leadership, there was very rarely a woman at that table. And I do think that there was this kind of scarcity mindset that was perpetuated within these workplaces, that there's only one seat at the table for a woman and you have to fight for it. And know what I learned and what I've seen, and really what has given me so much hope over the last decade, is that women are coming together to fight to get more seats at the table together. And you are much more effective working together than competing against each other.

And I've seen so many female leaders, now, who are really working to open up that pipeline and help other women. And I'm part of a lot of networking groups, and just the generosity—just with advice and guidance and really everything—is, I think, that's a little different than what I've seen in networking groups where it's men and women.

It's really this sense of ‘a rising tide lifts all boats’ and that we have a responsibility to be a part of that. And I've really observed that in the last few years. So I think that's really heartening. We still have a ways to go, I think, in terms of achieving gender parity. If you look at the Fortune 500, I can't remember what the percentage is, but it's in the single digits. And certainly, if you look at people of color, it's also abysmally small number when you think of the demographics of our country. So we still have a little ways to go there, but been heartened by some of the trends I've seen in recent years.

ilise benun

Yeah. Again, I have too many thoughts all at once. I mean, one thought is just about leading. You could talk very broadly about what it means to lead, even not without this idea of being a leader. Because when we talk about our lives, leading our lives, do we lead our lives in a way that is active or passive? Whether you're a man or a woman. I see both genders doing this. So I'm curious if you have a thought about just leading one's life.

Jennifer Barrett

You mean showing up as a leader in the way that you live?

ilise benun


Jennifer Barrett

Yeah. I mean, I think that there are a lot of pieces to being a successful leader in the workplace or wherever. Could be an author and be a thought leader ...

ilise benun

Mm-hmm, another way to think about it.

Jennifer Barrett

... and that's a form of leadership too. But there are a lot of those attributes or kind of the functions of being a leader in an organization that you can take into your own life too.

You want to have a vision for your own life. You want to know where you're going. You want to feel really good about it. And I think that kind of energy spills over into your environment too, and the people who are around you. So if you think of certain people who are really happy with who they are, where they are, where they're going, that's contagious. And other people want to be around that and be a part of it.

And I think once you sort of set the direction in your own life, and I've really found this to be true, if you declare it to other people: “this is where I want to go,” people just come out of the woodwork. People want to help. If you say, “My goal is to do X, Y, Z, I feel passionately about this,” other people want to help you. And so I think that's true no matter what it is in your life. You could be organizing a volunteer food drive or really anything that you feel passionately about and you want to take the lead on, you can get other people excited about it too. Or even your vision for your life, I think about ... This might feel like a silly example, but I had a real vision for where I wanted us to live as a family, and I sat down and wrote it out.

I wrote out a literal checklist of everything I was looking for in the next place we lived, and it was very specific. It was location-wise, where I wanted to be within, no joke, a six-block radius. It was a place with a lot of light. The space to have guests come over, which in New York is not a given. A dedicated nook or space for my office. A balcony, a roof deck, all of these things. I just wrote it all out on a piece of paper and kind of declared: “this is what I want.” And we're living in it, now.

And I'm not saying that just by declaring it, you make it happen. It's not like the secret, you imagine something, and boom, the secret, there it is. I think there's more to it. It's really hard to achieve something if you actually don't have a vision for what it is. You have to know what you want in order to recognize it when it appears or to get other people to help you achieve it.

ilise benun

Yeah. So that seems like a good place to put the bookmark here because I'm sure there will be more conversations. And it almost sounds like you just gave it, but I'll ask you the formal, “What is the baby step, then, to move in that direction?”

Jennifer Barrett

I think based on the conversation we have, it really is giving yourself the space and the time to think about what it is that you want for your life. Or what it is that you want in whatever position you're in, for the company you work for, or the company you own, for your life.

Creating that vision of where you want to go, and where you want to bring your team if you have one, in a year, in two years, in three years. What that looks like. Getting really clear on it ... so, viscerally, enough that you feel connected to that outcome.

And you don't need to know exactly what it is. It's more sometimes, you might describe the impact that you want to have. I think about Fidelity. We want to close—I want to; I think that I'm not alone at the company feeling this way—we want to close the financial literacy gap for the next generation of investors. That's a vision. To have that kind of impact would be incredible.

So if you start there and you say, “So what do we need to do in order to get to that point?” And you start to back into it, you might not know exactly how we are going to get there, but you want to be able to clearly articulate what that end goal is in order to rally other people around that, and then you'll start to put the pieces in place, the steps in place to get there.

ilise benun

And I would imagine as the head of content, you're in a good position to be able to do that, too.

Jennifer Barrett

I am. We're not there yet, but we're working on it.

ilise benun

That's awesome. All right. Well, thank you so much, Jen. This has been really thought-provoking. And I have a feeling I'm going to use this for one of my next retreats because it's exactly what I want to help facilitate for other people, which is part of my vision for my business also, which I've been working on.

Jennifer Barrett

No, I love that.

ilise benun

Thank you so much.

Jennifer Barrett

Well, thank you.

ilise benun

And tell people where they can find you online and your book and everything.

Jennifer Barrett

Sure. I mean, the book is sold wherever you buy books. It's called How to “Think Like a Breadwinner.” I have a site, jenniferbarrett.com. It's a little bit out of date because I haven't been ...

ilise benun

Been kind of busy.

Jennifer Barrett

... as focused on it. I've been a little busy. But you can find out more information about me there or on LinkedIn.

ilise benun

Beautiful. Thank you so much, Jen.

Jennifer Barrett

All right, thanks, ilise.

ilise benun

So the baby step Jen shared in today's episode is to carve out time to think about your vision for your own life and for your business at one year, two years, five years. You'll be surprised how much easier it will be to get there once you've articulated it. And if you want to build a thriving business on your own terms, the first step is to sign up for my Quick Tips at marketing-mentortips.com. Once you're on the site, you'll find lots of more resources, including my Simplest Marketing Plan. So enjoy and I'll see you next time.


Outro/Baby step

The baby step Jenn shared in today’s episode is to carve out time to think about your vision for your own life (and your business) at 1 year, 2 years, 5 years. You’ll be surprised how much easier it will be to get there once you’ve articulated it.

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