How to ask for more (money!) with Jennifer Barrett

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How can you never leave money “on the table” again when negotiating? 

It's simple: ask for more -- more than you need, more than you want, more than you expect.

But this seems to be one of the hardest things to do.

So in my second conversation with Jennifer Barrett, author of “Think Like a Breadwinner” (who will also be speaking at HOW Design Live in Nashville, Oct. 19-21), we talked about how exactly to ask for more.

We focused on negotiating and overcoming the money talk taboos and she shared exactly what I know you need: actual language to use when asking for more -- because it does take a certain finesse.

So listen here (and below) and learn….

Listen to our first conversation, Episode #416, here.

And here's the transcript of our conversation:

ilise benun
Hello Jenn. welcome back to the show.

Jennifer Barrett
Thanks so much for having me. I'm excited to be back.

This is part two of a conversation that we had not too long ago, based on your book, Think like a Breadwinner. I felt at the end of that episode, and I said this, there was just so much to talk about that I knew we would have a part two, So here we are, Please, for those who didn't listen to part one yet, tell us who you are, give us your elevator pitch -- I think things have changed a little since we talked last. So bring us up to date.

Jennifer Barrett
Sure, they have changed. I've actually taken a new job so I'm now the Head of Content at Fidelity, just a few weeks in, but enjoying it so far. And before I came here I had been the Chief Education Officer at Acorns for about five years. Before that I had a pretty long career in media. I wrote for the Times and the Journal, Newsweek, worked at NBC and then was the personal finance editor at CNBC before joining acorns.

So at heart. I am a journalist and I tapped, those instincts and skills when I was writing my book which is called "Think like a Breadwinner," and really encompasses my own experience, but then I interviewed over 100 women and did a good amount of research to boot.

And really the book came from my own wake up call. When I realized that what I had been taught was independence, actually, was not true independence, which is that there's a material difference between just being able to cover the bills and building wealth to support all the things you want in your life.

That's really the crux of the book -- how thinking like a breadwinner can really leave you feeling both empowered and having true agency over not just your money but your life.

ilise benun
And one of the things that drew me so much to your ideas, and the book and in the conversation also, is that marketing plays the same role for people who are self employed:  that the more you can provide for yourself, in terms of prospects in the pipeline, is very much like having savings in the bank, and it just frees you to make better decisions, not based on, let's say, desperation

Jennifer Barrett
I completely agree. I mean, the most empowering place to make decisions from is making choices that support the life you want, rather than making choices out of fear or, you know, being in a place of survival or desperation. So yes completely agree. I think there's a lot of overlap there.

ilise benun
And I know that your book is framed for women, based on the things that women are taught. But I have to say that I work with men who struggle from very similar mindset myths or challenges when it comes to money. And those are some of the things that I want to talk about but I'll just let you respond to this idea of, is it really just women, first?

Jennifer Barrett
Oh no. I focused on women in part because I do think that the socialization that we get around money, and the way we are brought up to think about our own financial capabilities, that is different for women generally than for men. But it is definitely worth pointing out that as a country we are failing in terms of teaching financial literacy to our population. I
t's not required. In the majority of schools most people never learn the basics of financial literacy. It's left to us to try and figure this out and this is really a basic life skill.

And so if we haven't been taught these basic skills by our parents or if we're lucky enough to have been taught some of these things in school, if we don't get that education. we become adults and have to suddenly make these choices around money and we're left making really uninformed choices and feeling a lack of confidence in terms of managing money. And on top of that, advocating for ourselves financially is not something that many of us are taught either.

And so both those things tend to play out when we're adults in sometimes really painful ways. Most Americans end up learning about money by making mistakes, learning from our mistakes. And we don't need to do that. So that's part of what I'm addressing in the book is that there are actually some very basic things you should know around money, some basic rules to follow.

And then, reinforcing the fact that we are not really brought up to be our own advocates, professionally or financially, and we really need to be, because no one else is really looking out for us. No one else cares as much about our money, or our careers, as we do. So we have to get comfortable advocating for what we need and then learning what we need to learn in order to make really informed choices,

ilise benun
That's a good segue to one of the things I really did want to focus on with you -- when you say, advocating for ourselves. One of the ways I think about that is negotiating. I was not taught how to negotiate as a child or by my parents or in school or anything. I was taught it eventually by a very smart person, who has been my teacher over the years and taught me many different things. And I try to teach negotiation to all the people that I work with, based on what I've learned and what I've experienced.

But I do want to talk about the mindset behind negotiating -- not even necessarily the practical aspects. I'll put one actual example in front of you and you can respond to it.

The idea of asking for more. When you're in a negotiation, and someone presents a number to you, whether it's a salary number or a project fee, or anything, you have to understand that they're not presenting their highest number. They're not presenting their ceiling; they're presenting their floor, because they perhaps expect to negotiate. My job, if I'm in that situation, is to ask for more. And some people are afraid of that. So to speak to that and maybe also to the question of how much more is appropriate.

Jennifer Barrett
That's such a great point. So I've been in management for about 13 years now. And one of the most eye opening experiences was when I moved from being on the other side of these negotiations to being the hiring manager. When you hire someone, there is typically a budget range, there is an assumption, especially when you start getting to mid level and senior level positions, that someone will negotiate. That is kind of baked into the budget for these roles.

And yet, when I was on the other side of it, when I was younger in my career, I didn't negotiate my first few jobs. I just assumed that they were giving me the best that they could at the time. I also had some fear around you know....I worked for Newsweek, and that had been kind of a dream job for me. So when I got the offer at Newsweek, I was a little afraid -- like what if they retract the offer if I asked for more?

So I didn't. I was just so thrilled to get the job and then -- I talked about this in the book -- I ended up working there for seven years, and I found out just before I left -- and this was certainly a factor in that decision -- that someone who had been hired in a similar role to mine, about five years in, was making more than 50% more than me!

It felt like a gut punch. First I felt stupid, I mean, I was thinking, "How could I have been working this long at a rate that now I know is lower than what I should have been paid? Why didn't I advocate more for myself?" But then, I also felt a sense of betrayal, because I had worked so hard for this company, I felt like I was so loyal and had just assumed that I would be rewarded with my pay.

And the fact is you can't make that assumption. I think this is where I see some of the gender differences, that, as women, when we were girls in school, we were rewarded for putting our head down and working harder, doing extra work, getting extra credit, led right to straight A's and pats on the head. And that is not the case in corporate America. Or if you're an entrepreneur or small business owner negotiating with clients, you are not paid necessarily just for being a good worker. You have to advocate for yourself.

And so that was one lesson -- that you have to advocate for yourself. Never assume that you are going to just work hard and be rewarded for that.

But the second lesson was there is a baked-in assumption in the budgets that there will be a negotiation, particularly on the more senior roles. And so you are literally leaving money on the table if you don't negotiate that salary. There is an expectation that you will. 

I think there is a certain finesse to it, like, "Oh, I was really hoping for more based on what your market rates are." Or, "My experience or what I made in my last role. Do we have some wiggle room here? Can we can we bring this up a little bit?" There is a way to negotiate where you're not putting someone on the defense but that this manager is kind of on your side, and the ultimate goal for both of you is that you take this role. So how do we get there together?

There were a couple stories lately -- there's one that sticks in my head about a woman who said that she asked for significantly more when she got a job offer. I think it was at Rolling Stone, and then she said they retracted the offer. I'm sure there's probably more to this story than that, but I do think you have to come into the negotiation having done your homework.You have to know what the market rates are for the skills that you bring and the role that you're filling. And then there is a kind of a finance aspect to it to where you want to position it as you and this hiring manager working together to get to a common goal, which is you taking this role and killing it in that role for this company,

ilise benun
Keeping in mind that most of my listeners are not looking for a J-O-B and not dealing with salaries at all, which means that often, what they're doing, the services that they provide, there's no actual market rate for it. Everyone charges something different, everyone pays something different. Even if there is a market rate, the market doesn't have a piece of paper where they're going to find the market rate. So, that makes it very tricky actually to negotiate a project fee, God forbid, an hourly rate, and for the most part, I am not a big fan of hourly rates anyway.

Jennifer Barrett
I am right there with you on that. Because I think you really want to focus on the project and the ultimate goal and what I've seen happen -- because my husband is on contract and being in the media and creative industries, I have many many friends and colleagues who are entrepreneurs and freelancers -- and it doesn't encourage you to work efficiently.

If you're being paid by the hour, you're encouraged to stretch out those hours. You're not rewarded for being more efficient. The second reason is if you are very efficient you should be rewarded for that. So be rewarded for the end results and not being paid by the hour,. Yeah that's my general feeling.

ilise benun
You're basically punished for being good and fast -- that's the way I think about it. But, back to this word "rewarded" -- because you were using it before and I had a lot of thoughts about it, that women expect to be rewarded or maybe even men. But to me it's less about the expectation of reward, and more that someone else is going to take care of me, someone else is looking out for my best interest. Even your example, "I assumed they were offering me the best deal or the best salary" -- why? Why would you assume that? Why would anyone assume that? That's the mindset piece I want to get at.

Jennifer Barrett
Of course, and I was pretty naive at the time. In my 20s and I think we all are in some ways. And I think, culturally, we're having these conversations more often, and having gone through two recessions now, we see how companies proclaim their loyalty to workers and then lay them off en masse. So I think everyone at this point is a little bit jaded and a little bit wiser to the fact that loyalty and hard work are not necessarily rewarded in that way. 

So you really need to look out for yourself. I do think that's a little different, especially for people in their 20s. Today it's more about building your own brand, and really thinking about each job as if you're taking a job as an opportunity, especially if you do want to become an entrepreneur or a contractor.

I think we've wisened up a little bit, as a country, but to your point, I do agree that there is a little bit of a "I will be taken care of mentality" that we see, again more in women, because that's the way we have been culturally conditioned. That our income is less critical, that at some point we will find a partner who will likely be the breadwinner.

These are sort of outdated assumptions but they persist and they can seep into our subconscious and inform the choices that we make. Because if we're making an assumption that our income is secondary, or that we won't have to take care of ourselves fully financially for life, we make different choices. One of the points I make in my book is to imagine if you were thinking like a breadwinner and you were raised to believe you would be fully responsible for yourself financially for life, and probably a family too, you would make different choices. At least I asked myself that question.

You know, when I had my own wake up call, and realized I would have made very different choices, even though I ended up getting married, and even though my husband initially earned more than me. I would have been in a much better position financially to have the things that I really wanted in my life had I've been thinking more like a breadwinner.

And so regardless of how your life plays out, it behooves you to think that way. Because then you know you'll be taken care of and I think, as you mentioned earlier, there are a lot of corollaries with being in business for yourself.

When I talk about financially taking care of yourself, I am talking about becoming less and less dependent on your paycheck by putting more and more of your money to work for you and building wealth. And I think there's an "apples to apples" corollary if you're in business for yourself or you want to be building wealth as you work. So you have that kind of cushion financially but also when you talk about building leads, and making sure that you're putting some of your energy into the tasks at hand and some of your energy into building your business, so it can be sustainable and sustain you.

ilise benun
I know you don't have a lot of time today and I have again so many more questions I want to ask you. Let me ask this one last question actually. But before that, I'll say that I'll have an opportunity to ask you all sorts of questions at HOW Design Live when you join me there for a fireside chat October 19-21 in Nashville. So thank you, I'm really looking forward to that and we'll definitely cover some of these things.

I wanted to go back to the idea of the mindset that is still persistent and ask you if young people who are just coming out of college or going into college now, in what is essentially a very info saturated, social media oversharing world, is it still taboo to talk about money details with either a friend or a family member? And a corollary question, "Are there any conversation starters you can suggest to get people to open up about these things and share more?" Because I do think that that's part of how we overcome some of these hangups,

Jennifer Barrett
I completely agree, I think that there has been a sea change in the last six months in terms of how comfortable people are talking about investing in particular, you can think cryptocurrency or stocks. There are a number of factors here but I think because that's become part of the popular lexicon now and so many people are talking about it, it's just become more acceptable to say, "What are you investing in?" 

This is not to say that I encourage day trading at all, and I think you have to be very careful if you're investing in cryptocurrency. But I think now there is just more dialogue among a much broader audience about, "How do you invest? What are you investing in?"

I think there used to be a real stigma if you weren't really comfortable about your knowledge of investing, you were hesitant to talk about it. I think we're getting over that a little bit, in part because crypto is complicated, meme stocks are complicated. And so if someone's asking, "What does this mean? Why did Gamestop go up?" -- there are a lot of lessons baked into that and it's a lot easier to ask a question like that than to say, "I don't even know how to open an investment account or get started."

There's still a little bit of shame, which is unnecessary, in not knowing what you feel like you should know about whatever money topic -- fill in the blank. And so the first step is really just being comfortable with the fact that the vast majority of Americans were never given this education and there's no shame in asking questions. So that's step one.

So ask a lot of questions, and who cares? There's really no shame in it, and you'll be surprised when you start talking to people, that almost everyone has some story about how they never learned XYZ and had to learn the hard way. So I think just getting over that hump is a big step.

I have a friend who runs a PR consultancy and she runs a workshop with other people who have their own businesses and they talk. She will say, "Okay, let's talk about what we charge." She said initially, no one wanted to talk about it, Because, you know, if, if one person said they charged X amount and another person charged less, they were embarrassed to admit it.

But then the more they talked about it, and they realized the gap in what they were charging and they started to talk about what accounts for that gap -- is it experience or is it just lack of experience asking for more. They started to get a lot of information on what the range was, and they had more confidence asking for higher rates. So a lot of people came out of these kind of informal gatherings with both information to ground them and a group of colleagues to support them. And they were much more confident asking for more.

I found it to be really helpful when I've freelanced as well, or even when I was speaking. I reached out to people and said, "What do you charge when people ask you to speak? What's normal?" I talked to a whole range of people and got a range of fees but then I had a much better understanding and thought, "Okay, this looks like where I am in this range based on my experience and other factors."

And so I had some information to lean on when I went into negotiation. So the first step is talking to other people who are in your area and asking them what they charge.

Also, it's also good to ask them what they think is reasonable. Because people can be a little funny about what they earn or what they charge. So one way to get into that is about what to charge for x y z. So you sort of separate it from the specifics. I think the corollary there if you're if you're working in a job or you're you're looking for a new job, I find it's much easier to say, "I'm interested in this job posting. I'm going for an interview. What do you think is reasonable as a salary for that role?" It separates it from, "What are you earning?" It takes the personal nature and the emotion out of it -- so you're using it as almost a hypothetical, like "What do you think is fair to charge in this scenario" which separates it from, "What are you charging your clients right now?"

ilise benun
A little bit of distance. All right, I actually have one more quick question. Is there still such thing as an investment club? Because I remember hearing about those a while back but lately I've been wanting to 
start one. 

Jennifer Barrett
Well if you start one, I'll be your first member. They do exist. I've mentioned in the book that there are some very large female-focused investment clubs, certainly many that are gender neutral clubs as well. And you can just Google investment clubs and look in your area, or start one yourself. Yeah I think that's still a thing, it's just that we don't talk about it as much, but I'm all for it. I think that we've gotten so good at helping each other build their business and their career. Imagine if we did the same with each other around building wealth, like, "Have you invested in a real estate? What have you found works for you? Are you investing in crypto? Are you investing in stocks and bonds? -- just having those conversations.

Obviously you want to turn to a trusted source to make sure that you're getting really good information as you're putting together your own investment portfolio. But I do think it can really behoove you to hear about other people's experiences on top of reading. I always say, go to Fidelity. We've got great information. Go to Investopedia. There are tons and tons of sources that are trustworthy that can give you the basics. But then talking to other real people about how they're doing it and what they've learned from their experience can be really valuable too.

ilise benun
And I want to share what I've learned because I've had such a good time learning how to invest and, you know, it's not that hard.

Jennifer Barrett
No, that's the big secret: investing is not hard.

That's the first thing I say in my investment chapters -- the biggest myth of all is that we've been taught it's this big, complicated thing and you need to hire a pro to do it. And that has really stopped so many people from being able to build wealth. And I agree. My mom and I talk all the time about our investments and compare notes. When you do learn something from investing, you want to share it and it's so valuable to get that insight from other people too. It's a way to bond you -- it's a social activity too. We share these lessons and you're both growing your wealth -- the whole group is growing their wealth at the same time. It's incredible.

ilise benun
All right, I'm gonna do it and I will keep you posted. And I'm gonna let you go back to your day J-O-B. I really appreciate your time Jenn and we will continue this conversation in Nashville together. I look forward to that. First, tell everybody where they can find your book first.

Jennifer Barrett
On any bookseller Amazon, Barnes and Noble or your local bookseller and you can get some more information on me at

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