How to Become Shameless (In the Best Way)

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1:33There's no safe like SimpliSafe. From Entrepreneur Media, this is Problem Solvers, a show in which entrepreneurs do what entrepreneurs do best, solve unexpected problems in their business. We were completely wrong. And I'm just like, it's not selling. It was like, we have to start from scratch. Watch. I'm Jason Pfeiffer, the editor-in-chief of Entrepreneur Magazine.

1:59My friend Jenny Wood is the most shameless person I know. And I mean that as a compliment. You want to find a person who just goes and gets it, who seems to have no fear of embarrassment, who's just willing to take the risk always? Well, you talk to Jenny Wood. I'm Jenny Wood. Wait, wait, wait, Jenny. Hold on. Not ready for people to hear your intro yet. First, I need to say this. I met Jenny about five years ago, and at the time she was high up at Google and was building this incredible career coaching program over there, and she had dreams of one day writing a book and building something for her own.

2:35And so, like many people, she asked me for advice about this or that. But I have never, never seen someone action advice like Jenny. Like, she took action on everything I said to her immediately. we would take hikes and she would come with a list of questions for me and would furiously take notes as we're like scaling rocks. And then, boom, she got a major book deal. She left Google. She is building things. And do you know how she did it? Well, among many ways, she was shameless, totally, completely shameless in the best possible way. Shameless in asking for help, not just from me, but from hugely accomplished people she did not know.

3:18Shameless in how she She promoted herself, shameless in the amount of money she asks for things, shameless in the way that all entrepreneurs need to be. Which is to say, you cannot go out there and be embarrassed or afraid or hesitant. You have to go out there with no shame, no embarrassment. Shamelessness is confidence in action. It's telling people without hesitation that you are worth it. And by the way, this is not me just opining myself on shamelessness. shamelessness is a part of her book, as you will hear in just a moment. And about that hearing in just a moment, this is a small but telling example of Jenny.

3:56So whenever I record a interview for problem solvers, I always start by asking the person I'm interviewed to introduce themselves. It's basically to get a little tape, little audio of them saying who they are in their own words. And they often do this with a kind of unsureness. Like sometimes they just say their name, like, hello, I'm Jason Pfeiffer. Sometimes they say their name and their title or something. But rarely, if ever, do you get the whole shameless package right out of the gate, like Jenny. Can I first just have you introduce yourself? Yeah, sure. I'm Jenny Wood, and I did research at Harvard Business School for three years, then went on to Google, where I spent 18 years climbing from entry level to executive, ultimately ran an operations team that sat between sales and engineering, And I have now put all of my energy into writing this book, Wild Courage, Go After What You Want and Get It.

4:52That helps people reclaim nine sizzly traits that create the bars of an invisible cage that keep them small. Weird, selfish, shameless, obsessed, nosy, manipulative, brutal, reckless, and bossy. I live in Boulder and I love to hike. I've got two kids who are seven and nine. I met my husband by chasing a stranger off the New York City subway, giving him my business card, and later getting hitched to him. Jenny, we're going to talk about being shameless and all the lessons that you have there. And you are going to reframe shamelessness as something that should not be feared or looked down upon, but actually a good trait.

5:31And I have to say to start, that was a pretty shameless intro. You packed a lot in there. Oh, yeah. Well, I mean, people say that authority matters, right? Like people like, why would people trust me if I'm some bozo off the street? Then like, what do they care what I have to say? Like, I've done a lot of things that I'm proud of. And using the phrase, I'm proud is one of the most powerful things you can do. Let's say you're pitching a client, right? And you've got this incredible testimonial from another client. Why not be shameless and say, I'm proud of this feedback that I just got from this client last week.

6:02I'd love to work with you too. The phrase I'm proud to me is one of the best two word phrases you can use. Another example, we had a nanny we were hiring. She filled out a form where we asked her a couple of questions so we could not waste time interviewing people who didn't meet the bar. And some open-ended question about what else do you enjoy to do? She said, because we were looking for someone who could also do house management activities too, cooking, cleaning, laundry. And she wrote, I'm an exceptional cook. That is a shameless word to use. And I swear, Jason, I hired her because of that, because we wanted someone to help with cooking.

6:37Who doesn't want an exceptional cook in their house? But how often would a candidate say, I'm exceptional at XYZ. I'm an exceptional coder. I'm an exceptional salesperson. I mean, that really makes you pay attention. Shameless. It's true. And also, who would say that they're exceptional at something unless they were exceptional at it? Yes. And even if you're a good cook, why not use the word exceptional, right? Like who's who's defining what exceptional shepherry is versus shepherry? We've we've invented a new word. Alert the James Beard Foundation. So that's true. Although I guess I would say, why wouldn't you use the word exceptional if you are not exceptional?

7:20The answer is because the next thing that will happen if someone believes that you are exceptional is that you will then have to cook for them. And it better damn be exceptional. Otherwise, you will have oversold yourself. And I think that that's something that people really fear is that they can't live up to the hype that they have put around themselves. Okay. And yet I find, I agree. I agree with what you're saying, but I think that's where the imposter syndrome comes in. All right. Sorry to hit pause, but we're going to take a short break for a word from our sponsor and then back with more from Jenny Wood.

7:57All right, we're back. And now here's more with Jenny Wood, author of Wild Courage. That's where the lack of confidence comes in. And I find that, you know, having coached tens of thousands of Google executives, non-executives, directly and indirectly, people outside of Google on leadership, influence and success, I have found that the bigger challenge is people living in fear, right? People not feeling confident enough. There's this study out of the University of Glasgow, 75 % of people feel a lack of confidence at work. So I think the bigger issue is often people not feeling they're good enough to even say that they're decent at something, right?

8:39As opposed to the people who use that superlative language. And you don't have to say exceptional. You can also say good, right? But people who don't feel like they even want to put the statement out there in fear of them not living up to it. And I think that holds so many more people back than... people saying it and overselling and then getting burned because they don't live up to their standards they've delivered or promised. It's almost like what you're saying here is, if you're going to err on one side, don't err on the side of underselling yourself. Err on the side of overselling yourself.

9:12And I don't just mean this for a job interview. Think about each week with your team or your boss or each team meeting you're in where rather than coming off of mute and sharing something that might be a really cool idea, you stay quiet you stay silent you think well it's probably not a good an idea good enough idea or maybe it's been shared before or maybe it's not innovative enough but you know what if you come off of mute and you say something even in front of your boss's boss at least you're playing it hot at least you're taking your shot like that is shame that is like you know the shamelessness every day that i think makes people successful is continuing to shoot your shot not thinking in darkness, but speaking in lightness, right?

9:52Like letting your ideas shine. And then if people don't like them, then you iterate on it, right? So you say, hey, I think we should... You work at an ice cream company. I don't know. You say, hey, I think we should start a vegan ice cream line. And maybe everybody thinks this is not the right idea for now, but maybe it inspires an idea for a soy ice cream line, whatever it is. I guess that's also vegan, but you get the idea. you're really doing some butchery to the world of food in this conversation so move on widgets my publisher said i had too many examples that i talk about widgets too often because of my economics background everything is like green widgets red widgets yellow widgets and then she's like can we talk about something besides widgets and then i started talking about ice cream a lot everyone likes ice cream all right so here let's let's let's back up for a our conversation, because you are full of ideas and also because we know each other so well, basically like took off on the tracks before we even set up where the station was.

10:54So I'm going to tell you this. Jenny, one of the reasons I was excited to talk to you, particularly about shamelessness today, was because when I hear shameless and I hear fear of shamelessness. The first thing that I flashed back to was a revelation in the early days of me having something to promote. And, you know, which is every entrepreneurial journey in some way or another starts with somebody now having a thing to sell and then having to get comfortable selling it. And I, you know, what would this have been? It might've been even just trying to get people to sign up for my newsletter or to hire me for a keynote or something.

11:40And I remember realizing this thing with this very particular person, which was that a couple years into me being editor-in-chief of Entrepreneur Magazine, I did a couple things with Tim Ferriss. I had him write something for the magazine. i had him comment on some stuff and then he was also on the cover this was all within like a maybe a year and a half span and i was really taken by how consistently he plugged things that he has like he almost used every opportunity whenever he would write something to try to turn people's attention towards uh and i have this framework that you can download at this um and this comes from episode 351 of my podcast.

12:33And you can check out... And as an editor, I found that stuff so annoying. Because I was like, would you stop pushing your stuff? Like, would you stop being salesy for a second? But then when it came my turn, it came my turn to start to promote myself, I thought back to Tim. And what I thought was, you know, and this is like a thing I've been trying to train my brain to do, which is to just, take as fact that if I'm seeing something in the marketplace and it's working, instead of arguing against why it works, like instead of trying to think of reasons that it shouldn't exist, why don't I start with it does work, so why?

13:14And so I'm thinking, okay, Tim Ferriss is extremely successful. He has driven millions of people to listen to podcasts and to buy books and stuff. So like this thing that he's doing clearly works. Why does it work? And the answer, I guess, is because if I'm just a consumer and I'm interested in what Tim Ferriss has to say, then he's giving me opportunities to get even more value. That's it. And I don't, as a consumer and a person who likes Tim, I don't actually find that annoying, even though as the editor, the guy who was like working on his text, I found it annoying, but a consumer doesn't. So then I thought, well, why don't I just do that?

13:47Why don't I just kind of be Tim Ferriss in the way that I can figure it out? And I just started doing that. I started dropping in, and you can get my thing here, and you can get, and you know what? Jenny, it works. It was shocking. It was shocking that it works. And that was my first introduction into what feels like shamelessness. Yeah, so I have an example of that. I wrote the book. It was nearly going to press. And a good friend of mine, whose work is awesome, Mo Bunnell, said, Jenny, I read your book. You do not have a single way for someone in the book to go from offline to online. You need to go back to your book and find multiple places in your book to include a URL, right?

14:33Like wildcouragebook.com slash resources. And I went back through and I added... Way to drop that in here right now. I added 17 mentions of wildcouragebook.com slash resources. And I am so glad I did. And mentioned throughout the book that I'm a keynote speaker and that I do consulting at Fortune 500 companies and other smaller companies and organizations and trade associations. and that I, you know, and I added a couple stories about keynote speaking and it's like, people don't know unless you tell them. Like people, think about the sign outside of someone's house when they're doing construction, right?

15:11That is full information. If you're driving by that house and you're considering a remodel, when you see that sign on the lawn out front, it saves you time. If you think this house is beautiful when it's done, like you want to know who's good. people are always looking for good talent. It's like I thought about this all the time as a Google executive because I'd hire tons and tons of people and it was really hard to find good talent and the candidates are always feeling so insecure or like, you know, who's going to hire me? How do I compete against these other candidates? But on the hiring end, I'm always thinking, how do I find the top talent?

15:48So if someone's got a sign outside their lawn telling me like, Like, hey, this is who we are. This is our work. Like that is helpful as the homeowner. If you're an entrepreneur and you're pitching your services, just remember, it is not so easy for the people on the other end to find someone as skilled, as high quality, as efficient, as friendly and as competent as you are. So give them the opportunity to know that you exist and then tell them nine more times. All of what you just said, there tracks. Tracks with my experience, and it makes logical sense. But it is going to run up against some people's feeling that nobody likes a braggart, that you can oversell yourself to the point where people just want to run away.

16:38Jenny, there's a reason that your book is structured the way it is, which is that you are taking these surprising positive tacks on terminology and qualities that we often think of as negative, right? That's a lot of what you're doing, right? Like nosy people think is negative. No, you're saying it's actually can be positive. So that's shameless. So people are thinking about shamelessness as a negative. Talk to me about why you think people do feel that and maybe what they're right about, right? Let's validate that there is possibly something bad about being shameless. So where are the lines that you're drawing that people can know if they're inside or outside?

17:21Yeah, that's a great question. So you absolutely can take these traits too far. Absolutely. And that's why I caution people to be mindful of trait traps. A trait trap. So these are the nine traits that can lead to a ton of success when used in a sane and savvy way. But if you take them too far, you will get burned, right? So, so trait traps are when you take it too far. And for shameless, yeah, of course, we all know that guy who is just obnoxious and, and too much and, and doesn't either doesn't back up the claim with the goods, right? Like, like has too much audacity or too much as we'd say chutzpah, right?

18:08But I still maintain that the vast majority of people live in way too much imposter syndrome and much more of a lack of confidence than an overabundance of confidence. Think about 10 people you do business with right now. Clients, partners, friends, colleagues. And in those 10 people, would you say more are actually over the top shameless in the classic sense of the word? Or more need you to push them and need you to say, no, go for it. That's a good idea. Why not? Like go ask that client for their business. Ask them for the upsell. Ask if you can partner on some new project. Which of those 10 people you have in mind right now, which category do they fall into more?

18:48Too shameless or not shameless enough? Hmm. It's a good question. You know, I'll tell you the kind of person that jumps to mind as you're saying that. And I think of a couple examples in my life of this kind of person, which is someone who is, they're like a quiet killer. which is to say that they're not bragging about themselves all over the place in an obnoxious way. But in the moments in which they need to convince someone that they are excellent, they are excellent at it. They have total confidence and they're not spreading it around scattershot. right i think that's that's that turns people off when someone is just a just bragging all over the place for sure they are they are instead cool and confident confident that they don't need to oversell themselves but man when it is time to sell they know how to do it they're really good at it and they have a full command over their value and they are they are almost as confident not selling when they don't need to be as they are confident selling to be and i find that's a very impressive skill.

20:01That's great. I agree. Yeah. Tell me how people can get there if they're not there. Take it back to me, guy who's like, I don't know how to pitch even a newsletter. Subscribe to my newsletter. I don't know how to pitch anything. I find that it's scary and I'm afraid that people are going to think that I'm obnoxious. And I had that moment of revelation by just looking at Tim Ferriss' work, but still, how do you start to do this? Yeah. Well, first it's a mindset shift. So let's actually put yourself back in your... The mindset shift is critical because I think what holds us back initially is the mindset of, you know, I'm not there and I'm not Tim Ferriss and who am I to even put my stuff out there in the world?

20:49Or why do they need another newsletter, right? There's lots on the internet around change management. Yeah, it's like, right. You're describing almost like arguing against yourself. Right. Before you pitch it, you start to imagine all the reasons why somebody wouldn't want you. Right. And so think how often we do that. How often we're our own worst enemy, right? And that's the thing is like, when we get into these fears, right? There are basically three fears that wild courage overcomes. Fear of uncertainty, fear of failure, fear of judgment of others, right? These nine traits, weird, selfish, shameless, obsessed, nosy, manipulative, brutal, reckless, and bossy.

21:23They're all living in fear of judgment from others, right? Like you don't want to be called shameless if you put your newsletter out there. You don't want to be called reckless, which to me is just erring on the side of action, right? It's in a good way. But, you know, so let's think about how you, if you are the one that's getting in your own way and you're working against yourself, well, what can we do to overcome that? Because it's good news. If you are the problem, you can also be the solution. So let's take you back to when you were first starting your newsletter or starting your own entrepreneurial endeavors.

21:55What was something that got in your way? I want you to think of a sentence that either starts with, I can't or I don't. That was based in fear. Anything that you felt like you were where Tim Ferriss was. Okay, so anything that starts with, I can't or I don't, that was a way you compared yourself in some way to someone who is bigger. Sure. Well, okay. The context here is, I will choose when I was first trying to pitch myself as a keynote speaker. And I started that journey because a friend of mine in PR, shout out John Beer, told me, he was like, Jason, you could easily get$10 ,000 a talk. And I was like, shut up.

22:39There's no way I can get that amount of money. And this was like a decade ago. And he was like, no, you could definitely get $10 ,000 a talk. And then, so what I did is I, I started, I came up with a talk. I practiced it a lot. I did it a couple of times for free. And then I got someone to tell me that they have a budget for speakers. And they said, what's your price? And what do you think I did? You said$10 ,000. I did not. That's probably what you would have done. You would have said$20 ,000. That's a percent. You would have said my fee is$20 ,000. No, I didn't do that. Instead, what I did is I said$5 ,000.

23:21And the reason is because, to go back to your prompt here where you wanted a statement that starts with, I can't or I don't. The statement in my head was, I don't think I'm worth that. Okay. So now take that statement and say it again. Add the word yet to it. I don't think I'm worth that yet. How does that change how you feel about what you just said? Well, this is an interesting thought experiment. I really like that shift. So though I have to tell you, I think that back then, to say I don't think I'm worth that yet is still to say, I don't think that I am worth$10 ,000 right now, but I know that I can be worth$10 ,000 later.

24:03Exactly. And so I'm still going to charge you$5 ,000. It's funny, yeah. Because I did feel confident that I could get there, but I definitely didn't feel like I was good enough at the time. But I like what you're saying by adding yet, because what you're doing is you're putting this moment onto a continuum, and you're giving it a purpose in a way, right? There's a way to look at this story where I just undersell myself, and that's that. There's another way in which I look at the story and I say, what I was doing was step stepping into the fullness of what I could ultimately sell first I did a couple free talks then I gave a 50 % fee talk and then I gave a hundred cent fee talk and that that gives it a that that that does this thing that I love which is that it gives me a sense of momentum like I'm like I'm building yeah exactly and I mean to be fair like we talked about you know how do you know when you're taking it too far I think I've fallen into the shameless a straight trap a lot in the last several months.

25:06I think I have pitched too high and I have lost deals. Like I have, you know, pitched that 20 when you said, you teased me rightly so that you wouldn't have pitched 10, you would have pitched 20. Well, I've done that. I've done that same type of thing and I have gotten zero. So, you know, I, I just had a, a talk where the deal was nearly done. Great fee. It was going to be... They then came back and said, could you do it at 3am in the morning? Your time, our audience is mostly Europe and Asia. And I was like, 3am in the morning? I was like, wow, this is really close to book launch. I don't know if I can lose a whole night of sleep.

25:45I'm like pulling all nighter to do this. And so I came back and said, could we do 6am? Figuring we'd land on 4.30 and then at least I could go to bed early and get a chunk. And they just came back. They're like, no, sorry, we've gone with somebody else. And so I was shameless, you know, I fell into a trait trap there where it's like, I, if I really wanted the money, I should have just said, yep, 3am sounds great. You know, where's the, where's the dial in and I'll be there. So I do think that like, I am not saying that this works every time, but I think that again, the vast majority of people will benefit from playing it a little bit hotter, right?

26:17Speaking up on that client call or saying$10 ,000 and seeing what happens. Oh, by the way, here's a real practical one. I wouldn't say any number. I would let them anchor first. What is your budget? How have you compensated speakers for this event in the past? You know, what is typical for you? Like the more you can do to get them to say their number first, gosh, the worst thing in the world is when an entrepreneur is pitching a project, they give their number and the client is like, oh, wow, amazing. I had 2x to spend, you know, versus what they just mentioned. So if we're getting real tactical, and I love to get practical, the more you can have somebody else anchor on the number first, then you don't even have to be shameless.

26:58Then you just react based on what they share. And then if we're talking negotiations, I also love this tool called the ping pong strategy versus the ping ping strategy. So ping pong is they say a number, you say a number, they say a number, you say a number. Ping pong, ping pong. Ping ping is basically, my dad taught me this when I was a kid, negotiating against yourself. So that would be if I say, I'm 20 ,000, but I could also do it for 15 ,000 if 20 ,000 is not in the budget. So it's ping, ping. You're hitting the ping pong ball twice. You never want to say a number and then negotiate against yourself with a lower number.

27:34Let them say another number. You might say, I'm 20. They might say, we only have 16. You land on 17, five. Instead, I went from 20 to 15 and you're never going back up to 20 once you say the word 15. Right. So that applies to any kind of entrepreneurial deal. Totally, totally. And I've experienced every part of what you just said. I remember the first time I got a fee above$10 ,000 for a talk, it was$15 ,000. And I thought I was killing it. And I flew down to Kansas or wherever it was. And the event was great. And then the event organizer actually drove me back to my hotel. and when we got to the hotel before I got out, she was like, hey, I just want to give you a little piece of advice, which is you could go higher.