261 | Your Invitation to Play the Game of Yes (7 Steps to Wealth, Step 4: Ask)

Hilary Hendershott: Well, hello, Money Lover! Welcome to my 7 Steps to Wealth podcast series. If you’ve already heard this introduction to the series and you don’t wish to hear it again, please just fast forward about two minutes. If you haven’t heard it yet or want to hear it again, here we go.

Hilary Hendershott: Many years ago, as I was digging myself out of financial oblivion and creating healthy money habits for myself for the first time, I realized that if I could master this thing called money, I would have something very valuable to share with the world. I mean after all, there is plenty of information about money out there in the world, yet most people still struggle with it. So obviously something is missing in the zeitgeist about money.

Hilary Hendershott: And there came a time in my financial life where I started to look more financially healthy than damaged. There came a time when my bank accounts started to contain 6- and 7-figure balances. There came a time when I could set big, really abundant goals for my business, work toward them, and reliably achieve them.

Hilary Hendershott: The way I would say that now is, I got into right relationship with money. I stepped into having power and influence with money. So as part of sharing the lessons I learned with money, I looked back on what I had accomplished–from where I was now, with a high credit score, a multi-million dollar home that my husband and I own, and a multiple 7-figure net worth–and I asked myself, “What are the exact steps I took to get here?”, “What specifically did I do differently to change my financial reality?”, and “How exactly did my money mindset and financial beliefs change?”

Hilary Hendershott: And I created a framework called the 7 Steps to Wealth. I’ve published that framework many times, in many formats. Episode 208 of this podcast contains the entire framework in one episode; it’s a great audio resource. There’s an interactive, multimedia eBook you can download if you go to the show notes for today’s episode. And I would love for you to do that. We talk about the 7 Steps in my Money Love Notes newsletter, which you can also subscribe to in the show notes.

Hilary Hendershott: But what I’m doing now is an entire episode on each of the 7 Steps. The 7 Steps in order are: Decide, Plan, Speak, Ask, Earn, Invest and Protect. I’ll publish this series with the steps in order, but not necessarily every week. So the point is to do a deep dive on each individual step because knowing the steps makes no difference. You have to actually put them to work in your life. So if you’re looking for a different step than the one I’m talking about today, and that step comes BEFORE today’s step, just look around in the recent episodes I’ve published. If you’re listening to these as they air, and you’re specifically interested in a future step, it’s coming.

[EPISODE]

Hilary Hendershott: Well, today we’re talking about the fourth step in the framework, and that is Ask.

Hilary Hendershott: This one is pretty simple. Yet for most of us it’s actually, really, really, really, really hard. That can be true, more or less, for every step in the framework, but I do feel like this one tends to be the most elusive. Some people are born with it, and some people just aren’t. And I think women are at a particular disadvantage. We’ll get to that. Wanting your life, your wealth, your money, your financial happiness to get bigger and better does require asking. You can’t do it on your own, and you can’t do it in a silo.

Hilary Hendershott: From the first step of this framework, Decide, it’s probably become quite obvious to you that you have to take an active role in building the kind of wealth that lasts. So what does it mean to ask for wealth?

Hilary Hendershott: Okay, it’s really secret. It’s really more of ask for what you want and ask for what you need that’s going to get you to wealth. But let’s talk about all of that.

Hilary Hendershott: Asking for wealth: If you are embodying the Ask step to this framework, it means you expect–that’s your expectation–to reach financial freedom. You are asking that of life. And it also means that you commit to requesting the participation or agreement of other people.

Hilary Hendershott: Simply said, there’s power in numbers. Other people currently possess literally the dollars and cents that you want and need to create your financial freedom. Them giving it to you is not them giving up their own financial freedom. But we’re also going to talk about that. You can accomplish more with the right people on your side than you can alone. You can do way more in the world when you’re not by yourself.

Hilary Hendershott: When I say it’s time to start asking, I’m talking about the kind of asking that comes with the expectation of delivery.

Hilary Hendershott: I have this image of my mind, and I may be dating myself, because I don’t see this game around anymore. But this game, it was Hungry, Hungry Hippos. Okay, you remember, and the little hippos would chomp at the marbles. Your goal was to get the most marbles in your little pocket. It’s like Hungry, Hungry Hippos, except in the game Hungry, Hungry Hippos, if you took a marble, you were taking marbles away from other people. Money isn’t that way.

Hilary Hendershott: That’s the thing is, money just represents value. So you’re running around asking to collect value in your store of bank accounts, investment accounts, like that, denominated in dollars, leaving the world a better place because you’re trading value for value. So the point isn’t to ask a random person on the street to give you $10,000. That would be a little crazy. You could do that. You’ll probably hear “no” almost all the time, and you might get 911 called on you.

Hilary Hendershott: I don’t know. I would assume that might happen if you ask for that 100 times, because you don’t really expect a “yes” if you just ask someone to give you $10,000. I’m talking about the kind of asks that put skin in the game, like asking for a client, or asking for a raise at work. I’m talking about asking someone to carpool with you so that you can save money on gas or decrease the amount of wear and tear on your car. I’m talking about asking VCs to invest in your startup company.

Hilary Hendershott: You need to actively pull in or call for increasing money, resources, and wealth over time. And the first step to this is really identifying what you want that you don’t have, right? It is okay to have an active and running list of the things you want and need that will make it easier and obvious for you to accomplish your goals.

Hilary Hendershott: The first time I really experienced the power of asking in my life was when I got really clear that I could not continue to pretend to the people in my life that I was doing alright financially. I wanted to show up and pay for stuff. I wanted to be fine. I wanted to be set. I wanted to be abundant, so I was pretending that I was, while in actuality what was happening was, I was disappearing all the money I earned and saved, and it was terrible. It was a terrible lie. So, showing up and being transparent felt like a huge ask. I mean, I was sort of asking for their forgiveness. I was asking for them to still think I was an okay person when I said, “This whole time I’ve been paying for dinner, when in reality I have $40,000 in credit card debt. I can’t do it anymore. I’d love to go out to dinner with you, but if we go out to dinner, you’re paying. Love you.”

Hilary Hendershott: And I really said that stuff. I didn’t say it that way each time, but sometimes I did.

Hilary Hendershott: So I got financially transparent. That felt like an ask to me. Then, when I started to build my business, I really had to fine tune and bulk, to use a weightlifting metaphor, I had to bulk up that Ask muscle. I was asking clients to come with me to my new firm, asking new clients to hire me constantly. Business owners don’t ask for a job once. They ask for a job every single day. I was also asking people to come work for me, to help build the firm. I’ve published almost 250 episodes of this podcast, or around 250 episodes.

Hilary Hendershott: That means I’ve asked hundreds, maybe more than a thousand people to be on my show with me, or to let me be on their show so that I could convince their audience that they should come listen to my show. I mean everyone who has participated with me in building this business has responded in the affirmative to some request or offer I have made them.

Hilary Hendershott: I hear “no” all the time. And you know what? I rarely even remember that it’s happened.

Hilary Hendershott: So this step that I call Ask is really about taking on the view, the desire, the commitment that makes asking for things come naturally to you. That may seem out of reach to you, I totally get it. However, I invite you to consider the first time you sat on the seat of a bicycle without training wheels on it, and put your feet on the pedals, the idea of balance also seemed out of reach to you.

Hilary Hendershott: So many people limit their abundance and their potential because they never ask for more. They never ask for what they want, let alone the things they actually need.

Hilary Hendershott: We suffer in silence because we don’t want to pressure other people, or be a burden, or put people out, which is really just not trusting people to say “no.” And then part of the insidiousness of it is that we honor, regard, and put people on a pedestal for suffering in silence. Right, like suffering in silence is a badge of honor to some people. No, we’re putting that badge away. We’re taking that badge off of our sashes, putting it on the desk, and wishing it well.

Hilary Hendershott: Now I get it, I do get it. Asking can be hard. Asking is harder for women. And I’ve always said this, asking is harder for women, because we’re taught not to make waves. We’re taught not to make noise. We’re taught not to be loud.

Hilary Hendershott: We’re taught to be happy with what we have; to make the best of things. I cannot tell you the number of times I’ve gotten eyebrows raised from people who use the word either assertive or aggressive–I haven’t heard aggressive in a few years–to refer to how I interact with people or in groups of people, right? And they don’t mean it as a compliment. We’re taught not to want a big, incredible life.

Hilary Hendershott: And I’ve said this before, but women even sometimes foist patriarchal values on each other, which is really sad. I mean, it’s actually really devastating.

Hilary Hendershott: Look. Be honest, if you’ve recoiled from or judged a woman for being bold and assertive and asking for what she wants. I am talking to you.

Hilary Hendershott: And the point is not to feel bad about it. Feeling guilty doesn’t help anything, but just recognize it for what it is so we can really just knock it off. I’m guilty of it myself in the past.

Hilary Hendershott: To some extent most of us actually believe that women should be content, little hard workers, whether we work in the office or at home, and the most complimentary, virtuous description of a woman is that she would give you the shirt off of her back.

Hilary Hendershott: It’s really a terrible metaphor. It’s really awful.

Hilary Hendershott: Really, like, I’ve seen this happen. Ask a hundred women what they would do if they won the lottery, 99 of them will tell you all the fancy ways they would give it away. Like they have specific charities and specific people to whom they would give away their lottery winnings. It’s insidious. I say, keep it for yourself… and ask for more.

Hilary Hendershott: I give money away every month and every year. Over the last 20 years I’ve given away tens of thousands of dollars. When I was broke, I had a $20 a month budget, or maybe it was 25 or 50, right, but I increased it over time. At this point I give away tens of thousands of dollars every year.

Hilary Hendershott: I give to individuals and charities and friends and their kids. And I’m able to give because I’m keeping what I need and want for myself, for my family, for my marriage, and for my child. Right? My cup is full. Get to that point, and then give from a place of being full. It’s a very different experience. Not only that, but if you’re really honest with yourself, when your cup isn’t full–even if you’re not talking about it out loud–you’re irritated. You’re under-slept. You’re under-resourced. Think about the energy that you’re able to bring to people, and you’ll probably–if you’re really honest and really take a look in the mirror–the energy that you’re bringing is a little bit stingy and a little bit of resentment.

Hilary Hendershott: And that’s the thing you’re bringing to the people around you when you’re under-resourced. Think about a time when you bought a friend a gift you couldn’t really afford, or gave a loan you couldn’t afford to lose.

Hilary Hendershott: And over time, the pain of having given that thing that you couldn’t afford to give, it really just grows. And resentment grows around it like a black little pearl. Right? We all know that this happens, and that is the other side of not having your cup be full. So really today, this episode, this podcast, this conversation is your invitation, almost almost your compulsion to either get to or commit to getting to a place where your cup is full.

Hilary Hendershott: Now, I’ve talked about before on this podcast several times, a particular challenge that I invite and recommend the people that I coach to take on in their life.

Hilary Hendershott: There’s two ways you can think of it. One is “the gift of a hundred nos”, also called the “game of yes.” How are we going to transform your relationship to hearing no, or perceiving that rejection? By the way, when someone says “No” to a request that you make, they’re not actually rejecting you. That’s part of the lesson.

Hilary Hendershott: But I invite you to take on asking for things so many times–and I literally mean track the asks that you make; the number of requests, invitations that you make–with the intention of hearing “no” 100 times.

Hilary Hendershott: Couple things this accomplishes–they’re really miraculous if you think about it. First of all, when you make “no” the goal, of course that’s the beginning of re-engineering what “no” means to you; what “no” feels like to you. Now I know that pushing back from a meal after my third piece of pizza doesn’t always feel good, but I can consciously take on a game of pushing back from the table a hundred times and celebrating my own discipline, my own win, my own self pride, right, and that begins to change how I relate to that thing that I don’t get, that I want, which is that third piece of pizza, or whatever it is for you that’s discipline.

Hilary Hendershott: In the same way, we have to, like I said, re-engineer how “no” makes you feel, what “no” means to you, what happens inside your body that you would reject asking for something just because you don’t want to feel that way.

Hilary Hendershott: So again, taking on getting to hearing “no” 100 times is just an alteration of thinking. And then the miraculous thing that happens, and I’ve never, ever, ever talked to someone who actually took this on, who didn’t say to me, “Hilary, first of all, I never got to a hundred nos, because along the way, my life got so much bigger, I had to stop playing the game.”

Hilary Hendershott: “Like I completely transformed what’s possible for myself, what’s happening in my business, what’s happening in my family, what’s happening in my friends group by just asking for the things that I wanted. And I thought that I would hear ‘no’, but I actually heard ‘yes.’ And then, in the granting of those requests, my life got so big that now I have a new problem called my life is abundant; my life is miraculous.”

Hilary Hendershott: So that is a challenge I highly, strongly recommend you take on today. Overcoming the struggle of being a person who doesn’t ask is worth it. It will pay huge dividends in your life.

Hilary Hendershott: Just really, after this podcast, or maybe right now, just take a 20-min break from listening to my voice. Think about all the ways that being terrified of hearing “no” limits you.

Hilary Hendershott: Think about all the things you don’t ask for, all the things you don’t have, all the hardships you experience and suffer in silence on your own because of the mentalities and strongly held beliefs I’ve talked about today.

Hilary Hendershott: Also, conversely, think about how free you would feel if you fully trusted people to say “no” when they mean “no”, and therefore allowed yourself to ask without hesitation. And you can really let go of the thinking that every ask leaves the person you’re asking worse off.

Hilary Hendershott: People love to give. People get value from contributing. The world is full of mutually beneficial partnerships that all had to get created by someone asking.

Hilary Hendershott: I have an incredible number of people bring abundance into their lives through just asking. Literally hundreds of people who listen to this podcast have emailed me that they asked for something and ended up getting 10 times what they initially even asked for. And that really is the secret gift of the yes game.

Hilary Hendershott: The goal here isn’t to develop a sense of entitlement or expectation. The world does not owe you anything, you don’t actually, quote, “deserve” anything. I mean, look, I use that word, too, and I know it’s galvanizing. I know it’s exciting. You know, ask, like “charge, what you deserve” kind of messaging. However, there is no measure of your value inside you, right? If I opened you up, I wouldn’t find a price in there. There isn’t something that you deserve from the world, and the world doesn’t owe you anything.

Hilary Hendershott: You’re an eager, optimistic, inspiring participant in the world. And people want to be around that, okay? You want to recognize and utilize the fact that there are things in life that require the partnership or support of other people to accomplish.

Hilary Hendershott: I couldn’t do really anything without the participation of either who’s managing childcare for me on a daily basis, or my husband, right? If I didn’t have childcare, appointments would get canceled, I would not be recording this podcast. It just wouldn’t happen. I need partnership at that very basic level to accomplish the things that I do in the world.

Hilary Hendershott: Immeasurable, really beautiful amounts of value get created on the planet through people trading something they have for something someone else has that each person values more than what they had originally.

Hilary Hendershott: It’s really lovely, and the only way that that gets initiated is through asking. I mean, if you think about it, the price tag on a piece of clothing at a retail store, at a boutique, right? That’s an ask.

Hilary Hendershott: That’s what they’re asking. You could think of it as a demand if it’s not negotiable, but it’s an ask. You could say yes or no. And that’s how you end up with a wardrobe full of clothes that you love is, you say yes to those asks.

Hilary Hendershott: So you go ask for something today. Remember asking is conceptual. It’s about wanting your life to get bigger and better, to expand and improve.

Hilary Hendershott: And it’s also tactical. Your desires for a bigger life, your picture and vision for what’s coming for you leads to the tactical aspect of asking. These are the conversations you have with people that are the catalyst that lead to opportunities and projects that expand your possibilities and your wealth.

Hilary Hendershott: Really, your Facebook and Instagram feed? Those are all asks. They’re asking for your attention, they’re asking for your click, they’re asking for your phone number, they’re asking for your purchase. The world is full of asks. Join the party.

Hilary Hendershott: Okay, so action steps. If you’re inspired by this conversation and recognize that it’s time to step out of suffering in silence.

Hilary Hendershott: I really, really invite you to take on the game of yes. The game of yes, formerly known as the gift of a hundred nos. Take on asking for things so many times that you hear “no” 100 times. Track them in detail. Date. Who did you ask? How did you ask? What did you ask for? What did they say?

Hilary Hendershott: It’ll change your life. Here are some types of things you can ask for to accomplish this step on your path to wealth.

Hilary Hendershott: You can ask for a raise at work. You can invite a prospective client to say yes to your contract. You can increase your prices if you’re a business owner. You can negotiate for anything, so that the offer is better for you. You can ask for and build business partnerships. You can ask VCs to invest in your company. You can ask 10 moms to join you in a wine or book club. You can ask for training to increase your technical skill set with the intention of raising your market value. You can ask for a schedule that allows you to get your work done and be home when the kids get off the bus.

Hilary Hendershott: These things might seem big. So here are some smaller examples where a “yes” or a “no”, both won’t alter your life dramatically, but also the “no” won’t feel like a big deal. You can create a nanny share to decrease each household’s childcare costs. I did that when my daughter was born, and I had to ask my nanny to participate and ask the other kids’ parents for that situation to work out.

Hilary Hendershott: You can ask someone to mentor you. I’ve done that. You can ask your husband where the investment accounts are. Ask your friend to make something you can sell at the charity auction. Ask someone to carpool with you. Negotiate the price of your new car, rather than assigning that task to your husband. You may think he’s better at it than you. That may be true right now. However, you can’t build your skill set if you continue to delegate.

Hilary Hendershott: You can ask your insurance company for better rates. You can ask your credit card company for a better APR.

Hilary Hendershott: By the way, I think I’ve done podcast episodes on almost everything that I just mentioned, so you could scroll through past published episodes and check those out.

Hilary Hendershott: And surprising things will happen. I once told a client that if she wanted to reach her financial goal–this really happened, I’m not making this up–I told her if she wanted to reach her financial goals, all she had to do was double her income. Now, did I think she was going to do that when I said that?

Hilary Hendershott: I’ll be honest, I didn’t. We both kind of chuckled. She said, “I want to get to X amount by X time.” I said, “Great, no problem. Double your income.” And I mean, we chuckled.

Hilary Hendershott: A month later she called me, and she said, “I quit my old job.”

Hilary Hendershott: Let’s say she was making 120 a year, she’s making $120,000. She said, “I quit that job, and then I went, and I applied for new jobs, and I said, my starting rate is $240,000 a year.” And she got it. She really did.

Hilary Hendershott: It blew me away, and it made me very happy for her. But I want you to know that a lot of times we limit our asks by what we think is possible. Go ask for stuff you think is impossible. We want to talk about changing your life.

Hilary Hendershott: I actually know someone who got medical school fully paid for because she asked for a tuition discount. She went in, said, “Can I pay less? Is there a way I can get a scholarship or a discount?” They took a look at her transcripts, or, like some other thing about some test score she had, and they said, “You know what? We’re gonna reimburse your tuition fully. Zero cost.” It happens.

Hilary Hendershott: The women who now work for me as my co-VPs of marketing, that whole thing got started in a very interesting way. They asked for a contract gig to a group that we’re all part of, a group of women, a group of moms. They wanted to repurpose content for me, which I happened to need at that time, so they could pay for Taylor Swift concert tickets. I was so charmed by their ask, I actually fell in love with them for the way that they asked.

Hilary Hendershott: And then our professional relationship continued to grow and develop and evolve. And now they’re like 60 or 70, or maybe more percent of their working hours are consumed by a contract with me, and I have strategic and tactical, full time marketers for the first time in my professional history.

Hilary Hendershott: It has been a real miracle, just because these two women got together and said, “I don’t obviously see the money for T Swift concert tickets in my bank account. Let’s go make a valuable offer to the marketplace, with the intention of paying for what we want.”

Hilary Hendershott: I felt like it was very synergistic, and it’s turned into a really great relationship.

Hilary Hendershott: Truly, the more you ask for, the better practiced and natural you’ll be in how you do it.

Hilary Hendershott: I promise you, you can get to a place where it doesn’t even phase you. Asks just come out of my mouth. Now, I’m not saying I make the biggest asks in the world; I’m not holding myself out to be the pinnacle of all askers. Right? But I don’t experience resistance, or I don’t experience emotional hardship about the possibility of hearing “no”, and if and when I hear “no”, I don’t suffer about that. That is definitely true.

Hilary Hendershott: So only you can answer, what do you want? Remember, asking is your empowered voice, knowing what you want and going out and getting it. It involves you and others in a dialogue, a decision, a process, and, in most cases, a goal.

Hilary Hendershott: I encourage you to do it inside your own integrity. Don’t stretch yourself beyond what is moral and virtuous to you, your moral code internally, right? So do it with integrity. And, know that asking is essential to reaching wealth.

Hilary Hendershott: So what can you ask for that would help you generate more wealth, more income, more investments, more free time, more happiness, more financial comfort, and build the life of your dreams?

Hilary Hendershott: It’s your life, it’s your money, and your plan, and it’s your future that’s on the line. And, I promise you no one else cares more about your money than you do.

Hilary Hendershott: I want to know what you’re going to ask for next.

Hilary Hendershott: So, assuming you’re not in traffic or doing something dangerous right now, take a second and open up your email app. Write me an email: hello@hendershottwealth.com. Hendershott has two T’s and no C. So it’s H-E-N-D-E-R-S-H-O-T-Twealth.com. Hello@hendershottwealth.com. We’ll be cheering you on, and we’ll meet you at our next step, Earn, when you’re ready.