Shout Out to Women: You Are Entitled to Sell!

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yes women, you are entitled to sell stuff.

“I just don’t wanna feel pushy, yaknow?”

^^^^ this is a sentence haunting the sales efforts of almost every woman business owner I know.

Myself included.

(At least, until fairly recently. And even then it never fully goes away.)

This constant fear of being, doing, or selling too much — even when it’s, uh, our literal livelihood — is an ever-present weight on women that adds extra pressure to the already-vulnerable experience of putting our work out there.

It’s the reason we send “just one quick email to test the waters” at the tentative start of a launch, and fold into ourselves like hermit crabs when we get don’t get quite the response we were hoping for.

Keeping Quiet When We Could Be Shouting

It’s the reason we feel guilty when someone outside of the industry (who would never be a customer anyway) mentions our FB ads are “annoying” or that we post on social media about our work “too much” for their liking.

It’s the reason why ONE negative response to a sales sequence can send us spiraling and questioning whether we should shut the whole thing down, even if we’re making money.

This struggle women face around feeling entitled to be paid (and paid well) for our work is a topic I’ve seen discussed most often in private FB groups, where it’s dug into like an open secret everyone’s been dying to tell.

We’ve all heard that wake-up call stat that men will apply for jobs they feel 60% qualified for, whereas women largely apply only to jobs they feel 100% qualified for.

It’s the Socialization, Baby

And while a lack of “confidence” is often cited as the reason for that statistic…

… It’s not so much self-doubt alone as it is women putting specific rules around how WE choose to sell ourselves — rules that men often aren’t culturally socialized to think about.

(Rules like “not being too in-your-face”, or “not sending too many emails”, or “making sure the ad copy doesn’t turn anyone off” <— because if you want to sell, you often NEED to be a little polarizing. And when you are: begone, non-buyers!)

I’ve seen mind-blowing numbers of women desperate for ways to make money without inconveniencing or offending… anyone. And it holds them back harder than any open or click-through rate ever could.

Some of the Best Convos Happen “After-hours”…

So when Margo, Maggie Frank-Hsu, and I started discussing women in sales offhand after a taping of #HAMYAW and Friends, we knew we had to go deeper, and give it an episode all its own.

Which is why we’re thrilled to be premiering our latest today: Women: You Are Entitled to Sell.

Our culture encourages women to be accommodating, which impacts how we sell and promote in our copy, our brand, and our sales strategies.

And so, the problem with women in sales is the problem with women in the world: we’re still working on feeling worthy of making demands, stealing the spotlight, demanding what we want.

Catch today’s episode all about the sucky process of selling as women, where we talk about…

A Few of My Favorite Parts:

1:25 What to do When Selling Feels “Annoying”

3:30 Why It’s A Good Thing If People DO NOT Like You

6:00 Women in Movies and TV are Un-relatable and Stupid and It’s Part of the Problem

7:27 Maggie (who’s also a mom of two boys) Explains How Our Biases Are Holding Us Back

8:40 Margo’s Jim Lovell Story (how we internalize the wrong things about ourselves that end up affecting how you show up in online AND what you believe about yourself and your capabilities) <– THIS IS MY FAVORITE PART OF THE EPISODE. MAYBE ANY EPISODE EVER, TBH.

11:03 Why Entrepreneurship Is The Best Form of Personal Development (For Women and Frankly Everyone Else)

And Now…Let’s Hear From the Full Spectrum!

Check out the episode, and while you’re over there, let us know:

Women and female-presenting friends: what’s been your experience with sales?

If you felt comfortable with selling right out of the gate, how has that impacted your journey?

If you didn’t, what (if anything) changed that, and how’s it been going?

And of course, men and male-presenting friends of #HAMYAW: we want to hear from you too!

My male marketing buddies are some of the loudest advocates for women unapologetically selling, so we’d love to get your thoughts: what are some ways you feel women suppress their own success in sales?

And do men have engrained doubts about selling, in your experience? If so, what are they?

And in the meantime: don’t be shy about gettin’ that paper ladies.

You were born to break rules.

Even if they’re your own.

Write on,

Episode Transcript

Can I try again? I’m like

Yeah, yeah, yeah.  

I’m hitting the 90-minute mark.  

You’re okay, baby. You’re okay, deep breath. You come back to center, okay? Take a sip of whatever’s near you. Have a crunch of your snack. We’ll come back online.  

Okay, okay.  

Your hair looks great.  

Thank you. That’s all that matters.  

It is.  

I hate this thing. It’s like an adult sippy cup. (laughs) Fuckin’ hate it. (upbeat music)

Welcome back guys for another episode of HAMYAW. And, this episode is actually a bonus episode of HAMYAW and friends with none other than the legendary Maggie Frank-Hsu.

Where we want to talk about why selling sucks so much when you’re a woman.

I think we have a lot to talk about here, about how women are socialized, about how our culture encourages us to be not pushy and accommodating, and all these things.

But, this is just a fantastic conversation that we hit record on after the last episode wrapped. So, we wanted to share it with you guys. Let’s dive in.  

So, we were talking about how women feel like they need to accommodate others. And how that affects how we sell.  


And, how we promote, and the way we come off in our copy. And, I think that this fear of inconveniencing others is something that we should talk about. I’ll dive into what we were talking about.

You were just saying in email, we don’t want to annoy people. And, I will share that I had a friend, recently actually, who was like, “This email feels like you’re trying to sell me on HAMYAW”. And Hillary and I were talking about it, and we were like…

That clout!  

Yeah, that’s precisely what I’m doing.

And so like one, that tells me I probably did a good job because you should never feel like you’re being sold. Here’s the thing. This is what I’m getting at.

When you’re not the market, it’s always gonna feel like a sales pitch. When you’re the market, it will feel seamless.

So like if I have hair that looks disgusting, and you sell a blow-out bar, I am gonna want what you have if I view my hair as a problem. That’s always gonna be something that’s interesting to me.

If I don’t view my hair as a problem, and you try and sell me on blow-outs, I’m gonna be like, “That’s really annoying.”

So like part of the re-frame we have to make is that your pitch doesn’t feel like a pitch to the market that needs it.

And you have to have that like tunnel vision, that the person that you’re talking to, is reading this, which is why you wanna come at it with respect and still have, you know, generosity and value-add in your emails, and the way you make your pitch.

But you still need to be making a pitch to them, to get them to take action because people are lazy. And I think the way that we socialize women in this country is antithetical to what we need them to do if they are going to succeed in business.  


You do have to have an element of, it’s gonna be inconvenient for some people. It’s going to come off as annoying to some people.

There are going to be very real consequences to you looking pushy, or what are those like terrible words that everyone says? Assertive. Aggressive. Intimidating.  

Bossy. Bitchy.  

Bossy, right!  

I take these as compliments at this stage in my career, so it’s very much like, “Oh perfect, you think I’m that, awesome!”  

But you graduated to that. Like

Yeah, exactly.  

No one started that way. Like now I hear it

Not at all.  

You meant executive leadership skills, it’s fine, I know what you meant. But in the beginning, we internalize that stuff and we’re like, “Oh no, I’m gonna offend someone.”

Like the one thing I have learned from studying under the people I’ve studied under is that like you do need an element of divisiveness. Like people need to not like you. If everyone likes you, then you’re doing a really bad job, at what you were trying to do.  

You’re not taking risks, you’re not, you’re not selling. Like you’re not doing a lot of things I think that’s so important for us to remember as well.  

But one thing that you kinda touched on and then jumped off of Margo is like, I think that, what I see, or the way that I frame it, and that I’ve seen it over and over in my clients, is like not feeling entitled to having a point of view.

What we sell, you know, is really like, a way of doing things or you know, helping someone with a problem right?

I see so much more in women and particularly I’ve noticed this a lot more after becoming a mother among other mothers, that like there’s just this erasure of, you know that, we just kind of feel like there’s a pressure, an internal pressure, an external pressure, societal pressure, just to not have a point of view.

To not have like something to say, and something to sell. A product, you know, that is our thing, that we created, that you know, this is why it helps this type of person. That there’s just like a lot of pressure. 

Yes, you know there’s this worry about bothering, but there’s this even deeper thing about just not being entitled.

There’s a podcast that I used to really, really like. They don’t do it anymore. But it was founded by two men. And I just thought like, it’s just some dumb idea, but they were really smart and the podcast was really great. And I just felt like, wow, they just thought, I can say what it is right?  


They don’t, I mean they’re not gonna care. It’s the podcast, Denzel Washington Is The Greatest Actor of All Time Period. (Hillary laughs) And it talked about each Denzel Washington episode, and they talked about how he’s a black actor, they’re both black so they talked about, you know, the implications of him being in different movies and being as big of a star as he is.

And there were so many angles right? But I just thought, “that’s such a good idea” and there are so many women who would’ve been like, “I don’t know.” I just felt like, wow, men just think, “Yeah, I’m entitled to do this. Let’s go do this.” Right?

That’s what you’ve done with HAMYAW too in a way. But like, I think that women are less likely to just automatically feel entitled to be like, “Yeah, I have this great idea. I wanna tell everybody about it.

Wanna know about this idea? Hey everybody!” You know? And I just really think that is totally about misogyny and the way that women are socialized differently from men.  

And pop culture. Like we don’t see a lot of like, “I’ve got a great idea” women in TV, movies


And even like, you know, in the digital space. Like women are in a lot of ways like supporting characters. And of course, we’ve got some great women-focused storylines going on. But I saw Quentin Tarantino’s Once Upon a Time in Hollywood and I’ve also been watching that series

I haven’t seen that.  

It’s pretty good. No spoilers. But there’s also this series on Amazon Prime called The Boys. And I’m looking at these female characters and I’m just like, “Oh my God!” They’re either dead because they’re motivating these superheroes, or the anti-superhero crew to like do the thing.

Or they’re like constantly crying, even though they’ve like had shitty lives because like that’s how we’re supposed to relate to them.

Or they’re evil. Like there’s not a lot of really productive female roles like in these films.

It’s a really sort of interesting thing, how far, when you think about the Bechdel test, when you think about movies and stuff that keep coming out, like, we have come so far but we still have so far to go.  


And I think that is, partially, like I think, cause I see a lot of parents now like encouraging their girls to like code and going entrepreneurship, and there’s a big push I know from every single mother I know about teaching their daughters to be ambitious and their boys to be respectful of women and all this stuff.

And I feel like this is the problem with women in sales is the problem with women in the world, which is the fact that we are still working on feeling worthy of making demands, of dealing with the spotlight, of demanding what we came for. Yes.  


I love the

And Hillary, as the mother of two young boys, I’ve heard more than once, online, and in-person, other boy moms saying things like, “oh well…” moms, women, saying things like, “Well you know, now there’s all this stuff for girls, what about boys? Like boys are so forgotten and stuff.” I’m like, boys are like, you know, they’re…

That’s the norm!  

Mean, and like everybody else is deviant and like, I just, it really boggles my mind. And they really feel that.

And I think that like it just shows you like how challenging it is because as soon as there’s any kind of progress people are like, “Oh I don’t like this. Like this isn’t the way it’s supposed to be. This is different.”

And women I think play a big part in holding back progress sometimes because they don’t have, they’re not like aware of the biases they have.

Everything you said about pop culture it’s really, it’s just women who are doing stuff like that, like the woman that does Fleabag, you know

[Margo and Hillary] Yeah.  

They’re like the exception that proves the rule.  

Yeah absolutely.  

I mean you see it, I mean back to us. It’s like kind of the same with selling.

Like I think that women who are really, really succeeding a lot of times sell to other women, but there aren’t that many crossovers where it’s just like yeah, everybody’s paying attention to her, everybody’s following her.  

I wanna make a connection so people don’t think we’re doing like just blatant identity politics here, of like

Oh right.  

When we say (laughs) cause like I worry about that sometimes.

But like when we’re talking about benevolent sexism or misogyny, I’ll give you a really like kind of silly example, but it’s very real about how we internalize the wrong things about us that eventually end up affecting how you show up online, how you show up in your brand, and what you believe about yourself and your capabilities.

So, when I was little, I grew up in Houston, and I really wanted to be an astronaut. So when Apollo 13 came out it was like my favorite movie. I was obsessed with this movie and I was like obsessed with Jim Lovell and Tom Hanks so like I did the thing that all little kids do where I like rented all of his movies, cause I was like chasing that feeling, and like did everything.  


So cut to like 28 years later, my mom just says as an aside, as a compliment, like how she knew I had such character cause the man I had a crush on was Tom Hanks and he’s not attractive.

And I was like, “Hold up, you thought I had a crush on Tom Hanks?” And she was like, “Yeah you were obsessed with him. I just thought wow, I raised like such a great daughter, that like she chose the one with character.” And I was like, “I wanted to be Jim Lovell.”  


“Like, I wanted to be Tom Hanks. How did you miss that?” And it was, it led to like a really interesting conversation but it reminded me of like those subtle things that happen along the way, that we internalize, like I’m not allowed to want this, this is not for you.

You’re too big for your britches. You’ve reached past the point. Like I’m trying to think about a movie about a female pilot that wasn’t steeped in how she overcame adversity and systemic oppression and like she… 

She doesn’t exist.  

Still be able to be a mom, still able to be a wife. So she did all the things. Like there isn’t actually a storyline where the fact that you’re a woman is left out. It doesn’t exist.

And so, when we look at, you know, how you feel about sales I know we’re talking about bigger level things but I want everyone to see the connection. Like these bigger systemic problems are part of why it’s hard to hit send on that email.  

[Maggie and Hillary] Yeah.  

And why it’s so important that you do it.  

[Margo and Hillary] Yeah.  

Even if it ends up in failure. Even if you mess up.

I saw on Instagram the other day someone said something like, you know, nobody’s waiting for you to, I think you guys said this already but like nobody’s waiting for you to do this stuff, like nobody’s watching, like what Margo said.

Like nobody cares, just like do it! Because nobody cares. Nobody cares if you don’t do it. Nobody cares if you do. It’s really your thing. It has to be your thing, you know?  


And I think women really have a hard time claiming.  

Yeah, and I think we just gotta get comfortable with the reality that we are in many respects starting not from zero but from a negative.

Cause when we are looking to sell and when we are looking to be out there in a bigger way we have to reprogram our brains to understand the way we’ve been raised, the way we’ve been shaped by culture, the way we’ve been taught to anticipate what other people have been taught to see from us. It is a really tricky experience, which is why, especially in the women’s space, entrepreneurship is the best form of personal development there is.  


You learn what kind of stuff you’re made of. Without all, everything else bugging you down.  



Totally agree. I mean, I think like, so few people recognize but like, you know, I worked jobs for you know, from the time I got out of school until five years ago, so, I don’t know, more than 10 years.

And just kind of kept what I felt was that like if I could keep doing this, but I always feel like I kinda get stuck in the same thing and I didn’t really feel like I was gonna figure out, I was gonna really, ahh, you know go to the next level, or something, or blossom.

And I think that part of it was me, you know, and taking responsibility for the ways I was limiting myself, but part of it is like where someone like me, you know someone who’s like a communications type of woman, fits in a company.

So yeah. I do think that entrepreneurship is the best form of personal development in that sense.  

All right, so, you guys, this has been a wonderful conversation on how gender and acculturation affects how you show up in business. How you sell, what your confidence level is, the things, the baseline for which we need to show up and do the work, and how to overcome those things.

Anyway, Maggie, thank you for inviting us to have this conversation. And thank you for being on this bonus episode.

I am Margo Aaron.  

And I’m Hillary Weiss.  

And this is… It’s Maggie.  


Oh, Maggie Frank-Hsu. I’m Maggie Frank-Hsu. (all laughing)  

And this is HAMYAW and friends. HAMWAY-A-F. If you liked this episode, please like it below. Comment. Share it with your friends. And subscribe to our channel. We will see you again in two weeks. Thank you.  

Bye for now.

Photo by Juliet Clare Warren

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