Getting Comfortable with Shameless Self-Promotion

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Talking about your business can be uncomfortable, but it's incredibly important to build awareness around what you love to do. In today's episode, positioning coach and creative director Hillary Weiss Presswood breaks down how to conquer resistance to selling and put yourself out there.

Hillary helps best-kept secret creatives find their most powerful position in the market - and use that to dominate their corner of the internet.

Website // Instagram // Twitter // Statement Piece Framework

The episode:

Katrina Widener: Hi everyone, and welcome back to the Badass Business Squad podcast. I am your host Katrina Widener and today I'm here with Hillary Weiss Presswood, which I'm so excited to have her on today. I wish you guys could see us right now.

Hillary Weiss Presswood: We are having a really good time.

Katrina Widener: We just like waxed poetic about all the randomness of life for like the last 15 minutes.

Hillary Weiss Presswood: We're talking about Prince! It's so exciting to be here. Thank you so much Katrina for having me. I'm so stoked, I can't wait to dive in today.

Katrina Widener: Yeah, thank you so much for coming! I'm excited to have you here! I'm trying to remember, I found your Instagram through one of our previous guest experts, Hunter.

Hillary Weiss Presswood: Oh, awesome!

Katrina Widener: She had posted something about yours. I had gone and followed and then have followed you for a while. And I was like, "You should come on the podcast and we should just hang out virtually."

Hillary Weiss Presswood: What a dream. Yeah hunter was actually my CMO for a couple years, so yeah. How delightful to hear she was on here too, yeah! I'm in good company, naturally. Amazing.

Katrina Widener: I also am really excited about the topic that we're gonna be focusing on, which is shameless self-promotion because I think there are a lot of people who are listening right now who maybe get a little uncomfortable doing self-promotion. But are really, as we were talking about before we started recording, moving into that heavily sales focused aspect of running a business, as opposed to just relying on referrals. And so I think that this is gonna be an amazing conversation for anyone who is listening.

So before we dive in, would you mind introducing yourself to everyone listening and just telling them who you are and what you do?

Hillary Weiss Presswood: Absolutely. So I'm Hillary Weiss Presswood, and I am a positioning coach and creative director. And positioning coach, I often get some looks about what that is cuz everyone understands creative direction, but what is a positioning coach? And the big bulk of work that I do is I work with small business owners, largely in the creative coaching consulting spheres, who are ready to do exactly what we're talking about today. Who kind of have built these businesses that are working through word of mouth, through referral. But what they want is to kind of create this next level brand, and to sort of become a thought leader even if they hate the word thought leader. Become a personal brand step out from behind sort of the avalanche of client work and actually start reimagining their business from the inside out.

So a lot of my clients move into strategy work, they move into higher ticket offers. They kind of create a really unique position for themselves in the market and it's really, really fun work. There are a few tiers of that sort of experience, but I like to call it reimagining the spinal cord of the business, basically.

Katrina Widener: Yeah!

Hillary Weiss Presswood: So what's the big idea? What's the specialty? Where do you wanna really focus your energy? What's the signature process we can build into everything? What's the messaging? What's the offer suite? How does it all link together? So that's a big part of what I do. And it's really, really fun because this is such a common experience I think, for creatives to kind of look around and realize that they want more for the business. They have more ideas to share. They have expertise. They're seeing people who don't know half of what they know skyrocketing in visibility, just because they're showing up and talking about this stuff. So there's a lot of deep dive work that we do.

It's such a joy, but it really is moving from that space of referral only business to sort of coming out and saying, "Here's who I am. Here's what I specialize in. Here's what I sell. Come buy my stuff." Which can be very intimidating for a lot of people. Especially if you have been referral based for a really long time, it can feel kind of anxiety inducing to suddenly have to put yourself out there. Cause people need to learn about what it's that you're doing. They need to learn about your specialty, especially if it's something extremely specific.

So I've been doing that for the last couple years. Prior to that, I was a copywriter in the industry for 10 years. So I know this transition very well. I'm really excited to dive into it today.

Katrina Widener: Yes, I love this so much. I also think this is so timely, cuz I've been talking a lot about trading time and energy for money.

Hillary Weiss Presswood: Yeah.

Katrina Widener: And getting out of that sphere of entrepreneurship and really moving into the place where like your business is working for you, your systems are working for you, your messaging is working for you. Essentially being like, "Let's reconfigure how we look at all of this and reposition."

Hillary Weiss Presswood: Yeah.

Katrina Widener: So it makes so much sense, and I think this is gonna be so helpful for people. Also, we're talking about shameless self-promotion, right?

Hillary Weiss Presswood: Yes!

Katrina Widener: People I know, get so uncomfortable with this. But it's like "No one's gonna buy your shit unless you're telling them that they can buy it."

Hillary Weiss Presswood: Yeah that rocks people's world when you remind 'em of that. Otherwise they have no idea. And there's also this myth of discovery, which we also see in the general creative world. Where it's like, "Are you actually legit if you had to go and like pitch yourself to somebody? Shouldn't you just get discovered in a mall as the new face of Givenchy? If your offers are any good shouldn't they just sell themselves?" like no, that's literally not how it works. That can be counterintuitive cuz we're speaking to people who are referral based right now.

But it's like if you wanna do things at a higher level? Because often I find referral based businesses are the sort of direct execution. So design, branding, copywriting, even coaching to a degree. I think when you wanna move into like a higher tier specialty, charge more. That referral network has to change because you're not serving that same client.

So I talk about shamelessness cuz people have a lot of resistance to selling, especially all the ladies and lady identifying people who are listening to this podcast. Because we're not socialized to ask for things, you know? We're socialized to just do and be caretakers and nurture, and the idea of putting ourself in front of somebody? Having that "Hire me," conversation. Having that "Pitch me," conversation, you just feel really awkward. But actually, you know, once you get into the swing of things, I find selling to be one of the most joyful parts of my business.

Katrina Widener: Ooh, I love that.

Hillary Weiss Presswood: You can really change your attitude towards it with time. But that's why we call it shameless self-promotion because, what do you run a business for if not to sell what you do?

Katrina Widener: Right!

Hillary Weiss Presswood: You know? Get shameless about it! It's way more fun, I'll tell you that.

Katrina Widener: It's also, it just feels so counterintuitive sometimes because I'm like, we all started our business because we wanna do the thing that we're selling. But then by not selling it we're actually spending way more time in the marketing world than we are actually executing the offer or whatever it is that we're trying to provide with people.

I know for myself as a coach, my mastermind is by far favorite part of my business. I love doing it. It's so fun, and so much gets done. I see so much progress get made. But if I'm not selling it, then I'm spending so much more time sitting in like the building it and in the like, marketing it.

Hillary Weiss Presswood: Yep!

Katrina Widener: But not in the doing of it cuz there aren't people in it?

Hillary Weiss Presswood: Yeah. Isn't that funny how that works?

Katrina Widener: Yeah.

Hillary Weiss Presswood: There's again this belief almost. If you have to sell hard, if you have to do a full launch, there's this weird counterintuitive self doubt that comes up that it's like, "Well people don't want it if I have to send multiple emails and make multiple posts." And I'm like, "Listen let me tell you something friend. One time I had a pair of shoes that I loved follow me in a Facebook ad for like a year." Every time I saw it I was like, "I gotta buy those shoes. I absolutely love those shoes." I wasn't like, "This brand is desperate, serving me this ad." But I just had to be reminded over and over and over. And that's another part of selling. It's yes, about making money and getting in front of people with what you do, but also it's building brand awareness around what you do. So people know when you're launching next. They know to refer people to you, all that good stuff. Why wouldn't you really, you know what I'm saying?

Katrina Widener: Oh, 100%. I'm just over here like, "Yes. Yes." We make up these stories around selling for ourselves, especially if it's not something we've been taught beforehand. And I look at a lot of entrepreneurs, especially creative entrepreneurs who started out being like, "Well I know how to do graphic design, so now I'm gonna be a designer. I've never been trained, I'm not well versed. I don't feel confident in this other part of entrepreneurship," which is the selling. The being sold on your own worth and being like, "I deserve to have this come to me also."

Hillary Weiss Presswood: Yeah.

Katrina Widener: And standing in that, I feel like is such a jumping off point when it comes to selling too. Like you have to really believe in the thing that you're selling.

Hillary Weiss Presswood: Yes.

Katrina Widener: And then it feels more like I'm just telling you about this really awesome thing that I love doing and less of like, "Please come buy from me, I need money."

Hillary Weiss Presswood: "I'm so sad." Yeah and that's also a big part of what I do in my positioning work. Because it's really about getting you connected to like, what is the specialty? What is the big idea? What are the offer suites? So you can fall in love with it! I find a lot of people who struggle to sell, and I'm sure you see this a lot in your work too, is that they struggle to sell because they're not clear. They're not clear on who the audience is. They're not totally confident in the outcomes or guarantees they can promise. They don't know how to explain their process. So selling just becomes like, "Money please," and it's a lot less fun when you're just like, "Hello I write copy. Want some?"

You know when you add detail to your pitch, when you develop your positioning, when you understand who you're talking to, what you're specializing in and how it benefits people? To your point, like it's become so much more fun to talk about cause you can just riff! With a little practice, of course. But you can get into the swing of things and really learn how to talk about this from other angles.

And this is also what I see, and maybe you've seen this in your work, I don't understand why this happens. I think it might be story brand's fault, but I have no confirmation for this. But people will sort of try to think about the story of their brand before they actually know what they're selling. They're like, "I need to be able to tell stories. How do I tell the strategic story?" and there's that big selling by serving kind of myth that was going around you know six years ago. Where it was like, "Well if you just serve people and just give them as much free content and tell great stories, you'll never have to sell! People will just buy even if they dunno what you sell, they'll just buy"

So there's a lot of deep patterning there, but I think especially as creatives, our instincts are to head to the creative place, which is the story, which is the visual brand. Which are all great things and all things that I help with in my work. But it's very much resistance to I think what feels like more technical, and more like nitty gritty business. The actual selling. People will market their faces off, you know? They will tell stories. They will create high value content, all of that. But when it comes to the actual selling, they pull the punch and they're like, "But I created all this content what's happening?" it's like, "You never explicitly told anybody to buy from you!" What's up with that! You know?

Katrina Widener: Right! I think oftentimes there's a story that people have in mind of like, there has to be some sort of really extensive sales funnel in place.

Hillary Weiss Presswood: Yeah.

Katrina Widener: Really like informative. "I have all of these emails set up and here's this lead magnet funnels them into this and then you get this and then it'll just sell!" And sure that does work and can work, but that's not the only way to sell and getting comfortable with selling has to come before you do the sales funnel work. I feel like there's this narrative in entrepreneurship...

Hillary Weiss Presswood: yes!

Katrina Widener: that there has to be this sales funnel. There's always a time and a place for some things, but we need to know that that time and that place is the right thing for us. And there has to be a strategic choice as opposed to "Here's more work I can hide behind, so I'm not selling."

Hillary Weiss Presswood: Yes. It's a sexy form of procrastination is what it is.

Katrina Widener: Yes!

Hillary Weiss Presswood: And it's also that I find a lot of folks in this category are very much perfectionist. They wanna do it well, they wanna do it the best. They take a lot of pride in their skills and their knowledge and being able to execute. And they also see their heroes in the industry selling this way. Creating the evergreen funnels, doing the tiny products, like whatever it looks like. And I remember that was a big wake up call for me because I went through this experience myself. I was in copywriting for a decade and I marketed myself, like I wrote. But I never really had to sell myself because people knew I was a copywriter. It was obvious what I did, and then they came to my website and they were like, "Here's my thing. Can you help me?" and I was like, "Yeah sure!" And I was like, "This is working so well, I'm such a good marketer!"

But the interesting thing about the switch was again, learning to talk about it explicitly and also learning that the sales process doesn't have to be a million miles long. I'm actually doing this right now, like I have a couple new offers in my suite. One's a 90 minute session and one's a VIP day. I've literally been selling it out of a Google doc, and this month alone I think we've done 20k in the last week? Just being like, "Hey here's the offer. Here's the sessions. You want it? I'll pass you on my team." People were like, "Yeah!" It's literally a Google doc with a loom video attached! I like sent an email to my list, "There's a new way to work with me. You want the details before it goes public!" People who put their hands up, I was like, "Hell yeah. Here's the Google doc. Let me give you a little walkthrough," and that was it! And I think that that's one of the first things I think we should be taught about sales, but we're not. I think that's a big reason why people get so afraid about sales and self promotion. It's like, "Oh no I have to have a whole team behind it. There need to be a million emails," and it doesn't necessarily need to be that way.

Also, and I think this is something that you teach as well, so much selling goes on in the DMs now!

Katrina Widener: Yeah.

Hillary Weiss Presswood: Like it doesn't have to be this big production. It can be a matter of getting someone in your direct messages and sending them a link to your calendar.

Katrina Widener: Right. Right!

Hillary Weiss Presswood: I have a couple friends of mine, and they will remain nameless cause I love them dearly. But they're always just on the cusp of releasing the next big funnel. They're always just on the cusp of doing the eight part series that they wanted to do on XYZ thing that hasn't happened yet because things get busy. They get distracted, client work picks up. So it's been hurry up and wait for a number of years now!

I think really thinking about how you can get clear and what you're selling in a way that gets you excited and how you can make your sales process simple. Again let's say it's a matter of offer, to DM, to calendar link. That makes the whole process of shameless self promotion so much easier and so much more fun. And I don't think people give them enough space to play with that, you know? Because they don't give themselves enough space!

Katrina Widener: I think it's interesting too. Like the last year and a half, I was offering these intensives.

Hillary Weiss Presswood: Yeah.

Katrina Widener: It's like three hours one on one with me, we'll do something really quick, work through your problem, move forward. Didn't have a sales page. It took me a while before I even had a calendar link set up officially. And it all started just cause someone was like, "Hey, can I do this with you? I'd really like to sit down and knock out this one project and then talk about long term stuff." and I was like, "Yeah sure. Sounds good." And those were so easy to sell because there was none of this like hoopla. Honestly also as someone who personally hates emails? I love sending emails. I love writing emails. I don't mind being the person creating the emails, but to receive emails? If you are a friend of mine and I have ever been on your newsletter and I unsubscribed it is not personal. Its a inbox boundary thing for me and I am a notification hound. I've almost zero notifications on any apps on my phone.

Hillary Weiss Presswood: Same.

Katrina Widener: It's just to simplify it. I think oftentimes we make it harder on ourselves almost as a self sabotage essentially, because then it's like, "Well I know how to to do this thing, but that thing over there feels like really nebulous and abstract, and I dunno how it actually operates or how to actually sell myself. So I'm not gonna go over there. I'm just gonna stay over here in my lane where I can create emails and feel good."

Hillary Weiss Presswood: Yeah. And there's also the issue I think of direct sales as well, and this idea of shameless self promotion too, is it is an incredibly vulnerable space to be in.

Katrina Widener: Mm-hmm.

Hillary Weiss Presswood: And it takes a lot of sort of mental work I think, to build up to showing up consistently in that way. Because sales yes, it's money and excitement and fun and conversations and vibes. But it's also rejection. It's also getting ghosted, you know? It's also having someone tell you "I'm not a fit for this, or I'm working with a competitor," and you have to learn to stomach that.

That is such an important skill in business to let it roll off you. You always hear this in mob movies where it's like, "It's just business. It's nothing personal." And it's like, "Yeah it feels personal, especially when you're the face of the company and the product. But I think it has so many benefits." So for those listening, if you're considering moving from a referral based business into a different specialty altogether, like I did. Or if you're looking to do higher level strategy work or higher packages that aren't a fit for your current market, you're gonna need to learn to sell. You're gonna need to learn to put yourself out there.

When I do this with my clients, often in Power Position which is the positioning work that I do, we have people do the Google doc offer and put it out to their email list or Instagram, even if it's a small community. And more often than not especially if they've been serving up content, people know what they do, and people follow them for that reason already even if their audience is tiny. There are usually buyers in that mix, you know? And they're always like, "Oh my God, they've been there this whole time!" And it's like, "Yes! Because you have to explicitly tell people." It's so important to remind yourself that's what all this is for. I mean, not all of it. But that's why you market. To create that list of primed people who know what you do, who respect you. And then you have to actually carry it over the line by making the sale.

And the reason why we talk about it as shameless self-promotion is like, why should you be embarrassed for making your business do what it does? Like you think McDonald's is embarrassed about the fact that it literally pumps out the smell of cheeseburgers into the world? No! McDonald doesn't care, you know? And I think the big fear is that again, that vulnerability, that fear of judgment. But more often than not the people you're worried who are gonna judge you are like friends and family?

Katrina Widener: Right! Right!

Hillary Weiss Presswood: "What if they see me and think I'm weird!" It's like, "Are they paying your bills?"

Katrina Widener: Yeah, no. Yeah.

Hillary Weiss Presswood: Okay. Problem solved. You're welcome. Block 'em I don't care. Nobody likes to be in that vulnerability. There's so much perfectionism. There's so much self-judgment. There's this myth of discovery and all these things coming into play. But the reality is if you don't have sales, you don't have a business. So why not get comfortable with it and why not make it fun? You know?

Katrina Widener: Right! There's so many things you just talked about that I wanna touch on. Number one, yes. That idea of getting comfortable with rejection? I always talk about it as like, there's 50% on me and 50% on the other person when it comes to making the decision to work together. I'm deciding whether or not you're aligned with me. I have just as much autonomy to choose whether or not a client is the best fit for me, as if I'm the best fit for them. When I'm hiring someone, if I decide to go with option A as opposed to option B, it's not because I think option B is like an annoying, desperate person who I absolutely hate and I'm like "Ugh I'd never work with you," It's just because option A is more aligned with me.

Hillary Weiss Presswood: Amen. Yeah again, it can feel so personal. Like you as a human and your value are being rejected when you're passed over for a project.

Katrina Widener: Yes.

Hillary Weiss Presswood: But in reality, and I'm so glad that you raised that point about thinking about when you're hiring people, cuz nothing taught me more about how in personal all this is than hiring my own team and hiring so many contractors over the years to do this work. Cause there's so many talented people out there. It doesn't even have to come down to skillset, you know? Cause two people can have identical skills, but like a different cadence of working. A different attitude that's more a fit for the company culture. Like there are a million little things and if you get rejected it's not cuz you're not good enough. It's just because the opportunity isn't a right fit for you.

It kind of reminds me of like college admissions? "I had all the requirements for this university and they said no!" It's like well you probably wouldn't have a good time on campus, and ideally where you go, you will. The people who say no to them create more space for the right people to come in, you know? If you're not a fit for a project and you get turned down for it, that's a great thing. It creates more space for you to actually find that perfect project. So you can have some fun and enjoy what it is that you're doing.

Katrina Widener: Yes! Yes 100% agree with everything you've said. Okay. So of course we're reaching the end of the episode. So I want to say for anyone who's been listening and is like, "Okay I'm on board. All of this sounds great. You've got me convinced. You're giving me like the why, but what is the how?" What would you respond for that?

Hillary Weiss Presswood: So I would challenge your listeners to consider just to give this a test run. To go on the social media platform where they have the most engagement and talk about one of your offers for three days. I'll give you some prompts.

So let's talk about a common objection about what it is that you offer and how you can turn that around on its head. Think about for example, I wouldn't pay for a copywriter because I can write words myself. I have the best words. What would you say to that person? Then with a prompt to DM you, because you have space in your schedule.

The second prompt, tell a story of a client who had great success working with you. Give 'em a little social proof. Tell that tale. Talk to them not just about what they achieved in terms of, you know, revenue, emotional stability, business growth or whatever it is. But also talk about how they got there. Where they were when they started, where they're going now.

Then the third prompt, I would say talk about the offer overall. What makes it really awesome? What are you so delighted about when it comes to your offer that you can't wait to tell people about? What excites you most about it? Where do you really nerd out? Talk about that. Talk a little bit about how the offer works, then get into the nerdy stuff. Give it a shot and see what happens.

Katrina Widener: Yes, thank you so much. I think that the actionable prompts are gonna be so helpful for people, but also just all of the information beforehand to help people get comfortable and shift that mindset a little bit of like, "How can I view marketing? How can I view selling myself as opposed to how have I been doing it in the past?"

Hillary Weiss Presswood: Yes. Exactly right.

Katrina Widener: This has all been absolutely amazing, thank you so much. Before we hop off, will you let everyone know where they can find you?

Hillary Weiss Presswood: Absolutely. And I at the end of every podcast interview I announce this is where I do my radio voice. So ahem... You can find me on Instagram at @hcweiss that's at H-C-W-E-I-S-S. And you can also visit my website at www.hillaryweiss.com.

And if everyone's like, "Why do you have two last names?" Weiss is my maiden name and Presswood is my married name, and I haven't figured out how to fully transition Hillary Presswood. So come say, hi. I love meeting new people if you enjoyed this episode, if you hated it also, okay. Come say hi too. But I would love to hear about something that you learned, if you wanna tell me if you had one big takeaway from the session or, let me know when you are creating those little shameless self-promotion posts that we just mentioned. I'd love to check 'em out and give you some feedback! So Instagram's usually the best place to find me, but I am everywhere. So come say, hi.

Katrina Widener: Well thank you so much for coming on. I really appreciate it.

Hillary Weiss Presswood: It was so much fun, thank you for having me. I hope to get to come back soon!