“I don’t want to sell too much, I want to be cool!”

Mar 7, 2025 | 44 comments

Questioner: I KNOW this course is going to be excellent and deliver tremendous value. And there’s this huge fear of coming off as too salesy or pushy in sharing it with my audience.

I want them to think I’m COOL. That I don’t NEED them to join. But I also know that they FUCKING NEED TO JOIN.

And I don’t want to “insult” them by being like, “Listen, your skills in this area are just not up to par, and if you get them up to par: 1) it’s going to be fun, 2) it’s not going to be that hard, and 3) most importantly, it’s going to make your offerings TEN TIMES BETTER and you are going to feel like you slayed a dragon.”

Lol. Ok, that’s pretty good—maybe I should use it.

But I think the key thing here is the fear of “insulting” them or calling them out.

Simone: Why would they join if their skills ARE up to par?

Questioner: Haha, correct. They wouldn’t.

It feels like I’m playing out some high school dynamic of worrying that they’re going to think I think I’m better than them and therefore not like me—especially since I’m selling in part to folks who I know personally / are colleagues.

Guess it’s an opportunity to blast through thaaaat.

Simone: Oooh, so this is about THIS belief… to be liked, I have to be small.

Questioner: 1000%.

Simone: (I fucking love marketing. It makes you work through allll your favorite shadows.)

If someone only likes you when you’re small, are they worth keeping around?

Questioner: UGH. Dammit. Not at all.

Simone: Are you worth being surrounded by people who love you in your bigness?

Questioner: Totally. And it’s one of the things folks love / reflect / are served and inspired by.

Simone: You sure?

Questioner: …Mkay.

Simone: Sounds like it’s time to allow people to either love you (and pay you) in your bigness, or fuck off…

Claim your ticket to the one-and-only live round of Truth or Dare.

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This is part of a Q&A series regarding the Mini Truth or Dare Challenge. Read the rest:

What if I don’t know what my offer is?​

​Can you be fierce without alienating people?​

​How do I get vulnerable without getting unsolicited coaching?​

​Why is my honesty getting crickets?​

​How do I get started writing when in limbo?​

​Is creative expression a “must”?​

​“I’m okay with my clients hating me for a while, but not my audience!”​

​“I don’t want to sell too much, I want to be cool!”​

​Unfiltered truth vs. “pain point marketing”​

​I’ve been silent. Help, give me a dare!​

​I’m being vulnerable… so why am I invisible?​

​Why can’t I just do the damn thing?​

​Why would my target market listen if I’ve failed?

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