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

Mar 7, 2025 | 591 comments

Questioner: Hi Simone, I’m taking your Truth or Dare for sure. I’m dying of boredom in the sameness of marketing.

I have been a “coach” for 15 years, but even I hate to admit it. Everything about the coaching world makes my skin crawl. Telling people that they’re all perfect and have everything figured out is a lie.

I have a background in the art world for 20 years. It was a place where I had to face my money trauma—triggered by it every day. The topic of money is a big, vulnerable one in my life, so I want to talk about it.

I talked about how, in my culture, so many feel stuck and crippled by their families—mostly because their families threaten to leave them nothing after they pass away.

I was the black sheep in my family, and even though that sounds normal in the West, it took me years of courage not to conform to society and not take a cent from my family.

That’s how I broke out of the norm and freed myself. I no longer feel that my family has any say over me or my work. And I’m 39 already!!

I feel like I’ve been open about some discomforts in my life in my marketing—including my mom’s mental illness, which plays a huge role in my life—but still, crickets.

And I don’t want to tell people how much I’ve made to get eyeballs, either. In fact, I’ve lost a lot of money — which I also didn’t want to admit — but I’m happy to tell. I just don’t know if people would still want to listen to me if I tell them how much I’ve failed.

Simone: 1. Who do you WANT to talk to? 2. Why do you want to talk to them?

Questioner: 1. I want to talk to the person I used to be — a “good Asian girl” who people-pleased because that’s how she derived her sense of worth, shaped by societal, cultural, and familial pressures. 2. My biggest resentment from my upbringing comes from being told what to do (dimming my light) when I knew I had so much more to shine.

Part of that was that, as a “good” Asian girl, I was expected to behave in certain ways—never swear, always be filial and well-mannered, and eventually find a “good” husband to marry. Preferably wealthy and educated.

I just want to say fuck that, I was born a rebel.

Simone: Is that “Good Asian Girl” you used to be not gonna listen to you if you tell her how much you failed? What does she need from you?

Questioner: She needs to see my courage. My path to fighting against it. She wants to know she’s not alone. That she’s understood.

I don’t even know if my fear is failing?! I think my fear is in not having my shit together. I’m not “coherent” enough. I don’t have an elevator pitch. And I’m not sure what I can actually offer to get people to pay me for my messiness.

My process has been messy af. But somehow, I made it here in my life, and I know I have the courage to be vulnerable. I’m just confused… Gahahahhahaa.

Simone: Would the “Good Asian Girl” you used to be judge you for not having your shit together? Would she want you to be “coherent enough”?

What I’m asking is—whose perception are you worried about when you have these fears? Is it her, or is it someone else? Are you writing for her in all of this? Or are you trying to do something else?

Questioner: Yeah no. She probably wants to see all this mess and know it’s okay to show that—even though I’m messy af—hey, I’m living a good life now.

But this brings up another deep fear of mine: showing others how privileged I am.

Even though my family is now in huge debt, when I was young, my family was what many would call wealthy. I went to private schools and had many material privileges.

I live in Asia and have childcare, and yet I’m still so tired from taking care of my kids—which I’m so afraid to admit.

Simone: Again—who? Who is “others”?

Look, here’s your only confusion: Who you really care about is speaking to who you used to be—that girl. You know why you want to speak to her. You know why it’s important.

And the minute you try to talk to her, all these other people come into the room, and you start looking at them instead of at that girl.

Questioner: Someone else, for sure. I’m afraid I won’t just be speaking to her, so I’ll have to be more “inclusive.”

For example, I’m afraid to say I serve Asian women—even though that’s really who I am.

I know many people outside of this niche wouldn’t agree with what I’m saying, and I find myself feeling frustrated having to defend myself to people who don’t get it. I also get attacked for what I say.

Now that you’re making me see that I’ve been trying to be as diplomatic as I can on the internet… I’m afraid to speak to just my old self.

Simone: Okay. So here’s your only problem.

You actually have a ton of clarity about exactly what you want to do and why it matters.

You’re just trying to be everything for everyone else at the same time—all of these other people who have NOTHING to do with your business.

You have a binary choice.

Do the business and show up for YOUR purpose, for YOUR person, for YOUR reasons.
Or try to make everyone else happy.

There is no in-between.

Questioner: Yeah, and making everyone else happy is impossible, so it’s not the path for me.

Simone: Exactly!

Questioner: Okay, I’ll keep speaking to my old self, then.

BTW, is it normal to sound like a crazy person talking to myself?

Because that’s really how I feel… when I’m writing newsletters and content for Threads. I just feel like I’m talking to myself and creating content for myself, and it feels like I’m in a bit of a bubble. Maybe that’s because I haven’t built my community yet.

Simone: I want you to write this out clearly—with pen and paper:

Who is my work for?
Why does this matter?
What do they need from me?

And you need to develop the discipline to tune out absolutely everyone else. Because they LITERALLY have NOTHING to do with your business.

Also… Is it bad to be a crazy person?

Questioner: Oh no, I quite enjoy being one!! I’m an oddball, and I love that for myself.

Simone: There you go. And who’s your business for?

Questioner: Okay, I’ll write this out right now.

I’ve done this exercise many times, but somehow, I fantasized about my target market too much—whereas I think I should just speak to my old self.

That’s the most comfortable and “authentic” I can be.

I’ve always envisioned my people to be ambitious, well-traveled, well-educated Asian women who are independent and whatever. But really, I should just be speaking to my old self—who was ALL OF THAT on the surface, but deep down, she wanted to be a DJ, loved electronic music, knew she was a rebel, wanted to be unique, and just wanted the freedom to be ME.

And THAT is who I’m speaking to.

Simone: This is NOT a “target market” exercise. You are never talking to a “type of person.”

People are complex humans. They are not demographics. Seriously, fuck that kind of thinking. Scrub it out of your brain.

Talk to your weird, crazy, rebel old self.

Because her liberation is your liberation.

Questioner: Omg, thank GOD for this…

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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!”