Questioner: Hi Simone! Thank you so much for creating T and D and your huge generosity in helping people work through any blocks too. It’s so helpful witnessing other people’s coaching!
I’m a self-aware hider and have gotten the email challenges—my block is that they all sound really good and I say, “Yeah, I totally should do them; I’m going to!” and then somehow I just… don’t. The day slips by and I think, “Okay, maybe tomorrow,” but in a surprise to no one, tomorrow never comes.
I’m struggling with how I could overcome this and actually just do it. Thanks in advance for any insight you’re able to share!!
Simone: You’re procrastinating for one reason: you don’t want to feel bad. Taking action involves being willing to feel bad. Doing brave things feels a little bad. You want to feel good. Asking me for advice feels good. Reading the emails feels good. At least, not bad.
Actually doing the thing feels bad. Be willing to feel bad.
Questioner: Oof, yes, this really cuts to the heart of it so precisely. Thank you so much for responding, I really appreciate it.
Do you have any suggestions for how to overcome the unwillingness of feeling bad? Logically, I know that hiding is giving me a fleeting sense of safety (the plight of the self-aware hider, I suppose), but I still get stuck in the gap between knowing and doing.
Or am I continuing to hide by even asking that question? And there are no tips besides just doing the damn thing? *shrieks in terror*
Simone: The last two sentences? Yes.
Questioner: Roger that!! Thank you so much
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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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Questioner: I have a menacing canker in my mind this morning…. when speaking my truth, why do I get so damn confrontational sounding?!?! Is that a thing?
I love work that gets into the grit and grunt of life and made it a belief that no one else is ready to do this work so they won’t buy from me. When I aim to express why they need to start going deeper, I end up getting confrontational with these people. It feels like I’m in a battle and wondering if there is another way to be in your face raw without yielding a sword all the time?
Maybe other folks in your T&D course or orbit feel the same?
Simone: Can you tell me what exactly is wrong with confrontational and wielding a sword?
Questioner: I don’t want people who follow me or receive my emails to feel like I’m coming at them. I’d like to confront without my system feeling like it’s gotta battle. If that makes sense. For example, “some of you aren’t doing the work, and it shows.” Was part of my last email talking about the collective shadow work needed for these times.
Simone: Ok let’s work on this particular shadow! The thing is, the world needs confrontations and battles. The world needs rawness. These are not failures or flaws or weaknesses to be perfected. They are part of the human experience. Putting aside problem solving for a minute, getting philosophical with me for a second… can you think of the VALUE and VIRTUE of things like going into battle, wielding a sword, being raw? Why they belong?
Questioner: Yes, I can see where there would be viable need for it. They belong for preservation of life, to fight for something that you believe will create a better world for others to exist, in hopeful harmony.
Simone: That’s right. Can you connect to the parts of you that stand up for that and give them appreciation and love and honoring? Once you do that, look at what you want to say. It’ll come out different.
Questioner: This makes a lot of sense. I stepped away today from an email with this in mind and came back to it. I naturally put my classy hider hat back on, but I’m becoming more and more aware of my emotions in this process.
Endless gratitude for your magic in the world. Thank you!!!
Simone: Also – what if you WERE just abrasive and aggressive? So what? Isn’t that genuinely a part of who you are?
Questioner: Gahhhhh – it’s totally a part of me. I get spicy and passionate about certain topics… there’s some layers beneath it all that hold me back. And my phrase for 2025 is “fuck it” my plant ally Nasturtium… so it’s time for me to get fired up and share what’s coming through.
Simone: If someone doesn’t love you at your fieriest and spiciest, raw and throwing swords, they’re probably not the people who’d be the MOST delighted to pay you and be radically changed by your work.
Questioner: Truth!! I’m going to lean into this. Thank you!!
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Questioner: I sincerely ask, for myself and from myself, what even is the point of “putting it out there” if it’s just for me and I’m glad it exists? This is what I personally wrestle with.
It’s the “people want to hear your story” that perhaps doesn’t sit the way I would (or would I?) like it to, in me.
Why would we put in the time and effort and energy it takes to “put our thoughts out there” – IG / blogging / YT / a book or whatever – if it were just for ourselves?
That act in itself drains the life force out of me (that just came out, and is something I will sit with). The moment any focus is on “putting it out there”, my desire for it diminishes.
To do it for myself and for the pure joy of it, I love it, I do it, presently and in alive flow. No reason to do it other than the joy of doing it for the sake of life force moving through me and a complete surrender to that.
But the moment agenda is put to it by “hmmm, the world needs this, let me put it out there”… then it becomes something else. Something that feels forceful and out of alignment.
Not that I don’t believe I hold gifted beauty & genius ability to add wonder to this world that has never existed before, because I DO. But the “must put it out there, it’s needed” feels like it’s coming from a place and push and rush and… it’s hard to put into words.
IF I feel inspiration at a certain point to put something out there, that is different, and that flows good in me. But if it’s from a place of pushing myself to put it out there, it’s sticky.
Simone: This is… exactly what i’ve been doing and teaching forever. Whether others need it has nothing to do with me, and when that becomes a thing in my creative process, it no longer belongs to me.
The reason we put it out there is because, for some people — not all — it feels stifling and like a violation of our creative drive, almost, to just keep it to ourselves.
Creativity — again not for all but for many — demands to be expressed out loud, shared, to take up space in the world. if that feels like a “should” and not like liberation, that path is not for you. you should not be sharing
So even when you put it out there in the world for many to see, it’s ultimately not for them, either. It’s for liberating what your creative work wants to do in the world
Questioner: I see, and agree.
It’s evident to me how I’ve benefited from the public release of the creativity of others. How gorgeous, and how grateful I am.
Putting things “out there” has felt like a “should” more than it hasn’t, which explains my current resistance to putting anything out there. I can no longer exist in that force.
But there may also be a bit of “who really wants to see my work anyway, and what if nobody cares” (even though that doesn’t feel true in my body, could be other life / karmic), so I will sit in contemplation of this.
“It’s for liberating what your creative work wants to do in the world” – this moves me, because I begin to see my “creativity” as a being of its own, and feel a shift as I digest that.
Like: my creative work wants to do it’s “own thing / own work / own journey”, and I just ALLOW it through me by honoring it – more than anything.
Simone: YES YES YES! Now your work is to sift through which part of the reluctance to show up is honoring the true impulse of your creativity, and which part is smallness
Questioner: Thank you, beautiful Simone! I’ve always found the sand mandala process of Tibetan Monks to ring deeply true in the core of my being. It’s been the foundation of most of what I do.
To create for the pure present joy of it. Then to wipe it away with surrender and effortlessness.
They throw the rest of the sand into the nearest living stream to be swept into the ocean to bless the whole world.
Perhaps that is what the outward expression of our inner creativity is: sweeping our beautiful creations (ourselves in all facets and essence) “into the ocean”, to bless the whole world.
Dispersing of it in whichever way feels true.
Simone: That is so so beautiful!
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Questioner: I’m a classy hider according to the quiz. I’m truthful to the point that I know my folks hate me for a while but know it comes from a place of care and love but this doesn’t extend to the space outside of my community! Would being truthful as in the 20 truths challenge – help with this?
Simone: If you don’t behave the same way you do inside your community out there in your marketing, how would the people who love it find you?
Questioner: Exactly! That’s what that line got me thinking. I don’t know what’s stopping me
Simone: “I don’t say these things in my content, because i don’t want people to ____” Fill this out 5 times
Questioner: Okay. I don’t say these things in my content because I don’t want people
To think I’m rude
To feel I’m inconsiderate
To think that I don’t feel their struggles are real
To think that I don’t regard what they are going through
To hate me
The last one struck a nerve!
I’ve had people hate me for a while when I say things they need to know but don’t want to hear.. But then I’ve had the buffer of being their coach in a space they chose to be a part of. How do I be okay with not having the same situation if I do sound rude? That would alienate people.. So it’s like people hating me without knowing the intent. That feels not good ….
Simone: Your paying clients probably hate you for a while when you say things they need to hear… because you performed a version of yourself that doesn’t do that in your marketing, so it was a shock to them when they suddenly got that version of you.
You didn’t alienate enough people in your marketing. And you didn’t draw in enough people who love you BECAUSE you tell them what they need to hear… all because you didn’t TRUST your audience
Questioner: I see how I’ve been trying to be that ‘nice girl’ all through…
Simone: Put very bluntly, you’ve been lying (by omission) in your marketing to bait people into joining your program who then get mad at you because what they got wasn’t what they were promised.
Either stand by your approach and trust the right people to get your intention behind your marketing and appreciate it and want to hire you for it, OR change your approach if it’s not something you can stand behind.
Everything else is a complicated dance of deception that’ll leave you hiding and your clients getting mad at you..
Questioner: Yes, there’s a gap between who I am as a coach and teacher vs who I am as a person running this biz
Simone: When you close that gap you’ll make more money and have happier clients. Deciding to trust yourself and trust your people is a choice.
Questioner: How can I start.. Or where do I start?
Simone: Start saying what you would say if you trusted the right people to “get you”, and were ok with everyone else leaving.
Questioner: Thank you Simone. This was really needed. I joined TD not knowing why, but knowing I wanted to do it. But I’ll start the truths challenge even before. I can’t wait to close this gap!
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I played with A.I. a lot in the process of creating Truth or Dare. My first time doing this with a course.
I think it is enormously importantfor creators and teachers to practice radical transparency in the role of A.I. in their work. So here goes.
Because I am only beginning to discover A.I., a lot of this process is fresh ongoing learning for me. And I want to tell you exactly how I used A.I. to help me create Truth or Dare, and what I am learning in the process.
The first reason is that radical transparency around topics like this is everything to me. If one of my own teachers used A.I. to help create a course, and they hid this fact from me — intentionally or not — that would feel icky to me. My cardinal rule of marketing is, “do unto others as you would have them do unto you,” so I am giving you the honesty that I would want from my teachers.
The second reason is that I think having honest and nuanced discussions about the benefits and dangers of A.I. is the only way we can collectively find our way into responsible use.
A lot of this is a new exploration and ongoing learning for me, so there are no definitive expert answers here. Only a transparent sharing my process and my learning.
That is all we should ever be doing anyways.
So, here’s what I did, and am doing. I used ChatGPT and Claude (paid version), and treated them like an assistant who would help me organize my thoughts, generate ideas, and spit out drafts of what I wanted to create.
I’m pretty cocky about my own intellectual capacity and output. I think I have the best fucking ideas in the world.
So there was no way I was ever going to turn to A.I. for help generating ideas. And whatever ideas it did try to give me sucked. It was nice to confirm that even the best algorithm can’t think anything like I do.
However, where I did find A.I. very useful: helping my ADHD brain get started. For creative ADHD folks, I think sometimes the biggest barrier is that we have these incredible ideas in our heads… and the idea feels so big, the possibilities so infinite, that we kinda get paralyzed. (Raise your hand, ADHD posse….)
When I fed it my big, hairy, ambitious ideas, it spit back out to me simplified breakdowns, summaries, and drafts. This was truly amazing for no other reason than that it reminded my brain that the next step isn’t so complicated, and that I could do it.
Those breakdowns and summaries were rarely usable, but seeing them in front of my eyes closed the gap between the brilliant chaos of my mind and the next functional step. And ADHD folks know: the ability to take the next functional step is EVERYTHING. It is the difference between a finished project and procrastinating for 5 years and being depressed and ashamed.
This did not change my usual creative workflow, but it SHORTENED the time it takes for me get through it. This was, honestly, super fucking cool and something I will continue to experiment with.
Here’s another thing I found.
A.I. wants you to be more concise, have better “flow”, use what I think of as more “standard American” language, remove obscure references, substitute big words with simpler words, and edit your sense of humor to a more mainstream and less edgy one.
But that ain’t me. My natural style is that my thoughts jump from place to place, not always neat linear order. I write run-on sentences, use uncommon expressions and big words, curse a lot, and have a specific sense of humor that isn’t for everyone. (I love poop jokes and sex jokes, what can I say.)
If I allow AI to edit these “different” aspects out of my writing, it no longer sounds or feels like me. At all. And the transmission of the feelingof Simone… is the most important thing to me. Because without that feeling, there is no human-to-human connection. And without that human-to-human connection, there is…. nothing.
So, whatever A.I. wrote, I ended up having to do multiple extensive rounds of edits, adding back the “Simone-ness”, and rewriting sentences the way *I* would say it, and in the sequence and the style that I would say it… to the extent that, by the end, it looked nothing like the original A.I. output at all.
But still, in the end, even after hours and hours of editing and re-writing…. it STILL took me way less time than it normally does. Why?
Because… the “shitty first draft” helped to kick my ass into gear, and into writing mode. And normally I just spend a lot of time in frustrated paralysis.
Once again, I confirm: A.I. is most useful for helping my ADHD brain to get started.
Having a shitty draft in front of me makes me go: “This is wrong, that sounds stupid, ewww i would never do that… let’s get to work fixing this!”
Another pitfall of A.I. is that, since it is so good at spitting out templates and frameworks, it makes it tempting for creators and teachers to instantly produce templates and frameworks for their people.
I could see how easy it would be for people to pump these out ad infinitum, and to dangle these as “more value” for people… especially if they lack creative confidence.
And sometimes, it really can be. I love a good framework… in the right time and place.
But for my course to be an honest reflection of my intellectual ability, I had to ask myself: what is genuinely essential for my people’s transformation? What genuinely comes from my brain, my ethos, the Culture of Me?
What would I produce entirely on my own terms, without A.I.’s. help? And how would I do it?
Anything outside of that, it was clear to me, did not belong in my business. And it was good to come to clarity about this.
I will never, ever have an A.I.-generated template that I pass off as my own. If I point you to a template that did not directly come from my brain, I will tell you so explicitly.
And anyway, if A.I. is so good at creating templates and frameworks that genuinely help people…
… instead of creating them that way and passing them onto your people as if they are your own, you could just tell them which prompts to use to generate them themselves.
In summary:
(1) I’m enjoying using A.I. to help reduce my ADHD overwhelm, sort through the brilliant clutter of my mind, and make it easier for me to see and take the Next Functional Steps,
(2) This is verrrrry different from asking A.I. to do the thinking or the creating for you, and I think we should all be rigorous about not handing over our creative sovereignty to A.I. while still allowing it to help us where it’s effective, and
(3) You will always know exactly what part of my courses are ME, and what has been aided by A.I., and to exactly what extent. I think it is critical, and I think we should all our teachers and creators to the same standard.
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It takes a certain set of skills to get a total stranger to stop the scroll and click on your link.
You need to learn that skill.
It takes an entirely different set of skills to get someone to say, “I don’t care if you’re selling a course called ‘Meditations on the Contents of My Wednesday Trash’, I’m buying it, because I know whatever you have is fucking gold.”
You need to learn that skill, too.
You need to be able to command immediate attention AND you need substance and depth that nourish long-term relationships.
Don’t let anyone talk you into giving up one for the other.
Here is what to know to not get scammed by business programs.
Or probably just generally a lot of bad life advice.
(1) If it sounds easy, it’s probably worthless.
Sales, marketing and copywriting are SKILLS. If you don’t respect them as skills, you deserve everything you get.
A lot of predatory, scammy business programs thrive on pretending that business isn’t overwhelmingly a game of skills.
Upgrade your branding using our templates!
Steal this proven strategy!
Follow this simple formula!
Use this customizable script!
Assume that, if it sounds like any idiot could do it and benefit from it, it probably is targeted to idiots.
And idiots don’t win at business.
(2) There are things that save time. But there are no real shortcuts.
You don’t need to invent calculus from scratch. It has already been invented, so all you need to do is go take a class on it. But, to pass the class, you’re going to need to do a lot of hard math problems where you get a lot of it wrong and study your mistakes.
apparently these gentlemen are competing for the position of “inventor of Calculus”
Likewise; you do not need to figure out the principles of copywriting from scratch. Not only have they already been figured out, you can actually just google them all online and learn for free.
However, to truly learn the skill of copywriting to the point where you can embody it comfortably in a way that feels like you as opposed to robotically following a theory or formula, use them flexibly, and create predictable results… you’re going to have to put in the work.
Uncomfortable work that requires experimentation, failure, and iteration.
And it will take you time.
Same is true of any skill.
And see what I said above about business. Business is overwhelmingly a game of skill, and if you don’t believe me, well, good luck. Can I also sell you a bridge?
A lot of people confuse “learning that saves time” with “magical shortcut.”
Often because learning is fraudulently advertised as magical shortcut. (If that is not explicitly said, it is implied.)
There are no magical shortcuts. There are no exceptions.
(3) Beware promises of simplicity and certainty.
In fact, the harder they push on the promises of simplicity and certainty, the more skeptical you should be. Because this probably means they probably don’t have much else to stand on.
Nothing is as seductive to the undiscerning customer as being told, “All you have to do is follow the exact steps I took to replicate the results I got.” Because this delivers two things that the primal brain desperately crave: simplicity and certainty.
Which leads us to why so many people feel bamboozled once they’ve bought business solutions. Because once you get into the weeds of things — of anything in life — nothing is actually simple, and nothing is certain.
It leaves you unprepared for the nuanced, multilayered work it takes to actually move your projects forward.
I’m not saying things can’t be simple. Actually, some of the best solutions are. I try to simplify my own frameworks and teachings as much as I can.
And I’m not saying that there aren’t things that don’t genuinely + significantly boost your odds of success. I don’t sell anything where I don’t have deep certainty that it is some of the best value that money can buy in the market.
But, in learning about a new program or product, watch how they address nuances.
The less nuance you can find, the less substance there will be.
I find that, in the typical business program, there is almost none of either.
Just endless echoes of regurgitated bro marketing.
(3) Stop seeking high reward with low input.
I see ad copy like this that makes me laugh and cry at the same time: “Even if you’re a total nobody with no special skills, no knowledge and no network, you could be quitting your job and earning six figures with content creation in 3 months.”
Oh really.
You do not have something that is highly valuable to others, and you want others to value you highly?
You are not willing to put in the work to develop a statistically exceptional skill set, but you want statistically exceptional pay?
In Korea, we call this a “thief’s mindset.” A thief feels entitled to something that they did not earn.
And when you have a thief’s mindset (seeking ‘get rich quick’ schemes, wanting big rewards with little effort, in other words), you are the easiest target for a fraudulent online business coach.
Do not be easily seduced to claim rewards that clearly don’t make sense in terms of how real world economics works.
Getting rich is not ever quick. (Believe me, the truly rich people of the world keep it that way.)
Getting 1% results does not ever come without top 1 percentile input (of some combination of talent, work ethic, privilege, luck, etc.)
Of course, there are exceptions. And they are as unlikely as winning the lottery.
And fraudsters get rich every single day, flattering people into thinking, “today is your lucky day. After all, don’t you deserve it?”
