The 8-week program for chronic yes-people
Practice saying no— before you have to.
Pleaseless gives you an AI coach to roleplay the conversations you've been avoiding. 8-week program. Personalized scripts. Built for people pleasers.
$79 one-time · 1 hour of AI coaching included · Upgrade to AI Coach Pro anytime ($19/mo, cancel anytime).
You've read the books. You still say yes.We do something different.
Personalized AI scripts
Tell the coach the situation. It writes you three script variations — gentle, direct, firm — based on your people-pleaser type.
Roleplay mode
Practice the conversation before you have it. The AI plays your mother, boss, partner — pushes back the way they will.
8 weeks. 5 minutes a day.
No live calls, no scheduled sessions. Daily lessons matched to your type, unlocked one at a time.
What it looks like
Type the situation. Get the words.
You: My sister keeps showing up unannounced and staying for hours. I love her but I'm exhausted.
“I'd love to see you — can we set up Sundays as our regular hangout? Drop-ins are tough with my schedule.”
“I need to ask you to text before coming over. I can't host unannounced anymore.”
“I'm not available for unannounced visits. Sunday at 2pm works — let's plan it.”
Two ways in.
Buy the program once. Add the AI coach when you need it. Drop it when you don't.
8-Week Program
- 8-week guided program (56 daily lessons)
- Quiz-based personalization (6 types)
- Boundary-script library
- 1 hour of AI coaching included
- Workbook PDFs
AI Coach Pro
- Unlimited boundary-script generation
- Unlimited roleplay sessions
- Daily AI reflection prompts
- Pattern detector across conversations
- Add to your program anytime
You don't need permission.You need a script.
Take the 2-minute quiz. Find your type. Start practicing.
Take the quiz