Build Your AI Life Coach

Configure a Claude Project as a persistent AI life coach with goal tracking.

Introduction

30 Second Summary

Everyone wants to improve themselves, but personal growth often stalls without someone to hold you accountable. A great coach asks hard questions, tracks your progress, and refuses to let you slide on your commitments.

In this project, you will build a fully configured Claude Project that acts as your personal AI life coach. You'll design a coaching system prompt, create structured knowledge files across five life domains, and run your first guided coaching sessions.

What You'll Build

A Claude Project configured as a persistent AI life coach with custom instructions, structured knowledge files, and conversation-based coaching workflows.

By the end of this project, you'll have:

  • A Claude Project with a comprehensive coaching system prompt that defines Claude's methodology and behaviour.
  • A knowledge file system with goal trackers across 5 life domains: career, fitness, relationships, spiritual growth, and hobbies.
  • A completed Discovery Session where Claude interviews you to define measurable goals from scratch.
  • Secret Mission: Add a Quarterly Retrospective system with a scoring rubric and trend analysis.

Are there any prerequisites?

You need an active Claude Pro subscription ($20/month) to access Claude Projects on claude.ai. The Free plan does not support Projects.

Create Your Life Coach Project

Every good coaching relationship starts with structure. Before Claude can coach you, it needs a dedicated space where it knows your goals, understands your methods, and remembers your progress across conversations.

In this step, you'll create a Claude Project that serves as your coaching workspace. You'll also confirm that project memory is enabled so Claude can carry context between sessions.

In this step, get ready to:
  • Create a Claude Project named "Life Coach".
  • Enable project memory for persistent coaching context.
  • Verify the project is ready for configuration.
Create the project

A Claude Project is a workspace that holds custom instructions, knowledge files, and conversation history in one place. You'll create one now to house your entire coaching system.

  • In claude.ai, find the left sidebar and click Projects.
  • Click New Project.
  • In the project name field, type Life Coach.
  • In the description field, type Personal life coaching across career, fitness, relationships, spiritual growth, and hobbies.
  • Click Create project (or press Enter) to save.

What is a Claude Project?

A project in Claude is like a persistent workspace. It groups conversations, custom instructions, and uploaded knowledge files together so Claude has consistent context every time you start a new chat inside it.

Without a project, every conversation starts from scratch. With one, Claude already knows who you are and what you're working toward.

Enable memory for the project

Claude's memory feature lets it synthesize key insights across your conversations. Each project gets its own separate memory space, so your coaching context stays isolated from other projects.

  • Click your profile icon or name in the bottom-left corner of claude.ai.
  • Select Settings.
  • Navigate to Capabilities.
  • Confirm that Memory is toggled on.

Why does memory matter for coaching?

Memory creates a daily synthesis of key insights from your project conversations. This means Claude can reference patterns and progress without you restating everything each session.

Combined with the knowledge files you'll upload in a later step, memory gives Claude both structured reference data and auto-generated context. The result is a coach that actually remembers your journey.

Don't see the Memory toggle?

Memory is available on Claude Pro, Max, Team, and Enterprise plans. If you don't see it under Settings > Capabilities, confirm that your account is on the Pro plan or higher.

help me find the Memory setting in my Claude account

Verify the project is ready
  • Return to the main claude.ai screen and check the left sidebar. You should see Life Coach listed under Projects.
  • Click into the Life Coach project.
  • Confirm you can see options for custom instructions and adding knowledge content (files or text).

You should see an empty project workspace with prompts to add instructions or upload content. This confirms your project is set up and ready for the coaching system prompt.

Project not showing in the sidebar?

Try refreshing your browser. If it still doesn't appear, click Projects in the sidebar to expand the full project list. Your new project should be at the top.

help me find my Life Coach project in the Claude sidebar

Your coaching workspace is ready. Next up, you'll write the system prompt that defines how Claude coaches you, including its personality, methodology, and conversation modes.

Write the Coaching System Prompt

Your Life Coach project is set up and ready. Now you need to tell Claude exactly how to behave when you chat inside it.

A system prompt (called "custom instructions" in Claude Projects) is the hidden set of rules Claude follows every time you start a conversation. Without one, Claude is a generalist. With a well-designed system prompt, it becomes a focused life coach that knows your domains, pushes back on vague goals, and runs structured sessions.

In this step, get ready to:
  • Write a comprehensive coaching system prompt that defines Claude's role and methodology.
  • Define three conversation modes: Discovery Session, Weekly Review, and Coaching Conversation.
  • Test that Claude acknowledges its coaching role in a new chat.
Open your project's custom instructions

Custom instructions are where you define Claude's persona and methodology for this project. Every chat you start inside the project automatically inherits these instructions.

  • Inside the Life Coach project, click the Instructions section (you may see it labeled Set project instructions or as a settings/edit icon depending on your interface).
  • You should see an empty text area where you can type or paste instructions.

What are custom instructions?

Custom instructions are text that Claude reads before every conversation in this project. They define who Claude is, how it should respond, and what rules it follows. Think of them as a job description for your AI coach.

Unlike regular chat messages that disappear between sessions, custom instructions persist permanently across all conversations in the project.

Paste the coaching system prompt

This prompt defines Claude's role as a direct and supportive coach, establishes the SMART framework for goal-setting, and creates three distinct conversation modes.

  • Copy the entire system prompt below and paste it into the custom instructions field:
You are my personal life coach. You are direct, supportive, and hold me accountable. You do not sugarcoat or give generic advice. You push me to be specific, honest, and action-oriented.

## Your Role
- Act as a professional life coach across 5 domains: Career, Fitness, Relationships, Spiritual, and Hobbies
- Reference my uploaded knowledge files for context on my goals, progress, and history
- Challenge vague statements. If I say "I want to do better," ask what "better" means in measurable terms
- Use the SMART framework (Specific, Measurable, Achievable, Relevant, Time-bound) when helping me set or refine goals
- Remember what we have discussed in previous conversations in this project

## Conversation Modes

### Discovery Session
When I say "Let's run a Discovery Session" or "Help me define my goals":
- Interview me one domain at a time (Career, Fitness, Relationships, Spiritual, Hobbies)
- For each domain, ask about: my current state, what I want, why it matters, what success looks like, what is blocking me
- Push back if my answers are vague. Ask follow-up questions until we reach something specific and measurable
- After covering all domains, generate updated goal files in the format from my templates

### Weekly Review
When I say "Let's do my weekly review":
- Walk through each domain one at a time
- For each domain, ask about: Wins, Misses, Insights
- Reference my goal files to check on specific targets
- After all domains, provide: overall assessment, pattern observations, top 3 action items for next week, and one accountability question
- Generate a progress log entry I can save

### Coaching Conversation
For any other conversation:
- Check what I want to work on
- Reference my goals and progress log for context
- Give direct, actionable advice
- End each conversation with a clear next step or commitment

## Communication Style
- Be direct and concise. No filler phrases like "Great question!" or "I appreciate you sharing that."
- Use a warm but challenging tone. Think: trusted friend who also happens to be a coach.
- Ask one question at a time. Do not overwhelm with multiple questions in a single message.
- When I am stuck, offer 2-3 concrete options rather than open-ended brainstorming.
- Celebrate real wins. Do not offer hollow praise.

## Rules
- Never fabricate information about my goals or progress. If you do not have context, ask.
- If I have not done a weekly review in a while, gently remind me.
- If a goal has not seen progress in 3+ weeks, flag it and ask if it is still relevant or needs restructuring.
- Keep responses focused. Coaching sessions should feel like a conversation, not a lecture.

What does this prompt do?

The prompt has five sections that work together to create a coaching experience:

  • The opening paragraph sets Claude's identity as a direct, accountability-focused coach.
  • "Your Role" tells Claude to use the SMART framework and reference your uploaded knowledge files for context.
  • "Conversation Modes" creates three triggers: Discovery Session (for defining goals from scratch), Weekly Review (for structured check-ins), and Coaching Conversation (for general coaching).
  • "Communication Style" prevents generic AI filler and keeps responses concise.
  • "Rules" stops Claude from making up progress data and creates proactive accountability nudges.

✔️ Awesome, I've got everything!

Great. Make sure the full prompt is pasted with no sections cut off, then move on to save it.

ⓧ I'd like to double check the full code

Here is the complete system prompt. Make sure your custom instructions field matches this exactly:

You are my personal life coach. You are direct, supportive, and hold me accountable. You do not sugarcoat or give generic advice. You push me to be specific, honest, and action-oriented.

## Your Role
- Act as a professional life coach across 5 domains: Career, Fitness, Relationships, Spiritual, and Hobbies
- Reference my uploaded knowledge files for context on my goals, progress, and history
- Challenge vague statements. If I say "I want to do better," ask what "better" means in measurable terms
- Use the SMART framework (Specific, Measurable, Achievable, Relevant, Time-bound) when helping me set or refine goals
- Remember what we have discussed in previous conversations in this project

## Conversation Modes

### Discovery Session
When I say "Let's run a Discovery Session" or "Help me define my goals":
- Interview me one domain at a time (Career, Fitness, Relationships, Spiritual, Hobbies)
- For each domain, ask about: my current state, what I want, why it matters, what success looks like, what is blocking me
- Push back if my answers are vague. Ask follow-up questions until we reach something specific and measurable
- After covering all domains, generate updated goal files in the format from my templates

### Weekly Review
When I say "Let's do my weekly review":
- Walk through each domain one at a time
- For each domain, ask about: Wins, Misses, Insights
- Reference my goal files to check on specific targets
- After all domains, provide: overall assessment, pattern observations, top 3 action items for next week, and one accountability question
- Generate a progress log entry I can save

### Coaching Conversation
For any other conversation:
- Check what I want to work on
- Reference my goals and progress log for context
- Give direct, actionable advice
- End each conversation with a clear next step or commitment

## Communication Style
- Be direct and concise. No filler phrases like "Great question!" or "I appreciate you sharing that."
- Use a warm but challenging tone. Think: trusted friend who also happens to be a coach.
- Ask one question at a time. Do not overwhelm with multiple questions in a single message.
- When I am stuck, offer 2-3 concrete options rather than open-ended brainstorming.
- Celebrate real wins. Do not offer hollow praise.

## Rules
- Never fabricate information about my goals or progress. If you do not have context, ask.
- If I have not done a weekly review in a while, gently remind me.
- If a goal has not seen progress in 3+ weeks, flag it and ask if it is still relevant or needs restructuring.
- Keep responses focused. Coaching sessions should feel like a conversation, not a lecture.
Save and test your system prompt
  • Click Save (or Save Instructions) to lock in your custom instructions.
  • Start a new chat inside the Life Coach project.
  • Type the following message to test that Claude has loaded your instructions:
What do you know about me so far?

Claude should respond acknowledging that it is your life coach, noting it does not yet have your goals on file, and offering to run a Discovery Session.

What should I see?

Claude's response should reflect the communication style you defined. It should be direct and concise, not generic or overly enthusiastic. It should mention coaching you across domains and reference that it does not have goal data yet.

If Claude offers to run a Discovery Session or asks what you want to work on, your system prompt is working correctly.

Claude responding like a generic assistant?

If Claude does not reference coaching, domains, or goal files, your custom instructions may not have saved. Go back to the project's instructions section and confirm your full prompt is there.

Make sure you started the chat inside the Life Coach project, not in a general Claude conversation. Check the project name at the top of the chat window.

Help me troubleshoot my custom instructions

Your AI life coach now has its methodology and personality locked in. Next up, you will create the knowledge files that give Claude structured data to reference across sessions.

Create and Upload Knowledge File Templates

Your coaching system prompt is saved and ready to guide Claude's behavior. Now Claude needs something to reference between conversations: your actual goals, templates, and progress history.

In this step, you will create a set of structured Markdown files that act as Claude's long-term memory. These files give Claude persistent access to your goals, review templates, and progress entries across every conversation in the project.

In this step, get ready to:
  • Create 7 Markdown knowledge files on your Mac with structured templates.
  • Upload all 7 files to your Life Coach project on claude.ai.
  • Verify Claude can reference every uploaded file.
Create your knowledge files locally

You will create 7 Markdown files that serve as Claude's external memory. Five are domain-specific goal trackers, one is a weekly review template, and one is a progress log.

You will use Terminal to create the folder and files, then open each file in TextEdit to paste its content.

  • Press Cmd+Space to open Spotlight search.
  • Type Terminal and press Enter to open it.
  • Move to your Desktop by running this command:
cd ~/Desktop
  • Create your project folder and move into it by running these commands:
mkdir life-coach-files
cd life-coach-files
  • Create all 7 empty Markdown files by running this command:
touch goals-career.md goals-fitness.md goals-relationships.md goals-spiritual.md goals-hobbies.md weekly-review-template.md progress-log.md
  • Confirm the files exist by running:
ls

You should see all 7 .md files listed in the output.

Don't see all 7 files?

Make sure you typed the full touch command on a single line. If you accidentally pressed Enter too early, run the touch command again with only the missing filenames.

help me create multiple files with touch in Terminal

Now you will open each file and paste its template content. Start with the career goals file.

  • Open goals-career.md in TextEdit by running:
open -a TextEdit goals-career.md
  • Select all existing content (if any) and paste the following template into the file:
# Career Goals

## Vision
[What does your ideal career look like in 3-5 years?]

## Current State
[Where are you right now? Role, skills, satisfaction level, challenges]

## 90-Day Targets
- Target 1: [Specific, measurable outcome]
- Target 2: [Specific, measurable outcome]
- Target 3: [Specific, measurable outcome]

## Weekly Actions
- [ ] [Recurring action that moves you toward Target 1]
- [ ] [Recurring action that moves you toward Target 2]
- [ ] [Recurring action that moves you toward Target 3]

## Metrics
- [How will you measure progress? Be specific.]

## Notes
- [Constraints, context, important decisions, rejected approaches]
  • Save the file with Cmd+S.

What is this template structure?

Each goal file follows the same framework. Vision sets the long-term direction. Current State anchors where you are today. 90-Day Targets give Claude specific milestones to hold you accountable to.

Weekly Actions are recurring habits, Metrics define how you measure progress, and Notes capture context Claude should know about. During the Discovery Session in the next step, Claude will replace all the bracketed placeholders with your real goals.

The remaining 4 goal files follow this same structure with domain-specific prompts. Repeat the open, paste, and save process for each one.

  • Open goals-fitness.md in TextEdit by running:
open -a TextEdit goals-fitness.md
  • Paste the following template and save with Cmd+S:
# Fitness Goals

## Vision
[What does peak physical health look like for you?]

## Current State
[Current fitness level, habits, challenges, injuries/limitations]

## 90-Day Targets
- Target 1: [Specific, measurable outcome]
- Target 2: [Specific, measurable outcome]
- Target 3: [Specific, measurable outcome]

## Weekly Actions
- [ ] [Recurring action that moves you toward Target 1]
- [ ] [Recurring action that moves you toward Target 2]
- [ ] [Recurring action that moves you toward Target 3]

## Metrics
- [How will you measure progress? Be specific.]

## Notes
- [Constraints, context, important decisions, rejected approaches]
  • Open goals-relationships.md in TextEdit by running:
open -a TextEdit goals-relationships.md
  • Paste the following template and save with Cmd+S:
# Relationship Goals

## Vision
[What do your ideal relationships look like? Partner, family, friends, community]

## Current State
[Where are your key relationships now? Strengths, gaps, patterns]

## 90-Day Targets
- Target 1: [Specific, measurable outcome]
- Target 2: [Specific, measurable outcome]
- Target 3: [Specific, measurable outcome]

## Weekly Actions
- [ ] [Recurring action that moves you toward Target 1]
- [ ] [Recurring action that moves you toward Target 2]
- [ ] [Recurring action that moves you toward Target 3]

## Metrics
- [How will you measure progress? Be specific.]

## Notes
- [Constraints, context, important decisions, rejected approaches]
  • Open goals-spiritual.md in TextEdit by running:
open -a TextEdit goals-spiritual.md
  • Paste the following template and save with Cmd+S:
# Spiritual Goals

## Vision
[What does spiritual growth mean to you? Mindfulness, faith, purpose, inner peace]

## Current State
[Where are you now in your spiritual practice or journey?]

## 90-Day Targets
- Target 1: [Specific, measurable outcome]
- Target 2: [Specific, measurable outcome]
- Target 3: [Specific, measurable outcome]

## Weekly Actions
- [ ] [Recurring action that moves you toward Target 1]
- [ ] [Recurring action that moves you toward Target 2]
- [ ] [Recurring action that moves you toward Target 3]

## Metrics
- [How will you measure progress? Be specific.]

## Notes
- [Constraints, context, important decisions, rejected approaches]
  • Open goals-hobbies.md in TextEdit by running:
open -a TextEdit goals-hobbies.md
  • Paste the following template and save with Cmd+S:
# Hobbies Goals

## Vision
[What hobbies bring you energy and joy? What do you want to explore or master?]

## Current State
[What are you doing now? What have you dropped? What are you curious about?]

## 90-Day Targets
- Target 1: [Specific, measurable outcome]
- Target 2: [Specific, measurable outcome]
- Target 3: [Specific, measurable outcome]

## Weekly Actions
- [ ] [Recurring action that moves you toward Target 1]
- [ ] [Recurring action that moves you toward Target 2]
- [ ] [Recurring action that moves you toward Target 3]

## Metrics
- [How will you measure progress? Be specific.]

## Notes
- [Constraints, context, important decisions, rejected approaches]

Why 5 separate goal files instead of one?

Splitting goals by domain keeps each file focused and easy to update. When Claude references your career goals during a coaching conversation, it pulls from a concise, domain-specific file rather than parsing through a single massive document.

This also means you can update one domain (like fitness targets after a race) without touching the others.

Now create the two structural files that power your review workflow.

  • Open weekly-review-template.md in TextEdit by running:
open -a TextEdit weekly-review-template.md
  • Paste the following template and save with Cmd+S:
# Weekly Review Template

Use this template every week. Start a new chat and say "Let's do my weekly review."

## Review Structure (per domain)

### [Domain Name]
- Wins: What went well this week?
- Misses: What did you skip, avoid, or fail at?
- Insights: What did you learn about yourself?
- Next Week Focus: What is the ONE thing to prioritize?

## Domains to Review
1. Career
2. Fitness
3. Relationships
4. Spiritual
5. Hobbies

## Coaching Output (Claude generates this)
- Overall Week Score (1-10)
- Pattern Observations
- Top 3 Action Items for Next Week
- Accountability Question to answer at the start of next review

## Review Cadence
- Weekly reviews: Every Sunday or Monday
- Update progress-log.md after each review

What does this template do?

This file tells Claude exactly how to structure a weekly review. When you say "Let's do my weekly review" in a project chat, Claude follows this template: walking through each domain, asking about wins and misses, then generating a score and action items.

The Coaching Output section defines what Claude produces at the end. The Accountability Question creates a bridge between sessions so next week's review starts with a check-in.

  • Open progress-log.md in TextEdit by running:
open -a TextEdit progress-log.md
  • Paste the following template and save with Cmd+S:
# Progress Log

Record a summary after each weekly review. This creates a running history Claude can reference to spot trends, patterns, and growth over time.

## Entry Format

### Week of [DATE]
- Overall Score: [1-10]
- Top Win: [Single biggest accomplishment]
- Top Miss: [Single biggest gap]
- Key Insight: [What you learned]
- Focus for Next Week: [Primary intention]

---

[Entries will be added here after each weekly review]

What is the progress log for?

This file starts empty and grows over time. After each weekly review, you paste a summary entry here. Over weeks and months, Claude can reference this log to spot trends like "you consistently skip fitness actions" or "your career score has climbed steadily."

Unlike Claude's built-in memory (which stores summarized insights), this file preserves your exact scores and observations in a structured, searchable format.

You can close all the TextEdit windows now.

✔️ Awesome, I've got everything!

Great. Make sure you have saved all 7 files inside the life-coach-files folder on your Desktop.

ⓧ I'd like to double check the full code

Here are all 7 files for comparison. Make sure your files match these exactly.

# Career Goals

## Vision
[What does your ideal career look like in 3-5 years?]

## Current State
[Where are you right now? Role, skills, satisfaction level, challenges]

## 90-Day Targets
- Target 1: [Specific, measurable outcome]
- Target 2: [Specific, measurable outcome]
- Target 3: [Specific, measurable outcome]

## Weekly Actions
- [ ] [Recurring action that moves you toward Target 1]
- [ ] [Recurring action that moves you toward Target 2]
- [ ] [Recurring action that moves you toward Target 3]

## Metrics
- [How will you measure progress? Be specific.]

## Notes
- [Constraints, context, important decisions, rejected approaches]
# Fitness Goals

## Vision
[What does peak physical health look like for you?]

## Current State
[Current fitness level, habits, challenges, injuries/limitations]

## 90-Day Targets
- Target 1: [Specific, measurable outcome]
- Target 2: [Specific, measurable outcome]
- Target 3: [Specific, measurable outcome]

## Weekly Actions
- [ ] [Recurring action that moves you toward Target 1]
- [ ] [Recurring action that moves you toward Target 2]
- [ ] [Recurring action that moves you toward Target 3]

## Metrics
- [How will you measure progress? Be specific.]

## Notes
- [Constraints, context, important decisions, rejected approaches]
# Relationship Goals

## Vision
[What do your ideal relationships look like? Partner, family, friends, community]

## Current State
[Where are your key relationships now? Strengths, gaps, patterns]

## 90-Day Targets
- Target 1: [Specific, measurable outcome]
- Target 2: [Specific, measurable outcome]
- Target 3: [Specific, measurable outcome]

## Weekly Actions
- [ ] [Recurring action that moves you toward Target 1]
- [ ] [Recurring action that moves you toward Target 2]
- [ ] [Recurring action that moves you toward Target 3]

## Metrics
- [How will you measure progress? Be specific.]

## Notes
- [Constraints, context, important decisions, rejected approaches]
# Spiritual Goals

## Vision
[What does spiritual growth mean to you? Mindfulness, faith, purpose, inner peace]

## Current State
[Where are you now in your spiritual practice or journey?]

## 90-Day Targets
- Target 1: [Specific, measurable outcome]
- Target 2: [Specific, measurable outcome]
- Target 3: [Specific, measurable outcome]

## Weekly Actions
- [ ] [Recurring action that moves you toward Target 1]
- [ ] [Recurring action that moves you toward Target 2]
- [ ] [Recurring action that moves you toward Target 3]

## Metrics
- [How will you measure progress? Be specific.]

## Notes
- [Constraints, context, important decisions, rejected approaches]
# Hobbies Goals

## Vision
[What hobbies bring you energy and joy? What do you want to explore or master?]

## Current State
[What are you doing now? What have you dropped? What are you curious about?]

## 90-Day Targets
- Target 1: [Specific, measurable outcome]
- Target 2: [Specific, measurable outcome]
- Target 3: [Specific, measurable outcome]

## Weekly Actions
- [ ] [Recurring action that moves you toward Target 1]
- [ ] [Recurring action that moves you toward Target 2]
- [ ] [Recurring action that moves you toward Target 3]

## Metrics
- [How will you measure progress? Be specific.]

## Notes
- [Constraints, context, important decisions, rejected approaches]
# Weekly Review Template

Use this template every week. Start a new chat and say "Let's do my weekly review."

## Review Structure (per domain)

### [Domain Name]
- Wins: What went well this week?
- Misses: What did you skip, avoid, or fail at?
- Insights: What did you learn about yourself?
- Next Week Focus: What is the ONE thing to prioritize?

## Domains to Review
1. Career
2. Fitness
3. Relationships
4. Spiritual
5. Hobbies

## Coaching Output (Claude generates this)
- Overall Week Score (1-10)
- Pattern Observations
- Top 3 Action Items for Next Week
- Accountability Question to answer at the start of next review

## Review Cadence
- Weekly reviews: Every Sunday or Monday
- Update progress-log.md after each review
# Progress Log

Record a summary after each weekly review. This creates a running history Claude can reference to spot trends, patterns, and growth over time.

## Entry Format

### Week of [DATE]
- Overall Score: [1-10]
- Top Win: [Single biggest accomplishment]
- Top Miss: [Single biggest gap]
- Key Insight: [What you learned]
- Focus for Next Week: [Primary intention]

---

[Entries will be added here after each weekly review]
Upload all files to the project

With all 7 files saved locally, you will now upload them to your Claude Projects knowledge section so Claude can reference them during coaching conversations.

  • Switch back to claude.ai in your browser.
  • Open the Life Coach project from the left sidebar.
  • Click Add content.
  • In the file picker, navigate to Desktop then open the life-coach-files folder.
  • Select all 7 .md files and click Open to upload them.

Select multiple files at once

Hold Cmd and click each file to select all 7, or press Cmd+A to select everything in the folder.

  • Verify all 7 files appear in the project's knowledge section.

You should see goals-career.md, goals-fitness.md, goals-relationships.md, goals-spiritual.md, goals-hobbies.md, weekly-review-template.md, and progress-log.md all listed.

Files not appearing after upload?

Make sure you clicked Add content from within the Life Coach project, not from the main claude.ai sidebar. Files must be uploaded to a specific project to appear in its knowledge section.

If a file shows an error, confirm it was saved as plain text (not rich text) in TextEdit. Re-save the file using Format then Make Plain Text if needed, then upload again.

help me upload knowledge files to my Claude project

Test file access

Before moving on, confirm that Claude can actually see and reference the files you just uploaded.

  • Start a new chat inside the Life Coach project by clicking the compose/new chat button.
  • Type the following message and send it:
List all the knowledge files you can see in this project

Claude should respond with a list that references all 7 uploaded files by name.

What should I see?

Claude's response should mention each of your 7 files: the 5 domain goal files, the weekly review template, and the progress log. It may also describe what each file contains based on the template structure.

If Claude says it cannot see any files, the upload did not complete successfully. Go back to the project's knowledge section and re-upload the missing files.

Your knowledge file system is in place. Claude now has structured templates to reference across every coaching conversation. Next up, you will run your first Discovery Session where Claude interviews you and fills these templates with your real goals.

Run Your Discovery Session

Your Life Coach project now has a complete coaching methodology and structured knowledge files ready to be filled.

The knowledge files are still full of placeholder text like [What does your ideal career look like in 3-5 years?]. In this step, Claude will interview you across all 5 domains to replace those placeholders with real, measurable goals. This is where your coaching system becomes personal.

In this step, get ready to:
  • Complete a Discovery Session conversation across all 5 life domains.
  • Get Claude to push you toward specific, measurable goals using the SMART framework.
  • Generate personalized goal file content and update your project knowledge.
Kick off the discovery conversation

A Discovery Session mirrors what a real life coach does in a first meeting. Claude will interview you one domain at a time, asking probing questions about where you are now, where you want to be, and what specific success looks like for you.

  • In the Life Coach project, click the chat input to start a new conversation.
  • Type the following message and press Enter to send it:
Let's run a Discovery Session. I want to define my goals from scratch across all 5 domains.

What happens next?

Claude will recognize the Discovery Session trigger from your system prompt and begin interviewing you. It starts with one domain (usually Career) and asks about your current state, what you want, why it matters, and what success looks like.

It will ask one question at a time. Answer honestly and in as much detail as you can.

Complete the full discovery

This is the most important part of the project. The quality of your coaching system depends entirely on how specific you are during this conversation.

  • Work through all 5 domains with Claude: Career, Fitness, Relationships, Spiritual, and Hobbies.
  • For each domain, Claude will ask about your current state, what you want, why it matters, and what is blocking you.
  • Let Claude challenge vague answers. If you say something like "I want to get fit," it should push you to define what fit means, what metrics matter, and what your 90-day target is.
  • Take your time. This conversation will likely be 15-20 minutes.

Get the most out of your session

Treat this like a real coaching session. The more honest and specific you are, the better Claude can hold you accountable in future reviews. If you do not have a clear answer for a domain, say so. Claude will help you explore what matters to you.

What is the SMART framework?

Your system prompt instructs Claude to use the SMART framework when helping you set goals. SMART stands for Specific, Measurable, Achievable, Relevant, and Time-bound.

Instead of "I want to read more," a SMART goal would be "Read 2 books per month for the next 90 days, tracking titles in a reading log." Claude will push you toward this level of specificity.

Claude not asking probing questions?

If Claude gives generic advice instead of interviewing you, it may not be reading the system prompt correctly. Confirm you are chatting inside the Life Coach project (not a general Claude conversation). You should see the project name at the top of the chat.

If that does not help, try sending: "Remember, you are my life coach. Follow the Discovery Session mode from your instructions and interview me one domain at a time."

Still having trouble? Help me get Claude to follow my Discovery Session instructions in my project.

Generate your goal files

Once you have worked through all 5 domains, Claude has enough context to produce structured, personalized goal files. These will replace the template placeholders in your project knowledge.

  • After finishing all 5 domains, type the following message:
Now take everything we discussed and generate updated versions of each goal file in the format from my templates.

What does Claude produce?

Claude will generate formatted Markdown content for each of your 5 goal files (Career, Fitness, Relationships, Spiritual, Hobbies). Each file follows the same structure as your templates: Vision, Current State, 90-Day Targets, Weekly Actions, Metrics, and Notes. The difference is that every section is now filled with your specific, measurable goals.

  • For each domain, copy the formatted output Claude provides.
  • Return to the project's knowledge section.
  • Remove the old template version of the goal file (for example, the original goals-career.md with placeholder text).
  • Add the new personalized content as a replacement. You can either paste it directly as a new knowledge item or save it as a .md file on your Mac and re-upload it.
  • Repeat for all 5 goal files: goals-career.md, goals-fitness.md, goals-relationships.md, goals-spiritual.md, and goals-hobbies.md.

Keep the same file names

If you re-upload files, use the exact same file names as the originals. Your system prompt references these files by their domain structure. Consistent naming ensures Claude can find and reference your goals in future conversations.

  • Verify all 5 goal files are updated by starting a new chat in the project and typing:
List all the knowledge files you can see in this project and summarize my top career goal.

Claude should list all 7 files and reference a specific, measurable career goal from your updated file. If it still mentions placeholder text, double-check that you replaced the old template with your new content.

Claude still referencing placeholder text?

Make sure you deleted the original template file before adding the new version. If both versions exist in the project knowledge, Claude may read the old one. Check that only one version of each goal file appears in your knowledge section.

Need help? Claude is still showing my template placeholders instead of my real goals after I updated the knowledge files.

Your Life Coach now knows who you are and what you are working toward. Next up, you will put the coaching system to work with your first Weekly Review.

Run Your First Weekly Review

Your goals are defined, your knowledge files are personalized, and Claude knows exactly what you are working toward. Now it is time to put the coaching system to work with a structured weekly review.

A weekly review is where the real coaching happens. Claude will walk through each of your 5 domains, check in on your targets, identify patterns, and give you concrete action items for the week ahead.

In this step, get ready to:
  • Run a full weekly review conversation across all 5 life domains.
  • Receive coaching feedback with pattern observations and action items.
  • Generate and save your first progress log entry.
Start the weekly review

The weekly review follows a structured format defined in your weekly-review-template.md file. Claude will use this template to walk through each domain systematically.

  • In your Life Coach project, click the text input area to start a new chat.
  • Type the following message and press Enter:
Let's do my weekly review.
  • Claude will begin walking through each domain using the review structure: Wins, Misses, Insights, and Next Week Focus.
  • Answer honestly for each domain. Claude will reference your uploaded goal files to check in on specific targets you set during the Discovery Session.
  • Work through all 5 domains: Career, Fitness, Relationships, Spiritual, and Hobbies.

What if I just started and have no progress yet?

That is completely fine. Even if you defined your goals only minutes ago, treat this as your baseline review. Your "wins" might be the act of defining clear goals. Your "misses" might be that you have not started any weekly actions yet.

The point is to practice the format and create your first data point. Claude will adapt its coaching based on where you actually are.

Get your coaching feedback

After you finish reviewing all 5 domains, Claude shifts from interviewer to coach. This is where you get the structured output that makes the weekly review valuable over time.

  • Once all domains are covered, Claude will provide an overall assessment of your week.
  • Read through the coaching output. It should include:

Why does the accountability question matter?

The accountability question creates a bridge between this session and next week's review. When you start your next weekly review, Claude will ask you to answer it first. This prevents the common pattern of setting intentions and then forgetting about them entirely by the following week.

  • If the coaching feedback feels too generic, push back. Ask Claude to be more specific about what it sees in your responses.
  • Note down the accountability question somewhere you will see it during the week.

Push back on vague coaching

If Claude gives a generic action item like "focus more on fitness," ask it to make it concrete. Something like "What specific action should I take on Tuesday to move toward my 90-day target?" will get you much more useful output.

Update your progress log

Your progress-log.md file is currently empty. This step creates the first entry, giving Claude a historical record to reference in future sessions.

  • In the same chat, ask Claude to generate a progress log entry by typing:
Generate a progress log entry for this week.
  • Claude will produce a formatted entry following the structure from your progress-log.md template: the current date, an overall score, top win, top miss, key insight, and focus for next week.
  • Copy Claude's progress log output.
  • Open your local progress-log.md file in your text editor.
  • Paste the entry below the line that says [Entries will be added here after each weekly review], replacing that placeholder text.
  • Save the file.

Now update the knowledge file in your project so Claude can reference it in future conversations.

  • Return to your Life Coach project's knowledge section.
  • Delete the old progress-log.md file from the project's knowledge.
  • Click Add content and upload the updated progress-log.md from your life-coach-files folder.

Why manually update the file?

Claude's project memory automatically synthesizes insights across your conversations. But memory stores summaries, not structured data. Your progress log file preserves the exact scores, wins, misses, and insights in a format Claude can reference precisely.

Over time, this running log lets Claude spot trends across weeks. It might notice your fitness score dropping for 3 weeks in a row, or that your career wins consistently come from the same type of action.

  • Verify the upload by starting a new chat and asking:
What does my progress log show so far?
  • Claude should reference your first dated entry, including your overall score and key focus for next week.

Claude does not see your updated progress log?

Make sure you re-uploaded the updated file. Editing the file locally does not automatically sync it to the project. You need to delete the old version from the project's knowledge and upload the new one.

Also confirm you are starting a new chat after uploading. Existing conversations may not reflect newly uploaded files.

Still having trouble? Help me troubleshoot why Claude cannot see my updated progress log file in the Life Coach project.

Secret mission

Add a Quarterly Retrospective System

Weekly reviews are great for staying on track, but they can miss the bigger picture. What if your coach could zoom out every 12 weeks and give you a brutally honest assessment of where you're actually growing versus where you're just going through the motions?

Clean Up Your Resources

Clean Up Your Resources

This project runs entirely within your existing Claude Pro subscription, so there are no additional ongoing costs. Decide whether to keep your Life Coach project active, pause your usage, or delete it entirely.

Resources you used:

  • Claude Project named "Life Coach" on claude.ai (includes custom instructions, memory, and 8 knowledge files).
  • Local life-coach-files folder on your Mac (contains your Markdown template files).

Keep everything running

No action needed. Choose this if you plan to continue using your Life Coach project for weekly reviews and coaching sessions.

  • Your Claude Project stays in your sidebar, ready for new conversations anytime.
  • Your knowledge files, system prompt, and project memory all persist across sessions.
  • Your local life-coach-files folder remains on your Desktop for future edits.

Pause - I'll come back to this later

There is nothing to pause. Your Claude Project does not consume resources when you are not actively chatting in it. Come back anytime and start a new conversation.

  • Your project, knowledge files, custom instructions, and memory remain intact until you return.
  • No charges beyond your existing Claude Pro subscription.

Delete - I don't want to use this again

Remove all project resources to start fresh.

  • Delete the Claude Project:
  • In claude.ai, click Projects in the left sidebar.
  • Click the Life Coach project to open it.
  • Click the three-dot menu icon in the project header.
  • Select Delete from the dropdown menu.
  • Click Delete in the confirmation dialog. This permanently removes the project, its custom instructions, knowledge files, and conversation history.
  • Delete your local files by opening Terminal and running:

macOS

rm -rf ~/Desktop/life-coach-files

Windows

rmdir /s /q "$HOME\Desktop\life-coach-files"

Nice Work!

Nice Work!

You just built a personal AI coaching system from scratch. Your Life Coach project is ready to hold you accountable, challenge vague thinking, and track your growth across every area of your life.

You learned how to:

  • Design a coaching system prompt that defines Claude's methodology, conversation modes, and communication style across Discovery Sessions, Weekly Reviews, and general coaching.
  • Build a structured knowledge file system with goal trackers, progress logs, and review templates that persist across conversations and give Claude concrete data to reference.
  • Run a complete coaching workflow from Discovery Session to Weekly Review, generating measurable goals and tracking progress over time.
  • Secret Mission: You added a Quarterly Retrospective system with a 1-10 scoring rubric and trend analysis that gives you a longitudinal view of your growth.

Ready to quiz yourself?