✨ Congratulations, crew!

You made it through the 14-Day AI Challenge. It sounded short and sweet on “paper,” didn’t it? Funny how two weeks can feel like a marathon once you’re actually in it. For those of you who stuck with it — thank you! I hope you learned something new along the way.

And if you’re someone who plans to circle back later when life makes room (hi, fellow real humans 👋), thank you, too. These posts will be here as a resource whenever you need them.

For our final day, I want to leave you with a different kind of gift: not another tool or prompt, but a moment of reflection. This experiment wasn’t just about AI — it was about creativity, discipline, and what happens when you simply commit to showing up.

The Lessons

Here are some of the biggest takeaways from this 14-day journey:

1. Better prompts = better results. Prompt structure matters. Every iteration gets you closer to clarity.

2. Iteration is normal. Each round of prompting sharpens your thinking and tailors the response to your needs.

3. Data privacy + bias = ongoing homework. Be mindful and keep learning.

4. AI ≠ autopilot. It’s a thinking partner, not a replacement for your judgment. Always check the facts.

5. Small experiments compound. Fourteen tiny posts add up to something meaningful.

6. Clarity comes from creating. Writing about AI daily helped me discover what I really think.

7. Your questions are everything. AI is only as sharp as the prompts you feed it.

What’s Next

This challenge isn’t the end — it’s just the beginning. Kindworks is diving deeper into big questions like:

• How is AI reshaping the future of work?

• What does AI and data privacy really mean for leaders and teams?

• How can automation (think AI agents) make our lives easier — without making things weird?

But I want this to be a two-way street. What do you want to see next?

• A 7-day deep dive into a single AI tool?

• A “build in public” series on what it looks like to consult with AI?

• Mini hackathon for community vibe coding?

• Or something totally different?

Thank You 💜

Thank you for being part of this experiment. Writing in public is always a little vulnerable — but it’s also a great way to learn and stay accountable.

If these 14 days taught me anything, it’s this:
👉 You don’t have to be an expert to start. You just have to start.

So, here’s to starting. And re-starting. And building the future of work — one experiment, and community member at a time.

Now it’s your turn: What should we explore next? Drop your thoughts in the comments — I’d love to hear them.

AI generated graphic

AI generated image

Hey Crew —

Day 12 was all about sharpening your prompt. Today we’re putting that sharper tool to work on something that brings me a ton of joy and momentum: building your 90‑day roadmap.

What’s a roadmap?

A roadmap is a high‑level plan for the next three months (or any time horizon that fits your world). It shows where you’re going and what “good” looks like.

We’ll pair it with OKRs—a lightweight framework I grew to love while at Microsoft:

• Objectives = big goals

• Key Results = measurable outcomes that prove you’re making progress

Think of the roadmap as your map, and OKRs as the checkpoints along the way.

Copy‑paste prompt: build your 90‑day roadmap

Drop this into your favorite AI tool:

You are a strategic planning coach. Help me create a 90‑day roadmap for [insert your goal/project]. Break it into 3 phases (Month 1, Month 2, Month 3). For each phase, suggest 1–2 Objectives (big goals) and 3–4 Key Results (measurable outcomes). Keep it realistic for a solo consultant with limited time. Write it in plain language, no jargon. Format as a simple table.

Optional upgrades

• Constraints: add hours/week, budget, or tools you already use.

• Style: ask for bullets only, or a table plus a one‑paragraph summary.

Example output (so you can see the shape)

Imagine your goal is to restore a 1960 Ford Ranchero (hey, a kid can dream). Your AI might generate something like this:

Now swap in your goal.

How to use your roadmap

1. Pick focus, not perfection. One or two Objectives per month is plenty.

2. Make it measurable. If you can’t count it, you can’t celebrate it.

3. Assume real‑life constraints. Solo capacity beats wishful thinking.

4. Review weekly. Check your KRs, adjust scope, keep moving.

Make it your own

Deep down you might be sitting on an idea, a career change, a new product, a team reset, or a personal project. Plug your goal into the prompt above and see what AI gives you. Use the output as a starting point to shape your roadmap and set OKRs—then iterate and have fun.

Want a template? Reply with your goal and I’ll send you a clean Notion/Google Doc you can duplicate.

— Emily

image generated by AI

Hey Crew,

We’re officially in the home stretch of this challenge! And today we’re circling back to one of the most important skills when it comes to working with AI: learning how to write better prompts.

On day 11, we talked about how useful AI can be for getting an executive level briefing for your role/industry. Pretty cool, right? I’m going to use that one tomorrow morning!

If you’ve been following along, you know that a “prompt” is just the instruction you give an AI tool. Simple enough, right? But here’s the secret: the way you phrase your prompt can make or break the usefulness of the response.

Think of it like ordering at your favorite coffee shop. If you walk in and say, “coffee, please,” you’ll get some coffee (or maybe a bunch more questions from the barista). But if you ask for a double tall vanilla almond milk latte, with two pumps of vanilla, you’ll get exactly what you want. Yum.

Now that we are on day 12, you’ve probably learned that AI works the same way.

Why Better Prompts Matter

When you first start out, it’s tempting to ask AI really broad questions, like:

“Summarize trends in my industry.”

And AI will give you something. But often it’s generic, fluffy, or just not that useful.

Now watch what happens when you add clarity and context:

👉 “Summarize the 5 biggest emerging trends in [industry] from the past 6 months. For each, explain why it matters and give one real-world example.”

Suddenly, your AI is doing focused work for you. You’re not just getting information—you’re getting insight.

A Simple Framework for Writing Strong Prompts

If you’re new to this, here’s a no-fail formula to make your prompts better right away:

1. Add a Role

Pretend the AI has a job title. Example: “You are a compliance officer” or “You are my Chief of Staff.”

2. Add a Time Frame

“In the past 6 months” is very different from “all time.”

3. Add an Output Format

Want bullet points? A table? A one-paragraph summary? Say so.

Try This Yourself

Here’s a before-and-after you can test:

❌ Vague Prompt: “What are some leadership trends?”

✅ Better Prompt: “Act as an executive coach. Summarize the 3 most important leadership trends emerging in the past year, and explain one action a manager could take for each.”

See the difference? The second prompt is sharper, clearer, and much more useful.

Today’s Challenge

Pick something in your own work—maybe it’s industry news, content planning, or brainstorming fall goals—and write one “before” and one “better” prompt. Notice how much more specific and valuable the output feels when you frame it right.

✨ The more you practice, the easier this gets. By the end of this challenge, you’ll not only know how to use AI, but you’ll also know how to ask for what you really need. And that’s the real magic (in AI and other parts of your life, am I right?)

👉 Tomorrow, we’ll take it one step further: using AI to help you draft a 90-day roadmap for your fall goals. Stay tuned—this one’s a game-changer.

Image created with AI.

Hey Crew,

Welcome to Day 11 of our 14-Day AI Challenge! 🙌

I’ll be real with you; it took me a minute to land on today’s focus. I toyed with:

• AI + spreadsheets (hello quick insights 📊)

• Responsible AI + privacy (always important 🔒)

• AI for competitive intelligence & research (👀 on your industry)

And while we will likely circle back to some of those before the challenge ends, today I want to dig into something super practical: using AI as your role-based research assistant.

Think about it, what if, instead of drowning in tabs and newsletters, you had an AI that:

• Gave you a morning briefing on the trends shaping your industry

• Flagged policy changes or new regulations that might affect your work

• Surfaced top headlines your execs or clients care about

• Even pulled competitor moves into a clean summary

Our community is diverse—marketing pros, events directors, therapists, educators, product leaders—so the details of how you prompt will vary. But across all roles, the questions are the same:

• Where is my field heading?

• What disruptions should I prepare for?

• Which policies or regulations could change the game?

✨ Instead of spending two hours piecing this together, let AI be your personal industry analyst. Think of it as your daily executive briefing, in plain English.

Today’s Challenge: Try These Prompts

1. Trends & Emerging Themes

👉 “Act as an industry analyst specializing in [industry]. Summarize the 5 biggest emerging trends shaping this space in the last 12 months. Include why they matter and one example for each.”
👉 “Give me a plain-language overview of what new technologies, consumer behaviors, or business models are disrupting [industry]. Rank them from most to least impactful.”

2. Regulatory & Policy Updates

👉 “You are a compliance officer. What are the newest regulations or policy changes in [industry/country] that leaders should be aware of in 2025? Provide a short summary plus links to source material.”
👉 “Create a briefing for executives on 3 recent regulatory developments in [industry]. For each, include: (1) what changed, (2) who it affects, and (3) a recommended next step.”

3. Top Headlines & News Scan

👉 “Summarize today’s top 5 headlines in [industry]. For each, explain why it matters for executives and what action (if any) leaders might consider.”
👉 “Pretend you’re my Chief of Staff. I need a daily 1-paragraph digest of the most important [industry] news for senior leadership. Keep it concise, with a focus on implications.”

4. Competitor / Market Intel

👉 “You are a market analyst. Based on publicly available news and reports, what major moves have [Competitor A, Competitor B] made in the past 6 months? Summarize in bullet points.”
👉 “Compare [your company] with [competitor] in terms of market positioning, recent launches, and strategic focus. Output a SWOT-style grid.”

5. Synthesis for Executives

👉 “Act as a McKinsey-style consultant. Create a 1-page briefing on [industry] that includes: recent trends, 3 regulatory shifts, and top headlines—all written for a senior executive who needs the highlights only.”

🔑 Pro Tips

• Always add a time frame (“in the past 6 months” vs. “all time”)

• Always add a role/context (“as if you’re a compliance officer…”)

• Always ask for sources when it comes to regulations or policy

👀 Imagine starting your day with this kind of clarity instead of playing catch-up. That’s the power of AI when you frame it right.

Your turn and I’d LOVE to hear from you!: Drop into ChatGPT (or your tool of choice), plug in one of these prompts, and see what kind of executive-level briefing you can get on your own industry.

Graphic generated by OpenAI’s DALL·E

Hey crew, welcome to Day 10!

Yesterday we gave our AI a sidekick role. Today, we’re going a little bigger — because sometimes, what you really need is less buddy and more project manager.

Program management = alignment + communication.
And let’s be real: that usually means wrangling updates from different teams, sifting through way too many docs, and trying to stitch it all together into something clear.

Good news: AI is actually shockingly good at this.

Here’s how your sidekick can step into program/project manager mode:

✨ Consolidate updates
Drop in three messy project updates and ask AI to create a clean, single-page status doc.

⚠️ Highlight risks + blockers
Instead of reading between the lines, ask AI: “What feels risky here? Where are the blockers?”

📣 Draft communication plans
Need to tell leadership one thing and your team another? AI can help you tailor updates for each audience.

📊 Create dashboards & summaries
Connect AI to your project tools (if IT lets you 😉), and it can automatically summarize tasks, deadlines, and trends.

👉 Today’s Challenge: Copy + paste three messy updates into your AI sidekick. Ask it to summarize the wins and the risks. Bonus points if you also ask for a version you could send to your boss.

Prompts for Each Scenario 🐈‍⬛

1. Consolidate messy updates → status doc
👉 Prompt:
"Here are three project updates from different team members: [paste updates]. Please consolidate them into a single status update for leadership. Make it concise, professional, and organized into: Wins, Risks, and Next Steps."

2. Highlight risks + blockers
👉 Prompt:
"Review these project updates: [paste updates]. Identify potential risks, blockers, or dependencies that could slow us down. Summarize in bullet points, and highlight the most urgent ones."

3. Draft tailored communication plans
👉 Prompt for Leadership Update:
"Summarize this project update for a leadership audience: [paste update]. Keep it high-level, focus on outcomes, and frame it as progress + risks."

👉 Prompt for Team Update:
"Summarize the same project update for the core team. Make it more detailed, action-oriented, and include specific next steps."

4. Create dashboards or summaries (when connected to tools)
👉 Prompt:
"Based on these project tasks and statuses from [tool]: [paste export/list], create a simple project dashboard. Organize by: Completed, In Progress, At Risk. Then summarize key insights in 3–5 bullet points."

✨ Pro Tip: Save your favorite prompt inside your AI sidekick (like a custom instruction or pinned note). That way, you don’t have to rewrite it every week — just drop in the new updates and hit go.

🔒 Quick PSA on Privacy & Responsible AI Use

Before you start feeding AI your project updates:

• Don’t paste in anything confidential, sensitive, or client-protected unless your organization has approved tools in place.

• Stick to patterns, summaries, and generic examples if you’re experimenting.

• If your company has IT-approved AI (like Microsoft Copilot, Google Duet, or Notion AI), use that for real work data. If not, treat free tools like ChatGPT as your practice sandbox.

• Always review and edit the AI’s output before sharing — you’re still the human in charge of alignment + context.

✨ Think of it like this: AI can herd cats, but you’re still the cat whisperer.

Shoot me a comment and let me know how you're doing. It's awfully quiet out there, crew.

Image: A retro robot assistant illustration, Rosie-inspired. Generated with AI (ChatGPT + DALL·E)

Hey everyone! Welcome to Day 9 of our journey. Today, we’re diving into something that I hope will spark some excitement: creating your own personal AI sidekick.

Yes, really! We’re talking about building a little digital assistant that’s customized just for you. This builds on the personal prompts we’ve been playing with so far — and takes it to the next level.

✨ The best part? It only takes a few minutes.
⚠️ The catch? Depending on the path you pick, it might require a subscription or asking IT to enable something in your workplace tools.

🧑‍🤝‍🧑 First, what the heck is an “agent”?

People throw this word around a lot, so let’s make it plain: an agent is basically AI that can either talk to you or do things for you.

Types of AI Agents

💬 Chatty Sidekick

• Description: A conversational helper that mostly just answers you.

• What It Can Do: Brainstorm ideas, answer questions, draft text.

• Other Terms: Conversational agent, chatbot

⚡ Task Runner

• Description: Goes beyond chatting and actually does things by connecting to apps/tools.

• What It Can Do: Send emails, update your calendar, pull data.

• Other Terms: Tool-using agent, workflow agent

🎯 Specialist

• Description: Trained for one niche domain or expertise.

• What It Can Do: Analyze X-rays, review contracts, run analytics.

• Other Terms: Domain-specific agent, vertical AI model

🤖 Autonomous Agent

• Description: Independent AI that takes a big goal, breaks it down, and keeps going without prompts.

• What It Can Do: Research, generate reports, monitor data.

• Other Terms: Autonomous agent, AutoGPT-style

👉 Today, we’re building your own Chatty Sidekick. Over time, you can upgrade it into a Task Runner or even an Autonomous Agent.

Option 1: The Freebie Route

Not ready to pay yet? No problem. You can still play!

• Try TextCortex (they have a free GPT Builder).

• Give your sidekick a name, role, and a few instructions.

• It won’t be as powerful as ChatGPT Plus, but it’s perfect for dipping your toes in.

Option 2: The Paid Quick & Easy Route (ChatGPT Plus)

If you’re ready to invest a little (~$20/month), ChatGPT Plus lets you create Custom GPTs right inside ChatGPT.

Here’s the fast path:

• Open Explore GPTs → + Create.

• In Create, describe what you want (the GPT Builder guides you).

• In Configure, paste in one of the instruction templates below.

• (Optional) Upload files (like policies or FAQs).

• Toggle capabilities: Web browsing, Image generation, Data analysis.

• (Optional) Add connectors/actions for task-running powers.

• Test it in the preview.

• Publish privately, with a link, or in the GPT Store.

⚡ Safety note: Be mindful if you add connectors. Only grant access to what’s truly needed.

Option 3: The Enterprise Route (Microsoft 365 Copilot Studio)

If your workplace uses Microsoft 365, you may already have Copilot in apps like Word, Outlook, and Excel. That’s handy for everyday drafting and summarizing — but if you want to build your own GPT-style copilot for your company, you’ll need Copilot Studio.

💡 Tip: Copilot Studio is an add-on license, so you might need to ask your IT team to enable it. Just say:

“Hey, can we turn on Copilot Studio so I can build a custom assistant for our team?”

How it works:

• Go to copilotstudio.microsoft.com and sign in.

• Click + Create Copilot, give it a name and set its language.

• Paste one of the instruction templates below as its “job description.”

• (Optional) Connect it to SharePoint, company docs, or FAQs.

• (Optional) Add actions with Power Automate.

• Test it, adjust as needed.

• Publish & share in Teams, your intranet, or even your website.

📝 Copy-Paste Instruction Templates

Here are three ready-to-use starting points. Just copy one into the Instructions (for Custom GPT) or Job Description (for Copilot Studio):

• The Organizer Sidekick

You are my personal digital sidekick. Your job is to help me stay organized, draft emails and posts in my voice, and summarize information clearly. Always keep your answers short, friendly, and practical. Avoid jargon.

• The Research Buddy

You are my research partner. Your job is to quickly find, summarize, and explain information in plain English. Always give me 3–5 bullet point takeaways, and suggest a next step I can take with that knowledge.

• The Motivational Coach

You are my encouraging coach. Your job is to help me stay focused and motivated during the day. Keep responses upbeat, supportive, and practical. Use positive reinforcement and end each response with a small action I can take.

🎯 Today’s Challenge

👉 Pick one path (Free, Paid, or Enterprise) and create your first custom AI sidekick.

Let me know how it went!
Which template did you choose — Organizer, Research Buddy, or Motivational Coach? Or did you make your own?

I can’t wait for you to meet your new digital teammates.

Ever been asked (or “voluntold”) to run an event? Team offsite, client workshop, company happy hour… it can feel like a lot.

And the same skills show up in real life too: baby showers, volunteer events, milestone parties. Today we’ll focus on work, but you can use these prompts anywhere.

How AI Helps:
Think of it as your planning buddy. Instead of staring at a blank page, let AI draft:

• Timelines

• Agendas

• Checklists

Today’s Challenge

Try one of these prompts and customize it to your needs:

• “Plan a half-day team offsite for 15 people, including icebreakers, lunch, and wrap-up.”

• “Provide me a full-day client offsite agenda. I want to include a discovery meeting, lunch, and a fun, low-key morale event at the end.”

• “Create a checklist for organizing a 2-hour volunteer event with 50 attendees. Include setup, volunteer roles, and teardown.”

Prompt Add-Ons

Want more detail? Add one of these at the end of your prompt:

Logistics & Checklists

• Add supply checklist with estimated costs

• Highlight deadlines and responsibilities

• Include accessibility considerations

• Draft a comms plan (invites, reminders, follow-up)

Creativity & Engagement

• Suggest morale-boosting activities

• Recommend relaxed venues/settings

• Add hybrid-friendly options

• Include wrap-up activities tied to goals

Professional/Personal Blend

• Tailor for nonprofit volunteer events

• Adjust for milestone parties (about 30 guests)

• Show a budget-friendly version under $500

• Make it family-friendly with kids’ activities

Data Protection Reminder

• Do not share personal info (names, emails, client details).

• Use placeholders like “Client X,” “Team A,” or “Lunch at [local restaurant].”

• Golden rule: only type what you’d share with a colleague.

Pro Tip for Free Plan Users

• Free users can turn off “Chat history & training” under Settings → Data Controls.

• When off, chats won’t train models, but they are still stored for 30 days for safety review.

• Free or paid, treat AI like a public workspace.

Shoot me a comment

• Are you guys still with me? Hit me with a comment and let me know if this resonates or is useful!

Three simple tracks to turn AI into real work wins: meetings, nonprofit grants, and one‑page authority assets.

Hey crew,

You’ve made it to Day 7 of our 14‑day AI challenge—who’s still with me? 🙋‍♀️ I hope this low‑pressure sprint has helped you dabble more effectively with generative AI. Over the past week we’ve explored ways AI can help when life gets lifey.

Quick Recap: Days 1–6

• Getting started: platforms + the core structure of a great prompt

• Self‑care ideas: using GPT for tiny joys (shoutout to the new pedi spots!)

• Meal planning: including reverse‑searching a beloved recipe from just the ingredients

• Mental load helpers: thank-you notes + school comms, simplified

• Career glow‑up: job search prompts and résumé refresh

• Declutter practice: your mind, your inbox, and even the hallway closet

Today’s Theme: From Me to We

It’s time to roll up our sleeves and point this energy at work. We’re tackling a few common professional scenarios where AI can be your quiet, competent assistant—no cringe, no buzzword soup.

Goal for Day 7: Create one tangible work asset in ≤45 minutes.

Pick one track below (follow your energy):

Track 1: Meetings & Calendar (keep it simple)

What you’ll make today: a cleaner week with prioritized meetings and focus time.

Copy/paste your next 2 weeks of meetings (titles + dates/times), then paste this:

Prompt:
“You are my calm chief of staff. Using the meetings below (next 2 weeks, add time zone]), do three things:

1. Prioritize each meeting with: Priority = High/Med/Low and Role = Decision / Input / FYI (1-line why).

2. For High and Decision items, suggest a prep block (15–30 min) scheduled before the meeting. Include: title, exact date/time, and a 3-bullet prep checklist (docs to skim, questions to answer, outcomes to clarify).

3. Mark any FYI/Low items that could be async and draft a polite decline I can paste.
   Keep the whole plan skimmable, grouped by date, and cap total prep time at ≤90 minutes for the week.”

Track 2: Nonprofit Grant (research & first draft)

What you’ll make today: a one‑page Funder Fit Brief or a 120‑word LOI.

Do this (20–25 min):

1. Pick one funder.

2. Paste key text from their guidelines into the prompt below.

3. Generate a checklist of eligibility, deadlines, word counts, attachments.

If you have 45–60 min: draft a short letter of inquiry (LOI) with request amount, 1 data point about need, 2–3 activities (example: “Run 12-week after-school soccer clinics (2x/week) for 120 middle-schoolers across 4 schools, led by USSF-licensed coaches.”), and 1–2 outcome metrics (e.g. 75% of participants meet daily activity guidelines by week 12.).

Paste‑ready prompts:

“From this grant text, list all requirements as checkboxes. Group by: Eligibility, Narrative sections (with word limits), Attachments, Budget rules, Deadlines.”

“Write a 120–150-word

LOI for [Nonprofit] in [city] serving [population]. Include problem (1 data point), approach (2–3 activities), outcomes (1–2 metrics), and request $[X]. Tone: clear and non‑jargony.”

Track 3: Authority & Assets (show your work)

What you’ll make today: a 1‑page case study or service one‑pager.

Do this (20 min):

1. Pick one recent win.

2. Fill this skeleton: Client • Challenge (2 lines) • Approach (3 bullets) • Outcome (numbers or quotes) • CTA.

3. Share as a Google Doc or LinkedIn post.

If you have 40–45 min: export to a clean PDF and add it to your LinkedIn Featured.

Paste‑ready prompt:

“Turn these notes into a 1‑page case study (your tone: clear, no fluff). Use bold mini‑headers: Client, Challenge, Approach (3 bullets), Outcome, CTA.”

Which GPT should I use? (easy picks)

Use any solid general model (ChatGPT, Copilot, whatever) and keep your instructions simple. These starter helpers work great:

• Calendar Co‑Pilot (for Track 1): “You are my calm scheduling assistant. Be brief. Help me protect focus, shorten meetings, and write polite declines.”

• Grant Scout (for Track 2): “You are a grants researcher for a small nonprofit. Extract requirements from RFPs, build a one‑page funder brief, and draft 120‑word LOIs in plain language.”

• Case Study Polisher (for Track 3): “You are a marketing writer for a boutique consultancy. Turn messy notes into a 1‑page case study with bold headers and specific outcomes.”

Tip: Save each as a custom GPT (or a pinned system prompt) so you can reuse it. (not sure you can do this with free subscription but definitely let me know!)

Just do it

• Let them stack meetings—you’ll stack outcomes - use AI to create boundary emails or determine if something can be asynchronous.

• Start tiny; ship something.

• Clear beats clever. One page > no page.

P.S. Free vs. Paid Tools

If you’re still on a free tier, amazing—use what you’ve got. If you’re using AI more and want to experiment, the $20/month paid plan can unlock things like custom GPTs and more capable models. Not required; just a lever if you’re ready to tinker.

Your Day 7 Checklist

• ☐ Pick one track

• ☐ Run the prompt(s)

• ☐ Ship one asset (email, case study, or system)

• ☐ Block next week’s Deep Work

• ☐ Post your win (1 sentence + screenshot)

If you try one of these, hit reply and tell me what you did—I love cheering for tiny, meaningful wins. 💜

If this helped, share it with a teammate.

We made it to day 6 of our 14-day AI challenge! Can we get a little round of applause (or at least a self-high-five)? 👏

Today’s challenge is brought to you by the letter D—as in Declutter.

Now, I don’t know about you, but as much as I wish I was Type A… I’m just not. Stuff piles up. Things get messy. And honestly? Decluttering is less a one-time achievement and more a practice—like yoga or meditation. Sometimes I’m flowing gracefully, sometimes it’s more like a face plant while trying for the crow pose.

That’s why today’s prompts are as much for me as they are for you. If only AI could declutter our closets in real life (I know people are building humanoids!). But generative AI can help us clear the mental, physical, and digital clutter so we feel lighter and more focused.

So, let’s channel our inner Marie Kondo and tackle three zones today:

✨ Declutter your mind — create focus and calm
✨ Declutter your space — hallway closet refresh
✨ Declutter your inbox — sanity over inbox zero

1. Declutter Your Mind 🧘‍♀️

AI Prompt (copy & paste):

I have these tasks: [list 5–8].  

Act as my calm prioritization coach.  

- Pick my Top 3 for today (impact × effort).  
- Write each as one clear sentence with a finish line.  
- Make me a simple 90-min schedule with breaks.  
- End with 2 things:  
   1) A short boundary script if someone tries to add more work.  
   2) A pep talk reminding me I’m already doing a lot, I’ve got this, and I deserve to feel clearer and more focused.  

2. Declutter Your Space 👟🧥

Let’s start small—your hallway closet.

AI Prompt (with photo upload):

I’m uploading a photo of my hallway closet.  
Act as a professional organizer for small spaces.  

Based on what you see in the photo:  
1. Describe the current state in 2–3 sentences.  
2. Suggest a simple 3-zone layout (Daily / Guest / Seasonal).  
3. Recommend what I should keep, move, or donate.  
4. Give me a 20-minute tidy checklist I can follow step by step.  
5. Suggest 2–3 budget-friendly storage ideas (like bins, hooks, shelves).  
6. End with one motivational one-liner to keep me going.  

3. Declutter Your Inbox 📬

AI Prompt (copy & paste):

Help me clean my inbox.  

1. Give me 3 simple rules I can set to auto-label or auto-archive:  
   - Newsletters  
   - Promotions  
   - System alerts  

2. Write 2 short, kind reply templates:  
   a) “Not now” → for when I can’t take something on.  
   b) “Delegating” → for when I’m passing it to someone else.  

3. Make me a 15-minute bulk-archive plan I can follow step by step (Gmail-friendly).  

You Got This 💡

✨ Progress over perfection.

Even as we lean in and learn how AI can help us with life hacks and little personal-assistant wins, let’s not forget: we’re juggling a lot.

Are we making progress? Yes. Even if it doesn’t always feel that way. Sometimes change looks like mulling, circling, or stalling before the breakthrough. And sometimes a closet (or inbox, or mind) has to get extra cluttered before we finally make the big shift.

You’re doing the work. You’ve got this. 🌟

Whether you’re eyeing a new role—or trying to help your grown-ass kid land a decent job—AI can be a surprisingly useful sidekick in the search. Sure, nothing beats activating your network (still the #1 move), but there’s something seriously confidence-boosting about sending out a résumé you know is polished and on point.

Just yesterday, one of our challengers tested this exact approach for her own résumé refresh—and it worked. That’s what inspired today’s challenge.

Step 1 (2–3 min): Find your dream job description & grab the keywords

Copy a job description and paste it into your AI with this prompt:

Prompt 1: Extract the 12–15 most important keywords/phrases from this job description. Group them as Tools, Core Skills, and Responsibilities. Keep it concise.
JD: [PASTE JD]

This gets you a cheat sheet of the exact language employers care about—no second-guessing.

Step 2 (3–4 min): Rewrite 3 bullets

Now, let’s upgrade some résumé bullets. Paste 3 bullets you want to improve and add this:

Prompt 2: Rewrite these 3 résumé bullets to align with the JD keywords—truthfully. Keep each under 2 lines, include scope + method + outcome. Do not invent facts; keep my achievements intact but clearer.
JD keywords: [PASTE LIST]
My bullets:
– ...
– ...
– ...

Pro tip: If you can, add one metric per bullet (time saved, revenue, adoption, cost, scale). If you’re not sure what to measure, ask AI this:

Prompt 3: Suggest realistic ways to quantify these bullets (e.g., # users, $ budget, time-to-delivery). Do not make up numbers—give me questions to ask or places to look to find them.
Bullets: [PASTE REWRITTEN BULLETS]

Step 3 (2–3 min): Headline + quick scan

Give your résumé a job-specific headline and summary. Prompt AI like this:

Prompt 4: Write a 10–15-word résumé headline and a 2–3 sentence summary that naturally includes 6–8 of the JD keywords. Then scan my bullets for: any missing critical keywords, any signs of keyword stuffing, and any formatting risks for ATS (tables/text boxes, odd fonts).
JD: [PASTE JD]
My bullets/summary: [PASTE TEXT]

What to keep (and what to skip)

✅ Mirror the employer’s language
✅ Keep verbs strong
✅ Let real results do the talking

❌ Don’t add tools you’ve never used
❌ Don’t cram a keyword 6 times
❌ Avoid fancy tables/graphics that confuse ATS

Done? Share your win - how did it go?🎉

Post one before → after bullet and one keyword you added that clarified your value.
Bonus: Update your LinkedIn headline with your new job-specific headline.

Writing is one of my favorite ways to clarify my thinking, dig deeper into a topic, and prepare myself to speak with confidence. But let’s be honest: whether it’s a thank-you note, a social post, or a paragraph for a grant proposal, writing can also feel intimidating.

AI as your brainstorming buddy or editor

That’s where AI can help. Think of it as your brainstorming buddy — a way to get past the blank page, polish your draft, or outline ideas. Personally, I like to start with my own words and then ask AI to review or suggest edits, but sometimes a quick AI-generated draft gives me the momentum I need.

Pro tip: Always make it your own. AI can help with structure, tone, or flow — but your heart and personal touch are what make writing land.

Day 4 prompts

Here are three prompt options to try for Day 4:

1. Nonprofit Focus (Donor/Supporter Note)
   “Help me draft a warm thank-you email to a donor who contributed to our nonprofit’s recent campaign. Keep it under 150 words, make it genuine, and highlight how their support directly helps our mission.”

2. School / Family Admin
   “Draft a short, kind, and clear email to my child’s school office letting them know my kid will be absent on [date]. Keep it polite and professional, around 3–4 sentences.”

3. Networking / Career Growth
   “Write a professional but approachable networking email to someone I met at a recent conference. I want to thank them for the conversation, mention what inspired me, and suggest grabbing coffee to continue the discussion.”

Each one shows how AI can save time and reduce the stress of staring at a blank page — while still leaving space for you to personalize before sending.

Five guidelines to protect privacy

A quick but important note on privacy: if you’re using AI to draft communications (especially in nonprofit or job-search contexts), keep these five guidelines in mind:

4. Don’t Paste Sensitive Information
   Never share passwords, Social Security numbers, health data, or financial account details. Treat the chat box like a semi-public space.

5. Know Where Your Data Goes
   Free or consumer AI tools may use your inputs to improve their models. Enterprise versions (like ChatGPT Enterprise or Microsoft Copilot within a corporate tenant) have stricter protections. Know which one you’re using.

6. Redact and Anonymize Before Sharing
   If you want help with an email or grant draft, swap names and details with placeholders like “[donor name]” or “[organization].”

7. Treat Outputs as Drafts, Not Finals
   AI text can sound convincing but may contain errors or “hallucinations” (side note, I recently learned that using the word “hallucinations” is not considered inclusive language — “ungrounded” is another way of speaking about it.) Always fact-check before sending anything important.

8. Use Secure, Trusted Platforms
   If you’re handling sensitive nonprofit or client data, use platforms with clear privacy protections (e.g., Microsoft Copilot, Anthropic’s Claude for Business, OpenAI Enterprise). General rule: If you’re an individual contributor - just make sure to leave the personal info out of your gen AI work.

AI is here to make writing easier, not replace your voice. Use it to clear roadblocks and free up energy for the parts of writing that matter most: connection, clarity, and authenticity.

Try a prompt and let me know how it went — reply to this email or drop a comment. Which one felt most useful for you? Any interest in diving deeper into how to use AI for any of these specific scenarios?

I don’t know about you, but in my house only one of the grown-ups is really good about meal planning. Hint: it’s not me.

I’ve had stretches where I dutifully sat down every Sunday to plan a week’s worth of meals. But lately it’s more like open the fridge, cross my fingers, and hope dinner makes itself.

The good news: AI can actually help us out here. It’s great at spinning up meal ideas, organizing shopping lists, and nudging us out of the rut of cooking the same three recipes on repeat.

Since Day 3 falls on a Sunday, it feels like the perfect time to play with meal-planning prompts. But first—let’s answer the big question…

What the Heck Does GPT Mean?

Factoid of the day: GPT stands for Generative Pre-trained Transformer.

Which, honestly, feels like an engineer named it (no offense, engineers). Wouldn’t “Smarty Robot Buddy” or “Recipe Genie” have been clearer?

In plain English:

• Generative = it can create new stuff (like text or ideas).

• Pre-trained = it learned from a giant pile of information already.

• Transformer = the type of model it uses to understand patterns in words.

So when you give GPT a prompt like “here’s my fridge—now what?” it’s basically scanning its giant playbook of food knowledge and remixing it for you.

Quick Refresher: Prompt Structure

A good prompt usually has:

1. Context – what’s the situation?
   “Here’s what’s in my fridge…”

2. Instruction – what do you want AI to do?
   “Make me a 3-day meal plan.”

3. Constraints/Style – how should it be done?
   “Keep it healthy, low fat, and include breakfast, lunch, dinner, plus one snack per day.”

4. Optional Extras – anything special?
   “Make it kid-friendly, or support hormone balance with calcium-rich foods.”

Prompt of the Day

Copy/paste and try this one out:

“Here’s what’s in my fridge [list items]. Can you create a healthy 3-day meal plan using these ingredients? Please include breakfast, lunch, dinner, and one snack per day.”

Super Fun Bonus Activities

• With text only: Try adding a dietary goal (like “help me build muscle” or “make it kid-friendly (I added “make sure meals support hormone balance and include calcium-rich foods to support bone density.”).

• With photos: Snap photo of what’s in your fridge → upload (easiest on mobile app) → prompt. The nice thing? AI won’t judge how packed and disorganized your fridge might be.

Beauty of a Hack for Instacart Users

• Go to Account → Orders in Instacart

• Open your most recent order

• Screenshot it

• Upload it to your AI tool (if your platform allows images)

• Add today’s meal-planning prompt and boom—personalized recipes.

Pro tip: the free versions usually have limits on photo uploads, so try text first if you’re testing things out.

Did AI help you come up with a meal plan this week — or even just for the next couple of days? I’d love to hear what you tried and what worked (or didn’t!). Drop a note in the comments and share your experiments. Thanks for being on this little journey with me — we’re learning together, and I hope you’re having a little fun too.

Weekends are a chance to hit reset. Instead of filling the day with errands, what if you designed a Saturday that was all about you? Sometimes it’s hard to know where to start — so let AI be your brainstorming buddy. Think of it as a way to tease out what lights you up and turn it into a day that feels indulgent, restorative, and just plain fun.

A bunch of us on this challenge are parents of kids that don’t need us the same way they used to (ahh, remember those days?). Maybe they’re grown and out of the house, or just on the path to independence. It can feel bittersweet — but it’s also a wonderful time to carve out space for yourself. Believe it or not, AI can be a surprisingly fun tool for this too!

Feel free to stick with the same platform you tried yesterday or test out another one.

Here are a few quick links:

• ChatGPT (OpenAI)

• Claude (Anthropic)

• Google Gemini

• DeepSeek

• Microsoft Copilot

Today’s Prompts

• Prompt 1: AI as your brainstorming buddy
  “Act as my brainstorming buddy. Ask me a few questions to help me uncover what I really enjoy (like favorite hobbies, foods, places, or activities). Then, use my answers to design a ‘treat myself’ Saturday plan that balances fun, rest, and something a little adventurous. Keep it realistic, like a schedule I could actually follow.”

• Prompt 2: AI as your day designer
  “I’m a mom of independent kids who don’t need me all the time, and I love <fill in your favorite things here: singing, being outdoors, shopping, sporting events, day spas…>. Design a Saturday all to myself that blends those interests into a realistic, recharging schedule. Include suggestions for specific activities, timing, and ways to make the day feel special.”

(Any Parks & Rec fans out there? Think of this as your personal ‘Treat Yo’ Self’ day, powered by AI.)

This second prompt works anywhere — just add your city or town and see what local gems pop up. You might discover activities or spots you’ve never thought about before.

Pro tip: AI is still just a robot. Definitely double-check that places it suggests are real and open before you jump in the car!

Share Back

Once you’ve tried one of today’s prompts, share a little piece of your ‘treat yo’ self’ Saturday plan in the comments. It could be your favorite activity AI suggested, a funny twist it came up with, or just the vibe of your ideal day.

I’m so excited to jump into this little experiment with you. Over the next 14 days, we’ll explore a low-pressure way to engage more deeply with AI — shake off intimidation, learn how to pick a platform, practice writing good prompts, and know what to expect along the way.

First, thank you for joining me. Let’s get curious, experiment, and most importantly — have some fun.

How the Challenge Works

• Week 1: We’ll get familiar with what generative AI is, explore the free tools out there, practice writing prompts, and try out personal use cases (meal planning, school emails, job hunting, etc.).

• Week 2: We’ll shift into work and professional life — how to use AI as an assistant, speed up admin tasks, and even get help on presentations.

What the heck is Generative AI?

Generative AI is like having a really well-read friend who’s read every cookbook, manual, and blog post.

• You give it a spark — a question, a task, an idea.

• It takes patterns it’s learned and creates something new: a draft email, a meal plan, a picture, even a bedtime story.

• It’s not “thinking” like a person. It’s more like supercharged autocomplete — guessing the next word, step, or image until something useful appears.

Sometimes it gets things wrong (like a friend misremembering a recipe). But most of the time, it saves you time, energy, and brain space. That’s why starting with low-stakes experiments — meal plans, quick thank-you notes, even tightening a toilet seat — is the best way to build confidence.

What Tools You’ll Need

For this challenge, you’ll want:

1. A platform to try (start with free options unless you already have a subscription). Check below for options.

2. Your imagination and lived experience — where could you use a little help right now?

   

Maybe you’re:

• Supporting a nonprofit that you volunteer with

• Figuring out your next career move

• Keeping up with back-to-school emails and kids’ schedules

• Looking for an assistant to lighten your workload

AI can help in all of these situations.

A Quick Glance at Four Starter Platforms

What’s a Prompt?

Think of a prompt as the recipe card you hand your robot helper.

• If you just say, “Make dinner,” you’ll get something random.

• If you say, “Make me a quick chicken stir fry with rice and broccoli in 20 minutes,” your AI helper knows exactly what to do.

That’s prompting — telling the AI what you need, in plain English.

For this challenge, think of prompts with three parts:

3. Role/context — who the AI should “be” (teacher, assistant, coach).

4. Task — what you want it to do.

5. Details/constraints — any specifics (style, length, tone).

Today’s Challenge

6. Pick a tool from the table above.

7. Try this starter prompt:

“Act as my personal assistant. Explain in simple terms what AI is, what’s happening ‘under the hood,’ and give me one fun way I can try it today using a free tool.”

8. Share what you discover! Drop a comment with the tool you chose and what surprised you about the response.

That’s Day 1. Tomorrow we’ll dive deeper into prompts and start applying AI to everyday “life stuff.”

This September, I’m launching something fun, approachable, and totally non-intimidating:

👉 Want a reminder when we kick off? Just pop your email below and you’re in.

Subscribe now

The 14-Day AI Challenge

A mini personal-to-professional adventure to help you explore how AI can support your real life—and your work—without the tech overwhelm.

What It Is:

A two-week guided series delivered straight to your inbox (via Substack) with one small prompt each day.

• 🧠 Week 1: Use AI to make life easier (think: meal plans, writing help, mental clutter clearing)

• 💼 Week 2: Use AI to plan your goals, set OKRs, and communicate with clarity

Each day takes just 5–10 minutes and is designed to build confidence, not dependency. No tech jargon. No AI hype. Just helpful, human-centered tools you can actually use.

Who It’s For:

• People who’ve opened ChatGPT… and froze (or those that haven’t even gone there yet)

• Leaders and changemakers who want to use tech with intention

• Nonprofit folks, purpose driven brand leaders, PMs, consultants, and curious humans

• You, if you want to start the fall grounded and clear-headed

What You’ll Walk Away With:

✅ A clearer understanding of how to write useful AI prompts
✅ Tools to make content, communication, and planning smoother
✅ A 90-day roadmap draft for your fall goals
✅ (Maybe a few silly AI-generated vacation ideas too)

Start Date: September 12, 2025

👉 Want in? Subscribe here and you’ll get all the challenge posts sent to your inbox when we kick off.

You can also bookmark this page or forward to a friend who might want to join too!

Until then, keep stay curious!
—Emily