The When seriesBy Shane Stanford

Practical prompts for what happens next.

LIFE GETS
MESSY.
GO DEEPER.

For the days you do not have the answers.
Start with a better question.

Two collections. Ten books in each. One useful next step.

Front cover of When You Feel Lonely Around Everyone, by Shane StanfordFront cover of When You Keep Waiting to Feel Ready, by Shane StanfordFront cover of When You've Just Broken Up With Someone, by Shane StanfordBetter
questions.
Real life.
A book for the moment you are in.

Not sure what is next?You do not have to figure it all out today.Start here.

20 books shown

For the moment you are in

THERE IS A BOOK
FOR THIS PART.

Ten books for familiar personal situations, from a breakup to starting again. Each book stands on its own.

10 of 10 books

Front cover of When You've Just Broken Up With Someone, by Shane Stanford

When You / 0164 prompts

When You've Just Broken Up With Someone

For the message you keep rewriting, the evening that feels too long, and the practical pieces that still need arranging. The conversations start from your actual day rather than a generic list of ways to move on.

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Front cover of When You Keep Putting Yourself Last, by Shane Stanford

When You / 0364 prompts

When You Keep Putting Yourself Last

For the automatic yes, the request you struggle to answer, and the needs that slip to the bottom of the list. The aim is a choice that includes you, while respecting other people and real responsibilities.

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Front cover of When You Feel Behind in Life, by Shane Stanford

When You / 0564 prompts

When You Feel Behind in Life

For borrowed deadlines, milestone comparisons, and the feeling that everyone else has already arrived. The conversations separate a social timetable from a priority that is actually yours.

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Front cover of When You Keep Waiting to Feel Ready, by Shane Stanford

When You / 0864 prompts

When You Keep Waiting to Feel Ready

For the draft nobody has seen, the start you keep postponing, and a definition of ready that moves as you approach it. The book separates necessary preparation from extra reassurance.

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Front cover of When Work Takes Over Your Life, by Shane Stanford

When You / 0964 prompts

When Work Takes Over Your Life

For work that continues after the working day, priorities that do not fit, and the life you want to make room for. Advice to log off is incomplete when income, staffing and other duties are part of the picture.

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Front cover of When You're Starting Again, by Shane Stanford

When You / 1064 prompts

When You're Starting Again

For changed circumstances, practical loose ends, and a next step that does not need a five-year plan. Starting again does not mean starting with nothing.

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For what you want to do next

WHAT DO YOU
WANT TO DO?

Ten books for practical goals, from money and work to family, learning, health and travel. Each book stands on its own.

10 of 10 books

Front cover of When You Want to Take Control of Your Money, by Shane Stanford

When You Want / 0164 prompts

When You Want to Take Control of Your Money

For a balance you know and bills you do not, a budget that misses an ordinary week, and a money conversation that becomes personal before the figures are clear. Start with a smaller question than sorting everything out.

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Front cover of When You Want More From Your Career, by Shane Stanford

When You Want / 0264 prompts

When You Want More From Your Career

For work you want to change before you can name the part that matters, and for applications that should still sound like your experience. Sometimes the next step is a form. Sometimes it is a question you have not asked.

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Front cover of When You Want Better Relationships, by Shane Stanford

When You Want / 0464 prompts

When You Want Better Relationships

For words that come out as criticism, friendships you want without keeping a tally, and disagreements that need one useful next step. Better relationships can start smaller than fixing everything.

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Front cover of When You Want Family Life to Work Better, by Shane Stanford

When You Want / 0564 prompts

When You Want Family Life to Work Better

For the small part of the day that creates more friction than it should, and for routines that stopped fitting when work, care or home changed. There is no single family shape behind these pages.

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Front cover of When You Want to Get Your Life Organised, by Shane Stanford

When You Want / 0664 prompts

When You Want to Get Your Life Organised

For the task you remember at the wrong moment, the plan that forgets travel and preparation, and a system that has to survive a change in time or energy. Start with what you want to find more easily.

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Front cover of When You Want to Learn Something New, by Shane Stanford

When You Want / 0764 prompts

When You Want to Learn Something New

For courses you have saved and not started, explanations that slip when you try to use them, and learning that has to fit the life you already have. The useful question is what you want to be able to do.

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Front cover of When You Want to Travel More, by Shane Stanford

When You Want / 1064 prompts

When You Want to Travel More

For a trip that has to fit your money, time and needs, with room left in the day. Wanting to travel more can start with one journey that suits the life you have.

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More than a list of questions

DO NOT JUST ASK.
GET SOMEWHERE.

A book. A conversation with ChatGPT. Something useful to take into your day.

01

Start with your moment.

Find the situation that sounds like today. Copy the starting prompt and add the details you want to share.

02

Make the answer fit.

Use a deeper question. Correct the assumptions. You direct the conversation, and you can disagree with it.

03

Take one next step.

Leave with a small action, clearer words or a question to check. Every exercise includes a stopping point.

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SMALL QUESTION.
USEFUL SHIFT.

A broad question leaves the answer with nothing to hold. Here is where book 08 begins. Try it as it is, or make it your own.

Open this book
WHEN YOU / 08A START

Define what ready would mean.

You cannot describe the feeling you are waiting for.

Help me define readiness for one specific action through something I can observe, rather than a feeling of certainty.

Two collections. Your next chapter.

YOU DO NOT NEED
TO BECOME SOMEONE ELSE.

You need a question that meets you where you are. The When You books and the When You Want collection by Shane Stanford turn everyday situations and goals into focused conversations, with room to question the answer and choose your own next step.

Explore the collection

Before you turn the page

GOOD
QUESTIONS.

How do the two collections differ?

When You explores familiar personal situations, from overthinking to starting again. When You Want explores broader goals, including money, careers, relationships, learning, health and travel. Each collection has its own books 01 to 10, and every book stands alone.

What is in each book?

Each book contains 64 exercises in eight chapters. Every exercise includes a starting prompt, two follow-ups, a correction line, a practical next step and a stopping point.

Do I need to know how to use AI?

No specialist knowledge is needed. Choose a prompt, type it into a text chat and add only the context you are comfortable sharing.

Where can I buy the books?

Both collections are being prepared for sale. Confirmed listings will be added when they exist. This site does not take payment, and the buttons marked coming soon do not open a shop.

What are the companion pages?

Each book prints a link such as whenseries.com/companion/01. That page confirms you are in the right place. The complete exercises stay in the book.

Are these books therapy or professional advice?

No. They are tools for reflection and practical planning. The series is independently produced and is not affiliated with or endorsed by OpenAI.

YOUR NEXT CHAPTER
STARTS WITH A QUESTION.

Find your book