You Don’t Need a Plan — You Need Imagination to Design the Life You Actually Want

“Most people decide what’s impossible before they even try what’s possible.”
— Debbie Millman, renowned professor at SVA and designer

What if one exercise could change the way you see your future?

This piece brings together the million-dollar questions from an insightful podcast episode with Debbie Millman and Mel Robbins, layered with powerful inquiry from the Fulfillment module in Co-Active Coaching.

These are not productivity hacks. Not vision board fluff.

These are radical, imagination-opening questions designed to help you design a life based on possibility, not probability.

Whether you’re in your 20s or 60s, standing at a crossroads or craving reinvention, these questions are your starting point.

Why Questions to Imagine Matter

Designing your life isn’t about having the “right” answers.

It’s about asking better questions—questions that make space for your truest desires.

You don’t need a strategy to start.

You just need the courage to admit what you really want.

Wake Up in 10 Years from Now

“It’s September 16, 2035. In 10 years from now. You open your eyes. Where are you?”

Don’t overthink it. Don’t future-proof it.

Just write.

Let your imagination lead. Let the details get sensory:

Light. Smell. Sound. Texture. Silence. Connection.

What if everything you wanted had already come true?

Ask Yourself:

• What kind of light comes through the window?
• Who’s with you—or not?
• What do your sheets feel like?
• What does your home look like?
• What does your morning smell like?
• What are you wearing?

Now layer in Co-Active:

• What do you appreciate most in this scene?
• What values are being honored here?

💬 Try this:

“I wake up in a small house and an art studio in the woods. I hear trees and birds. I make coffee slowly. There’s no rush.”

Live in Your Perfect Day

“What Does Your Day Look Like in 10 years?”

• Where do you go to work?
• Do you walk, bike, drive, or Zoom?
• Do you travel for your job?
• What kind of conversations do you have?
• What excites you about your work?

💬 Co-Active prompt:

What part of this day makes you feel most alive?

Find Love that Nurtures You

“What kind of love do you need?”

• Constant? Quiet? Wild? Respectful?
• Who are you with? And why do you love them?
• How do you feel in their presence?
• What kind of love do you offer in return?
• Who do you allow yourself to be around them?

💬 Prompt yourself:

“In this future life, love looks like…”

And now ask:

What would it be like to fully receive the love you long for?

What Do You Choose with Money

“What is your relationship with money?”

• How much do you need? How much do you want?
• What would you do with it?
• What’s the first belief you need to change about money?

💬 Prompt yourself:

“What if money became a tool for beauty and generosity?”

💬 Fulfillment layer:

What value do you wish your money reflected more clearly?

What Are You Practicing?

“What have you developed mastery of?”

Mastery takes time. Years. Maybe decades.

What have you given yourself permission to love long enough to master?

• What have you stuck with — even when it was slow?
• What took time but felt worth it?
• What are people thanking you for?

Please note: It’s okay to hold many interests. It may take longer — but you’re allowed to enjoy the process.

💬 Reflection:

“It took ten years, but now I…”

💬 Co-Active lens:

What is your soul calling you to stay with, even now?

What’s Been Hiding in You?

“What are five things you would do if you knew you could not fail?”

• What would you try, launch, create, or become?
• What would you say yes to and no to?
• What would you stop apologizing for?
• What have you secretly dreamed about for years?

💬 Reflection tip:

• Don’t censor. Don’t worry if it “makes sense.”
• What dream have you been quietly denying?
• Notice which ones make you laugh, blush, or tear up.. That’s the one to write more about.

Listening to Your Desire

“What are you jealous of?”

Jealousy is not ugly. It’s a flashlight.

It illuminates a life you secretly want.

• Who do you admire, and why?
• What part of their life calls to something in you?
• What does their life reveal about what you secretly want?
• What would your jealousy say if it had a voice?

💬 Ask yourself:

“What does my jealousy want me to notice?”

What Are You Telling Yourself You Can’t Do?

“What are you telling yourself you can’t do… that you actually can?”

• What voice holds you back?
• What has that voice protected you from?
• What has it helped you survive?
• What would change if you thanked it and chose anyway?

💬 Knowing what you know now, ask yourself:

“What are you choosing now?”

A Personal Exercise in Imagining the Impossible

This isn’t a worksheet.

It’s an invitation to imagine.

Light a candle. Get quiet. Write slow.

Read the questions like poetry.

Pause where your breath catches.

You don’t need to answer them all.

Just the ones that won’t leave you alone.

What Happens After the Vision

You close the notebook. You take a walk.

Maybe nothing changes.

Or maybe…

You begin noticing where you’re shrinking.

You begin listening to what you’ve been denying.

You start hearing your own longings again — under the noise.

You begin giving yourself permission to want without needing proof.

You stop asking how.

You start asking what if.

You Don’t Need More Confidence. You Need Imaginations.

We’re not here to be efficient.

We’re here to be fulfilled.

We’re not here to shrink to fit the space.

We’re here to take up space — beautifully, unreasonably, with color and courage.

You don’t need a five-year plan.

You don’t need to make it make sense.

You just need to want what you want.

And say it out loud.

CREDITS & INSPIRATION

🌀 The questions in this piece draw from:

• Debbie Millman’s 10-Year Visioning Exercise, as shared in her design classes and the Mel Robbins Podcast
• The Co-Active Coaching Fulfillment Framework, from the Co-Active Training Institute’s curriculum

To both bodies of work: thank you for the questions that crack us open.

🌱 One Last Question:

“If not now, when?”

If something stirred while you were reading — even just a little —

and you’d like to explore it with someone who knows how to sit with the unknown,

I’d be honored to hold space with you.

Let’s begin with a gentle conversation.

— Jay