For the in-between moments

Turn what-ifs into brave next steps.

The Maybe Project™ is a framework, a book, a podcast, and a coaching practice for anyone standing in the fertile space between doubt and determination.

Book Workbook Podcast Soundcheck Coaching Speaking Instagram LinkedIn
Rob McLoughlin
Maybe
Turn What-Ifs Into Brave Next Steps
The Book
★★★★★

Maybe: Turn What-Ifs Into Brave Next Steps

A self-help book built around the seven-stage Maybe Loop — a framework for moving through uncertainty with honesty, courage, and grace. Written for anyone who has a question they can't shake and isn't sure what to do about it.

"Wonderfully thoughtful and actionable book. To anyone else who has the book and has just been letting it whisper, 'maybe, maybe, maybe' — just read it already!"
— A Reader
"Every page of this book reminded me of all the maybes along my career that became the start of something magical. If you want to explore your maybes, maybe it's time for you to read it too!"
— A Reader
Companion Workbook
The Maybe Pages
A Workbook for Your Own Maybe
The Companion Workbook

The Maybe Pages

The companion workbook — nine chapters of prompts, exercises, and reflection space to turn a "maybe…" into a step you actually take. It's built to pair with Maybe: Turn What‑Ifs Into Brave Next Steps, but works just as well on its own.

Working through it? Pair it with the Seven-Day Maybe Challenge — one small experiment to try over seven days.

The Maybe Loop™

A seven-stage framework for working through the decisions that matter most — not by eliminating uncertainty but by moving through it honestly. The loop is not linear. It breathes.

01
Spark of Possibility
The moment a question arrives that won't stop tugging at you.
02
Emotional Weather
Mapping the feeling beneath the question before you strategize.
03
Navigating the Unknown
Learning to move without a complete map or guaranteed outcome.
04
Taking Action
One real, testable experiment. Not a leap — a brave next step.
05
Framing the Transformation
Naming what actually shifted — not what you hoped would shift.
06
Wisdom from the Journey
Harvesting what you now know that you couldn't have known before.
07
What's Next
The loop opens again. The next question is already forming.
∞
The Loop Returns
Maybe is a practice, not a finish line.
"Maybe" is the fertile space between doubt and determination — the moment before a life changes shape. — The Maybe Project™
Free, by email

Try the Seven‑Day Maybe Challenge.

Pick the maybe you keep circling. You'll get one short email with a small experiment to run inside the life you already have. Then take the next seven days to try it and see what your maybe actually wants.

You'll also get the Maybe newsletter on Substack. Unsubscribe anytime.

Almost there. Confirm your subscription in the Substack tab that just opened, and your challenge will be on its way.

Ways into the work.

Whether you're just discovering the framework or ready for guided 1:1 work, there's a way in that fits where you are right now.

Read

Maybe: Turn What‑Ifs Into Brave Next Steps

The book gives you the complete framework. The Maybe Pages is a separate, standalone companion workbook with space to work through your own live question.

Listen

The Maybe Podcast

Conversations that sit with uncertainty instead of rushing past it — new episodes on Spotify and Apple Podcasts.

Follow

Instagram & LinkedIn

Follow along for the ideas and moments in between episodes, plus updates on the book, workshop, and speaking.

Coming Soon

Maybe Sessions — The Workshop

A 90-minute live experience — in person or virtual, solo or with your team — walking the Maybe Loop through four parts: Riff, Verses, Chorus, Bridge. Something new is on the way.

You're on the list. Confirm in the Substack tab that just opened.
Speak

Turning What-Ifs Into Brave Next Steps

A talk on the word underneath the work: "maybe" comes from "it may be" — not a hedge, but an opening toward what you're able to become. Rob speaks on the Maybe Loop and courageous movement for organizations and leadership teams navigating change. It's a loop, not a ladder. Available for keynotes and workshops.

The Maybe Podcast

★★★★★

Episodes that sit with uncertainty instead of rushing past it — conversations designed to create room for resonance, reflection, and recognition.

"You don't need a complete life overhaul to make meaningful change — just the next right step." — A Listener
The Maybe Podcast
Maybe Is the Power to Become
Major decisions rarely arrive with cinematic clarity. This episode sits inside the messy middle of change — including the Seven-Day Maybe experiment — and shows how to right-size your next step without needing to know everything at once.
Jul 29, 2026 · 16 min
Maybe It's Time to Experiment
Introducing the Seven-Day Maybe Challenge — a way to turn an idea into a small, real experiment inside your current life. No big leaps, just repeatable steps and a focus on what you want to learn, not what you need to prove.
Jul 22, 2026 · 6 min
Maybe Not Everyone Needs to Be in My Orbit
On the people and spaces that shape how a maybe feels — some expand you, some quietly shrink what you're willing to try. Includes a simple mapping exercise to protect early possibilities and give them room to grow.
Jul 15, 2026 · 6 min

About Rob McLoughlin

Author, speaker, podcast host, songwriter, and decision intelligence researcher. Creator of The Maybe Project™ and founder of DCDR.

If something keeps tugging at you — that is enough to begin. — Rob McLoughlin
Background

Two decades at the intersection of data and humanity

For two decades, Rob has helped companies and creatives understand how real decisions get made — especially the ones that don't fit neatly into job titles, social posts, or five-year plans. Over time, he became most interested in the decisions that break those frameworks — the ones that reshape what we think we want. With Maybe, he brings that work into the room and onto the page.

Author

Maybe: Turn What‑Ifs Into Brave Next Steps

Plus The Maybe Pages, a separate companion workbook.

Speaker

Keynotes & Workshops

Bringing the Maybe Loop to teams and leaders.

Host

The Maybe Podcast

Weekly conversations with uncertainty.

Coming Soon

Maybe Sessions

Live 90-min workshop.

Also By Rob

DCDR — Decision Intelligence

Rob's organizational work lives at DCDR, his decision intelligence consultancy. DCDR helps brands, teams, and leaders make better decisions in uncertainty.

New Book · Coming Late 2026

Coherence: Align Your Story, Data, and Decisions

Rob's next book applies the same instinct behind Maybe to organizations — closing the gap between the data a company has, the story it tells, and the decisions it actually makes.

You don't have to know everything — just the brave next step.

Start with the Soundcheck, get the book, or reach out directly. The Maybe Project™ is here for the question you can't stop carrying.