Turning Lived Experience into a Year-Long System
The messy, honest beginning of building a 365-day guided journal.
You never get clarity before you start.
You get it once you’re in motion.
Today proved that.
Last week’s announcement felt like the beginning but today is when the project actually became real. Not glamorous-real, not polished-real, but the kind where you sit with a blank page, start pulling on threads from your own life, and watch an entire vision begin to form.
What Today Looked Like
Today is only my second real day of working on this journal, and I’m still finding my rhythm; still figuring out how I want to shape this thing and what direction feels honest.
Most of today wasn’t “writing a book.” It was uncovering.
I went back through almost everything that’s helped me grow over the last three years:
the books I’ve read (close to a hundred)—in case you are interested, I will include at the bottom of the article :)
three full notebooks of daily journaling since July 14, 2022
quotes I’ve saved
notes I’ve written in airports, coffee shops, and random side streets
the 3-month letters I write to my future self
every Substack article I’ve published in the last nine months (over 45,000 words)
Today was mostly about retrieval; pulling all of that into one place, realizing how much raw material already exists, and seeing how it might all come together.
I also drafted the Editor’s Note and an early mission statement for the journal, trying to clarify what this book is supposed to feel like:
Not pressure.
Not perfection.
A steady companion in a loud world.
A place to slow down, breathe, and hear your own voice again.
The Hardest Part So Far
Somewhere in the middle of all of this, I hit the first real “oh wow” moment of the project.
It’s one thing to grow privately—to fill notebooks, write letters to yourself, experiment with habits, and publish essays as you go. It’s another thing entirely to turn that lived experience into a clear, simple system someone else can actually use.
That’s the part I’m wrestling with right now.
This is my first “book”. My first project at this scale. And I feel a real responsibility to do it well. I don’t want this to be another journal full of random prompts or vague positivity. I think there’s a gap for something that weaves together the themes that have actually mattered in my life: presence, awareness, identity, stability, discipline, money, joy, resilience, purpose.
Right now, I’m exploring a 12-month structure that reflects that journey. Something like:
Presence & Awareness
Understanding Yourself
Past & Core Beliefs
Stability & Foundations
Habits & Discipline
Identity & Values
Self-Talk & Self-Respect
Connection & Community
Happiness & Simple Joys
Resilience & Discomfort
Systems & Intentional Living
Future Self & Purpose
None of this is final yet, just the themes that keep rising to the surface as I sift through the past few years.
The breakthrough today wasn’t “figuring it all out.”
It was accepting that my job isn’t to force everything into a perfect structure.
It’s to take what’s been meaningful in my own growth and translate it into a year-long roadmap that genuinely helps someone else.
Three Things Worth Sharing
1. What I Worked On (Building the Foundation of a 12-Month Transformation Journal)
I spent today assembling the foundational pieces of the journal: reviewing nearly 100 books, three years of daily journaling, 45,000+ words of Substack writing, personal letters, saved quotes, and notes. I drafted the Editor’s Note, shaped the early mission, and started mapping the 12-month arc that will guide the entire book.
2. What I Learned (The Real Challenge of Creating a Growth System)
The hardest part isn’t writing, it’s distilling. Turning lived experience into a clear, practical system forces you to ask, “What actually helped me move forward?” Today reminded me that clarity comes through action: by sorting, refining, and repeatedly showing up.
3. A Recommendation for You (Start Your Own 30-Day Growth System)
If you want to improve your life, here’s a simple framework to use right now:
Pick a theme for this month (presence, discipline, clarity, stability).
Choose one daily anchor habit (5–10 minutes: journal, walk, stretch, read a page).
Do a weekly check-in:
What moved me forward?
What held me back?
What one small adjustment will help next week?
Simple systems create real change. You don’t need a full blueprint to start; you just need a direction.
A Quick Question for You
If you had a year-long journal designed to help you become someone you’re proud of…
What’s one theme you’d want it to spend more time on?
Reply to this E-Mail. I’m building this in public for a reason. Your answers genuinely shape where this goes.
I Almost Forgot!
Here’s the list of books I have read in the last few years :)
A
The Alchemist — Paulo Coelho
The Almanack of Naval Ravikant — Eric Jorgenson
Atomic Habits — James Clear
As a Man Thinketh — James Allen
The Art of Spending Money — Morgan Housel
The Art of War — Sun Tzu
B
Broke Millennial — Erin Lowry
Bounce Back — Travis Mills
Building a Second Brain — Tiago Forte
Breaking Free From Broke — George Kamel
The Body Keeps the Score — Bessel van der Kolk
C
The Comfort Crisis — Michael Easter
D
Deep Work — Cal Newport
The Defining Decade — Meg Jay
Die With Zero — Bill Perkins
Discipline Is Destiny — Ryan Holiday
Don’t Sweat the Small Stuff — Richard Carlson
E
Ego Is the Enemy — Ryan Holiday
Endurance — Alfred Lansing
The Energy Bus — Jon Gordon
The Emotion Code — Bradley Nelson
Everything Is F*cked — Mark Manson
The 48 Laws of Power — Robert Greene
The Four Agreements — Don Miguel Ruiz
The 4-Hour Workweek — Tim Ferriss
Feel-Good Productivity — Ali Abdaal
Failing Forward — John C. Maxwell
FIRE for Dummies — Michael J. Withey
F
First-Time Home Buyer: The Complete Playbook — Scott Trench & Mindy Jensen
Four Thousand Weeks — Oliver Burkeman
G
Good to Great — Jim Collins
Greenlights — Matthew McConaughey
GRIT — Angela Duckworth
The Go-Giver — Bob Burg & John David Mann
H
The Hard Thing About Hard Things — Ben Horowitz
The House Hacking Strategy — Craig Curelop
How to Win Friends & Influence People — Dale Carnegie
The Happiness Advantage — Shawn Achor
I
Ikigai — Héctor García & Francesc Miralles
I Will Teach You to Be Rich — Ramit Sethi
Into the Wild — Jon Krakauer
L
Leaders Eat Last — Simon Sinek
Living a Non-Anxious Life — John Mark Comer
The Last Lecture — Randy Pausch
M
Meditations — Marcus Aurelius
The Millionaire Next Door — Thomas J. Stanley & William D. Danko
The Millionaire Real Estate Investor — Gary Keller
The Millionaire Fastlane — MJ DeMarco
Man’s Search for Meaning — Viktor Frankl
The Magic of Thinking Big — David Schwartz
The Most Important Thing — Howard Marks
Notes on Being a Man — Scott Galloway
N
Nowhere for Very Long — Brianna Madia
Nexus: A Brief History of Information Networks — Yuval Noah Harari
Never Finished — David Goggins
O
The Obstacle Is the Way — Ryan Holiday
Outlive — Peter Attia
P
Plan Your Prosperity — Ken Fisher
The Psychology of Money — Morgan Housel
The Power of Now — Eckhart Tolle
The Pathless Path — Paul Millerd
The Power of Your Subconscious Mind — Joseph Murphy
R
Range — David Epstein
Real Estate Investing for Dummies — Eric Tyson & Robert S. Griswold
The Richest Man in Babylon — George S. Clason
Right Thing, Right Now — Ryan Holiday
The 5 Types of Wealth — Sahil Bloom
S
Same As Ever — Morgan Housel
Set Boundaries, Find Peace — Nedra Glover Tawwab
Stillness Is the Key — Ryan Holiday
Stop Working & Start Investing — Logan Allec
Set for Life — Scott Trench
The Simple Path to Wealth — JL Collins
Start With Why — Simon Sinek
Strangers to Temptation — Scott Gould
Shoe Dog — Phil Knight
The Subtle Art of Not Giving a F*ck — Mark Manson
The Surrender Experiment — Michael A. Singer
T
Think Again — Adam Grant
Think & Grow Rich — Napoleon Hill
The Tipping Point — Malcolm Gladwell
To Shake the Sleeping Self — Jedidiah Jenkins
The Three Questions — Don Miguel Ruiz
Tuesdays With Morrie — Mitch Albom
10% Happier — Dan Harris
The 80/20 Principle — Richard Koch
The 5AM Club — Robin Sharma
U
The Untethered Soul — Michael A. Singer
V
Vagabonding — Rolf Potts
W
Wealth Your Way — Wealth Your Way Insights
What Makes Sammy Run? — Budd Schulberg
Why We Sleep — Matthew Walker
The Wisdom of Insecurity — Alan Watts
Thank You
Thanks for being here.
Thanks for reading.
Thanks for following along as I build this thing from the ground up.
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Great read, Ryan.
Great list of books as well! I recently finished Die With Zero by Bill Perkins and is up there as one of my favorite reads. Gives a very different, but refreshing perspective on finances and life.
Hi Ryan, wow what an adventure. Thanks for showing your progress and I look forward to reading more of your posts as well as seeing what your book is. I saw a few familiar books I have read in your list.