Present and Progressing | Ryan | Substack

📓 Present & Progressing Journal

I Wrote 250,000 Words in My Mid 20s

Looking back now, here are three important lessons I learned.

Dec 29, 2025 • Ryan

365 Journal — Build Log #5: Building the System Beneath the Journal

Month 3, belief work, and the decision to index years of frameworks before moving forward

Dec 22, 2025 • Ryan

Designing the Journal From the Inside Out

Finishing Month 2, building the first interior layout, and switching between two very different versions of my brain this week.

Dec 15, 2025 • Ryan

Building a 365-Day Journal: The Breakthrough I Didn’t Expect

Day 3 of building a year-long guided journal in public, and the moment everything became clearer.

Dec 11, 2025 • Ryan

Turning Lived Experience into a Year-Long System

The messy, honest beginning of building a 365-day guided journal.

Dec 4, 2025 • Ryan

Why I’m Writing a 365-Day Guided Journal

and why I’m building it in public

Dec 1, 2025 • Ryan

🧠 Mindset & Growth

Your New Year’s Resolution Is Going to Fail

The life you want doesn't begin on January 1st. It will begin on an ordinary day when you finally decide to start.

Jan 5 • Ryan

I Get to Do This

A mindset shift that makes life feel lighter, even when nothing around you changes.

Dec 7, 2025 • Ryan

30 Things I’m Starting to Understand

Five new lessons, twenty-five that built the foundation.

Nov 17, 2025 • Ryan

Living Between Two Truths

How contradictions shape growth, balance, and who we become.

Oct 20, 2025 • Ryan

⚙️ Systems & Discipline

Do the One Thing You’re Avoiding

How tackling the smallest avoided task builds the kind of confidence that lasts.

Nov 24, 2025 • Ryan

Keep It Simple, Stupid.

A framework for staying grounded in a world that never stops moving

Oct 27, 2025 • Ryan

How to Love Your Life Without Waiting for It to Be Perfect

A simple framework for noticing what’s already good, even in the middle of the hard stuff.

Oct 6, 2025 • Ryan

Let’s Have an Honest Talk About Motivation

Why chasing motivation will always let you down, and what to focus on instead.

Sep 29, 2025 • Ryan

💬 Reflections

Why High-Achievers Still Feel Lost (Even When Life Looks “Good”)

A shared reflection for people in their 20s

Jan 12 • Ryan and Amy Stanborough

I Wrote Letters to My Future Self for Nearly Two Years. Then I Asked AI to Analyze Them.

A $0 self-reflection habit that gave me more clarity than most life coaches.

Dec 8, 2025 • Ryan

The Reality Audit

How to close the gap between what you expect, what you perceive, and what’s actually happening.

Nov 10, 2025 • Ryan

10 Hard Truths About Being a High-Achiever in Your 20s

You can be smart, stable, and still feel completely lost.

Aug 11, 2025 • Ryan

💼 Life Design & Clarity

The Luckier You Are, The Nicer You Should Be

How to keep your surface area for luck expanding through generosity.

Nov 3, 2025 • Ryan

What Would You Do With a Year Off?

A thought experiment to uncover what you’d Stop, Start, and Double Down on when work isn’t the center of your identity.

Sep 22, 2025 • Ryan

From Decisions to Opportunities

Why growth isn’t about finding the perfect mountain but saying yes to the right climb.

Sep 15, 2025 • Ryan

Increase Your Surface Area for Luck

How small acts of reciprocity compound into opportunities you can’t plan for.

Sep 8, 2025 • Ryan

Join 400+ readers learning to live with more clarity and consistency. New essays every Monday morning at 7:30 AM EST.

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