New Year’s resolutions are infamous for their failure rates. Most of them don’t make it past February, leaving many of us feeling frustrated, unmotivated, and defeated. I’ve been there—starting the year with grand ambitions, only to lose momentum as the days pass and life gets in the way. But over time, I realized something fundamental: most resolutions fail because they demand rigid commitment without allowing room for real-life challenges, learning, or growth.
As someone who identifies as a Rebel (a personality type from Gretchen Rubin’s framework), I’ve always resisted being told what to do—even by my past self. Traditional systems of goal setting, with their rigid schedules and prescriptive rules, just don’t work for me. I crave freedom and flexibility, but I also want to feel rooted in purpose and meaning. That’s why I created the Rooted Freedom Way.
This system gives me the freedom to choose what I want to do each day while staying grounded in the context of my larger goals and future vision. It’s not about imposing rules on myself; it’s about building a framework that allows me to adapt, experiment, and grow—all while making real progress toward meaningful objectives.
The Rooted Freedom Way was born out of my own struggles with goal setting, and it’s shaped by years of experimentation and inspiration from systems like SMART goals, OKRs, Tiny Habits, and the PARA organizational framework from Tiago Forte’s Second Brain. Today, this system is the foundation of how I manage everything from improving my health to pursuing professional growth. It’s designed to help you create meaningful change in your life while honoring your unique way of working.
The Rooted Freedom Way didn’t appear fully formed. It evolved out of years of trial, error, and a realization that traditional goal-setting approaches weren’t working for me. In fact, it started as an experiment—a way to sidestep the all-or-nothing mindset of New Year’s resolutions.
Like many people, I used to make big, ambitious resolutions every January. But, like most people, I found myself abandoning those resolutions by February. The problem wasn’t a lack of motivation—it was the rigidity of the goals themselves. Resolutions demanded year-long commitment without giving me the flexibility to adapt, learn, or even decide if I wanted to continue. By February, I’d feel like a failure for falling off track, and I’d ditch the goal entirely.
To solve this, I began experimenting with what I called New Year Experiments. Instead of committing to a resolution for the entire year, I committed to a one-month experiment that would end on February 1st. This allowed me to test new habits, diets, or routines without feeling trapped by them. If I liked what I tried, I could keep it. If I didn’t, it was only one month—I could endure almost anything for that long.
Over time, these experiments evolved. I realized that one month wasn’t always enough to see meaningful results or fully evaluate the impact of a new habit. So, I extended the timeline to three-month sprints. These quarterly cycles gave me the space to test ideas, gather data, and adjust my approach in a way that felt intentional and sustainable. I wasn’t committing to a rigid year-long plan, but I was staying focused long enough to make real progress.
One of the most powerful examples of this is my ongoing work to manage my cholesterol. Each three-month sprint involves sticking to a diet and exercise plan, testing my lipid levels at the end of the period, and using the results to adjust my approach for the next sprint. While this experiment is still underway, it’s already helped me lose 15 pounds and improve my 5k running time by two minutes. More importantly, it’s shown me how effective iterative goal-setting can be when combined with reflection and flexibility.
At the heart of the Rooted Freedom Way is a balance between two seemingly opposing forces: freedom and roots. For me, these two concepts aren’t in conflict—they complement each other.
As a Rebel, freedom is non-negotiable. I thrive on the ability to choose what I do each day without feeling constrained by someone else’s expectations—or even my own past decisions. Traditional productivity systems often fail Rebels because they rely on rigid structures, routines, and rules that feel restrictive and oppressive.
But complete freedom, without context or purpose, can feel aimless. That’s where the “roots” come in. My actions are rooted in a larger vision—a purpose that keeps me grounded and focused on what matters most to me. These roots provide stability and direction, allowing me to make choices each day that align with my long-term goals while maintaining the flexibility to adapt as I learn and grow.
The Rooted Freedom Way is built on this philosophy: it’s a framework for freedom. Instead of imposing strict schedules or rigid routines, it creates a flexible structure that supports exploration, experimentation, and autonomy while ensuring progress toward meaningful objectives.
This philosophy is reflected in every aspect of the system:
This balance of freedom and roots has made a huge difference in my ability to stick with goals and make meaningful progress. It’s why I can wake up every day and feel excited about what I’m working toward—not pressured by the weight of a rigid plan.
The Rooted Freedom Way is designed to balance structure and flexibility, giving you the freedom to choose your daily actions while staying aligned with your long-term goals. It’s built around five key components, each serving a specific purpose within the system:
# Rooted Vision: [Name of Vision]
## Description
- What is your big-picture, emotionally resonant goal for the year?
- Example: *"Become a healthier, stronger, and more resilient version of myself."*
## Why It Matters
- Why is this goal meaningful to you?
- Example: *"I want to feel strong and capable in my body, handle life’s challenges with resilience, and enjoy long-term health."*
## Associated Waypoint
- `#g[yy]-[descriptor]`
- Example: `#g24-health`
# Quarterly Milestone: [Name of Milestone]
## Description
- What is the specific, measurable objective for this quarter?
- Example: *"Stick to a heart-healthy diet and complete 3 runs per week."*
## Why It Matters
- How does this milestone support your Rooted Vision?
- Example: *"This will improve my cardiovascular health and help me build habits that support long-term resilience."*
## Associated Waypoint
- `#g[yy]q[x]-[descriptor]`
- Example: `#g24q1-nutrition`
# Building Block: [Name of Project]
## Objectives
- What do you aim to accomplish during this period?
- Example: *"Track meals daily and complete three 5k runs this week."*
## Freeing Actions
- What are the key daily tasks tied to these objectives?
- Example:
- *Monday: Plan meals for the week.*
- *Wednesday: Run a 5k.*
## Associated Waypoints
- Relevant tags for this Building Block:
- Example: `#g24q1-running`, `#g24q1-nutrition`
A Freeing Action is the one small, impactful task you choose each day to move closer to your goals. This practice ensures daily progress without overwhelming you with long to-do lists. The key to Freeing Actions is simplicity and alignment—they must directly support your current Building Block, Quarterly Milestone, or Rooted Vision.
A successful day begins the night before. The Flow Tracker supports this by splitting each day’s entry into two parts: a planning section completed the evening before, and a reflection and action-setting section completed the following morning. This structure ensures that you wake up with clarity and direction while still leaving room for flexibility.
Evening (Planning for Tomorrow):
## Grounding Review
- Progress: Completed a 5k run. #g24q1-running
- Lesson: Running in the morning gives me more energy throughout the day.
## Freedom Alignment (Planning for Tomorrow)
- Intention: Focus on consistency over speed in tomorrow’s workout.
Morning (Review and Choose Your Freeing Action):
## Freedom Alignment (Morning)
- Freeing Action: Complete a 3-mile jog at a relaxed pace. #g24q1-running
Throughout the Day:
Repeat the Cycle:
Example Flow Tracker Daily Entry
## Freedom Alignment (Morning)
- Freeing Action: Complete a 3-mile jog at a relaxed pace. #g24q1-running
## Grounding Review
- Progress: Completed a 5k run. #g24q1-running
- Lesson: Running in the morning gives me more energy throughout the day.
## Freedom Alignment (Planning for Tomorrow)
- Intention: Focus on consistency over speed in tomorrow’s workout.
This simple yet powerful process helps you start each day with clarity and intention, while still honoring your need for flexibility and autonomy.
Evaluate your progress at the end of a week, month, or quarter to identify lessons and plan your next steps.
# [Weekly/Monthly/Quarterly] Review: [Time Period]
## Progress Summary
- What did you accomplish during this period?
- Example: *"Tracked meals daily and completed 11 out of 12 planned runs. #g24q1-nutrition #g24q1-running"*
## Wins and Lessons
- Wins:
- Example: *"Found a new running route that’s more enjoyable."*
- Lessons:
- Example: *"Need to prepare meals on Sunday to avoid weekday takeout."*
## Adjustments
- What changes will you make moving forward?
- Example: *"Add cross-training to prevent repetitive strain."*
The Pivot Template is your tool for documenting changes in your approach when new challenges, insights, or opportunities arise. It ensures that adjustments are intentional and still aligned with your larger goals.
Here’s how to document a pivot step by step:
# Pivot: [Name of Project or Building Block]
## Original Plan
- What was the initial plan?
- Example: *"Complete three 5k runs this week to support Q1 milestone."*
## New Information
- What led to the pivot?
- Example: *"Work commitments reduced available time for exercise this week."*
## New Plan
- What is the updated strategy?
- Example: *"Switch to two shorter runs this week and add a weekend run."*
## Connection to Milestone and Vision
- How does this pivot still support your Quarterly Milestone and Rooted Vision?
- Example: *"This keeps me on track for consistent cardiovascular activity while adjusting to a busier schedule."*
The Pivot Template ensures that changes in your plan are intentional, documented, and still aligned with your Rooted Vision and Quarterly Milestones.
Document the outcomes of completed or abandoned goals for future reference.
# Rooted Vision Archive: [Name of Vision]
## Summary
- What was your Rooted Vision?
- Example: *"Become a healthier, stronger, and more resilient version of myself."*
## Outcome
- Was the vision achieved or abandoned? Why?
- Example: *"Achieved. Built a consistent exercise routine and improved resilience through mindfulness."*
## Lessons Learned
- What did you learn from pursuing this vision?
- Example: *"Big progress comes from small, consistent steps."*
# Quarterly Milestone Archive: [Name of Milestone]
## Summary
- What was the milestone?
- Example: *"Stick to a heart-healthy diet and complete 3 runs per week."*
## Outcome
- Was the milestone achieved or abandoned? Why?
- Example: *"Partially achieved. Stayed consistent with diet but missed 2 runs due to illness."*
## Lessons Learned
- What worked, and what didn’t?
- Example: *"Need more flexibility in workout plans to account for unexpected setbacks."*
#g[yy]-[descriptor]
for Rooted Vision (e.g., #g24-health
).#g[yy]q[x]-[descriptor]
for Quarterly Milestones (e.g., #g24q1-nutrition
).To implement the Rooted Freedom Way, I use a series of templates stored in plain text files with Markdown. These templates make it easy to stay organized and consistent:
With these components, the Rooted Freedom Way creates a framework for freedom and purpose. It’s a system that helps you stay focused on what matters most, adapt to new information, and make consistent progress toward your goals.
One of the best things about the Rooted Freedom Way is its simplicity. It doesn’t require special tools or apps—it works just as well in a physical journal as it does in a sophisticated digital system. However, my personal setup is in Obsidian, a powerful, Markdown-based note-taking app. I use plain text files, organized using Tiago Forte’s PARA structure from the Second Brain framework.
Here’s how you can set up the Rooted Freedom Way in Obsidian—or adapt it to any note-taking app you prefer.
Organizing your notes effectively is crucial for implementing the Rooted Freedom Way. I use the PARA structure, categorizing information into Projects, Areas, Resources, and Archives. The Rooted Freedom Way functions as an Area, containing all related materials.
This structure ensures that everything related to the Rooted Freedom Way is easily accessible and logically organized.
Rooted Freedom Way/
├── 2024/
│ ├── Rooted Vision.md
│ ├── Q1 Milestone.md
│ ├── January Building Block.md
│ ├── Flow Tracker/
│ │ ├── January/
│ │ │ ├── 2024-01-01.md
│ │ │ ├── 2024-01-02.md
│ │ │ └── ...
│ │ ├── February/
│ │ │ ├── 2024-02-01.md
│ │ │ └── ...
│ │ └── ...
├── Archive/
│ ├── 2023/
│ │ ├── Rooted Vision.md
│ │ ├── Q1 Milestone.md
│ │ ├── Flow Tracker/
│ │ │ ├── January/
│ │ │ ├── February/
│ │ │ └── ...
│ └── ...
├── Templates/
This structure is simple, scalable, and easy to implement in any note-taking tool, such as Obsidian or plain text systems.
Every component of the system is stored in plain text files written in Markdown. This makes the system:
I use a clear, consistent naming convention to keep files organized:
rooted-vision-[year].md
(e.g., rooted-vision-2024.md
)milestone-[year]-q[quarter]-[descriptor].md
(e.g., milestone-2024-q1-nutrition.md
)block-[year]-[month-week]-[descriptor].md
(e.g., block-2024-01-w1-running.md
)flow-[date].md
(e.g., flow-2024-01-15.md
)Waypoints are the tags I use to link actions, reflections, and notes to specific goals. They help me track progress and maintain alignment across the system.
#g[yy]-[descriptor]
for Rooted Vision (e.g., #g24-health
)#g[yy]q[x]-[descriptor]
for Quarterly Milestones (e.g., #g24q1-running
)For example, if a daily note includes progress on my Q1 milestone for running, I’ll tag it with #g24q1-running
. Later, I can use Obsidian’s search or plugins like Dataview to gather all notes related to that milestone.
All components of the Rooted Freedom Way are managed with templates (see the previous section for details). Here’s how I apply them:
The Rooted Freedom Way emphasizes iteration and learning, so regular reviews are essential:
While I use Obsidian, this system works with almost any app or setup:
With this setup, the Rooted Freedom Way becomes more than a system—it becomes a part of how you work, reflect, and grow. By combining the simplicity of plain text with the power of tools like Obsidian, you can tailor this framework to fit your life.
The beauty of the Rooted Freedom Way is its versatility. Whether you’re working on personal health, professional growth, or creative projects, this system gives you the tools to stay focused, adapt to challenges, and make meaningful progress. To illustrate how it works, here are some real-world examples from my own life.
One of the most significant ways I’ve used this system is to address my cholesterol. This is an ongoing experiment, but the Rooted Freedom Way has helped me create a sustainable approach to improving my health.
## Grounding Review
- Progress: Completed a 5k run. #g24q1-running
- Lesson: Running in the morning is more energizing than evening runs.
## Freedom Alignment
- Freeing Action: Prep tomorrow’s meals. #g24q1-nutrition
- Intention: Stay consistent with small, daily steps.
While this experiment is still ongoing, it’s already helped me lose 15 pounds and improve my 5k time by two minutes. More importantly, it’s taught me the value of iterative progress and reflection.
I’ve also used the Rooted Freedom Way to manage creative projects, like writing articles or working on larger publishing goals.
## Grounding Review
- Progress: Finished the article draft. #g24q1-writing
- Lesson: Writing in focused 90-minute blocks helps me stay productive.
## Freedom Alignment
- Freeing Action: Edit the first section of the eBook. #g24q1-writing
- Intention: Take small, steady steps forward.
Finally, the system has been invaluable for professional development. For example, I recently used it to focus on improving a technical skill I’d been procrastinating on.
## Grounding Review
- Progress: Finished Module 2 and implemented one exercise. #g24q1-skills
- Lesson: Hands-on practice makes concepts stick more effectively.
## Freedom Alignment
- Freeing Action: Build the first draft of the portfolio project. #g24q1-skills
- Intention: Focus on creating, not perfection.
Across all these examples, the Rooted Freedom Way succeeds because it:
This system isn’t just about achieving goals—it’s about creating a meaningful, intentional way of working and living.
The Rooted Freedom Way stands out from other productivity and goal-setting systems because it’s built for people who crave autonomy and flexibility while still wanting to make meaningful progress. It’s designed to work with you, not against you, especially if you resist rigid plans or traditional approaches to productivity.
Here’s why this system works so well:
The Rooted Freedom Way is ideal for people like me—Rebels who resist being told what to do, even by their past selves. It gives you the autonomy to decide what’s right for you each day, while rooting your actions in a larger purpose.
This system isn’t about perfection or strict adherence to a plan. It’s about freedom, growth, and intentional progress. It’s a way to design a life you love, one choice at a time.
The Rooted Freedom Way isn’t just a productivity system—it’s a philosophy for how to live and grow. It’s a framework that empowers you to act with purpose while giving you the freedom to adapt, experiment, and discover what works for you. By combining reflection, flexibility, and alignment with your deeper values, this system turns goal-setting into a meaningful, sustainable process.
Starting your Rooted Freedom journey is simple. Here’s how to get started today:
Every day, take a moment to reflect and realign using the Flow Tracker. Every week, assess your progress and adjust your Building Blocks. Every quarter, evaluate your milestones and plan your next steps. With each cycle, you’ll learn, grow, and move closer to your vision.
The Rooted Freedom Way isn’t about perfection—it’s about progress. It’s about creating a life that aligns with your values, one choice at a time.
Imagine what your life could look like if you had the freedom to choose your actions every day, with the confidence that those actions were leading you toward something meaningful. What could you achieve? How would you grow? The Rooted Freedom Way offers you that opportunity.
Start today. Root your actions in purpose. Embrace the freedom to grow.