An (Im)perfect Plan

My story about transforming my relationship to my to-do list, and instead started focusing on what I really care about.

I was taught to make lists at the tender age of eight. In a moment of overwhelm, my mom helped me write down what I wanted to pack for a family vacation. That list made me feel calmer, more in control. Ever since then, I have been a devoted to-do list maker.

A bet.

Several years ago, a colleague and I talked about our love/hate relationship with our lists. We agreed to track the number of tasks on our daily to-do lists for a week, then report back on our average at the end of the week.

Our respective to-do lists included an average of 12 tasks per day. That was just the work-related items. We didn’t even track our personal and home/family items, that would be just too much.

Just. Too. Much.

We made a bet to reduce our list maximum to nine items per day (work-related tasks). It felt like a win at the time, but looking back on it, it gives me a yucky feeling.


Lists, lost.

When the pandemic hit, I felt totally unmoored. I was working full-time as a project manager, going to art school at nights and on weekends, and finding my way through chronic eye pain. I kept making lists, but they were sort of worthless as I triaged my way through each day.

In a moment of desperation, I bought a copy of The Bullet Journal Method book by Ryder Carrol. I read this book with a fervor that caused my highlighter to actually dry out. I decided to try it.


When I began Illustrated Journaling

Here’s what happened when I journaling with illustrations instead of only making to-do lists:

  1. Goals from my heart, not my head. I created a list of my values, and my personal goals. I was horrified to realize that my work goals were not on the list. At all. What was on the list? Make art, lots of it. And start my own small business. What a WILD IDEA! I wrote it all down.

  2. A Plan. I made a loose plan for how to work toward my most important personal goals, not just my daily job tasks. What do you know? Over the next two years, I was able to finish art school AND start my business.

  3. A whole me. Most importantly, I started using my daily plan as a sort of synthesis for my life, which had felt split between work, art, and family. In one notebook, I wrote my daily list, my journal, my sketches, lettering practice, work notes, art school notes. EVERYTHING. I was going through a notebook every two months, but that was fine with me. I finally felt like one person, not like three people living three different lives, all competing for my focus and attention.

Looking back, I realize that this experience fundamentally changed how I think about planning. I stopped asking myself how to get more things done and started asking a different question: Am I making time for the things that really matter to me?

That shift—from productivity to purpose—continues to shape how I approach my own projects and how I work with coaching clients today.


Productivity vs. purpose

Me in my studio, probably coming up with another big idea.

Me in my studio, probably dreaming up a scheme I will sketch in my journal later.

I have a note hanging in my studio that reminds me that perfection does not equal prolific. As a recovering perfectionist, I need that reminder often.

I've learned that being productive doesn't necessarily mean making progress toward something meaningful.

Whether you're developing a new program, leading an initiative, starting a business, or making a significant change in your life, the challenge isn't always figuring out how to do more. Sometimes it's about getting clear on what matters most, deciding what deserves your attention, and giving yourself permission to let the rest go.

That's the kind of planning I believe in: Enough structure to help you move forward, with plenty of room for imagination and creative thinking.


Need someone in your corner?

Have a big idea or meaningful project that's struggling to move forward?

Through my Creatively Plan coaching services, I help changemakers turn ambitious ideas into achievable goals. Together, we'll clarify what matters most, explore possibilities, identify priorities, and create a realistic path forward that works for you.

Want more ideas like these? Subscribe to my free newsletter for practical planning tools, creative perspectives, and inspiration to help you bring your ideas to life.


Previous
Previous

Illustrating history

Next
Next

You are creative. Really.