The Real Reason Your Systems Keep Failing (It’s Not the App)

Let's go back in time to Savannah in college. My backpack consisted of 2 planners, a notebook with a never-ending brain dump, and a binder for each class. My phone consisted of 3 todo apps, an intense Google Calendar (color coded and everything), and Apple Notes full of gibberish. My computer had folders with different styles of digital organization, a Google Drive with warnings of full capacity, and Microsoft OneNote. I used every form of weekly planning, organization, and brain dump trick I could get my hands on. I spent more time organizing my todo list than I did doing the todo list. Color coding my multiple planners and trying out different layouts was a favorite pastime. Spending time in the office section of a store? Full of dreams for the day I could afford it all. Somehow I graduated summa cum laude and it certainly wasn't because I was on top of it all. I just knew how to not sleep and push the work through. Organized Chaos is what we called it.

What I didn't realize is that I wasn't searching for the best productivity and organization hack. I was searching for me.

WAIT — before I lose you, I know that sounds all "woo-woo," but I promise it is more than that.

My assistant and I with our Tour Binders for Elf! The Musical.

After college I went on a Broadway Tour of Bullets Over Broadway and no matter how hard I tried to force the need for all these fancy organization and todo list tools, I just wasn't living the life for them. The simplicity of tour is that your life is kind of "done" for you. No cooking, no booking hotels, no home cleaning. You're focused on the show and living on the road. So reluctantly all those amazing planners and notebooks I bought went into boxes under my bed at my mom's house. And there they stayed.

Instead I found myself learning a lot about people. I saw how human connection and the rhythms in which people worked differed from the east to the middle to the west. I learned how to change the order in which I gave directions to adapt to the people receiving them. I have a lot to thank touring for in life, but sparking a deep curiosity about people may be one of the biggest.

Arriving in NYC — and Back to Square One

Let's fast forward to arriving in New York City. I quickly found myself juggling freelance design, electrician work, and the harsh reality of living in such a large and expensive city. Suddenly the planner was back — but it wasn't working at all. My color code made no sense and life changed so quickly the planner went out of date the next day. Being organized became the most important thing, especially with my calendar. I swore I would only double book myself once. I swore I'd arrive at the wrong theatre only once. Intentions were good, but the system wasn't.

So I asked a few seasoned electricians how they did it. Their way didn't work — it wasn't clean enough for my design work that needed to track meetings and carve out homework time.

I asked a few designers how they did it. Their way was more project-based, when mine needed to be daily with all the electrician work layered on top.

And then I started noticing something fascinating. Every single person's system was completely different. Someone thrived with just an updated Google Calendar with Google Tasks, etc. Someone else had a long Apple Notes list. Someone else had a physical planner for notes and tasks plus a Google Calendar. It all depended on how people actually worked and what their schedule actually required.

The people I viewed as most successful weren't using the best app or the trendiest planner. They knew how their own system worked for them — and they didn't care about the status quo, the new awesome planner that just dropped, or how college taught them to be productive.

That was the moment everything shifted for me.

The Self-Discovery Journey Nobody Told Me I Needed

So I went on a self-discovery journey — through trying everything out, reading books, taking quizzes and paying close attention to myself. Unknowingly I found a huge passion: taking the human curiosity I gained on tour and combining it with personal hacks.

I wanted to understand myself on a deep level. I wanted to know when I hit my creative peak during the day, whether I worked best in long or short sessions, whether I needed accountability. Turns out — no, I actually dislike accountability. I like having control over my own todo list. My process is one of purpose and chaos together. I love trying new things, understanding them, and then leaving them on the side of the road when they've served their purpose. Change energizes me where it drains most of my friends.

Here's what actually created my systems:

• Human Design may have been the first tool that really helped me gain vocabulary around the things I was consciously and unconsciously learning about myself. It was described to me as: "If astrology is the story of your life, Human Design is the strategy of your life." Astrology always felt a little too predictive for me. But Human Design gave me language I could accept, adapt or decline.

• The Enneagram didn't work for me — but I know so many people it has genuinely helped. What I did learn was that taking quizzes felt so in-the-moment for me. I got a different result at home than I did at work. But again — vocabulary, language. Learning that my brain operates in completely different spaces depending on my environment was its own kind of huge.

• The Four Tendencies by Gretchen Rubin — how a person handles both inner and outer expectations — has told me more about people and how they work than almost anything else I've encountered. This one is especially useful for understanding your clients and the people you work with.

• Atomic Habits by James Clear helped me with routines, with achieving goals without completely bouncing from one thing to the next, and with choosing purposefully rather than reactively.

• Vanessa Van Edwards, Profit First, Four Thousand Weeks, the Money for Couples Podcast, Find Your Why, Three Word Rebellion — and honestly so much more. The learning never stops and I wouldn't want it to.

My Notion homepage in 2024, it’s changed a bit since then, but this was the first year I really found a way to include all three focuses together.

What Self-Knowledge Actually Changes

Every tool I've picked up has added vocabulary to my life. Vocabulary that created acceptance when I differed from the norm. Vocabulary that helped me help others far more efficiently. Vocabulary that created patience I definitely lacked before — because not everyone moves as fast or as chaotically as I do.

And here's the thing that changed most practically: I used my unique preferences and strengths to create systems I wanted to use and worked like I did.

Once I understood that I thrive on variety not routine, that I need lists both physically and electronically, that chronic illness means some days the whole plan has to flex — I stopped building systems that asked me to be someone I'm not. My Broadway career, my business, my health management — none of it is held together by the perfect app. It's held together by years of paying attention to myself and building around what I actually found.

My systems still change every year because every year I discover more vocabulary about myself. Every month my schedule needs shift. Every day my energy fluctuates. That's not failure — that's how it's supposed to work.

The First Step Isn't Finding the Right App

If you've tried every app, every influencer's morning routine, every color-coded system — and nothing has stuck — it's not because you're a failure. It's because those things weren't designed for you. And you may not have had the vocabulary yet to adjust them for yourself.

The first step to creating a system that actually works is getting to know yourself. It's trial and error. It involves trying things that seem "not your style" at first. Honestly, trying something that fails is more valuable than succeeding immediately — because failure gives you opinions you didn’t know you had.

Start there. Everything else gets easier once you do.

And if you want help building a system around the person you actually are — not the person productivity culture thinks you should be — that's exactly what I'm here for. The tea chat is free, thirty minutes and a real conversation.

Here for you,

— Savannah

P.S. — If a mid-year reset sounds like what you need right now, I'm putting together something for July. Stay tuned.