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The Messy Journey: From Notion, Obsidian, and Trello to Asana – And Why I’m Done

Let me be clear: I’m not a perfectionist. I’m an ADHD enthusiast who thrives on chaos, coffee, and the occasional “aha!” moment. When I first tried Notion for task management, it felt like a miracle. I’d create boards, add checklists, and imagine myself as a productivity wizard. But then I switched to Obsidian for my writing, and suddenly I was juggling notes, projects, and a growing list of “I’m done” tasks. Trello had its charm—visual boards, drag-and-drop simplicity—but it felt like a game of Tetris where I was both the player and the target. By the time I’d mastered Trello, I realized I’d traded one mess for another.

So, here’s the truth: I’m done with Notion, Obsidian, and Trello. I’ve moved on to Asana, and it’s not just about being “more productive.” It’s about finding a system that works for me, even when it feels messy. Let me break down why this transition felt like a necessary evolution—and how it’s reshaped my approach to work, family, and creativity.

The Problem with “All-in-One” Tools

I used to think that a single tool could solve everything. Notion, for example, was my go-to for brainstorming, organizing ideas, and tracking projects. Obsidian helped me write deeply, but it was a bit too abstract for managing tasks. Trello, while visually appealing, felt like a game of “if you can’t beat them, join them.” I’d spend hours tweaking boards, adding reminders, and reorganizing to fit my evolving needs.

The issue? I was constantly trying to be perfect, but I wasn’t. As a dad, I’ve learned that perfection is a myth. My kids don’t expect me to be flawless, and neither do I. When I switched from Trello to Asana, I realized that the tools should reflect my personality—messy, iterative, and deeply human.

Asana: A System That Fits My Brain

Asana is a tool that’s not designed for perfection. It’s built for collaboration, clarity, and flexibility. I love its ability to break down complex projects into manageable tasks with deadlines. Here’s how it’s helped me:

  1. Deadlines as a Compass
    Asana’s calendar view is my favorite. I can set deadlines for tasks, track progress, and see how each project is evolving. Unlike Trello, which often feels like a race to the top, Asana lets me slow down and focus on one task at a time. I’ve learned to prioritize, not just plan.

  2. Team Collaboration with a Side of Chaos
    I’ve been managing projects for clients, and Asana’s team boards are a lifesaver. I can assign tasks, set milestones, and track who’s doing what. It’s not a rigid system—it’s a living document that adapts to our needs. My kids used to say I “mess up the timeline,” but now I’m more intentional about keeping things on track.

  3. Less Overhead, More Flow
    With Asana, I’ve cut down on the noise. Trello’s clutter made me feel like I was trying to manage everything, but Asana’s clean interface has helped me focus. I can spend more time on creative work and less on administrative tasks.

The ADHD Side of Productivity

As a dad, I’ve always been a workaholic—until I realized that productivity isn’t about being “on” all the time. Asana has helped me balance my work and family life in ways I never expected.

  • Time Blocking for Focus
    I’ve started using Asana to block time for specific tasks. For example, I’ll set aside 2 hours each morning to tackle client deliverables and 1 hour for family time. It’s not about being “productive” in the traditional sense, but about creating structure without stress.

  • The Art of “Done”
    I’ve learned to embrace the concept of “done.” Sometimes a task is complete when it’s finished, not when it’s perfect. Asana helps me track progress and celebrate small wins, which has made the process feel less like a grind.

  • Coffee as a Sidekick
    I’ve found that coffee is my best friend. Asana’s interface can be overwhelming, but when paired with a cup of coffee and a good book, it becomes a tool for creativity rather than chaos. I’ve even started using Asana to track my writing projects, which has been a game-changer.

Lessons from the Messy Transition

Switching to Asana wasn’t a smooth process. I spent weeks trying to figure out the best way to organize my tasks, and there were moments when I felt like I was losing myself in the chaos. But here’s what I’ve learned:

  • Flexibility is Key
    Asana doesn’t require me to be a “tool expert.” I’ve used it for everything from client timelines to personal projects, and it’s worked well. The more I use it, the more I understand its strengths.

  • The Power of Imperfection
    I used to think that a tool had to be “perfect” to be useful. But Asana has shown me that imperfection is part of the process. I’m okay with a messy board, a slightly off deadline, or a task that’s just “in progress.”

  • Parenting and Productivity Go Hand in Hand
    As a dad, I’ve realized that productivity isn’t just about work—it’s about balance. Asana helps me manage both my professional and personal life, which is a huge win.

A Final Word: Embrace the Mess

I’m not here to sell Asana or tout it as a miracle tool. I’m here to share my story—and the messiness that comes with it. It’s not about being “tidy” or “efficient.” It’s about finding a system that works for you, even if it takes some time to figure out.

So, if you’re feeling stuck in a tool that’s not working for you, don’t be afraid to try something new. The key is to stay true to your personality and let the process evolve.

And if you’re like me, you’ll find that the messiness is actually what makes it human.

Cheers to coffee, chaos, and the occasional “I’m done” moment. 🥤✨