Overwhelmed and Overloaded: The Struggle to Organize My Inherited Chaos of Files

When I first opened my dad’s hard drives, I felt both excitement and overwhelm. With decades of scattered courses, tools, and resources, the first real challenge wasn’t learning—it was organizing. Here’s how I’m tackling the chaos and turning this digital inheritance into something meaningful.
Messy computer desk with scattered notes
When I first looked at the hard drives my dad left me, I felt like I had inherited a treasure chest of knowledge—but no map to navigate it.

With 20 years’ worth of courses, tools, and resources scattered across dozens of external drives, I quickly realized that the first challenge wasn’t learning—it was figuring out where to start.


The Weight of the Legacy

The Initial Excitement
At first, finding these drives was exhilarating. Every file felt like it held the potential to transform my life. But that excitement quickly gave way to overwhelm.

One drive alone contained hundreds of folders with cryptic names like “Final-Version-v3.2.” Multiply that by 12 drives, and I was drowning in files before I even started.

Emotional Layers
This wasn’t just about organizing files—it was about honoring my dad’s passion and making something meaningful out of his investment. Knowing how much thought and money he’d poured into these drives made me feel an added pressure to get it right.

It’s hard to describe the emotional weight of realizing that what he left behind wasn’t just information; it was his belief in me.


The Challenges of Organizing

Disorganized Files
Some files were labeled perfectly, like “Affiliate Marketing Millionaire,” but others were complete mysteries—“project_plan_final” gave me absolutely no idea what it was.

To make matters worse, there were countless duplicates, outdated materials, and incomplete courses. Trying to make sense of it all was like untangling a giant knot with no clear ends.

No Clear Starting Point
Do I start with the biggest course? The most recent one? The one that looks easiest to tackle?

Having so many options led to paralysis. Every choice felt like it might be the wrong one, and that kept me spinning in circles.

The Time Commitment
Even skimming a single course’s video files could take weeks. Multiply that by the sheer volume of materials, and it felt like I’d need years to sort through everything.


My Process (So Far)

Breaking It Down
To avoid being completely overwhelmed, I decided to tackle the drives one by one, starting with one of the most recent.

I created an inventory using Airtable, logging each course, its topic, and a rough estimate of its content. This helped me see what I was working with and start identifying patterns.

Tools I’m Using

  • Airtable: To catalog everything and track my progress.
  • AI Tools: For transcribing video files and pulling out key takeaways.
  • Cloud Storage: To back everything up and avoid losing anything in the shuffle.

Lessons Learned
One of the first lessons I had to accept was to stop aiming for perfection. I didn’t need every file perfectly labeled or every course fully understood before I could start learning and applying the lessons.

Small Wins
After hours of sorting, I found a course on affiliate marketing that was so well-organized it felt like a breath of fresh air. That small win gave me the momentum I needed to keep going.


Tips for Tackling Overwhelm

If you’re facing a massive project of your own, here’s what I’ve learned:

  1. Start Small
    Pick one drive or one folder and focus on completing it before moving on to the next. Breaking it down makes the task feel more manageable.
  2. Use Tools to Your Advantage
    Tools like Airtable and transcription software can save you time and keep you organized. Automating parts of the process helped me stay motivated and avoid burnout.
  3. Focus on the Goal
    When it feels overwhelming, I remind myself why I’m doing this: to honor my dad’s legacy and build a better future for myself. Keeping that purpose in mind keeps me grounded.

Conclusion

Organizing this inheritance isn’t just a logistical challenge—it’s a mental and emotional journey. Every step I take feels like I’m getting closer to turning this overwhelming collection of files into something meaningful.

If you’re tackling a big project like this, it’s okay to feel stuck. The key is to keep moving forward, one step at a time. ✨ 

About the author
Aly Macklin

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