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Beyond the To-Do List - Productivity for Work and Life

Shawn Lemon on Digital Organization: Find What You Need in Seconds

Beyond the To-Do List - Productivity for Work and Life

Erik Fisher

Business, Entrepreneurship, Self-improvement, Careers, Education

4.5875 Ratings

🗓️ 11 September 2025

⏱️ 47 minutes

🧾️ Download transcript

Summary

Shawn Lemon is the founder of The Digital Organizer, where he helps individuals and teams eliminate friction and chaos in their digital workflows. In this episode, we go deep into digital file systems, tool audits, naming conventions, AI clutter, and the underestimated cost of daily digital disorganization.

This isn’t about color-coding your folders for fun—it’s about recovering your focus, time, and mental energy by organizing your digital life on purpose.

In this episode, we cover:

  • What Digital Organization Actually Means: It’s not about perfection—it’s about finding what you need in seconds, not minutes.
  • The Core Four Systems: Files, email, passwords, and communication tools. Nail these, and everything else falls into place.
  • Solo Business vs. Teams: Why even solo entrepreneurs create hidden chaos—and how to stop duplicating effort across tools.
  • Avoiding the Frankenstein Stack: How tool sprawl (Google Docs + Dropbox + Box + iCloud…) is draining your time and brainpower.
  • The Pitfalls of AI-Generated Clutter: As creation gets easier, organizing what you make becomes more important than ever.
  • How to Tame GPT Projects and Prompts: Why you need a training folder, naming conventions, and even visual breadcrumbs for your GPT knowledge base.
  • Digital Hoarding is Real: Most businesses only use 5% of their files regularly—find that 5% and prioritize from there.
  • The Real Cost of Disorganization: How wasted time and duplicated work affects your bottom line—and what to do about it.
  • How to Make Digital Organization a Project (Not a Forever Problem): Treat this like a sprint, not a slow drip. Get in, get organized, and get back to work.
  • Focus Over Friction: Why triaging your tools, tasks, and systems one at a time is the fastest way to reclaim productivity.


Whether you’re a solopreneur juggling too many tools or a leader managing team chaos, Shawn’s approach can save you hours a week—and a ton of mental load.

Start with his quiz at thedigitalorganizer.com/beyond to find your digital organization score and get free access to his file organization guide and resource library.

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Transcript

Click on a timestamp to play from that location

0:00.0

Your first great love story is free when you sign up for a free 30-day trial at audible.co.

0:05.5

That's audible.co.ukesl-wondery. Hello and welcome back to Beyond the To Do List, a podcast about productivity.

0:32.9

I'm your host, Eric Fisher, and I'm excited to welcome back to the show, Sean Lemon, the digital organizer.

0:39.7

And we're diving a little deeper into digital organization, touching on things like the

0:44.8

pitfalls of the AI generated clutter. We're all using AI and we're all copying and pasting stuff

0:50.8

out of it. But then isn't that just creating many more documents that we need

0:54.6

to keep track of? We also talk about how to make digital organization a project and not an

1:00.0

ongoing forever problem, and why even solo entrepreneurs create this hidden chaos when it comes to

1:07.6

digital organizations versus teams, and how to stop duplicating effort across all

1:13.7

your tools. So whether you're a solopreneur juggling too many tools or a leader managing

1:18.3

team chaos, Sean's approach can save you hours a week and a ton of mental load.

1:26.7

Well, it is my privilege to welcome back to the show.

1:29.8

Sean,

1:30.2

Lemon, Sean, welcome back to Beyond the To-Do List.

1:34.0

Thanks, Eric.

1:34.8

I'm excited for a conversation today.

1:36.2

I am too.

1:37.0

So you're the digital organizer.

1:38.4

You've been on the show before.

1:39.3

We talked all about digital organization.

1:41.6

Let's do a quick overview of, okay, obviously digital organization is

1:47.1

important. Not in like a, well, definitely in a, I mean, Venn diagram crossover into some minimalism

...

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