Podcast Summary:

This Can't Be That Hard - Ep. 354: The Importance of Organizing Your Business with Ashley Pendergraft
Host: Annemie Tonken
Guest: Ashley Pendergraft (Systems Over Stress)
Release Date: Feb 3, 2026

Main Theme & Purpose

This episode explores the transformative power of organization and systems for entrepreneurs and creative professionals, especially photographers. Host Annemie Tonken sits down with Ashley Pendergraft, founder of Systems Over Stress and an expert in Airtable, to unpack how functional, supportive systems can revolutionize your business operations—making daily work less stressful and more sustainable, no matter your brain wiring or business niche.

Key Discussion Points & Insights

1. The Permission to Find Your Own Way

• Ashley’s Backstory & Philosophy (04:45 - 06:58)
  • Ashley shares her neurodivergent background (ADHD, depression) and how a diagnosis in 2020 reframed business struggles not as personal failings, but as system-based issues:

    “It’s not a you problem, it’s a systems problem.” (05:46, Ashley)

  • Letting go of shame around being “bad” at tasks—many times it's just that the right system isn’t there yet.

2. Functional vs. Fun Organization

• Dopamine Chasing vs. Productivity (09:30 - 12:20)
  • Annemie and Ashley distinguish “fun organization” (buying new planners, color-coding, endless prepping) from “functional organization” (processes that streamline real work).
  • A key insight: Constantly switching tools or reorganizing for fun actually stunts growth and efficiency.
  • Quote:

    “When you’re looking for fun and dopamine, especially in your systems...you’re really stunting your growth, because you’re restarting all of the time.” (10:38, Ashley)

3. Establishing a Central “Source of Truth”

• First Game-Changing System to Set Up (12:54 - 14:22)
  • The breakthrough almost everyone experiences: having a single, central place for all leads and client information.
  • Many use multiple tools and notes, resulting in scattered info and lost time—streamline this with a central profile for each client.
  • Quote:

    “Having that one central spot where everything about the client lives totally changes your relationship with your business.” (14:08, Ashley)

4. Customizable Tools vs. All-in-One Solutions

(16:48 - 21:59)

• Discussion around CRMs like Dubsado/Honeybook versus the flexibility of Airtable for managing evolving business models.
• All-in-one tools have limitations; specialized tools may serve you better, even if it means juggling a few.
• Ashley’s approach: View software as a team member and strategic investment.
• Quote:

  "...software as a team member. $500 for software—if you are bringing in $50,000 in revenue—like, that is worth it to have a streamlined, automated tool..." (20:11, Ashley)

5. True Organization Is About Searchability, Not Perfection

• Overcoming Messiness Anxiety (21:59 - 25:03)
  • You don’t need every tool (Canva, Google Drive, etc.) perfectly organized—create an accessible system (e.g., an Airtable “Quick Links” table) that keeps essential info at your fingertips.
  • Empower your business by making Airtable (or your system of choice) the hub for everything: SOPs, links, content, clients, etc.
  • Quote:

    “Airtable is our source of truth for everything...anything we need is in Airtable. That’s just the rule of our business.” (24:10, Ashley)

6. Organizing for Longevity, Not Just Today

• Sustainable Organization & Future-Proofing (26:40 - 28:36)
  • Annemie’s experience closing her business underscored the pain of not having old info organized—set yourself up now, not just for convenience, but for long-term peace of mind.
  • Ashley emphasizes that centralized systems not only help the owner, but also make it easier to delegate and scale.
  • Quote:

    "If you have somebody come into your inbox and say, 'Hey, I need that gallery from two years ago,' ...you or a team member can go into that place and say, 'Oh, here’s the link. No problem.' ...those little client experiences are better, your peace of mind is better." (27:31, Ashley)

7. Getting Started: Simple Action Steps

• Ashley’s Post-Recording Advice (00:55 - 02:29, referenced at top)
  • Start by noting moments in your workflow that feel unnecessarily hard or time-consuming—track friction points, no matter how small.
  • Quote:

    "Those dumb little things that feel too small to even pay attention to...can add up. ...Those are the things that save you the most time and energy." (01:28, Annemie paraphrasing Ashley)

Notable Quotes & Memorable Moments

• On self-acceptance and systems:

  “When I looked at everything as: it’s not a you problem, it’s a systems problem, the shame went away." (05:45, Ashley)

• On functional organization:

  “If we just stopped seeking the fun, new stuff in tools and tech and organization and just sat down and got our work done...your business would grow so much more.” (11:13, Ashley)

• On focusing on functionality over perfection:

  “Airtable is our source of truth for everything...anything we need is in Airtable. That’s just the rule of our business.” (24:10, Ashley)

• On future-proofing:

  “If you want. If you’re in this business for the long haul, you want to have that documented place... you’re gonna get more clients, it builds.” (28:21, Ashley)

Timestamps for Key Segments

• 00:55 — Actionable advice: log friction points in your workflow
• 04:45 — Ashley’s personal and professional journey
• 09:30 — Fun vs. functional organization & habit pitfalls
• 12:54 — First powerful organizing system to create: central client info
• 16:48 — Specialized tools vs. all-in-one solutions
• 21:59 — Making searchability/process more important than perfect order
• 26:40 — Annemie’s experience closing her business and the pain of insufficient past organization
• 27:31-28:36 — The benefits of streamlined systems for client service and scaling

Resources & Where to Find Ashley

• Ashley’s Business: Systems Over Stress
• Best places to connect:
  • Instagram & Threads: @systemsoverstress
  • Offers: Airtable templates, courses, consultations, group programs

Episode Takeaway

Organization isn’t about making your desk look pretty—it’s about building systems that actually support you, your creativity, and your long-term business health. Shift your focus from chasing fun, shiny new tools to implementing simple, functional, and sustainable organization. Start by noticing workflow friction—and remember, the best system is the one that works for you, not the one that looks best on Instagram.

(Summary prepared in the original spirit and actionable tone of "This Can't Be That Hard" and the captivating energy of Annemie and Ashley’s conversation.)