Podcast Summary: ADHD-ish with Diann Wingert

Episode: Shifting Smoothly with ADHD: Stop Task Switching Stress – ADHD Tips That Actually Work
Date: July 15, 2025

Overview of the Episode

In this episode, Diann Wingert tackles the crucial—yet often overlooked—challenge for ADHD entrepreneurs: transitioning smoothly between different types of work. As the final installment in the "Momentum" mini-series, this episode explores the hidden costs of tough transitions, the science behind ADHD and task switching, and practical, actionable strategies for maintaining momentum in a business world that demands constant context changes.

Key Discussion Points and Insights

1. The Strain of Context Switching with ADHD

• Diann illustrates a typical, chaotic workday—the constant bouncing between client calls, content creation, admin, and emergencies—resulting in mental fatigue:
  • Quote: "My brain felt like scrambled fricking eggs... Not because any individual task was so difficult, but because the constant switching context was exhausting." (04:15)
• Highlight: For ADHD brains, context switching isn’t a rare inconvenience—it’s the job description for entrepreneurs.

2. The True Cost of Tough Transitions

• Smooth transitions are vital for maintaining business momentum; tough ones “kill momentum” and leave entrepreneurs feeling “busy but you don’t have much to show for it.” (06:35)
• Three common transition struggles are personified:
  • Task Switching Whiplash (Blake): Losing time and energy moving between different work modes.
  • Context Switching Chaos (Marcus): Confusion between multiple clients and projects, leading to mistakes and lost time.
  • Re-Entry Friction (Maya): Losing momentum after a break, with old notes feeling like a foreign language.

3. ADHD and Transition Difficulties

• ADHD brains have “higher task switching costs,” longer recovery times, and struggle with working memory and cognitive flexibility:
  • Quote: “All those years that we’ve spent bragging about our miraculous multitasking abilities, we were only fooling ourselves.” (15:25)
• Tough transitions are cumulative: energy lost on early switches worsens later transitions, leading to full-day exhaustion.

4. The Transition Bridge System

• Foundational Strategy: Don’t jump from task to task—build “bridges” to carry you smoothly from one context to another:
  • “The jump might be faster if you make it, but it requires a lot of energy... a bridge takes more effort up front...but it gets you across safely, consistently, and with a lot less energy expenditure.” (21:05)
• Once built, these bridges make future transitions easier.

a. Breadcrumb Trails

• For daily switches: Leave minimal breadcrumbs—one sentence on where you left off, one on the next step, key links/files.
  • Example: “Just finished reviewing Q3 metrics. Next step is creating the presentation deck. Spreadsheet is in the Q3 folder.” (23:20)
• For project transitions: Write status notes with key decisions, next steps, and deadlines—enough so you don’t have to relearn everything.
• For extended breaks: Record a two-minute voice memo, update project management, and set a realistic re-entry day.

b. Transition Rituals

• Micro (within the same session): Simple pattern breaks (stand, stretch, get water, change playlist, 3 deep breaths).
• Macro (between different project types):
  • Clear workspace (physical and digital)
  • Review new goals
  • Set intention and gather materials
  • Takes 5-10 minutes but prevents confusion (30:10)
• Emergency or planned breaks: Triage must-do tasks, lower standards, ask for help, and PLAN reentry.

c. Context Switching Strategies

• Creative ↔ Admin: Build 10–20 minute buffers, shift environment/tools, match to energy level.
• Client A ↔ Client B: Review notes, close unrelated files, say their name aloud and, if possible, look at their photo (pattern interrupt).
  • Quote: “Right before you start work on the new Client project, say their name out loud. Seriously? It is a seriously effective pattern interrupt.” (40:35)
• Intense ↔ Low-focus: Use lighter tasks as a bridge post-deep work, don’t shift into intense work without recovery.
• Multiple projects: Use visual cues (color coding, different folders), batch similar tasks, quick regular check-ins to keep projects “alive,” resist switching just because something is hard.

d. Building in and Honoring Transition Time

• Typical guidelines:
  • 5–10 min for tasks within the same project.
  • 15–20 min for switching projects.
  • 20–30 min for switching clients.
  • 30–45 min for major context shifts.
• Quote: “It’s time you are already spending. You’re just spending it inefficiently through false starts and rework.” (55:15)

e. Recovery After Disruption

• Don’t immediately try to catch up; start with a pen-and-paper brain dump, then ease your way back in, calibrate standards, and reintroduce transition rituals stepwise ("parfait style").

Real-World Application Examples (65:30–72:00)

• Managing client work vs. your own business:
  • Dedicated time blocks, clear transition rituals, different locations/setups, end-of-block notes.
• Seasonal transitions:
  • Transition “week” with distinct phases: close out old projects, brain dump, plan, then reengage.
• Re-entry after illness/vacation:
  • Multi-day ramp-up; allow 70% productivity for first week back.
• Daily task management:
  • Planned transitions with rituals and buffers; use different playlists, locations, and end-of-session notes for smooth handoffs.
• Multiple client projects:
  • Client-specific days/blocks, setup time for reviewing notes, colored folders, and buffer time.

Notable Quotes and Memorable Moments

• On context switching as a job requirement:
  • “When you are running a business, context switching is not occasional or optional. It is the freaking job description.” (04:50)
• On ADHD task switching cost:
  • “Neurotypical brains can often power through rough transitions... ADHD brains? Not so much. For us, these costs are higher and our recovery time is longer.” (15:05)
• Why you need breadcrumbs:
  • “Every time you come back to a project and you didn’t leave proper breadcrumbs, you have to spend precious cognitive energy just remembering where you were.” (13:55)
• Patterns, not tools:
  • “Different types of transitions require different rituals—there’s no one tool for all uses.” (34:55)
• On embracing buffer time:
  • “I know this seems like a lot of time you just don’t have... But can I give you the real truth? It’s time you are already spending. You’re just spending it inefficiently.” (55:15)

Takeaway: The Four-Part Smooth Shift System

1. Intentional Boundaries – Dedicated time and space for task types or clients
2. Transition Rituals – Small, repeatable actions that signal a mental shift
3. Breadcrumb Systems – Notes, checklists, or voice memos for re-entry
4. Buffer Time – Explicit scheduling of transition periods

Resources Mentioned

• Diann’s new Start Stop Shift Toolkit—a system designed specifically for ADHD-ish entrepreneurs, available via the show notes.

Summary

This episode reframes the ADHD entrepreneur’s struggle not as a failure of focus, but as an energy management issue related to unbridged transitions. Diann offers strategies—from simple notes to mindful rituals—that, when consistently applied, can turn exhausting, scattershot days into maintainable, energized, and productive work rhythms. The key message: Smooth transitions are your leverage for sustainable business momentum—and your sanity.