Podcast Summary:

ADHD-ish with Diann Wingert
Episode: Starting Strong with ADHD: Overcoming Procrastination & Task Avoidance to Get the Ball Rolling
Date: July 1, 2025

Overview

This episode kicks off a three-part series exploring the "unholy trinity" of ADHD struggles in entrepreneurship: starting, stopping, and switching gears. Host Diann Wingert, a psychotherapist-turned-business coach with extensive experience helping ADHD-ish business owners, takes a deep dive into why starting projects is uniquely difficult for those with ADHD traits—and lays out practical, actionable strategies to overcome the cycle of procrastination, impulsive launching, and sustainability fears.

Key Discussion Points and Insights

1. The ADHD Starting Paradox (00:35)

• ADHDers have two opposing “starting problems”:
  • Analysis Paralysis: Endless planning, research, and preparation, never actually launching (“I want to make sure I have everything figured out first.” — Renee, [07:34])
  • Cannonball Starting: Impulsive action with minimal planning, leading to panic when details unravel (“He sold founding memberships and then spent the next three months in panic mode…” — [09:20])
• Core insight: Both strategies are rooted in the SAME fear: not being able to SUSTAIN what they start.

2. Anatomy of Over-Planning (10:38)

• Illusion of productivity: Planning feels responsible, but can be an elaborate form of procrastination (“It’s an elaboration of procrastination, wearing a productivity suit.” — Diann, [12:30])
• Perfection trap: The more one plans, the higher the stakes get; nothing feels ready enough.
• Safety in the hypothetical: As long as an idea stays in “planning,” it can’t fail (“It’s Schrodinger’s business idea…” —[13:50])

3. Risks of Impulsive Launching (15:00)

• Chasing dopamine: Excitement ≠ clarity. ADHD brains love newness and can conflate action with informed action.
• Inevitable crash: Realization of unpreparedness leads to doubt, research spirals, or bailing out.
• Link to “stopping problems”: Impulsive starts risk quick burnout or loss of confidence.

4. The Sustainability Fear (18:45)

• It’s real and justified: ADHDers have often started projects that fizzled.
• Misplaced focus: We try to sustain motivation, momentum, or “perfect conditions”—all inherently unsustainable.
• Key mindset shift: What IS sustainable is tiny, imperfect action.

5. The Messy Start Method (20:18)

• Antidote to both extremes: Not perfect prep, not pure impulse—“informed action with built-in course correction.”
• The “2% + 20%” Formula:
  • 2% Effort: Teeniest, tiniest action (“If you want to start a podcast, 2% effort is recording a two minute voice memo about your idea…” — [22:27])
  • 20% Planning: Just enough research to avoid obvious blunders—NOT exhaustive research.

Five-Minute Blind Spot Check ([28:00])

• Five quick reflection questions to address before acting:
  1. What’s the actual outcome I want?
  2. What’s the biggest thing that could go wrong, and can I live with it?
  3. What do I need that I don’t have (skills, tools, people, time, money)?
  4. Who is my first customer, user, or audience for this?
  5. How will I know if it’s working?

“That’s it—five questions, five minutes. If you can’t answer all five, you’re overthinking or you’re not ready to start yet.” — Diann ([31:50])

6. Mood-Independent Starting Systems (33:42)

• Motivation is fickle: Build systems that work when you’re NOT “feeling it.”
• Key steps:
  • Starting Signal: External cue (time, place, ritual) that triggers work regardless of emotion.
    (“She only starts new projects in her car, in a coffee shop parking lot…” — [34:50])
  • Pathetically Small First Step: “So small you’d feel ridiculous not doing it.”
  • The Two-Minute Rule: Work for two minutes, then give yourself permission to stop.
  • Always have the next tiny step ready: Prevents decision fatigue.

7. Built-in Course Correction (39:50)

• Check-ins: Schedule regular “review points” (after a week, two weeks, etc.)
  • Ask:
    1. Is this working toward my goal?
    2. What have I learned that I didn’t know?
    3. What needs to adjust based on what I’ve learned?

8. Emergency Protocols for Getting Unstuck (43:10)

• Overthinking: Set a 25-minute timer, start with what you have, allow yourself to suck.
• Impulsive leap: Do a five-minute check, get perspective (not permission), sleep on big-money decisions.

9. Making Sustainable Starts Real (47:00)

• Focus on daily contact, not daily perfection:
  • "You're trying to sustain the practice of showing up imperfectly and course correcting as you go along." — Diann ([49:10])
  • Some days are 2% energy, some 80%—ALL count.

“Everything counts. The goal is not to maintain your peak performance. It is to maintain contact with your project even when you don’t feel like it.” — (49:45)

10. Real-World ADHD-ish Starting Examples (51:10)

• Launching a Course: Don’t build the whole thing. Test one lesson with three people, then iterate in a group setting.
• Marketing Campaign: Post ONE thing on ONE platform with a single offer. Evaluate. Iterate.
• New Service: Offer a solution to one person, document the process, inform future offerings.
• Podcasting: Record five short takes on your phone before investing in gear or artwork.

11. Common Resistance Reframes (55:50)

• “But what if it’s not good enough?”
  • “Version 1 is supposed to suck—the job is to teach you what version 2 should look like.”
• Fear of Judgment:
  • “You’ve already judged yourself more harshly than anyone else ever will.”
• Wasting Time:
  • “You’ll waste more time planning the right thing than testing the wrong one.”
• Sustaining Perfection?:
  • “You can’t. But you can sustain small, consistent actions with course correction.”

Notable Quotes & Moments

• On starting problems:

  “We ping-pong between the two of them like we're in some kind of productivity hell.” — Diann (01:44)

• On analysis paralysis:

  “You know everything about your industry except how it feels to actually show up and do the fricking work.” — (03:49)

• On impulsivity:

  “You launch yourself into the deep end without checking if there’s even water in the pool.” — (04:45)

• On perfectionism in planning:

  “It’s an elaboration of procrastination, wearing a productivity suit. I know that hurts.” — (12:30)

• On course correction:

  “This is not about judging your progress...it’s about staying responsive to reality instead of stuck on your original plan.” — (42:30)

• On sustainability:

  “The real problem with sustainability is that we’re often trying to sustain the wrong things.” — (18:00)

• On action:

  “Everything counts. The goal is not to maintain your peak performance. It is to maintain contact with your project even when you don’t feel like it.” — (49:45)

Important Timestamps

• 00:35: Introduction to the “ADHD Starting Paradox”
• 07:34: Renee’s story (analysis paralysis)
• 09:20: Mark’s story (cannonball starting)
• 20:18: Introduction to the “Messy Start Method”
• 22:27: What “2% effort” looks like in practice
• 28:00: The Five-Minute Blind Spot Check
• 33:42: Mood-independent starting systems
• 39:50: Built-in course correction and check-ins
• 43:10: Emergency protocols for overthinking and impulsivity
• 47:00: Mindset shift on sustainability
• 51:10: Real-life ADHD-friendly “starting” examples
• 55:50: Addressing common objections and fears

Tone & Style

Candid, irreverent, supportive, and practical—Diann uses humor (“productivity hell”, “pathetically small first step”), tough love, and real-world stories from clients and herself to make complex psychological and practical ideas relatable and doable.

For Next Episode

Next up: “Stopping Smart”—knowing when to end, launching imperfectly, and course correction when you’re in over your head.

Summary Takeaway

Starting strong as an ADHD-ish entrepreneur is all about tiny, intentional actions and building systems that guide, not stifle. Planning and impulsivity are both traps if left unchecked: find the actionable middle by embracing mess, course correcting along the way, and redefining what it means to ‘keep going.’