Overcoming the Fear of Starting: Embracing Imperfection

Welcome to ADHD-ish, the podcast for ambitious entrepreneurs whose brains work a little differently.

I’m your host, Diann Wingert, and today we’re kicking off “The Momentum Series,” a deep-dive into what I like to call the “unholy trinity” of ADHD business struggles: starting, stopping, and switching gears.

Ever find yourself stuck in a never-ending planning phase, or maybe leaping headfirst into a project before you’re actually ready?

You’re not alone—it’s what I call the ADHD starting paradox, and it’s a challenge so many of us face. In this episode, we’ll break down why we get trapped in either over-planning or impulsively diving in, and explore the real fear that’s driving both: “What if I can’t keep this up?”

I’ll introduce you to my messy start method—a practical, low-pressure approach that ditches perfection and procrastination for real results. You’ll learn the 2% + 20% formula for action and discover foolproof systems that don’t depend on your mood.

Plus, I’ll walk you through concrete steps, emergency protocols for when you’re stuck, and real-world examples to get you moving—whether your challenge is launching a course, starting a podcast, or finally reaching out to those dream clients.

By the end of this episode, you’ll have practical strategies to overcome your biggest starting hurdles, and set yourself up for momentum that actually sticks. So if you’re ready to get your ass in gear, let’s jump in!

Episode Overview — What to Expect:

The Two ADHD Starting Problems:

• Analysis paralysis: Getting stuck in endless planning and research
• Cannonball starting: Diving in impulsively without enough prep

Why Both Approaches Set Us Up For Failure:

• Perfectionism and over-planning create pressure and stall action
• Impulsivity leads to chaos, burnout, and stopping problems

The Real Root: Sustainability Fear

• Why ADHD entrepreneurs fear they can’t keep things going—and why this fear is rational (but surmountable!)

The Messy Start Method:

• Diann’s proven “2% + 20%” formula to get unstuck
• How to combine just-enough planning with tiny, immediate action

The Five-Minute Blind Spot Check:

• Five quick questions to avoid overthinking or reckless starting

Mood-Independent Starting Systems:

• How to set up external cues and “pathetically small” first steps
• Using the two-minute rule for unstoppable momentum

Built-in Course Correction:

• How to schedule check-ins and adjust your approach without self-judgment
• Emergency protocols for when you’re frozen or tempted to leap in blindly

🎙️Mic Drop Moment: 

"The more you practice starting small and adjusting as you go, the more sustainable, quite literally, everything becomes. Because you're not depending on the perfect conditions, or the perfect mindset, or the perfect motivation. You're depending on real systems that work even when you're tired, distracted, or overwhelmed."

Help me help you

I am creating a FREE Start -Stop-Switch toolkit. Click here to complete an anonymous 30-second survey on your Starting Struggles to let me know what you need most. 

Don’t know Diann Wingert?

ADHD coach, former psychotherapist, and business strategist for neurodivergent entrepreneurs. Diann combines her professional expertise and lived ADHD experience to offer practical strategies for entrepreneurs whose brains work a little differently. Through her podcast and coaching, she’s passionate about helping others embrace their unique strengths and build sustainable businesses.

© 2025 ADHD-ish Podcast. Intro music by Ishan Dincer / Melody Loops  / Outro music by Vladimir /  Bobi Music / All rights reserved.