Boredom-Proofing Strategies to Keep Offers Fresh

Ever launched a program, course, or membership that once set your heart on fire, only to find yourself completely over it just as it starts running like a well-oiled machine? If you’re an entrepreneur with ADHD, this scenario is all too familiar. 

In this straight-talking solo episode, Diann Wingert unpacks why boredom hits hardest when your business finally starts working—and what to do about it. 

7 Things You’ll Learn From This Episode:

The Real Reason You Get Bored: Learn the neuroscience of ADHD boredom and why your brain craves novelty (hint: it’s about dopamine, not discipline).

The “PROOF” Framework:

A practical tool to help you decide if it’s time to renew or release your business offers.

How To Build Boredom-Proof Systems: Discover strategies to rotate, redesign, and reinvent your business model so you stay engaged long term.

Strategic Delegation & Role Redesign: Find out how letting go of the dull stuff (or handing it off!) can reignite your passion—and even grow your business.

Permission to Evolve: Why shifting your focus is not failure, but good business and good self-care.

Want your entrepreneurial journey to last? Build boredom-proofing in from day one.

• Alternate focus areas each quarter.
• Design offers so they evolve or rotate naturally.
• Proactively plan breaks, new challenges, or learning cycles.

And, most importantly, give yourself grace when you need to pivot, change, or retire offers. Evolution isn’t failure; it’s strategic adaptation.

Fun Fact from This Episode:

Did you know that constraints—NOT unlimited freedom—are actually better for the ADHD brain? Giving yourself playful “rules” can boost creative energy and bring the spark back to your work.

Next Steps: 

Download the FREE cheat sheet and put the PROOF framework to work today. 

Re-listen to Ep #277_ “The Soulmate Phenomenon: How ADHD Fuels Idea Infatuation In Your Business”  It’s the other side of the same coin! 

Mentioned in this episode: 

Episode # 288 “ADHD is Not Just in Your Head: Exploring Embodied Neuroscience” with Dr Miguel Toribio-Mateas 

About the Host

Diann Wingert is a seasoned psychotherapist-turned-business coach who blends neuroscience, entrepreneurial strategy, and real-life ADHD experience.

Her specialty? Helping entrepreneurs design businesses around their brains, instead of fighting them.

She’s the creator of The Boss Up Breakthrough coaching framework, where she brings actionable wisdom to entrepreneurs with ADHD who want a stand-out, sought-after, profitable business built on their unique brilliance, without burning out.  

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