Welcome back to ADHD-ish! In this episode, host Diann Wingert sits down with marketing strategist, copywriting expert, and podcaster Erin Ollila.

This convo is all about pop-up offers—and how adding a dose of novelty can transform your business. Inspired by her own ADHD-driven creativity, Erin shares the thought process behind developing two unique, time-limited offers just before a major launch.

What sets these pop-ups apart? They’re quick, strategic, easy to implement, and build on skills and systems Erin already uses in her daily work.

Together, Diann and Erin unpack the benefits and pitfalls of pop-up offers, the importance of strategy, and why a well-designed “quick win” can boost both business and client satisfaction.

You’ll hear how Erin’s ADHD-fueled ability to make rapid decisions, build connections, and see opportunity in white space on her calendar led her to a set of mini-offers that serve both her capacity and her clients’ need for immediate results.

If you’ve ever felt stuck between launching new programs or just want to shake things up in your offer suite, this episode is gold.

Here’s what you’ll learn from this episode:

1. What the heck is a pop-up offer? Erin breaks down how these limited-time, ultra-focused offers work—and why they’re not just a glorified sale.
2. Why pop-up offers are a dream for ADHD entrepreneurs. Ever feel compelled to act on a spark of creativity? Learn how to channel that energy in ways that actually make sense, earn money, AND feel fulfilling.
3. The strategy behind a successful offer It’s not just about the excitement; Erin is all about blending impulsivity with real business strategy so your pop-ups support your bigger vision.
4. How to create quick wins for your clients (and for YOU!) Discover ways to design services that give instant gratification and long-term results—yes, even for things like SEO and content strategy.
5. What to do when things don’t go as planned Real talk: Erin and Diann discuss what happens when nobody buys right away and how to adapt without losing your momentum.

About our Guest:

Erin Ollila is a content strategist & conversion copywriter with 15+ years helping brands and publications connect through strategic content. She’s the founder of EO Copy Co., the host of the “Talk Copy to Me” podcast, and a fellow entrepreneur with ADHD.

Connect with Erin:

Website - LinkedIn - Instagram

Was this episode THE ONE that is prompting you to leave a 5-Star rating and review? Do it! Here’s the link for Apple or Spotify: https://lovethepodcast.com/adhd-ish

Already left your review and want to share a comment on Spotify? I’d love to hear from you and respond personally to every one!

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

No one launches their own business in search of exhaustion. But for so many of us with ADHD-ish tendencies, overworking, over-delivering, and over-researching often become our default—especially when our own sense of “enough” is broken or never got calibrated in the first place.

This episode goes deeper than productivity advice; it’s about safety, self-worth, and learning what sustainability truly requires.

I share the real reason our inner “enoughness meter” is so hard to find—and how you can start recalibrating it for sustainability (not burnout).

Sometimes, the pursuit of “above and beyond” is really about chasing safety, not satisfaction.

What you’ll learn:

1. Why your “enoughness meter” is so damn hard to read.

Diann Wingert explains how, for entrepreneurs with ADHD, it’s not about laziness or lacking motivation—a lot of us just genuinely can’t judge when a task is finished.

2. The two main tracks that shaped your patterns:

Are you the “overachiever” always collecting gold stars, or the “compensator” trying to cover every base (and then some) out of fear of dropping the ball? Maybe both? You’ll discover your origin story—and why it matters.

3. The “Enough Already” Framework (it has five parts!).

Get real, actionable tools—like calibration questions and the Enough Algorithm—to help you finally stop overdoing and start celebrating what’s truly “good enough.”

4. How to tell the difference between flow state and fear state.

If you keep working because you’re energized, great! If you’re pushing through out of anxiety or fear, Diann Wingert shares how to spot the signs and what to do instead.

5. How to set micro-commitments and collect EVIDENCE that enough really is enough.

Try out the practical scripts and journaling prompts, and learn to recalibrate that internal workload meter (it CAN be done!)

Mic Drop Moment:

"Enough isn't about lowering your standards. It's not about doing mediocre work, striving for the bare minimum, or simply not caring enough to do better. It is about directing your excellence strategically instead of indiscriminately."

Try It With Me

Pick your area. Make a micro commitment. Collect your evidence. And then—here’s my ask—email me and tell me what happened when you stopped at enough. I want to hear where you struggled, what surprised you, and how it felt when it finally got easier.

We’ve run past the finish line for too long, measuring our value by exhaustion instead of impact. Now’s the time to recalibrate.

And if you want the full road map, join me on ADHD-ish—I’m here every week, sharing the hard-earned lessons I’ve learned (sometimes the hard way), and cheering on every step you take towards “enough.”

Ready to try? I’d love to hear your story. Email me at diann@diannwingertcoaching.com or DM me on LinkedIn

About the Host:

Diann Wingert (she/her) is a seasoned coach, consultant, and the creator/host of ADHD-ish. Drawing from her many years of experience as a former psychotherapist, business owner, and someone who thinks "outside the box," Diann is known for her straight-talking, no-nonsense approach to the intersection of neurodiversity and business ownership.

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

Welcome to another episode of ADHD-ish!

Today, host Diann Wingert is joined by psychologist and viral TikTok creator Dr. Dante for a raw, insightful look at the "Neurodivergent Edge"—how ADHD traits transform not just personal relationships but entrepreneurial success.

In this conversation, Dr. Dante shares the story behind his celebrated term "neuro baddies," celebrating the honesty, intensity, and creativity that neurodivergent women bring to the table.

Together, Diann & Dante explore why society’s negative perceptions of ADHD traits miss the mark, how trauma bonds form, and how rejection sensitivity and perfectionism can be reframed as superpowers in both love and business.

You’ll hear candid stories, hard-hitting truths about justice sensitivity, and practical wisdom on breaking free from toxic relationships—plus, a message for neurodivergent women struggling with self-acceptance.

If you’ve ever wondered how your different way of thinking can be your biggest asset, this episode will inspire you to name it, claim it, and embrace the title of“neuro baddie” proudly.

What’s Inside This Episode?

Here are 5 keys you’ll learn in today’s convo:

1. The Origin of "Neurobaddies": How a spontaneous ADHD thought in the grocery store parking lot became a viral, empowering movement for neurodivergent women.
2. Why Neurodivergent Women Make Amazing Partners: Honesty, hyperfocus, and genuineness—discover why these traits are actually super attractive (not quirks to hide!).
3. The Narcissist Trap: Neurodivergent traits can make women more vulnerable to toxic relationships, but knowing the signs gives you real power to protect yourself.
4. Entrepreneurial Superpowers: How “all-in” energy, justice sensitivity, and relentless action drive success in business (yep, your ADHD traits are an asset!).
5. Healing Starts With Self-Trust: Why learning to trust yourself is the real game-changer, despite years of negative feedback.

Guest Bio:

Dante Assad Williams, PsyD (Dr Dante) is a Minneapolis-based psychologist, adjunct professor, entrepreneur, and social media influencer who highlights the unique strengths of neurodivergent women in relationships and in business.

With lived experience as a neurodivergent (ADHD) man, and a viral TikTok following built on his unapologetic appreciation for "neuro baddies," Dr. Dante brings authenticity, deep understanding, and hope to every conversation about mental health, relationships, and business. His body of work is centered on neurodivergence, trauma, and holistic masculinity.

Connect with Dr Dante:

TikTok - Instagram - 5 Keys to Know if You’re a Neurobaddie

Fun Fact from the Episode:

Dr. Dante named “neurobaddies” on a whim in a 10-second TikTok video? He didn’t expect it to go viral—but now, it’s a movement with merch on the way! (Yes, T-shirts are coming!)

Is it time to build more balance and sustainability into your business?

I have two openings for one-on-one coaching engagements, starting this month. The first step is scheduling a free consultation where we talk about your goals and see if we are a good fit. Click here to book yours now.

And, don’t forget to

As we wrap up 2025, it seems like everywhere you look, it's all about reflection journals, vision boards, 90-day planners, and goal-setting frameworks.

If you're feeling absolutely nothing (or, let's be real, maybe a little guilty it's not working for you), I’m right there with you.

So, instead of one more system to make you feel “less than,” I’m serving something totally different—a simple, honest inventory. Just three lists: Energy, Money, Time. Here’s the breakdown:

Energy Inventory

1. What gave you energy this year? What absolutely drained you—even if it was profitable or “successful”?
2. Which tasks, clients, or projects left you jazzed up… and which made you want to flee the building?
3. Notice the patterns. Pattern recognition tends to be a skill that ADHD brains excel at.

Money Inventory

1. What actually made you money, versus what you thought should make you money?
2. Which offers did people really buy? Where did revenue flow in from? What’s gathering dust (subscriptions, courses, tech) in your digital library?
3. If most of your money came from one thing, but you spent all your time on everything else—this is info, not failure.

Time Inventory

1. When did you do your best work? Was it in performance windows that don’t match “normal” business hours?
2. Was your magic at 10 pm in the car, Friday mornings, or after a walk or shower?
3. This is about gathering intelligence, not shaming yourself. Design your days around your actual brain, not someone else’s ideal.

Subtraction is Strategy

Every time I let go of what wasn’t working, the good stuff got even better. So maybe your “stop doing” list is more important than any “to-do” list. Eliminate the clients, offers, or systems that drain you, no matter how much they pay. Permission granted to not start that newsletter, podcast, or YouTube channel you’ve been “planning” for two years.

Final step:

Commit to ONE thing that’s already working and carry it forward. Whether it’s sticking to your creative window or leaning into your night owl energy, just one thing that fits your brain. For me, it’s this podcast.

No pressure, no massive goals, no breakthroughs required. 2026 is happening no matter what. Go in knowing what energizes, pays, and fits your unique brain—and that’s your built-in advantage.

Mic Drop Moment:

“We're great at building these complex offers that we think people want. We spend months perfecting the positioning, creating the fancy framework, building out the whole fricking thing. And then we're genuinely shocked when that simple little thing we threw together in an afternoon is the one that actually makes more money.”

About the Host:

Diann Wingert (she/her) is a seasoned coach, consultant, and the creator/host of ADHD-ish. Drawing from her many years of experience as a former psychotherapist, business owner, and someone who thinks "outside the box," Diann is known for her straight-talking, no-nonsense approach to the intersection of neurodiversity and business ownership.

Enjoyed the...

What This Episode Is About

If your brain generates ideas faster than you can execute them, this conversation will make you feel seen. Sarah runs five businesses and has developed a systematic approach to managing what I call the "burden of creativity"—that relentless flow of inspiration that can fuel or derail you, depending on how you work with it.

This isn't about picking one lane or shutting down your creative engine. It's about building frameworks that let you honor your ideas without drowning in them.

Who This Episode Is For

1. Founders juggling multiple business ideas or revenue streams
2. Creatives who struggle with follow-through despite abundant inspiration
3. Consultants and coaches who feel scattered across too many offers
4. Anyone who's been shamed for having "too many interests."
5. Serial entrepreneurs who want to build interconnected businesses without burning out

The Big Idea

Having an ADHD brain means you're wired for abundant creativity. The challenge isn't generating ideas—it's knowing which ones deserve your energy and how to move them from concept to completion without burning out or abandoning ship halfway through.

Sarah's approach: treat your ideas like they matter, but give them structure so they don't hijack your focus.

What to Listen For

The Reality of Being a Creative Polymath

For many ADHD entrepreneurs, being interested in multiple things isn't a distraction —it's how they’re built. Sarah explains why being a polymath is actually an advantage in today's business landscape, as long as you set boundaries around what gets your attention.

The "Catching Butterflies" System: Capture, Connect, Structure, Iterate, Express, Reflect

Sarah walks through her six-stage process for managing creative output. It starts with capturing every idea without judgment, then moves through connecting related concepts, building structure around the keepers, iterating on them, expressing them in the world, and reflecting on what worked. Simple in concept, powerful in practice.

Using AI as Your Digital Thought Partner

Both Sarah and I use AI tools (ChatGPT, Claude) to externalize our thinking. Instead of letting ideas swirl in our heads, we dump them into our AI assistants to help us organize, connect dots, and build project folders. It's like having a patient colleague who never gets tired of your tangents.

The 3D Jenga Model for Interconnected Projects

Rather than treating each business or project as a standalone tower that could topple, Sarah visualizes her work as a 3D Jenga structure. Each piece supports the others. When one idea doesn't work out, the whole thing doesn't collapse—the remaining pieces actually get stronger.

Energy Management Over Time Management

Reflection isn't self-indulgence—it's how you build a feedback loop that keeps you moving forward. Regular check-ins about how you feel, what your vision is, and whether your projects still serve that vision help you stay aligned instead of spinning your...

Is it possible to have a brain wired for entrepreneurship, but actually thrive best within traditional employment? In this insightful episode, host Diann Wingert flips the script on the common narrative in both the ADHD and business worlds: that entrepreneurial traits automatically mean you should start your own business.

Instead, she explores the concept of intrapreneurship—bringing creativity, innovation, and entrepreneurial spirit into an existing organization—and how this path might be the most strategic decision for many ADHDers.

If you’re wrestling with the decision to go solo or stay employed, give this episode a listen. It just might give you permission to build a life—and career—that truly works for your brain.

Three key takeaways:

Entrepreneurial traits ≠ Entrepreneurial career:

You can be creative, visionary, and disruptive without having to start your own business. Don’t fall for the myth that employment is “settling.”

Intrapreneurship unlocks impact & stability:

Express your entrepreneurial strengths inside an organization. Lead without authority, innovate processes, and treat your role like you own it—while benefiting from structure, resources, and a steady paycheck.

Signs that traditional employment isn’t right for you:

Not everyone is meant to shine as an intrapreneur. If every manager is a nightmare, structure feels suffocating, or your best ideas die in committee, maybe going solo is your move. But it’s all about matching your brain and real life with the right path—not shame, not hustle-culture FOMO.

Workplace roles & cultures where ADHD-ish traits thrive:

Look for product development, business strategy, internal consulting, startups, project-based work, or innovation labs. Go where experimenters are rewarded, hierarchies are flatter, and outcomes matter more than bureaucracy.

Mic Drop Moment:

“Infrastructure isn't the enemy of innovation. Structure, when it's the right structure, is what lets your brain do what it does best without getting derailed by all the shit you hate doing."

Action Step:

Take 10 mins for honest self-reflection. Where do you really do your best work? What structure supports you? Then, make the choice that serves your life—not LinkedIn optics or anyone else’s expectations.

About the Host:

Diann Wingert (she/her) is seasoned coach, consultant and the creator/host of ADHD-ish. Drawing from her many years of experience as a former psychotherapist, business owner, and someone who thinks "outside the box," Diann is known for her straight-talking, no-nonsense approach to the intersection of neurodiversity and the world of work.

Enjoyed the Episode?

Share your thoughts! Leave a review and let Diann know what resonated, challenged, or inspired you. Your feedback helps ADHD-ish reach more listeners who need to hear these honest conversations.

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

Diagnosed recently with both ADHD and autism, Cat Orsini’s candid storytelling takes us on a journey from feeling like an outsider to building a thriving business based on authentic relationships, automation with heart, and radical self-acceptance.

In this interview, Cat reveals her unique approach to business—one that centers curiosity, genuine connection, and meeting people where they are (with a little tech magic to make life easier and more fun).

You’ll hear not just the triumphs, but also the complex, sometimes messy moments of “unmasking” and designing a business that fits your actual brain and values, not someone else’s idea of success.

Episode Highlights:

Strategic Relationship Marketing vs. Automation

Cat breaks down why automation and relationship-building aren’t mutually exclusive—and how smart systems can let neurodivergent business owners focus on authentic, meaningful connections.

Attract, Don’t Chase

Move over “hustle culture.” Cat and Diann discuss how building genuine relationships and letting people self-select nurtures business without the creepiness or pressure of hard selling.

Neurodivergent Thriving in Business

How Cat’s ADHD and autism traits fuel her ability to notice patterns, create unique solutions, and support her clients in efficiently reaching their goals.

Automating the Human Touch

Learn how emails, follow-ups, and event workflows can be automated, freeing up energy for one-on-one connections with those who are ready for deeper engagement.

Ethical Reciprocity & Non-Bro Marketing

Cat outlines how heart-centered reciprocity builds lasting relationships and why neurotypical tactics often miss the mark for neurodivergent individuals.

Meet our Guest: Cat Orsini

Cat Orsini has an MBA, is a master-certified coach, an entrepreneur, and co-author of the book "Experts Never Chase."

She specializes in relationship marketing, strategic conversations, and building automated systems that allow her—and her clients—to focus on human connection over busywork.

Through radical acceptance of her neurodivergence and trauma history, Cat has crafted a career and life that honors her strengths and refuses to squeeze herself into a neurotypical mold.

Links & Resources:

• Connect with Cat on LinkedIn
• Learn more about Cat Orsini and her work
• The Book Cat Co-Authored - Experts Never Chase

Know someone who identifies with ADHD + Autism (officially diagnosed or not…)?

Think this episode would inspire them? Here is the link to share it with them, in the most comfy way possible: https://bit.ly/episode-blog-292

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

Welcome back to ADHD-ish! In this episode, host Diann Wingert sits down with her client Steph Cotrell for a candid and relatable discussion about what it really means to build—and rebuild—a business when you have ADHD traits and life throws you curveballs.

Originally hired to help Steph Cotrell grow and scale her successful business, Diann quickly uncovered some uncomfortable truths about her business model, specifically how her notion of collaboration revealed a lack of boundaries, which led to burnout.

Their coaching journey took an unexpected turn as Steph was faced with redefining her work, grappling with exhaustion, and eventually reshaping her business to prioritize authenticity, personal connection, and family in the wake of a heartbreaking loss.

Together, they explore the challenges of managing emotional labor, the reality of ADHD-driven blind spots, and the courage it takes to rethink your path when everything changes.

If you've ever felt caught between ambition and overwhelm or questioned how your neurodivergence shapes your entrepreneurial journey, this episode is for you.

Here are 3 key takeaways from this conversation:

Scaling “as-is” can scale your problems, not just your profits: Before trying to grow, pause to check if your foundation—relationships, workload, boundaries—truly supports the life you want.

• Give yourself permission to redefine success: It’s not all-or-nothing. You can reshape business relationships and paths to fit changing needs, values, and energy levels.
• Clarity fuels action: The sooner you move from overthinking to taking action (even messy, uncertain steps), the faster you learn, adapt, and build the business—and life—that truly work for you.

Mic Drop Moment:

"You don't have to be the glue holding all of this together. If you enjoy working with them, work with them, and if you don't, don't."

Connect with Steph Cottrell:

Website: https://www.blueelephantcreative.com

LinkedIn: https://www.linkedin.com/in/bluelecreative/

How Steph discovered me:

ADDItude Magazine webinar: “How to Build a Business That Works for Your ADHD Brain”

Want to hear more Client Success Stories? Click here for the custom playlist

Is it time to redefine your success as a business owner with ADHD?

I have two openings for one-on-one coaching engagements, starting in January. The first step is scheduling a free consultation where we talk about your goals and see if we are a good fit. Click here to book yours now.

And, don’t forget to leave a comment on Spotify (I personally respond to every one) or leave a review so more ADHD-ish business owners can find THE podcast full of real talk and real solutions for neurodiverse business brains.

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