Planner constraints and the tiny squares method

Too often, those of us with ADHD (and, honestly, just about anyone striving for success) fall into the “check the box and move on” mentality, downplaying our achievements and racing toward the next goal. Sound familiar?

In this episode, host Diann Wingert and returning guest Risa Williams, LMFT, challenge listeners to radically rethink what counts as a win. What if making a sandwich, sending a tough email, or—even better—taking a moment for self-care, can be celebrated as much as those big, flashy milestones?

If you’ve ever felt like your wins don’t "count," or you’re stuck on the productivity treadmill, this episode is your sign to embrace a kinder, more sustainable approach.

3 key takeaways from our conversation:

• Redefine Productivity: Success isn’t just about big goals—it’s about acknowledging every step, even the small ones. Practicing this daily fosters confidence and decreases imposter syndrome and chronic dissatisfaction.
• Combat Dismissiveness: Many of us grew up being dismissed or dismissing ourselves. Start catching that dismissive inner voice. Replace it with gentle validation—give yourself credit the way you’d celebrate a friend’s progress.
• Track and Celebrate Progress: Write down 3–5 tiny accomplishments every day. Over time, this simple act retrains your brain to notice and remember your efforts, fueling motivation and staving off burnout.

Mic Drop Moment:

Many high achievers with ADHD also battle imposter syndrome. Why? Because they literally cannot remember the many incremental steps it took to get results. If you don’t witness your own progress, you can’t internalize your success. The result: even evidence-based accomplishments don’t “count,” fueling the endless treadmill of “not good enough.”

About Risa Williams, LMFT

Risa Williams is a licensed therapist, a time management expert, and an award-winning book author of six self-help books. She's also the host of The Motivation Mindset Podcast (Apple, Spotify). Risa has been featured as an expert in Forbes Magazine, Wondermind, Wired, Bustle, Psychology Today, and Business Insider. She's also a busy mom of two and a university professor.

Connect with Risa:

Website - Instagram - Motivation Mindset Podcast

Ready to put it into practice?

Ultimately, reframing tiny wins is an act of reclaiming joy and validation from a world conditioned to withhold or diminish them. The results are worth it—greater momentum, resilience, and happiness. So, what tiny win will you celebrate today?

Risa Williams’ Tiny Wins Journal - Tiny Wins digital mini-course

Rick Hanson’s Book Buddha’s Brain

If You Take Just One Step

The act of writing down tiny wins and then reviewing them is what rewires the narrative in your brain. Do it out of skepticism, if that works. Gamify it, make it defiant, or treat it as an experiment. And because we know accountability makes it real, DM me on LinkedIn, email me, or leave a voice message on my website.

Your ADHD-ish host, Diann Wingert

Diann Wingert has decades of experience as a psychotherapist and serial business owner, and is now a sought-after coach to entrepreneurs with ADHD traits. Her style is direct, strategic, and always honest—peppered with the insight of someone who lives and breathes the ADHD experience.

Sharing is Caring

Know a fellow business owner who is on the productivity dreadmill, always moving on to the next project without celebrating their success? They might need this wake-up call, too, so be a pal and share the episode. Here is a link to make it easy.

© 2026 ADHD-ish Podcast. Intro music by Ishan Dincer / Melody Loops / Outro music by Vladimir / Bobi Music / All rights reserved.