Developing Confidence as a Business Owner: a Client Success Story with CherylAnn Crego

Balancing multiple enterprises often leads neurodivergent entrepreneurs to doubt their capacity and leadership abilities. In this episode of ADHD-ish, host Diann Wingert sits down with client CherylAnn Crego to highlight how an ADHD small business owner can cultivate genuine confidence while running multi-passionate ventures.

Discover how embracing small windows of time, reframing a delayed diagnosis, and practicing targeted mindset tools help establish sustainable momentum. If you are a business owner with ADHD seeking empowering ADHD business coaching to step into leadership with clarity and ease, this client success story provides actionable inspiration.

EPISODE HIGHLIGHTS & TIMESTAMPS:

01:20 - Developing Confidence as a Business Owner

07:45 - Overcoming Imposter Complex for ADHD Entrepreneurs

15:30 - Tailoring Business Systems for ADHD Success

22:15 - Self-Trust and Decision-Making in Business

28:50 - Sustainable Growth for the ADHD Founder

Here are three key lessons from CherylAnn’s story for anyone managing multiple responsibilities while living with neurodivergence:

Embrace the “Nooks and Crannies” of Time:

You don’t always need a full day or a perfect schedule to make progress. CherylAnn leverages unexpected gaps in her day to move projects forward—proving that momentum can be built in the margins.

Growth Can Mean Letting Go:

Sometimes leadership requires making tough calls, like sunsetting a beloved business. CherylAnn shared how being honest about capacity and leading family and team members through disappointment is true leadership—and it’s okay to grieve business decisions. She also shares some vulnerable moments while talking about letting go of ego in service to growth.

Confidence Can Be Cultivated (at Any Stage):

Even as an experienced therapist, CherylAnn found new confidence by being open to coaching, embracing affirmations, and reframing challenges as opportunities to grow.

A Different “Take” on a Delayed ADHD Diagnosis

Cheryl Ann reflects on her midlife ADHD diagnosis and discusses how learning to build life strategies before even knowing she had ADHD turned out to be a hidden blessing.

For me, some of the most satisfying things about sharing the experience and outcomes from our work are how CherylAnn came to see herself in a new way, how she embraced the role of being “the boss,” and why finding the right support (and having a little fun) is essential when choosing the right coach, especially for someone who is accustomed to figuring things out on their own.

Client Bio

CherylAnn Crego is the co-founder of Chef Kent Getzen, a consulting business she started with her husband, whom she lovingly refers to as “the talent.” Together, they travel across the country teaching schools how to cook from scratch, source ingredients locally, and develop essential cooking skills.

Like many individuals with ADHD, CherylAnn is multi-passionate and multi-talented. In addition to being the CEO (and business brain) of the consulting business, CherylAnn is also a licensed psychotherapist in private practice, is in the midst of writing her first book, and has an extensive background in the performing arts.

Mentioned during the interview

• John Sovec - Diann’s friend and therapist who used to work for Disney
• Disney Front of House & Back of House distinctions
• Neurodiversion 2025 - the conference in Austin, where we hung out in person
• ADDitude Magazine - the leading website for resources and support for ADHD

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

Is it time to build YOUR confidence as a business owner with ADHD?

I have two openings for one one-on-one coaching engagements, starting in October. 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.