Developing Confidence as a Business Owner

6 snips

Sep 30, 2025

CherylAnn Crego, a therapist and multi-business owner, dives into her journey of building confidence while managing several ventures. She shares how embracing small time windows led to significant progress, and how hard leadership decisions, like sunsetting a beloved business, shaped her growth. CherylAnn also discusses the power of affirmations in nurturing confidence and reflects on her delayed ADHD diagnosis as a hidden advantage in crafting life strategies. Her candid insights offer inspiration for anyone navigating the complexities of business and neurodivergence.

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INSIGHT

Momentum In The Nooks And Crannies

CherylAnn uses ADHD-driven shifting of focus to “fit things into the cracks” of her day and get tasks done.
She leverages short gaps to build momentum across multiple businesses.

INSIGHT

Delayed Diagnosis Can Force Useful Workarounds

CherylAnn views her delayed ADHD diagnosis as a hidden blessing that forced practical workarounds.
Those early strategies shaped durable habits that now support her productivity.

ADVICE

Use Affirmations To Build Confidence

Use affirmations intentionally to build confidence and reinforce identity.
Pick specific, practiced phrases and post them where you'll see them daily.

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Today’s guest, CherylAnn Crego, joins me on the ADHD-ish podcast for a Client Success Story episode. She first heard me speak on a webinar for ADDitude Magazine called “How to Build a Business That Works With Your ADHD Brain” and decided to reach out a short time later. In this episode, CherylAnn and I share the outcomes from our six-month coaching engagement.

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.