Problem solving and reinvention late in life. Coach Diann Wingert Talks with Heather Vickery on The Brave Files Podcast.

From Problems to Possibilities

With Featured Guest

Diann Wingert

Clarity • Reach • Zest

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Problem solving and reinvention late in life. Coach Diann Wingert Talks with Heather Vickery on The Brave Files Podcast.

From Problems to Possibilities

With Featured Guest

Diann Wingert

Clarity • Reach • Zest

Blog divider

Top Takeaways From This Episode

  • You always end up where you are because of where you’ve been.
  • Our relationship with failure needs to be a conscious decision that it’s just an experiment.
  • Use your past experiences to create the best version of yourself, even if those past experiences are painful. You can control the narrative.
  • Forgiveness is a gift we give ourselves
  • Change the direction of your life by embracing Gratitude.
  • Many entrepreneurs have ADHD and many people with ADHD become entrepreneurs – use it to your advantage.
  • It’s never too late to change your career path.
  • Therapy is about insight and coaching is about transformation.

Reinvention and Resiliency

At a time when her peers were retiring and settling down, Diann Wingert decided to go back to school and change careers altogether. After moving from many corporate jobs to the nonprofit sector, to then owning her own therapy practice, Diann decided to become a coach.

Therapy vs. Coaching

Unlike most coaches, Diann has a background in psychotherapy before becoming a coach. Thus, she quickly learned there was a vast difference between the two​. Therapy is about insight and coaching is about transformation.

“I don't think bypassing any legitimate emotions is healthy.”

– Diann Wingert

Neurodivergent Solopreneurs

Combining her knowledge in psychotherapy with her newfound passion for coaching entrepreneurs, Diann quickly found her niche working with neurodivergent entrepreneurs. She strives every day to help her clients convert their negative attributes into positive ones.


Diann, just like the rest of us, experiences challenging times. Instead of letting her past weigh her down, however,  Diann is grateful for all of her past traumas and experiences. She believes deeply that she wouldn’t be who she is or where she is without those past experiences. 

The Driven Women Podcast

Join certified coach, former psychotherapist, and ADHD-powered entrepreneur, Diann Wingert for your weekly dose of no-BS straight talk that will take you from driven but distracted to focused, fired up, and flame retardant. Caution: Listening to this podcast will be detrimental to your limiting beliefs and may result in the enlargement of your possibilities for success.

Connect with Diann 

Diann Wingert is a coach, and mentor who specializes in helping driven female entrepreneurs to eliminate distractions, leverage their zone of genius and finally reach their true potential.

You can find Diann on her website where you can find out how to become a client of hers for coaching. You can also hear some amazing stories on her podcast, The Driven Women Podcast. Of course you can always drop her a line on Instagram or Facebook!

Giving is Good

As somebody who chooses to celebrate by taking sunrise hikes, it comes as no surprise that Diann’s first charity of the week is The Nature Conservancy. Founded in the U.S. through grassroots action in 1951, The Nature Conservancy has grown to become one of the most effective and wide-reaching environmental organizations in the world. Thanks to more than a million members and the dedicated efforts of our diverse staff and over 400 scientists, we impact conservation in 76 countries and territories: 37 by direct conservation impact and 39 through partners.

Can’t pick just one!

This week, Diann has chosen to support two different charities. Drawing from her experience in both Portland and Los Angeles and seeing the homeless population explode she has chosen to also support Habitat for Humanity. Habitat for Humanity is a global nonprofit housing organization working in local communities across all 50 states in the U.S. and in approximately 70 countries. Habitat’s vision is of a world where everyone has a decent place to live. 

Habitat works toward our vision by building strength, stability, and self-reliance in partnership with families in need of decent and affordable housing. Habitat homeowners help build their own homes alongside volunteers and pay an affordable mortgage.

"Our relationship with failure needs to be a conscious decision that it’s all just an experiment."

- Diann Wingert

Meet your Host, <em style="color:teal">Heather Vickery<em>

Meet your Host, Heather Vickery

Heather Vickery is an award-winning business owner and global leader with over 20 years as an entrepreneur. She leverages her entrepreneurial skills and expertise to coach individuals towards greater personal and professional fulfillment by helping them leverage their fear into intentional bravery. Heather says “When we choose bravely, on purpose, we choose bigger, have bigger successes and it’s contagious” A celebrated public speaker, Heather inspires audiences and empowers attendees with the tools they need to live bold and successful lives through creating balance, time management, mindfulness, as well as countless systems, strategies, and boundaries. She’s the author of Gratitude Journal: Shift Your Focus and Grow Grateful: A Gratitude Journal for Kids and Families. Heather is also the host and executive producer of The Brave Files Podcast.

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