What happens when you have bought all the courses, taken all the programs, followed all the conventional “wisdom” and your business is technically “working” but you’re not attracting as many perfect-fit clients, making as much profit, or having as much fun as you expected?

Find out the answer to these questions and more in this episode of the Driven Woman Entrepreneur Podcast.

In this episode, you will be able to:

Find out how to unblock your business potential and create your Boss Up Breakthrough
Tackle the conquer the entrepreneurial mindset challenges that hold you back
Discover the power of tailored solutions in business coaching for optimum results.
Identify the three crucial stages of transformation: Clarity, Commitment, and Confidence.
Differentiate yourself in a competitive market by leveraging your unique brilliance.

The Boss Up Breakthrough

My signature coaching program, the Boss Up Breakthrough provides entrepreneurs with the guidance and tools necessary to streamline their businesses, identify their unique strengths and goals, and focus on what truly matters for long-term success.

Clients often have many great ideas, leading them to pursue multiple goals and projects simultaneously. However, this approach can result in missed opportunities and unfinished business.

I advocate for a flexible structure, creating order from chaos without telling clients what I think they should do. Through the Boss Up Breakthrough, entrepreneurs learn to focus on their most profitable ideas while creating an organized, simplified, and profitable business model that highlights their unique value.

This approach prevents burnout and ensures that businesses can adapt in response to changes in the market or clientele needs, all while maintaining a sense of organization and direction.

One of the core elements of achieving success with the Boss Up Breakthrough is addressing and overcoming negative mindset issues. Limiting beliefs, perfectionism, and fear of criticism or rejection are common problems that entrepreneurs face and can significantly impact their ability to grow and excel.

Recognizing one's own biases, blind spots, and attachments is an essential step in evaluating and improving one's business. This requires entrepreneurs to view their operations objectively and see where they may be slowing themselves down or hindering progress.

Other helpful episodes if you’re thinking about working with me:

Ep #152 - From Visionary to Implementer: A Client Success Story https://bit.ly/episode-blog-152

Ep #143 - What to Expect During a Free Consultation https://bit.ly/episode-blog-143

Ep #139 - How to Know if You’re Coachable https://bit.ly/episode-blog-139

The Boss Up Breakthrough is my signature coaching framework and the one I use with both my 1:1 and group coaching clients. At this time, I am only accepting 1:1 clients and the first step is to schedule a free 30-minute consultation right here: https://bit.ly/calendly-free-consultation

Have you heard? I launched a PRIVATE PODCAST and you can listen to it from the same podcast player where you enjoy this one! It’s called “Show Up Like a Boss” and you can grab it right here: https://bit.ly/show-up-like-a-boss

Not ready to work together but want to see more of my content? Subscribe to my weekly Linked In newsletter here: https://bit.ly/TDWE-Newsletter

TLDL: Time stamps for the impatient among us...

00:00:00 - Introduction to the Boss Up Breakthrough

00:03:26 - The Importance of Structure and Flexibility

00:17:08 - Is the Boss Up Breakthrough for You?

00:20:47 - Clarity Stage

00:23:39 - Commitment Stage

00:33:19 - Confidence Stage

00:38:54 - Understanding Your Business from the Outside

00:41:03 - The Cult of Mass-Marketed Advice

00:43:34 - Conclusion

Mic Drop Moment:

To Boss Up means taking full ownership of your life and directing your time, energy, effort, and resources toward your goals. - Diann Wingert

Podcast reviews really do motivate me to keep creating this show & bringing you awesome guests and no-BS solo episodes, so if you are a regular listener and haven’t left one yet, what are you waiting for?

Apple: https://apple.co/2BZDFzc

Android: https://bit.ly/TDWE-podchaser

New & Brag-worthy!

With all the podcasts geared toward female entrepreneurs out there, I was thrilled to learn that Feedspot.com included me on their list of the top 30. The Driven Woman Entrepreneur Podcast is #6, Check it out! https://bit.ly/3LwoEVL

The Next Fed Chair In Focus… And Mike Wilson’s 2026 Market Playbook 12/4/25

CNBC's "Fast Money"

Rumors Over Trump's Fed Chair Pick

The AI-powered Podcast Player