Diann Wingert
Business Coach for Ambitious Outliers
My jam is helping neurodivergent entrepreneurs, creatives & independent professionals create a profitable, sought-after business in their zone of genius
How I became a business coach
I left a successful career as a psychotherapist because I wanted to shift the conversation from problems to possibilities, from focusing on healing to focusing on growth.
I specialize in coaching & mentoring entrepreneurial individuals who are ready to move beyond their current level of success and know that their past therapy has helped them get ready to do so, but staying in therapy is not the answer.
Think of me as a business strategist, coach, mentor and trusted advisor, all rolled into one. It’s a powerful combination.
How coaching helps neurodivergent entrepreneurs
Most gifted, creative, and brilliant individuals struggle to reach their true potential.
You know you are capable of so much more, but don’t quite understand how you may be unconsciously holding themselves back, or why.
There can come a tipping point when it’s too painful to keep settling (and watching others less brilliant pass you by…) or we stay frustrated, resentful and depressed.
I help those who are ready to close the gap between where they are and where they truly want to be.
Why I left my successful psychotherapy practice
I struggled with unidentified neurodivergence and a specific learning disability, in spite of being in gifted classes, leading to decades of masking, perfectionism, false starts and confusion.
Three kids, two divorces, and a few rounds of therapy later, I got a late in life diagnosis of ADHD, started working with a business coach and learned why therapy had helped me heal from past trauma. but was not moving me forward toward my most important goals.
My background as a therapist and serial business owner means you will grow as a business owner while we grow your business. I won’t be your therapist, but you will definitely benefit from my having been one.
What You Can Expect From Working With Me
NO BULLSHIT
One of my favorite clients called me "The Speaker of Uncomfortable Truths." Here's why: I am very direct, intuitive and insightful & value honesty above being liked. It’s also why I screen my clients before inviting them to work with me, because not everyone is comfortable with this approach.
PLAYFUL
One of the ways I balance my intensity is with humor. My core concepts are full of analogies and metaphors, sarcasm and colorful language. Taking action with uncertainty and doubt is work, but I make it fun.
Uncovering and highlighting our best work takes courage and I help dial the fear factor down.
WALK MY TALK
I'm not only a coach and former therapist, I'm a serial business owner myself, so I've not only got killer credentials, but lots of lived experience. I'll never ask you to do something I'm not doing myself and love knowing I can shave years off your learning curve, so you get further, faster.
Business coaching can be powerful when you find the right fit.
Let's connect and find out.
Schedule a no-cost, no- obligation consultation. It's like a first date without the awkwardness, I promise.
I will only invite you to work with me if I am 100% confident I can help and you're ready to make it work.
What some of my clients have to say about me
"Diann is a great business coach who will kick your butt when needed, and help you see why you are not achieving what you are wanting to achieve. She will help you develop your idea, not hers or some popular trending business plan."
~Jancina Dyer
"Diann combines the insight of a therapist with the skillset of a business strategist. Her ability to read between the lines and uncover what was behind my procrastination and indecision was spot-on. You'll walk away with actionable steps. The time spent is focused and not a minute is wasted. Well worth it!
Our VIP Day was like a gateway drug...I will be back!"
~Heather Frechette-Crowley
"I was able to focus on my most profitable service vs chasing too many revenue streams at once. I hired a CRO and let go of two people who were not moving the company forward. I started facing conflict instead of dodging it and throwing money at the situation. I negotiated an exit strategy and then turned down the offer because it was not right for me.
I'm more confident about standing in my own boundaries, unapologetically. (most of the time!) I was able to shift the narrative around business growth decisions into a more positive and factual perspective. I am less hard on myself about perceived shortcomings and able to see them as assets."
