Meet Sherry Winn

We caught up with the brilliant and insightful Sherry Winn a few weeks ago and have shared our conversation below.

Hi Sherry, we’re so appreciative of you taking the time to share your nuggets of wisdom with our community. One of the topics we think is most important for folks looking to level up their lives is building up their self-confidence and self-esteem. Can you share how you developed your confidence?

Confidence comes from the awareness that you are worthy. You were born worthy and don’t have to prove your worthiness to anyone. We think that we have to reach a particular title, obtain a number of awards, or make a certain amount of money to be worthy. What if we didn’t need to do any of that? What if we realized that because we came from love that we are love?

For years I sought confidence through achievements. I was a college valedictorian, a two-time All-American, a two-time Olympian, and a national championship basketball coach and still felt that I wasn’t good enough. Through a change in beliefs, I discovered true confidence, because I didn’t need anybody else to define my worthiness.

Once you understand that nobody else can validate you as much as you need to validate yourself, you are on the way to emotional freedom and the capacity to achieve your goals.

Great, so let’s take a few minutes and cover your story. What should folks know about you and what you do?
Most people would describe themselves as what they’ve achieved, and while I have written best selling books, spoke to audiences as large as 14,000, and provided leadership workshops for multi-billion dollar companies like McDonald’s, that is not who I am.

For other people, those achievements might be important. And, of course, I have enjoyed them, but they do not make me a better person. What makes me a better person is the time I’ve invested into self-development.

When I speak at events, coach executives, or lead workshops, I bring authenticity and positive energy that is impactful and influential, because of who I’ve become. When you invest in yourself, you offer more to others. This is the secret of leaders who get the best from their team members–they are not looking for anything from their team members. They are then able to support their team members to become the best versions of themselves.

There is so much advice out there about all the different skills and qualities folks need to develop in order to succeed in today’s highly competitive environment and often it can feel overwhelming. So, if we had to break it down to just the three that matter most, which three skills or qualities would you focus on?

First, it is good to acknowledge that we are on a journey, and that we will never be done. There is always another lesson to be learned, another layer of ourselves to uncover, and another challenge to overcome. For me, this was an important skillset–to know that I am both perfect as I am and imperfect as to whom I can become. To sit in this duality and feel good about it is an essential awareness.

The second lesson is to unconditionally love myself. This is challenging, because we are raised in an environment that often teaches us that we are loved when or if we do certain things. I was loved more when I brought home straight A’s, cleaned the house, or was named all-state in basketball. I learned to place conditions on myself which led to judgment and self-punishment.

The third quality that is essential is forgiveness of self and others. When we stand in judgment of ourselves and others, we cannot move forward, because we are stuck in the past. To move forward requires letting go of what has already occurred.

Who has been most helpful in helping you overcome challenges or build and develop the essential skills, qualities or knowledge you needed to be successful?
When I was in my teens and early 20’s, I suffered from depression and suicidal thoughts. I was in survival mode, which meant that I couldn’t accept the good things and people that were around me. I saw everybody and all events as the enemy. I was in fight or flight mode for ten years.

What changed me was books. I read hundreds of books which changed my belief system and allowed me to look honestly at who I was and how my belief systems impacted my joy, peace, serenity, and success.

Once I understood that it was me that stood in the way of my happiness, I invested in coaches who saw the mind, body, and spirit as one. They were able to help me see the belief systems that kept me from living the life I desired.

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