Proud2Bme | Confidence is a Journey, Not a Destination: An Interview with Jess Weiner

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Confidence is a Journey, Not a Destination: An Interview with Jess Weiner

By Chelsea Kronengold--Considered this generation’s “go-to authority” on women, girls and confidence, confidence expert Jess Weiner serves as Dove’s Global Self-Esteem Ambassador and the CEO of Talk to Jess, a consulting and strategy firm. As CEO, she advises global brands on the issues facing today’s women and girls. After feeling inspired by her TEDx talk on The Confidence Myth, I contacted Jess about her journey to confidence and her advice for young adults struggling with confidence, standards of beauty and unrealistic media messages.

To learn more about Jess, or to join the Talk to Jess community, visit

Chelsea Kronengold: Tell us about your work and your journey to self-discovery.

Jess Weiner: When I was a young girl, I struggled with body image issues and self-doubt. I drew inspiration from these experiences and started a conversation and a community where we could make positive changes. 10 years ago, I became the Dove Self-Esteem Project’s global ambassador. I wrote the curriculum for our self-confidence workshops and travel the world facilitating these conversations for millions of women and girls.

As a social entrepreneur and consultant, I work with Fortune 100 and 500 companies to help them better understand the issues impacting women and girls in today’s culture. We help translate these trends into better products, campaigns and marketing, to ultimately empower women instead of repeating damaging stereotypes. I strongly believe that in order to generate meaningful change, we have to work from the inside out.

CK: What is The Confidence Myth? What are some myths about confidence that you’ve challenged?

JW: The Confidence Myth is the oversimplification of one’s personal relationship to confidence; the idea that all we need to do is ‘get confidence’ in order to maintain it for the rest of your life. But much like a gas tank for your car, the feeling of confidence must be replenished and filled up over time.

We spend so much time talking about ‘getting’ confidence, that we often ignore the most important component--the how. In reality, confidence is a journey, a manner of traveling, not a destination. And the truth is, that journey is messy and involves a lot of hard work.

We often hear hollow messages like “You go girl!” “Be true to yourself!” “Be confident!” They are what I call, “S.F.S.N. - sounds fabulous, signifies nothing.” These messages tend to ignore the most important part of the journey to confidence--the HOW we get there. The real. The raw. The messy. 

CK: Many young people have a hard time differentiating between confidence and arrogance, can you explain the difference?

JW: Arrogance is the fa├žade of having it all together and emanating an air of superiority to those around you. It’s egocentric and self-absorbed. True confidence is knowing who you really are because you are on a constant journey toward self-discovery. It’s about owning your flaws and being vulnerable about whom you really are. Confidence is raw and authentic.

CK: What is the relationship between confidence and (a) beauty, (b) perfectionism and (c) the media?

  1. You can still love yourself on the inside and care about outer beauty, but outer beauty is not what ultimately defines you. Beauty fades for all of us eventually, which means it’s not a currency to take to the bank, character is.
  2. Confidence is not perfection. And the journey to confidence won’t look perfect either. It will be messy, and it will likely be hard, but it will ultimately be worth it.
  3. I think the media often portrays a very limited idea of what confidence is and looks like. When we recognize and celebrate diverse stories and types of people in the media, we can inspire confidence in more people by validating and reflecting who they are in what they consume. It is also important to me to motivate a discussion around media literacy. The media isn’t responsible for instilling confidence in our children or in us, we are. The more honest we are about our personal responsibility in this conversation, the better.  

CK: In your TEDx talk, you encourage society to talk about the price we pay for really being ourselves. Can you expand on this?

JW: It’s the risk you take when you embark on a journey of self-discovery and learn who you really are. That takes vulnerability, which might lead to embarrassment, failure, judgment, pain-–what you encounter won’t always be pretty. But ultimately our struggles lead to our greatest joys and it’s so important to be transparent about what our journeys look like–-nothing worthwhile comes easily.  

CK: The road to self-confidence is often long and arduous. What are little things young people can do today to start feeling better about themselves?

JW: My advice would be to enjoy the moment. Enjoy your moment. When something good happens to you, soak it in and wallow in the goodness happening now. Believe that you are worth it and remind yourself that you are allowed to feel good. Cherish those good moments during the long journey.

Let's not pretend it's that easy just to stop worrying, but let's change the amount of worry and substitute it for something else. You could put your energy toward something you really love to do that excites you. And when you think about it like that, that's really manageable. Look at the energy we spend on obsessing and worrying about how we look and assign it to something else in our lives.

CK: As an activist, you’ve faced some critical judgments both online and offline. What are a few ways you’ve protected yourself from negativity?

JW: When it comes to online media, I think critically about what I consume and I know how to navigate the distracting messages. It’s important to remember that our online lives are a filtered reality of our actual lives. Knowing this allows me to take a step back and remove myself from a negative online situation. On social media, I work to promote a positive community where people can find sources of inspiration and empowerment. My Facebook community loves when I highlight uplifting moments and celebrate signs of progress in our culture.

I’m actually a very private person offline and mostly surround myself with a few close people whom I trust. These positive relationships in my life, coupled with activities that keep me mindful and grateful, protect me from the negativity of others.

CK: You’re working within the media to change the media. How have you seen the media evolve and what still needs to be done?

JW: It’s amazing to see that the brands I work with are so open to creating a positive shift in the way women and girls are portrayed in the media. This openness shows that the media is looking to show women and girls a better world through the messages they receive.

I’m seeing good things happening in the media every day, but there are always those moments that remind us of all the work that still needs to be done. I think any time we can bring humanity back into the conversation, and we can be less like robots and more like people, we can help companies see that the girls and women who are seeing their products want the same thing. They want the connection. They want to feel seen and recognized and celebrated. There's enough space in the larger culture to celebrate all forms of beauty.

CK: Lastly, what makes you confident and Proud2BYOU?

JW: Exploring all the different sides of who I am makes me confident. I am an entrepreneur and a creative being, and I’m so grateful that I am able to embrace, celebrate and explore the many sides to who I am and what fulfills me. 

About the blogger: Chelsea is a body image and eating disorder scholar and activist, currently pursuing a master's degree in clinical psychology from Columbia University's Teachers College. In addition to her studies, Chelsea is a consultant and program administrator for NEDA’s implementation of The Body Project. Prior to working on The Body Project, Chelsea coordinated the inaugural and second annual Gainesville, FL NEDA walks and served as the Proud2Bme National Outreach Coordinator. Chelsea has spoken on behalf of NEDA and Proud2Bme about her personal struggles with binge eating disorder and body dissatisfaction to media platforms such as Huffington Post Live, Seventeen Magazine, WebMD and SiriusXM Doctor Radio.

Also by Chelsea:

#ImNoAngel Campaign

Are Plus Size Models Not Plus Size Enough?

BED & Doctors: From Stigma to Support


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