338: Embrace Uncertainty With Jess Estrada

Jess Estrada is a sought-after writer, strategist and public speaker, focused on personal branding, social media, networking Embrace Uncertainty With Jess Estradaand blogging. She created FreshJess.com, a Seattle-based life & style blog, in 2008 to offer a unique perspective on life, health and style in the Pacific Northwest. By day, she works as the digital media manager for a nonprofit family foundation.

Jess used to define herself based on other people’s definition.  She would agree to what people told her to do for better or for worse.  When she decided to quit her job with no plans of what to do next, that is when she embrace uncertainty and had the confidence to go in the direction of her dreams which has made her the successful woman she is today.


Jess Estrada is a sought-after writer, strategist and public speaker, focused on personal branding, social media, networking and blogging.

Cultural Background

Jess is of Filipina descent.

Favorite Self Confidence Quote

Act as if.

Act as if.

Definition of Self Confidence

Self-confidence as a muscle. Like our body’s muscles, it takes constant work and repetition to build strength in our self-confidence. It’s easy to quickly lose the strength we’ve built when we don’t make it a priority. Self-care, positive self-talk, and being able to trust in yourself are the foundation of self-confidence, and those are what I turn to whenever I feel overwhelmed, defeated, or otherwise doubtful in my skills and capabilities.

Her Life Before the Discovery of Self Confidence

Jess spent most of her time looking to others to help her shape her perception of self; who she was, what she should be doing with her life. It was probably easier to look outward instead of inward to help answer those tough questions! She listened to what people told her she was good at doing, their recommendations of what kinds of things she should be doing, and agreed with what most people thought of her (for better or for worse.)

The “AHA” Moment

Jess abruptly left a job she was really unhappy with and didn’t know what her next steps would be. It was frightening at first to not have her next thing lined up, but it turned out to be the most exhilarating and freeing time in her career (so far.)

She took on consulting projects while also pursuing professional blogging – brand partnerships, speaking gigs, writing jobs, etc. It was the first time in her life that she really listened to her intuition, then figured out how to ask for or make the things she wanted come to life. It was truly a time of manifesting her destiny – and her self-confidence had to be there (and high) constantly for her to believe in herself enough to go after it all.

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Her Life After the Discovery of Self Confidence

It’s an ever-evolving journey. Jess had many highs and even more learning opportunities. No matter how many times or how low she feels, somehow she always finds her way back to channeling her self-confidence to power her towards her goals and dreams.

The One Self Confidence Tip For the Listener

Focus on positive self-talk and taking care of yourself. Society does a great job in itself of putting women down, downplaying our influence and importance, picking at our bodies and our deepest insecurities, and creating an environment for deep shame and doubt. We don’t do ourselves any favors by perpetuating that cycle in our minds. You are the key to creating a healthy relationship with your self!

Interview Links

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