Have you ever stood at the precipice of a dream, the wind of possibility at your back, urging you to leap? That’s where Jean-Eva from Book of Love Canada found herself, and she’s here with me to recount the exhilarating climb from side hustles to entrepreneurial success. Our recent Boss Talk event was a cauldron of candid […]

Confidence, Live

March 14, 2024

[LIVE] Boss Talk: Seasons of Entrepreneurship w/ Jean-Eva Dickie Part 1/2

Embarking on the year with a surge of energy, I found myself navigating the electrifying but daunting post-New Year wave. Discover how a slower pace isn’t just okay, but sometimes necessary, as I recount the thrill of launching ‘Confidently You’ and the meticulous planning of our Spring Retreat in Barbados. PLUS  the gratitude that comes […]


January 18, 2024

Small steps to big success in 2024

Ever feel the call of the open road, the thrill of the unknown, or the lure of the unconventional? I’m taking you on an adventure with Ashley O’Connor, a registered nurse turned Health & Fitness Coach, as she shares her exhilarating journey through her first year of full-time entrepreneurship and nomadic living.  Imagine booking a […]


December 14, 2023

[INTERVIEW] The Entrepreneur Adventure: Crazy + Confused w/ Ashley O’Connor

Let’s flip that narrative together and sprinkle a dose of joy amidst the seasonal chaos. I’m sharing my personal toolkit to navigate through this bustling period, with a firm focus on what lights your spirit rather than on obligatory bullshit.  As we navigate the shared weight of this season, arm yourself with strategies that will help […]

12 Days of Confidence, Confidence

December 8, 2023

12 Days of Confidence: Day 8🎄

EP. 1

What is confidence? Where can I find some?

The scoop on where I lost my confidence.

ep. 3

When you're feeling like you're not enough.

EP. 45

[LIVE] You are enough. You are doing enough.

EP. 76

my favorite

Featured Episodes

Tune In!







"Disney World might be the happiest place on earth but The Self(ish) Retreat is one of the safest places on earth to share your true self. All parts of you are welcome at the Self(ish) Retreat. It's an opportunity to make new friends and bond on a deeper level with old (and new) friends. You're guaranteed to learn something new about yourself. Jess takes care of all the details of the weekend so you can focus on turning inward and getting what you need out of the retreat."

Jamie Says:


"You NEED to work with Jess. No question. In the 4 months I have been working with Jess so far, my business and I have grown EXPONENTIALLY. Four months ago, I was just talking about the idea that I might start a business, and now I have left a career that wasn’t aligned for me, committed to the adventure of a lifetime, found my niche, launched my business, and rediscovered WHO I AM in the process. I promise you, YOU WILL NOT REGRET choosing 1:1 coaching with this powerhouse woman. Just make sure that you are ready to GROW more than you thought possible."

Ashley Says:

Leave a review in the apple podcast app

Take Me There!