The Myth of the Perfect Leader with Jessica Drogosz

If you’ve ever paused on your next chapter because you think you need to be “more ready” or “more perfect,” this one’s for you. My dear friend, multi-hyphenate creative and mentor Jessica Eileen Drogosz joins me to dismantle the myth that leaders must have it all together before they lead. From building associate teams and separating brands to launching a heart-led coaching offer, Jessica shares the real (and often messy) middle—where clarity, courage, and connection are forged.

So many of you are standing on the edge of your next season—coaching, teaching, creating a course, or simply showing up more boldly online. If perfectionism has been your speed bump, consider this your green light. Progress—not flawlessness—is what builds mastery, self-trust, and momentum.

In this episode, we cover:

• The myth of perfection and why showing your humanity actually builds more trust.

• Following the “whisper”—how to recognize the nudge that it’s time for your next thing.

• Making space for multipassionate work: running successful photo brands and stepping into mentorship.

• Leadership in real life: humility, owning mistakes, and building systems with your team.
  Identity first, strategy second: creating from the future you (website, offers, and voice) before you “feel ready.”

• Micro-leaps & progress tracking: simple daily practices that compound into big outcomes.

• Social media resistance: sharing vulnerably in a new container without overthinking it.

• Coaching with depth: why inner story work belongs before scaling strategies.

You don’t need a perfect plan to lead—you need your imperfect, present self and one brave step. If you’re ready to move from dreaming to doing, go follow Jessica and book a clarity call. And if you want coaching around identity, mindset, and strategy for your next season, my door’s open too. Let’s build the future you—starting today.

Meet Jessica

Jessica Eileen Drogosz is a multi-hyphenate creative with over 14 years of experience turning vision into reality through artistry, strategy, and soul. As the founder of For Just a Moment Weddings and Our Days Photo and Film, she has traveled the world documenting love, legacy, and human connection—blending refined editorial style with honest, documentary storytelling.

Beyond photography her work has always been about more: helping others step fully into their story, create with truth, and embrace the beauty of becoming. Through her Undone & Becoming coaching, Jessica supports women and creative entrepreneurs in moving from uncertainty to clarity, from dreaming to doing. She offers strategic guidance, grounded mentorship, and bold encouragement to help others take their next leap—with heart, purpose, and integrity.

Connect with Jessica

Jessica’s Instagram
Jessica’s Substack
www.jessicaeileen.com
www.ourdaysphotoandfilm.com
www.forjustamoment.com