This week on High, Low, and Unexpected, Shaun sits down with Kelsey Converse, a New Hampshire-based elopement photographer, business coach, and founder of the Biz with Boundaries program. Kelsey is a powerhouse entrepreneur who went from leaving her corporate 9-to-5 to rapidly scaling a six-figure creative brand—but her rapid rise came with a steep learning curve about what it actually costs to "have it all."

In this episode, you’ll hear:

The "Dream Life Achieved" High: Kelsey celebrates her current reality as a new mom to a six-month-old boy, living the exact balanced life she once envisioned. She shares how years of front-loaded hustle and extreme curiosity about strategic growth allowed her to step away from corporate limitations, travel to 10+ countries a year, and now build a business that fully supports her family timeline.
The "Six-Figure Blindspot" Low: A raw look at the deception of vanity metrics. Kelsey opens up about her first massive $100k year in 2021, where comparison-driven hustle led her to book 43 weddings and 15 sessions. Despite the financial win, she describes the breaking point of working from 5:30 AM to 8:00 PM every day, experiencing public breakdowns, and missing her best friends' weddings—forcing her to completely redefine her version of success.
The "Superwoman Backlash" Second Low: What happens when you try to fix your capacity problem by aggressively expanding? Kelsey vulnerably shares the heavy reality of 2023: onboarding two associate photographers simultaneously, managing a rental property, launching an education branch, and navigating a heartbreaking pregnancy loss under the weight of chronic cortisol and stress.
The "18-Month Astrologer" Unexpected: A funny, perspective-shifting moment where a hometown friend brings an astrologer to a gathering, sparking a conversation about the upcoming transitions that await Kelsey. Shaun and Kelsey unpack the beauty of the unknown, the necessity of personal therapy, and why learning to sit in the neutral "in-between" zones of life is an entrepreneur's greatest asset.

Kelsey’s journey is a necessary wake-up call about why we must stop using social media algorithms to measure our self-worth. Whether you are trying to cross the six-figure line or learning how to scale back to protect your peace, this episode will challenge you to look introspectively, get curious about your pain, and determine what "enough" truly looks like for you.

Listen now on High, Low, and Unexpected.

🎙️ Want to learn more from Kelsey? Track her journey and find out if that 18-month prophecy comes true by following her on Instagram @kelsconverse or visiting KelseyConverse.com.