“What's mud season?" Never heard of her.”  That was my first thought—and my first clue this wedding was going to be unlike anything I'd planned before.

While working on Jackie’s high-glam, Vogue-inspired Chicago wedding, her sister Johnie got engaged—and suddenly, we were planning our first set of sister weddings. Jackie went big-city chic; Johnie wanted mountains, fresh air, and her favorite people surrounded by nature.

Six months later, I’m in Aspen. It’s snowing. I’m about to board a gondola with their parents—10 of us total—headed 11,000 feet up a mountain. (Did I mention I’m afraid of heights and had never been on a mountain before?) Turns out, pushing past your comfort zone is part of the job.

We brought 32 vendors together—only two from Chicago. The rest? Sourced, vetted, and aligned to our HBIC standards. Staffing included four from Chicago, two from Denver, and two locals from Aspen. Eight days on-site for a three-day wedding, timed perfectly over Fourth of July weekend.

Biggest takeaways? Altitude sickness is real. Gondolas don’t leave room for anything extra. And yes, I’d absolutely do it again.