Power Half Hour: Leaning into Event Chaos

Event planning is chaos. Startups are chaos. So why not lean into it? Welcome to the Power Half Hour, where we share stories, laughs, and maybe even a lesson or two along the way. Grab a cocktail, sit back, and let’s dive into the world of events, weddings, and corporate chaos.

A Toast to Millennial Chaos (and Boxed Wine)

The Power Half Hour is proudly fueled by boxed wine—because why not? Millennials know how to make the most of what’s available, and whether by birth or spirit, everyone in this conversation is a millennial (or close enough).

The conversation kicks off with Rocio introducing today’s guest, Jen, who’s no stranger to the world of event planning. The connection between Jen and the team goes back years, with friendships formed through industry work, weddings, and life transitions.

From Weddings to Corporate Events: A Planner’s Journey

Jen first crossed paths with the team while being interviewed to be a “day-of” wedding coordinator—correction, a wedding coordinator (because let’s be real, there’s no such thing as just 'day-of' planning). The relationship quickly evolved, and over time, Jen became a trusted name in the Chicago event planning scene.

Jen started her business in 2016, having already spent seven years in the industry. Originally from Milwaukee, she brought her expertise to the Chicago market, where she quickly built a reputation. Her ability to balance personal connections with professional execution made her one of the go-to recommendations for weddings.

Weddings vs. Corporate Events: The Emotional Divide

The conversation takes an interesting turn as the group discusses the differences between wedding planning and corporate event planning. While both require extreme attention to detail, weddings carry a different level of emotional intensity.

One of the key distinctions is that weddings happen once—there are no second chances. Every detail, from the color of the linens to the placement of the cake, is scrutinized. Corporate events, on the other hand, are often annual or biannual, meaning there’s room for improvement and iteration. If something doesn’t go perfectly, there’s always next year to adjust.

Jen shares an experience where she had to deal with a particularly interesting corporate event dynamic: the involvement of helicopter parents—but not just any parents, the parents of 21-year-old investment banking analysts.

“We literally got an email into the food and beverage email that we managed from someone's mother,” she recalls. “It was from his mom. I don't remember what she was checking, but it was like dietary restrictions.”

Wedding Planning as a Bootcamp for Corporate Success

Despite the chaos of weddings, Jen argues that anyone who has mastered wedding planning is better equipped for corporate event planning. The level of detail and problem-solving required in wedding planning translates well into the corporate world, where high-level executives expect seamless execution. However, there’s a fundamental difference: in corporate events, you’re often dealing with experienced professionals rather than emotionally charged families.

While wedding clients may obsess over the color of napkins, corporate clients are more likely to care about logistics, budget efficiency, and execution. But at the highest level, even corporate events can have their version of irrational concerns—like whether the hotel’s mixed nuts are salted or unsalted.

“You are thinking about things that only, you know, the person who is the executive assistant to the so-and-so who's really going to care about the nuts being unsalted versus salted.”

The Recovery Time Factor: Weddings vs. Corporate Events

In weddings, there’s no do-over. If something goes wrong, that’s it. Corporate events, however, come with built-in recovery time. Mistakes can be addressed in a post-event debrief, and improvements can be implemented in the next iteration. In weddings, the stakes feel higher because for most people, it’s (hopefully) a once-in-a-lifetime experience.

The Favorite Corporate Event

Jen shares one of her favorite corporate events—well, technically not corporate, but a highly niche gathering. It’s a group of 150 women who own agencies in a specific industry and also happen to be deeply religious. The combination of professional ambition and faith-based values makes it a unique event to manage.

Interestingly, this isn't where Jen met her podcast co-host—though that event was another networking opportunity specifically for women entrepreneurs.

Women, Business, and Poker Nights

The discussion shifts to a growing trend: women in business embracing poker nights. These gatherings bring together badass businesswomen who are learning to play poker, smoke cigars, and, in some cases, make high-level networking moves in a traditionally male-dominated environment. It’s part skill-building, part rebellion, and entirely fascinating.

Jen shares how she works on the vendor side for a recurring event that happens twice a year, moving across different locations from the East Coast to the West Coast. Unlike weddings, where a planner is expected to have deep knowledge of creative elements like floral arrangements and linen options, corporate planners often focus more on logistics and execution. The creative aspects are usually driven by brand teams, leaving planners to facilitate rather than dictate the vision.

The Corporate Chaos and the Event Planner’s Rush

While some planners prefer one side over the other, the reality is that both wedding and corporate planning come with their own brand of chaos. Weddings are highly personal, with a long planning process leading up to one intense day. Corporate events can be equally demanding, with planners needing to handle last-minute requests—like needing twelve breakout rooms in an hour.

“How did you not know that you needed 12 breakout rooms?!” Jen laughs.

The Future of Event Planning: AI, Logistics, and Food Trucks

As the discussion shifts to event logistics, Jen reflects on how AI has become a helpful but imperfect tool. “I use it as a brainstorm buddy,” she explains. “But just so everybody's aware, if you're thinking about using AI to be your travel agent, a lot of times they, it will spit out restaurants that have been closed for five years.”

The group also discusses the never-ending challenge of food trucks at events.

“And every single year it would be like, ‘Well, can't you make something happen?’” Rocio shares. “And I feel like this is a sign of how good at my job I was because they would get no’s from my team and then they would call me.”

Wrapping Up: The Power of Adaptability in Event Planning

Whether planning weddings, corporate events, or large-scale conferences, the ability to adapt, problem-solve, and embrace the chaos remains at the heart of the industry. The conversation highlights the ever-changing landscape of event planning and the resilience required to navigate its challenges.

As planners continue to push boundaries, innovate, and refine their processes, one thing remains clear: event planning is not for the faint of heart—but for those who thrive on adrenaline, it’s the ultimate rush.