The Planner’s Passport - Wedding Planners, Travel Agents, Decades of Stories

This week, we talk about… well, everything and nothing at all, which is basically our specialty.

We catch up on Megan’s time up north Wisconsin, one of Jen’s former make-out sessions, and why you should always walk up the hill when your boyfriend tells you to. (Spoiler: proposals happen on hills.) We get into upcoming travel plans, pooping on vacation, Groupon purchases, Mexican food cravings, and of course, JAMAICA! Come travel with us.

SPECIAL ALERT: If you’ve been thinking about advertising with us, now’s your moment. Get in at the basement level and grow with us because this elevator is going up.

So no, it’s not nothing. It’s everything. It's hilarious. And it’s very us. Press play.

This week, we’re joined by Jesse Lyon of Lyon Mental Health—a therapist, dream interpreter, and hilarious human who somehow made talking about the subconscious feel like a party.

Lyon Mental Health

@lyonmentalhealth

This week on The Planner’s Passport, we’re talking timelines—specifically, how much time you really need to plan a wedding. Whether you're stretching things out over 18 months or sprinting toward an 'I do' in six weeks, there are perks and pitfalls on both sides.

Longer planning timelines might sound like a dream (hello, options), but with time comes the temptation to overthink everything. Shorter timelines force quick decisions, streamline the process, and reduce waffling—but they also come with logistical curveballs and fewer available vendors.

We break it all down: from decision fatigue to vendor availability, budget impact to emotional whiplash. And in true fashion, we absolutely go off the rails at least once, possibly more. You already know.

Whether you're a type-A planner or a last-minute lover, this one’s for you.

This week on the pod, we’re joined by one of our OG listeners —  Heather Cook Elliott! To say that Megan and Jen are as mutually obsessed with her as she is with us? A massive understatement.

Heather is a Milwaukee-based wedding and portrait photographer whose work is rooted in real connection, thoughtful storytelling, and capturing people as they truly are. She’s the kind of person who shows up fully behind the camera and in life, and we absolutely adore her.

In this episode, we dive into Heather’s origin story, what it’s like building a creative business with soul, and why we all can’t stop giggling through this whole conversation. Spoiler: Heather’s coming with us to Jamaica. Are you??

 Tune in for major bestie energy, industry insight, and a whole lot of love.

On this episode of The Planner’s Passport, we’re joined by the brilliant and deeply intentional Alysia Cole—stylist, image coach, and founder of Alysia Cole Styling. Together, we dive into the world of wedding fashion, but not in the way the industry usually tells it.

Alysia brings her signature warmth and wisdom to a conversation about how brides can show up as their fullest selves on their wedding day—no matter their size, shape, or where they fall on the traditional beauty spectrum. We talk about the emotional journey of finding a gown, why so many brides feel pressure to conform to a certain “bridal look,” and how Alysia helps clients reconnect with their body, style, and confidence throughout the process.

From breaking down outdated beauty standards in the wedding market to redefining what it means to feel beautiful in white (or not), this episode is a celebration of self-expression, empowerment, and choosing style over expectation. If you’ve ever felt unseen in bridal fashion—or you’re ready to reclaim what your wedding day should feel like—this one’s for you.

This week, we’re joined by the wildly talented and hilariously cheeky Rachal A. Duggan, the creative genius behind Rad Illustrates. Known for her signature butt drawings (yes, you read that right), Rachal is an illustrator, author, and workshop leader who brings her one-of-a-kind style to everything from comics to custom wedding art.

We dive into how Rachal started drawing butts, what it’s like being a creative vendor on a wedding day, and the unexpected chaos of live event sketching.

From editorial and branding illustrations to teaching private drawing workshops, Rachal does it all and somehow makes it all hilarious. Tune in for puns, laughter, and an honest peek behind the (butt) curtain of wedding day artistry.

Follow her work on Instagram and TikTok @radillustrates.

Last week, Jen popped off about moms (and no, Megan still does not agree with her).

This week? Megan’s the one telling it like it is. And honestly? We're. Here. For. It.

She’s in her villain era, y’all. We’re talking wedding industry awards and how (surprise!) a lot of them are paid for. Not saying the people winning don’t deserve the spotlight, but it’s worth knowing there’s usually money behind that shiny badge. Transparency matters, and Megan’s not holding back.

Tune in! Why? Because it’s so fun when Megan spills the dirt.

To be clear, Megan does not sign off on any of this. This is 100% Jen’s story arc... from superhero to supervillain wedding planner.

Now, Jen actually loves most moms. But in her experience, a few bad apples spoiled the bunch so much that she no longer works with parents unless they’ve been fully vetted.

But this episode isn’t just about mom drama (although yes, a few wild stories are shared). It’s really meant to help moms navigate the modern wedding planning journey. A lot has changed since their own wedding days... and let’s just say, some of them struggle with that. So this one’s for you, moms. We’re here to help so that you don't become a Momzilla.

Oh! We also spend a solid 15 minutes talking about “John Smith” (name changed to protect the extremely attractive but not-so-innocent boy everyone had a crush on in high school).

You don’t want to miss it.

We’re fangirling a little harder than usual this week, because our guest isn’t just TikTok-famous—he’s also one of Jen’s former grooms… twice. (Ah, the joys of COVID-era weddings.)

Marco Braun—aka @marcosfunhouse—joins us to share the story of his two celebrations, what it was like planning during a pandemic, and how he accidentally became the internet’s vintage recipe king. Oh, and did we mention that Hilary Duff bought him and his husband their registered china after he went viral for being the world’s biggest Lizzie McGuire fan?

We talk about love, weddings, internet fame, and yes… a very passionate discussion about mayonnaise. It’s hilarious, heartwarming, and everything you didn’t know you needed today.

🎙️ This Week on the Podcast: We're Going Tropical, Baby! 🌴

Pack your sunscreen and questionable swimwear—we're taking this podcast to The Bahamas and want YOU to come with us! In this episode, we spill the (piña colada-flavored) tea on our upcoming getaway to Sandals Royal Bahamian. Think snorkeling with sea turtles (or at least aggressively friendly fish), late-night karaoke that may cause permanent secondhand embarrassment, and tropical drinks with umbrellas that are fancier than our actual wardrobes.

We're giving you the inside scoop on what it's like to party podcast-style in paradise, how to snag your spot on this sandy adventure, and why your mom, best friend, or mildly chaotic partner absolutely needs to come too. It’s happening November 30–December 3, and it’s going to be legendary… or at least mildly sunburned and extremely fun. 🌞🎤🌊

Want more info or to get your room on hold?

Reach out to Megan at [email protected] or check out our trip page at http://www.daretodreamtravelwi.com/join-us-bahamas.html

See you on the beach! 

Megan & Jen