Episode 46: Planning a Stress-Free Vacation with Nick loper
In this episode, podcast host and side hustle expert Nick Loper shares how thoughtful, early planning can turn family travel from chaotic to calm. From booking flights nearly a year out to letting kids scroll through Airbnb listings, Nick offers tips that make vacations more fun and less frantic.
Nick and Hannah discuss the mental load of travel logistics, the power of anticipation, and how being intentional with your calendar can reduce stress before the trip even begins. Whether you're dreaming of spring break or booking last-minute hikes, this conversation will inspire you to make planning part of the joy.
Key Takeaways
Put it on the calendar. If it’s not scheduled, it likely won’t happen.
Anticipation matters. Planning ahead helps you enjoy the trip before it begins.
Involve your kids. From researching destinations to picking the Airbnb, it builds buy-in.
Narrow your scope. Use things like school calendars to limit decision fatigue.
Start small. A day hike or weekend drive counts, too!
Quotes
“If you don’t put it on the calendar, it doesn’t happen.”
“Anticipation is half the fun.”
“Planning isn’t just about logistics—it’s about creating joy.”
“Our kids love helping pick the Airbnb — they’re focused on bunk beds and TVs.”
“Let the kids help plan. They’ll be more engaged and excited.”
Resources Mentioned
Side Hustle Nation – Nick Loper’s platform for earning extra income through side hustles.
The Side Hustle Show Podcast – Nick’s podcast sharing real-life side hustle success stories and tips.
Heron House Management – Virtual house management for busy families: we handle your to-dos so you can focus on what matters most.
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This episode of De-Stress the Nest is sponsored by Heron House Management.
About Heron House Management:
Heron House Management is a virtual house management service that takes the stress out of your busy life by taking on your mental load and managing your To Do list. We provide fractional virtual house management for busy families at 10, 15 and 20+ hours/month.
Meal planning, signing up for kids activities, scheduling doctor's appointments, finding a house cleaner, planning your kid's birthday party, getting quotes for that home renovation project, or scheduling a monthly date night with your significant other and so much more. We do it all!
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[00:02] Hannah Morgan: Welcome to De-Stress the Nest, a podcast for busy parents where experts share bite-sized tips on how to create systems that minimize stress at home. I'm your host, Hannah Morgan.
[00:16] Hannah Morgan: Today’s episode is sponsored by Heron House Management — the first-ever virtual house management service that lightens your mental load by handling your to-do list with monthly subscriptions of 10, 15, and 20+ hours per month. From meal planning and doctor’s appointments to birthday parties and home projects, Heron House Management helps busy families reclaim their time and live their best lives. Learn more at heronhousemanagement.com.
[00:30] Hannah Morgan: Nick, I'm so excited to have you on today's show. Let's start by hearing a little bit about who you are and what you do.
Nick Loper: Excited to be here! I'm the side hustle guy. For the past 12 years, I’ve been hosting The Side Hustle Show at sidehustlenation.com, where I uncover creative ways to make extra money. I love geeking out on things like: How did you come up with that idea? How did you get customers? It’s been an absolute blast, and I’m thrilled to get paid to do work I genuinely enjoy.
Outside of that, I married my high school sweetheart, and we have two boys—one going into fourth grade and one into second. We’re soaking up a beautiful Pacific Northwest summer while still trying to get work done and find that elusive balance.
Hannah: Thank you for joining us today, Nick—we’re excited to chat. You’re going to share some of your favorite tips and perspectives on how to make trips less stressful, and how the planning process can actually be a key ingredient to a fun vacation or excursion. So let’s talk about it.
Nick: Yeah! Travel has always been a favorite hobby of ours. If we’ve got extra money in the budget, our default is: “Let’s go explore someplace new,” or visit friends and family. It’s been a big part of our identity, and we’re trying to instill that in the kids.
Even though we remind them—don’t get used to always hopping on a plane! That’s not necessarily the norm. But we do want them to understand the value of travel, exploring new areas, and seeing different cultures.
One of the biggest benefits, I think, is the psychology of having something to look forward to. It’s like signing up for a half marathon. Now you have to train, but you also get the anticipation.
We often book trips 6–11 months in advance. Airline tickets usually open about 330 days out. So if you’re on it and have the miles, you can plan really far ahead. Sometimes we already know what we’re doing for next spring break.
And once the kids hit school age, those seasonal constraints actually helped us narrow our options. Without them, it felt way too open-ended—like, “Where do you want to go?” The whole world is an option, and that made it harder to decide.
Hannah: Yes! I’ve read that most of the joy people get from a vacation actually happens before the trip—just from the anticipation and planning.
When you’re traveling with kids, things don’t always go according to plan. I’m guilty of last-minute planning—which surprises people because I’m so Type A!
But I get overwhelmed by all the options, and it’s hard to commit. I’ve been trying to train myself to plan ahead. You enjoy the anticipation, and you have time to make solid plans without the last-minute scramble.
This is such a great reminder. Can you tell me about a trip you planned far in advance that went smoothly—and maybe some highlights as a family?
[04:20] Nick: Day-to-day, we’re more like, “What are we doing tomorrow?” It’s a little chaotic. I’ll text my brother like, “Hey, we’re going on a hike—leaving in 25 minutes.”
Hannah: So your pre-planning is exclusively for vacations?
Nick: Exactly. Daily life is spontaneous, but big trips get the full planning treatment.
This year, we went to Japan. We booked it 10–11 months out when we found a great mileage deal for flights.
Our youngest was supposed to be our Duolingo guy and translate… that didn’t pan out. But we did watch a ton of travel YouTube videos. Things like “Top 10 Things to Do in Tokyo with Kids” or “Best Food Spots in Kyoto.”
When we saw those places in person, the kids recognized them from the videos and got really excited. They even made their own shortlists.
I think it’s the same for adults—without context, a museum or monument can be kind of boring. But when you understand what you're looking at, the experience is totally different.
Hannah: That’s fantastic. Getting the kids involved not only makes it more fun—it helps with behavior and engagement. They feel ownership when they’ve helped plan.
We’ve mostly traveled along the East Coast, but we’re taking the kids to Colorado this summer, and I’m really excited.
Shout out to my house manager—she’s planned so much of it. It’s been a game-changer. I can focus on what we actually want to do, because I’m not overwhelmed by logistics. She emails me options, I give the green light, and it’s done.
Nick: That sounds like a dream.
Hannah: When my husband and I first started dating, we took a totally spontaneous trip to Colorado about a month in. We just drove around and had the best time.
This trip is kind of a full-circle moment—going back with our kids to places that were meaningful to us. Eventually we’ll do the big cross-country drive, but right now, I love being able to focus on the fun parts.
I’ve been deep in TikTok looking up “5 Fun Things to Do in Denver” and stuff like that. It’s fun to do that kind of research!
Learning another language, though? That’s impressive. I’m amazed it was even attempted.
Nick: It lasted a week, maybe! But we’ve got a Paris trip coming up this fall, so maybe he’ll pick up French instead.
Oh—and one thing the kids love is scrolling through Airbnb listings. They’ll say things like, “This one has an arcade machine!” or “Look at the size of that TV!”
Meanwhile, my wife and I are looking at reviews, cost, and location. The kids are just like, “Does it have bunk beds?”
Hannah: Yes! My daughter gets excited if a rental has a pink room.
There’s this quote I love (I wish I remembered who said it): Always have a trip planned, so you always have something to look forward to.
Nick: Totally agree. That’s how we try to live.
Hannah: So for any of our listeners deep in summer chaos—this is your invitation to open up that school calendar and start planning for fall break, winter break, spring break… even next summer.
That way, you can actually enjoy the planning process instead of stressing out.
But hey—there’s always room for a last-minute hike, too, right?
Nick: For sure. What we’ve learned is if you don’t put it on the calendar, it doesn’t happen. That planning piece is key—not just for logistics, but for having something to look forward to.
Hannah: Yes! Well, thanks so much for joining us today, Nick. Many happy travels to you and your family.
Nick: Cheers!
Hannah Morgan: Thanks for listening to De-Stress the Nest — the podcast where experts share bite-sized tips on how to simplify your life. Don’t forget to subscribe and tune in every Tuesday for more ways to make home feel easier.
