How to Have a Win-Win-Win Family Trip

Last week we went to Los Angeles for our youngest son’s college orientation at Loyola Marymount University. He got accepted on a partial design scholarship—something he earned through grit, consistency, and building his own creative business from scratch. Predominantly, upstairs in his room, without us having much to do with any of it… He’s been designing merch, album covers, flyers, clothing, and doing photography for music artists across the city. All from his bedroom. All self-taught. All heart. I’m proud of him.  

Let that land for a second. This wasn’t just a school visit. It was a milestone moment. I never did anything like this when I was his age. And my father wasn’t alive to see me off to college. 

So we decided to make a family trip out of it. Kate, Harper, and I. Our older son is studying abroad in Florence, so he couldn’t make it—but he was with us in spirit, group texts, and Instagram stories.

This wasn’t about sightseeing or cramming in tourist stops. It was about being together, staying on rhythm, and leaning into the kind of travel that aligns with how we want to live.

How We Travel Now: Houses Over Hotels

One thing we’ve learned over the years: hotels don’t work for us anymore. We’re not in that phase. We like being together. We like space. We like having a kitchen. And honestly, I can’t stand paying super high rates for tiny rooms (and we need two rooms at this point), outrageous valet charges, and overpriced breakfasts that don’t taste half as good as what we eat at home.

So we rented a perfect little cottage in Venice—right on the border of Marina del Rey and Venice Beach. About 50 yards from the sand. It had everything we needed, cost significantly less than the hotel I had originally planned to book, and gave us the exact feeling we were looking for: this is our home base.

Lesson: The way you travel reflects the way you live. Choose comfort, simplicity, and intention over flash.

Stat: 76% of travelers say renting a home gives them a deeper connection to the place they’re visiting. And I believe it.

Keeping the Routine, Even on the Road

I bring my routine with me. It’s not the enemy. It’s my solace, discipline and consistency. It grounds me and enables me to feel like myself wherever I am in the world. 

As soon as we landed, we went straight to Erewhon. Stocked up like we were setting up camp for a week: eggs, turkey, Greek yogurt, fruit, vegetables, juices, a few frozen items for smoothies. We make it feel like home. Food is fuel. It’s also a family. It’s routine. It’s grounding.

I’m always up by 6 a.m., even on vacation. I walked the beach. Did breathwork using my XPT Life App. Took it all in. And even though we had food at the house, I like to find a great local coffee shop wherever we go. In this case, Great White.

I’d go out early, get my coffee, do some people watching, and bring Kate & Harper home a cappuccino or a pastry. We’d start the day that way. Together.

Lesson: Your environment doesn’t control you. You carry your habits with you. Build systems that travel well.

Training at the Mecca, and Then Some

Friday morning I dropped into Gold’s Gym Venice—the Mecca. That place still holds a special energy. You walk in and feel the history, the intensity, the no-BS vibe.

Saturday morning I trained at Hume—an upscale, members-only performance facility that was kind enough to grant me a guest pass. Incredible design, great energy, clean, minimalist, and dialed-in. The kind of place that understands what modern, mature, performance-oriented guys want from a gym.

Even when I travel, I’m trying to hit as many of my 6 F’s as I can—fitness, family, finance, food, fashion, and fun. That’s the Midlife Male ethos. It’s not about being jacked or extreme. It’s about being healthy, consistent, and showing up at a high level across the board.

Podcasting, Presence & Powerful Conversations

Friday, I  drove to Jen Cohen’s house to record an episode of her Habits and Hustle podcast. Jen’s been a guest on Midlife Male, she’s like a female version of me and we spent two hours talking about stuff I’ve never discussed anywhere else.  Not sure how she’s gonna edit it into something comprehensible, but it’ll be entertaining. That much I can assure you.  While I was there, Kate and Harper went out for the day—shopping, exploring, making memories of their own. Afterward, we all met up for dinner at Gjelina on Abbot Kinney; one of our favorite restaurants with amazing food and great vibe. The people watching along Abbot Kinney is stellar.  

We also stopped into One Golden Thread, one of my favorite apparel companies and one of my favorite people—Jeff Scult. Jeff recently had me on his Drops of Gold podcast, and it was great for Kate and Harper to meet him and to check out their new retail space. It’s not just clothing—it’s art, philosophy, and expression.

A Morning with Gabby & Laird

Sunday morning, I drove to Malibu to Gabby Reece and Laird Hamilton’s home to record for her podcast. I sat with them in their kitchen, drinking Laird Superfood coffee, having real conversation—about life, longevity, love, health, marriage, presence, parenting, and performance.

Gabby and Laird are the real deal. There’s no performance. No filter. Just two people living in alignment. Their space is like a human optimization sanctuary—plunge pool, sauna, ocean energy, open windows, intentional choices everywhere you look.

And then I saw it—Laird’s INEOS Grenadier truck. Actually, two of them. One for him. One for Gabby. Rugged. Beautiful. Functional. It was love at first sight. That truck is now on my bucket list.

But more than the gear, it was the feeling: this is how life can be when you build it on purpose.

Stat: According to the Harvard Study of Adult Development, the #1 predictor of happiness and health in later life is the strength of your relationships. That morning was about more than a podcast. It was about connection. Reflection. Alignment.

Lesson: Build your life with the same care and intentionality you bring to your workouts or your investments. The return is greater than money—it’s joy, meaning, and energy.

Dodgers, Sunshine & Lessons in Perspective

That afternoon, we bought tickets to see the Dodgers play the Cubs. I never regret an experience. But let me offer a tip: buy your seats on the Dodgers’ side of the stadium. We were on the visitors’ side and got blasted by the sun for two hours before it dipped behind the upper decks.

When I buy tickets, I’m very specific. I like to sit in the front row of the second level—great view, not obstructed, close enough to see the action, far enough to breathe. That’s how I experience life, too. Observant. Engaged. Selective. Present.

Stat: 89% of people say they’d rather spend money on experiences than material things. And they’re right. The money comes and goes. But the memory of watching a game with your kid in the sunshine? That sticks.

Lesson: Buy the ticket. Take the trip. Don’t wait for the perfect moment—it’s already here.

Style Stop: Dover Street Market, L.A.

We made a trip down to Dover Street Market in the Design District—because no visit to L.A. is complete without a little style inspiration. This is Harpers thing.  He curates the spaces and places we go.  The space itself is a work of art. Part gallery, part boutique, part fashion playground. Everything is curated to perfection—from the emerging designers to the established icons, to the architecture and layout itself.

We browsed, tried things on, and soaked up the creative energy. It’s one of those spots that doesn’t just sell clothes—it sells culture. Whether you walk out with a new piece or not, you leave with ideas, perspective, and a refreshed take on what style can mean – mainly for him and Kate, but I pick up a few pointers for me on how to make it work in midlife: intentional, expressive, and uniquely yours.

Where We Ate (and Loved Every Bite)

One of the things we value most when we travel is food. Not just the quality, but the experience around it. The vibe. The people. The routine. The memory. In L.A., we didn’t just eat—we curated our meals the same way we curate everything else: intentionally, joyfully, and with appreciation.

Great White was our go-to for breakfast. Amazing cappuccinos, great people-watching, and maybe the best pancakes we’ve had in a long time. We ended up going back for dinner—and it did not disappoint. The burger, the steak, and the cod were all exceptional. Casual, cool, and absolutely nailed the balance between comfort and quality.

Gjelina never fails. Still one of our all-time favorites. The pizza, pasta, and chicken were perfect. It’s one of those places where you linger a little longer, where the food and atmosphere just make you want to stretch the moment.

MRKT was a standout—made even better thanks to our incredibly kind and generous friend, Seb Terry, who surprised us by sending over a bottle of champagne. Incredible vibe. Thoughtful, attentive service. The steak, the fish, the pasta, and the must-have crispy potatoes? All dialed in. Everything on that table had intention and soul behind it.

We hit up Salt & Straw multiple times for ice cream. A couple scoops, some laughs, a little walk on Abbot Kinney after—it’s the kind of simple joy that just feels right.

Erewhon Market was our go-to grocery hub. We shopped there the way other people might shop Rodeo Drive. Stocked up on staples for the house, grabbed a few of their prepared items, smoothies, and enjoyed the atmosphere that somehow turns grocery shopping into a scene.

Gjelina Takeaway, right next door to the main restaurant, was perfect for lunch on the go. Their pizza and sandwiches? High-level. It’s fast, it’s fresh, and it’s every bit as good as sitting down next door.

And then there’s Gjusta. A market, a bakery, a vibe. Fresh food, great coffee, and that warm, lived-in feeling of a place that locals love and travelers wish they had back home.

What I Packed (and What I Didn’t)

I pack light. I bring what works. No fluff. No “just in case” gear. Only essentials. But LA essentials because I give a shit and want to look cool, without looking like I’m trying to look cool.  That’s so midlife and fortunately I have Harper to style me and Kate to cringe at me.

It’s simple. Versatile. Comfortable. Stylish. Just like how I try to live.

Reflections from the Middle

This wasn’t just a trip. It was a checkpoint. A reminder.

When I was 23, I was sitting at the bar of Rodeo Bar in NYC during the production of Two Ninas, The first movie I produced, next to Amanda Peet, who played one of the leads. She looked at me and said, “I just hope I make it.” I said, “Same.”  We were both kids, just starting out. And it was hard. 

Now I’m 52. I’m married. I’ve got kids. I’ve built three businesses. I’m lying in bed in Venice Beach watching Amanda Peet on Apple TV in a new show and I don’t even know the name of but its about midlife and crisis and she got caught fucking her trainer, divorced Jon Hamm, who then lost his job because he banged some underling at his wall street firm and its a colossal shit show that gives me agita so I turned it off and am now annoyed I’m even writing about it. Life comes full circle like that.

Stat: Men in their 40s and 50s report the lowest levels of life satisfaction across every major happiness study. But the curve goes back up. Dramatically. If—and only if—you lean in (and stop watching crap on tv, reading about it, watching the news and consuming volumes of social media)

Here’s What I Know Now

  • Routines are freedom. Build them so well they travel with you.
  • Presence is power. Bring it everywhere.
  • Comfort is earned. But it doesn’t have to be complicated.
  • Family is the mission. The rest is strategy.
  • Time is your most valuable currency. Spend it wisely.

We didn’t just go to L.A. We experienced it. Together. On purpose. And we came back more connected, more grounded, and more grateful than ever.

midlifemale
midlifemale
Greg Scheinman
Founder, Midlife Male
52. Husband. Father. Entrepreneur. Coach
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