Entering the Last Stretch & Calling a Travel Audible

Greetings from Colares, Portugal! Nearly three months have flown by since my last update, and we’re now in month nine of our thirteen-month adventure.

Since writing about our special time in Bali, we have traveled throughout Vietnam, Thailand, Australia, and just wrapped up an amazing two weeks in Sri Lanka. The overarching theme has been constant:

Fast travel without schooling provides a high-low intensity that is more appreciated after the fact. 

Slow travel with a short-term school gives us the most joy. There, the kids connect with inspiring teachers and peers from diverse cultures, while Tye and I have the space for our routines and activities that refill our tanks and make us the most balanced.

The school also provides an immediate and strong community. You meet the most interesting people and form fast friends.
I was catching up with a high school buddy who lives in Byron Bay. I was telling him about how different it is to strike up conversations with people when world schooling. He got excited, “Well, yeah, it makes so much sense. The first question you are asking all these parents is essentially, ‘How did you get here?’” I hadn’t thought about it in those simple terms, but that is almost always the first question, and you never get tired of hearing the answers. Both because it’s interesting and you’re also trying to glean some insight or secret they have on how to live a best life.

By the way, this is the second time I have met up with a high school friend I haven’t seen in 20 years, and immediately, it felt so fun and effortless. It makes me think about being more intentional about putting myself in places that open up more of these previously dormant relationships — where the other person truly knows you at your core. I don’t know, but there is something there to call out.

So in knowing the formula with what made us happy, we started to question our planned travel to go to New Zealand, followed by a long stay in South America. We had found some schooling options, but nothing that seemed consistent or vouched for by people we trusted. 

We decided to open up our search and came across a school in Portugal with short-term options that met everything we were after. It was a forest school with an emphasis on outside time and project-based learning. 

And just like that, our Peyton Manning Omaha audible was called. 

It’s 24 hours from Sydney to Lisbon, so we knew we wanted to break up the trip. We decided on Sri Lanka after hearing great things about a world school and stories about the beautiful surfing beaches and nice people. 

Luckily, all three checked out. Sri Lanka felt a lot like Ubud.

A small, but cool story from Sri Lanka.
The ride to school is a fun, easy scooter through rice fields and jungles. Almost nobody is on the roads. You sometimes see big lizards and monkeys on the route.
There is a fruit stand along the road, and this sweet older lady stands outside, always smiling at us.
One day after drop-off, I pulled over and ordered a smoothie. While taking down a non-liquid, mushed-up banana smoothie, the woman asked if I wanted to return for breakfast. She said she just needed an hour's heads-up. This is all in broken English.
That night, I whatsapped her that I would come with my daughter in the morning. I told Lou about a nice lady who would make us breakfast. The food would likely be different, and probably lots of it, but that’s what it was all about. Lou was fully on board.
We scootered up to the lady waiting for us. We sat down, and she just kept bringing plate after plate. Our first bite was the spiciest, gnarliest-tasting thing. The woman came over right after and asked how it was. Lou looked her in the eye with a big grin, and said, "It’s good, it's good." The lady leaves, and we smile at each other. Inside, I'm beaming with pride at how she handled herself.
The rest of the food was incredible.
We talked about how we probably wouldn’t stop at someone’s house for breakfast on our morning walk to school in Austin and how the world is a pretty big, wild, and awesome place.
We then had a 10-minute ride through windy roads to Lou's school, with her behind me, giving me a good, loving squeeze. It was a top 1% way to start the day.

After Sri Lanka, we made a quick 2-day stop in Dubai and celebrated Tye’s 40th. It was a great couple of days, and also a place I never need to go back to again.

We then flew to Lisbon and have been in Colares (40 minutes from Lisbon) for the last couple of weeks. We will be here for three months, and it feels so great to know we will be in one place for a bit! 

We’re two weeks into the school, and it’s living up to our expectations. The kids spend a lot of time outside in nature, and there are kids from all over the globe. The teachers are so nice and passionate about what they do, and most importantly, the kids seem very happy to be there.

Tye and I have the time during the day we crave. Beyond having the time for health, I have the space and environment to think about how to insert myself in this wild, crazy world that seems to be reshaping itself.

Before the trip, Tye and I created four themes around which to focus our intention. Here are some recent thoughts on each.

Theme 1: Create compassionate and resilient kids.  Raise capable, good humans.

The theme that continues to dominate most cycles. So many threads feel open and alive. I’ll dig into a couple that may not be the most important, but are top of mind.

Despite a newfound conviction in the uselessness of much of what is taught in traditional schooling, it’s hard to ignore the pull to be Lou’s ‘Don’t let her fall behind from arbitrary second-grade curriculum’ teacher.
I often feel defeated on how to navigate. It’s a daily battle and negotiation to get a small amount of willing time from her. I lose my patience and hate myself for it. It’s the opposite compared to when I teach the kids tennis. With tennis, I can spot and celebrate the smallest gains (e.g., subtle movement to a ball, starting to take the racket back earlier, etc.). When it comes to foundational reading/math, for whatever reason, it’s just harder to stay patient and celebrate the small wins. 
It’s hard to let go of Lou being in some race — that I’m not doing my job if another 8-year-old is reading Harry Potter on their own while we’re struggling to get through a few pages together.
It’s getting easier to stay patient, though. I am hooked on seeing her progress and get more confident in herself, even if it feels like 1.25 steps forward and 1 step back. I have seen the pace of what can be accomplished with 1:1 learning, so I now understand that large ground can be made up in a short amount of time. Though hard, it’s super rewarding as long as I control my reactions.
In thinking about Lou’s sweet, inviting, and active energy, what has helped me the most is watching and rewatching Ted Robinson’s Ted Talk, ‘Do Schools Kill Creativity?’(78M views). He tells a story about a girl who grew up to be the uber-successful choreographer of Cats and Phantom of the Opera. For the first part of schooling, it felt so hard for her to keep up. Then, a friend doctor told her mother there was nothing ‘wrong’ with her; she was just meant to be a dancer, someone who needed to move to think.
Lou is very much a creative person who thrives when she is moving and social. She’s incredible, excelling in all the areas that matter the most on the human scale. I need to keep getting better. I write this out as a reminder.

I was recently listening to Chris Sacca on the Tim Ferris podcast. I have always loved listening to him. Before the trip, I even downloaded all his podcast interviews I hadn’t heard before because his storytelling feels so substantiated and evergreen.
This one was the best yet. It’s packed with laugh-out-loud takes on approaching the modern state of living, with most of the content about raising his three kids.
He recently moved to Bozeman, Montana, to be in an outside-minded community that is more resistant to the phone/social media epidemic. He compares the combo to “fentanyl-laced cigarettes.”
He set up a desktop computer in the living room that faces out, and kids can communicate with their friends that way.
His analogy feels right, and his solution to still allow kids to communicate with friends seems like a good one. I remember the excitement of coming home to see what friends and girl crushes were on AOL Messenger.
He goes deep on the importance of kids being kids. To get in trouble. To go through formative experiences vs. the pull to stay atop the academic leaderboard.
I just kept nodding my head throughout. It felt good to hear someone I have a ton of respect for validate so much of what Tye and I are thinking through.

Lastly, revisiting a small sub-theme from the first post around trying to find good movies we can watch as a family. This remains a thing.
Many times when we finish a full day, we have an hour before bedtime routine, and a good movie with the kids sounds fun. The problem is we have run out of ChatGPT prompt ideas that return more options like Sound of Music and Mary Poppins. We can only watch Matilda so many times.
So, we have decided to bypass the 8 or 12+ rating with more mature classics. Movies like The Martian, Father of the Bride, and Big.
Yes, we have to occasionally hit the fast-forward button when you forget Tom Hanks getting to second base in Big, but we’ll take the kids squealing when seeing a kissing scene vs. the new Pixar junk or newer movies depicting phones and social media as the cool norm.
Though last night, we were watching Father of the Bride Part II, and had to explain to the kids what menopause was 🤦🏻.

Theme 2: Be our best selves with each other.

I was chatting about marriage with a buddy the other day, and Bill Murray’s legendary bachelor party speech came up. It’s worth watching or rewatching. He offers advice to a group of recent college graduates who are attending the first bachelor party of their friend group.
He recommends that before getting married, you travel the world with your partner and visit hard-to-get-to places. When you return, if both are still in love, you get married at the airport.
While already married, Tye and I are passing this test in spades. Especially with kids in the equation, more gratitude and appreciation have emerged for how our individual strengths complement each other to form a complete, loving partnership.

However, with such an expanded, shared set of experiences, we’re feeling our hardest test to be our best selves as we navigate what comes after.

So much still feels ‘messy’ as we try to weave this newfound sense of adventure and presence with the kids into a future that doesn’t leave us feeling lost when the journey ends.
Tye and I have very different approaches in how we try to unravel or come up with solutions. There’s not a right way, just different. We can both get triggered despite the best intent from the other.
Similar to the thread about staying patient with Lou, we both control how we go about the process. It doesn’t need to be filled with any conflict or resentment because there are legit, varying views. We both acknowledge and love how these differing views push, balance, and shape the other. But right now, it’s a challenge to keep that mindset always on when going through big conversations and decisions.

Theme 3: Lean into family adventures (the good, the bad, and the boring).

Though it’s only been months since time spent in Thailand, Vietnam, and Australia, it feels like a long time ago. Lots of adventure. Below are some top moments.

Theme 4: Seek out personal exploration and professional curiosity.

The past three months have been filled with mostly fast family travel. When pockets of personal space open, I continue to lean into padel and especially in Byron Bay, was able to get in a bunch of surfing days.
Actually, the same friend who lives Byron, had another good line around surfing. We were talking about how humbling it is to be out there and how I still feel like such a beginner despite how many times I’ve gone out. He jumped up, “Dude, I’ve now lived here for 20 years and I’m still a beginner. But the thing is, you’re enjoying the best arena in the world.”
That landed. So much so that I pushed Tye to get into the surfing game in Byron after she didn’t have the best experience in Costa Rica a few years back. It just feels like something with the potential for us to enjoy as a family in years to come. Tye is a good snow boarder who spent a year in Denver going into the mountains every weekend. Beyond that, she can figure out angles and positioning in a way that comes so much easier for her than me.
She obliged to the push, and sure enough, she started to get up with ease, overcoming the paddle fatigue and occasional wave beat down.
In Sri Lanka, we had a fun couple days trying to figure it all out together.
The surfing conditions in Portugal have not been great since we got here, but excited to see the differences with wet suits and a stronger Atlantic Ocean.

On the professional curiosity front, it feels so good to have a home base with the kids in school, where I am feeling the timing and urge to LEAN in. The other day, we were on a guided e-bike mountain tour with a cool guy who had started several types of interesting small businesses. We were talking about all the highs and lows throughout his career that spanned starting a hostel in Bali to traveling the world with a filming business. After he gave us the download and without much thought I responded, “Wow, you have done a lot of adventure with your ventures.” For some reason, I’d never viewed my professional experiences in terms of adventures. Reframing them that way has helped to understand why it tugs at me so strongly—and why I’m thrilled to finally have the time to dive into the next one.

If you get a sec, drop me a response with a quick update from your world or reaction to any part of the post. We have space in our Airbnbs if anybody is coming or wants to come to Portugal :).

Best,
Scott