I don’t think there’s an exact tipping point where you become certified as proficient in life navigation. Looking back on things that I’ve managed to do without Darwinism getting in the way, I do however feel like I’ve been fairly successful in most things. And there have been certain crystallizing moments of self-awareness: at sixteen I navigated Paris solo in search of my father. Working the BOS-CDG route, dad’s crew schedule found him intersecting in the city when I happened to be up there for a few days (I was a study abroad student in Grenoble). His flight was late though, and this being 1993, I had no way of knowing this without making some complicated phone calls. So I wound up crisscrossing Notre Dame and his hotel near the Javel metro stop—always missing him. It was this day-long traversing coupled with a fledgling French that suddenly caused me to realize that I was figuring things out. Not bad for a Mashpee kid.

But because life is a multilayered and long continuum of learning stuff, the things that helped me as a teenager won’t necessarily drag and drop into the challenges I face in my 40s. Of course, the ensuing decades have certainly presented me with experiences that have helped to build my confidence. Whether it was learning to ride a motorcycle or failing my first qualification board as a Surface Warfare Officer, I believe that every experience offers the chance for a boost. But still, now that I’m an adult and still out there doing this life living thing, there remain plenty of obstacles that give me pause. 

Last week I went on a mini-adventure with my little brother to the Iberian Peninsula. I’ve been there before, but this was his first time and I wanted to ensure that we had fun. A few days into the trip, we were set to fly from Lisbon to Malaga. The night before we were due to fly, it dawned on me that we could probably squeeze a look into Gibraltar for a few hours once we landed in Spain. 

Up until that moment, I had not given this detour a thought. In advance of our departure from London, I’d laid a sound foundation of Tetris pieces that formed the bones of our trip. But for this modification, I obviously had no research under my belt. On the morning of our flight, we sat in the Lisbon airport. I tapped at my phone to do a quick search of how best to visit Gibraltar. In a matter of minutes, I learned that it was best to park in Spain and walk across the border. And it was no ordinary walk—you do it on a runway that doubles as the main drag into Gibraltar. Truth be told, it all sounded a bit Hitchhiker’s Guide to me. 

As I said before, the successful execution of past travel tasks has helped me to become the reasonably confident traveler that I am. I do not fear driving a car in a foreign country, nor do I fear not knowing the language. I also firmly believe that, even if I were completely stripped of my belongings and were left destitute in a town square, people would come over to help. The world is full of possibilities—and I believe in the goodness of others. I also believe that we humans have, for the most part, furnished a society that is quite user friendly; so even if I don’t know exactly what to expect in facing something new, I go on faith that things will be figured out.

But even as we drove along the coast of Spain, I harbored an element of low-grade stress in my gut. This always happens—particularly when I am traveling with someone like my brother. Someone with whom I share more than just a work trip relationship. Maybe it’s because I feel an added sense of responsibility, but I really want things to go smoothly. I don’t want to lead us down a path that leaves everyone else wondering, “what were they thinking?”  Like it or not, I’ve gained a reputation as a seasoned traveler. But that doesn’t mean that I know what the hell I’m doing.

But the worry I felt in modifying our itinerary really shouldn’t have had me stressed. Intellectually, I understood this. Furthermore, my brother of all people is someone who excels in teasing out my weak points and reinforcing them. While in Lisbon, we were walking at sunset down Rua Augusta, enjoying the changing light. As I was aiming to shoot a photo of the archway looking into Praça do Comércio, some damn fool was walking around nearly naked in Native American garb. He was chasing down people he judged to be taking his photograph without his consent. His look did not interest me, but it turns out he was in one of my shots. My brother, the part-time goalie and full-time sibling, instinctively formed a barrier between the naked man and me while I went on cluelessly metering the light in the sky.  My point is that my brother is a travel buddy who should not cause me stress. 

But I am also his big sister.

Of course, the rest of the story is that our Gibraltar deviation was uneventful and marvelous. We did just enough research to know that sharing a taxi to the top of the rock would yield the best return for our short timeframe. And our taxi was shared by a lovely couple from Northern Ireland who were there to elope, as well as a couple with a daughter who was mobility-impaired. Our driver was a Gibraltar native who shared all kinds of interesting facts—to include views of the Atlantic and the Med, the drydock down below where my ship once went into repair, as well as a cemetery where a few of the fallen from the Battle of Trafalgar still lie. And yes, the Barbary macaques. Every bit of it felt special. 

As we walked back across the border to our car in Spain, the border guards barely glanced at our passports. It was a sunny yet windy day, and we crossed a few streets and climbed back into our little Citroën C3. It was all easy. My creeping malaise was ill-founded. The planet had confirmed its user-friendly application once more. 

I suppose that it all sounds quite foolish to have harbored any concern at all in this space of a few hours. It’s not like we were attempting something exotic or daring. We weren’t members of a Shackleton expedition. And it was nothing like the drive north I once enjoyed, going from Dakar to Nouakchott where the only road was a desert with random Bedouins we would stop along the way to ensure we remained pointed in the right direction. What, me worry?

But I don’t like to get cocky about things.  I’d also like to think that I have a healthy enough respect of the world to know that I remain a mere mosquito who is bumping about the planet with colorful nail polish and cute clothes. Things can happen that are beyond my control. But I do believe that the world as a whole conspires to help—both in this small journey as well as the larger more metaphorical ones. For now, I’m just glad that my brother is safe back in New England and I can go back to worrying about myself. What’s more, we can look ahead to more off-script life adventures. They really are the best.