I set out on a three-week trip to Portugal with the majority fully planned. Lisbon and Madeira were smooth, structured, and exactly how I like things. Then I tried something new. I booked only two nights in São Miguel, thought I would hop over to Porto for six days, and then left four days completely open. No plan. Just see what happens.
It sounded exciting. Adventurous. Maybe even a little movie-like.
It was not.
When the Experiment Fell Apart
I do best with structure. Flights, hotels, logistics, when those pieces are in place, I feel free. Without them, I feel scattered.
When I arrived in the Azores, the regret hit immediately. Two nights in São Miguel were way too short. I could not decide where to go next, nothing felt right, and I fell into decision fatigue. That is when I changed the plan. I pushed Porto out a week and stayed longer in São Miguel.
I loved and hated that decision. I got more time on the island, but it also came with flight changes, hotel stress, and hours of scrambling. Yet that is what led me to the best part of the trip.
The Mistake That Turned Into a Gift
Extending gave me five full days in São Miguel. That island refuses to be rushed. The volcanic lakes, the cliffs that looked unreal, the fields so green they almost glowed, it all forced me to slow down.
I stopped reading, stopped listening to podcasts, and just walked. Miles and miles. I could have rented a car, but when every corner takes your breath away, slowing down is the gift.
Facing My Own Head
Here is what I did not expect. Being with my thoughts was not calming. It was draining. I realized how much of my anxiety comes from replaying conversations and analyzing things that do not need analyzing.
Five days were not enough to fully quiet my mind, but it showed me something important. Growth is not clean or romantic. It is uncomfortable, messy, and it takes time.
Of course, I had moments of magic too. Like the time I jumped into the ocean with new friends, even though I had no swimsuit. Or when I found a mountain pool fed by a waterfall with no one else around. Both moments happened because I created space for them.
What I Will Do Differently Next Time
This trip did not change the fact that I love control. And I am okay with that. As I told a friend later, “Structure is not weakness. It is what allows me to actually enjoy the freedom around it.”
Here are the lessons I will keep with me:
- Set a baseline. Flights and hotels need to be booked so I can relax and enjoy the trip.
- Respect the time it takes. Some places and experiences cannot be squeezed into two days.
- Always pack a swimsuit. Enough said.
The Real Takeaway
Spontaneity sounds romantic, but too much of it can unravel you. Structure gives stability. Flexibility creates discovery. Both matter in travel and in business.
Right now, leaders everywhere are being pushed into experiments with AI. Some work out. Some do not. But every attempt teaches us something about where structure helps and where letting go is better.
São Miguel did not turn me into a carefree wanderer. It reminded me that balance is the real goal. Too much control holds you back. Too much chaos pulls you apart. Growth happens in between.
At StringCan, we help leaders and companies find that same balance between structure and experimentation. If you are ready to create space for growth in your business, let’s talk.
