My time here on this solo personal retreat is winding down. Today, I would visit the high points of the city (high as in elevation).
I didn’t want this chapter to tie up without some reflection.
So I’m asking myself some key questions.
Stop 1: Esplanada da Graça
Lisbon, the city of seven hills, is dotted with “miradouros,” high points to get spectacular views of the city. “Esplanada da Graça” is a “miradouro” 700 feet from my apartment (and promised breakfast,) so I packed my backpack to beat the rain and headed out.
I cringed as I looked at the steep stairwell to the top. A British dad and young son came skipping down like it was nothing.
Christ. Here we go.
I’m 5 weeks out from surgery, so it felt ok to tackle the stairs today. I rested on the landings, and took my time. Surprisingly, my breathing stabilized pretty quickly. Murals along the way reminded me “You are not alone.”
I mean, I pretty much was.
It was still 8am.
Esplanada do Graca, Lisbon
The vista opened up to sweeping views of Sao Jorge Castle. It’s one of the few tourist attractions open on a Monday, so I decided to tackle that next. I see it from my apartment everyday, the flag flapping in the wind, beckoning me to come visit.
Today was the day.
Stop 2: Sao Jorge Castle
The Moors built Sao Jorge Castlein the mid-11th century as a defense stronghold. Like many buildings, it had several owners, including the Christians. A royal palace until the 16th century. It fell into ruin during the 1755 earthquake. It was restored in the 20th century. Today , it’s a national monument.
It was still early, so I bought a ticket on the spot. There was NO LINE.
The castle sits in the middle of a buzzing city, yet inside its walls, there's stillness.
Sao Jorge Castle, Lisbon
Sao Jorge rises above the city. As I walked the ramparts, I thought about how this solo retreat elevated me out of my day-to-day, affording me a new perspective on things.
This view of Lisbon— both literal and metaphorical — let me see how far I’ve come.
For starters, I’ve worked my ass off for 50+ years. I deserved and have earned this time.
“You can only connect the dots looking back.”
The watchtowers were built to see what was coming, not just protect what was. I thought about my time here since April 1st: strategic visioning for the next chapter in business and life. I thought about
What kind of impact do I want now?
What kind of work lights me up now?
Who am I becoming?
At the exit, there is a Sao Jorge chapel. I went in, sat in a pew with my journal.
I wrote "What I Leave Behind"
Emotions, identities, patterns, or expectations such as:
“The pressure to always be strong.”
“To be who I was before surgery.”
“The version of success that no longer fits me.”
I wrote "What I’m Walking Toward"
New beliefs, identities, or ways of showing up:
“Creating from softness instead of hustle.”
“Building a business that feels like art.”
“Letting the healed version of me lead.”
Then I wrote
“I came to Lisbon to slow down. To listen to the version of myself I could only hear when the world got quiet.
This castle has been many things: a fortress, a ruin, a royal home, a place of silence, a place of watching.
And maybe, so have I.
I leave a part of me here. I return softer, wiser, and more myself.
I am not who I was. I am not yet who I will be. But I honor exactly who I am now.”
Stop 3: A Loja Azul, A Ceramics Shop
Portugal is known for its ceramics. I walk into shops like these and think, “How the hell would I get a piece like this home?”
I settled for a poster and postcards from artist Eva Halffers. I can’t break them.
