“There’s a trail that goes up the coast where you walk from one small town to the next. Wanna do it?”
Such a potentially cool and interesting experience…it was a quick and easy yes for me.
My roommate all through college and best man in my wedding has worked internationally for the last 15 years and I’ve visited him at every stop of his journey from Seoul to Beijing, Copenhagen to Singapore. In early 2020, what started out as an annoying toothache, unpredictably twisted into a cancer diagnosis, radical surgery, many months of chemo in Singapore during COVID lock down, and a very different perspective on life.
Earlier this year, with his 5 year scan showing him cancer-free and his decision to take a “gap year” to travel the world and visit friends, we chose Portugal to meet up and celebrate.
I didn’t really look at what I said yes to until about a month before the trip. That’s when I learned what we would be doing was a segment of El Camino de Santiago, a pilgrimage up the Portuguese and Spanish coast through a series of small towns and villages dating back over 1200 years.
This is also when I learned that our “walk up the coast” was actually a half-marathon a day 100km hike with some pretty serious elevation. Cue a bit of mild panic. Better get some new shoes and some hikes with a loaded pack in asap.
I went in with no agenda or intentions outside of spending a lot of quality time with a quality human and to remain open to whatever experiences revealed themselves. Only now as I pause to reflect, are so many lessons crystallizing and presenting themselves to me, and I hope you may find some helpful in your own journey.

10 Lessons from El Camino de Santiago:
Lesson #1: Say yes to interesting things (before you can talk yourself out of it) and then figure it out.
The best decisions in life often happen before you have time to talk yourself out of them. My “yes” to the Camino happened in about three seconds, long before I actually knew what it was. Say yes to the interesting invitation, then do what it takes to make it work. You will often surprise yourself with what you can do.
Lesson #2: Great friends with rich shared experiences are the marker of a life well lived.
25 years of friendship and now 21 different countries together, but walking and talking for 100km was really special. The marker of a life well lived isn’t the number of people you know or who know you, it’s the depth of shared experiences with the people who matter.
Lesson #3: You get stronger as you go.
Your shoulders recover, blister(s) pressure subsides, legs stabilize. Then you stop and everything tightens up and hurts. Then you do it again. What feels impossible on day one becomes easy routine by day three. The same is true for any meaningful challenge in life. You adapt, you endure, you get stronger as you go. Don’t let the early pain prevent you from future progress.
Lesson #4: It’s easier, but certainly not better, to just stare at the ground right in front of you with tunnel vision.
There was a continual pull to zone out, stare down at the path, and put one foot in front of the other. It’s physically and mentally safer that way, less intrusive thoughts, less likely to stumble. But that’s not the point. Life is meant to be experienced head up and eyes open, even if that means we may sometimes trip and fall. That’s the only way to notice the truly beautiful things and people around us all the time.
Lesson #5: Any time you pass another pilgrim or local, it’s always the same greeting: “Buen Camino.”
A powerful connecting phrase wishing for a “Good Path”; a good, safe, and meaningful journey. We are all walking on this journey of life together. How might we all encourage each other to each have a “Buen Camino” on our own paths more often?
Lesson #6: The beauty of our humanity lies in all the things we share together.
We all came from different places for different reasons. But as we sat enjoying our meals with the same joy of completing another challenging leg, the mix of languages created something beautiful. The cacophony of all the different dialects filled the cafe and my soul. In an ever-polarizing world, look not for our differences but for our similarities. When you find them, you find what truly matters.
Lesson #7: There is immense energetic power of everyone moving together towards the same goal.
Hundreds of pilgrims from dozens of countries, all walking the same ancient path toward Santiago. Different stories, different reasons, but the same direction. There’s something powerful about being part of a collective movement toward a shared destination that you can feel in your soul. Where can you bring more clarity and alignment to your purpose-driven leadership?
Lesson #8: Every city, like every person, has a story and history that shapes their approach in the present day.
Once you start to learn about the scars from yesterdays, you begin to understand how they shape todays. The last 500+ years of Portugal’s rise and fall in global dominance can be seen in just one cathedral’s mismatched stones, charred pillars, red-painted ceiling, and lack of typical ornamentation. Earthquakes, fires, and tsunamis; plagues, inquisitions and massacres, leadership, succession, and ideological battles…all left their physical mark and cultural influence. Easier to see in buildings and cities, harder yet more important to understand in people.
Lesson #9: You will typically find what you look for.
When things go sideways…missing a turn and getting way off course, a majorly delayed flight, a misdirected drop-off location (all of which happened on this trip), do you fixate on what was supposed to be or embrace the opportunity of what now can be? All of our “disasters” actually led to some of the coolest conversations and discoveries of the trip.
Lesson #10: The Camino is the destination. How we walk through life is our life.
The journey itself was the point, not just reaching Santiago. Every step, every conversation, every moment of struggle and beauty, that was the experience we came for. The same is true for life: how we choose to walk through it becomes the life we actually live, one step and one moment at a time.
I hope at least a few of these lessons connect and resonate with you. That they offer a new perspective or maybe just a reminder of things you already knew but are easily forgotten.
If you have someone in your life who has faced their own battles: health, loss, challenge, or change, I hope you take a few moments this week to reach out and celebrate life with them in whatever way you can. Don’t wait for the perfect moment or convenient timing or a trip to Portugal. Say yes to spending quality time with quality people while you can however you can.
We’re all walking this path together, one step at a time.
Buen Camino,
Derek