Owen Dornan

Owen Dornan

Guide

Current Country

United States 🇺🇸

Current City

Chicago

Intuition

Cultivating inner knowing

A question currently animating me about the inner life/spirit is:

How can I move past friendships to create room for new connections?

September 11, 2025

A question currently animating me about the outer world/universe/multiverse is:

How can I be an entrepreneur that creates meaningful change while the world around me is not focused on meaningful change?

September 11, 2025

The practices I’m finding most helpful at the moment are:

Creating Music/Art,Meditation,Other

September 11, 2025

A moment I noticed my inner light kindled this month was:

Coming back to my room at 3 am after leaving at 8 am. This showed me how special the conversations I can have are and how much the people around me matter to me.

September 11, 2025

A moment I noticed my inner light dwindled this month was:

Staying fixated on my negative emotions and not allowing myself to move on.

September 11, 2025

Courage

Aligning action

Assumptions I'm examining right now are:

Other

September 11, 2025

I originally assumed:

I used to think that friendships take contenous effort and are hard to maintain and create.

September 11, 2025

These assumptions are changing:

Now I sense that friendships evolve in just the way they are supposed to. Some take a long time to create while others may happen right away. Some naturally drift out of your life and others you have to fight to keep in your life.

September 11, 2025

A moment I stepped out of my comfort zone this month was:

Going to play intramural football(Soccer) where everyone else was way above my level.

September 11, 2025

Compassion

Engaged Empathy

Something that is helping me build trusting relationships here is:

How you continuously showed up to the Tuesday sessions.

September 11, 2025

Digital Detox Retreat

Number of days I've gone without technology

Number of days I've gone without technology

89

Being intentionally away from technology and distractions has taught me:

You dont miss as much as you think. When you arrive back in technology after a long hike or being away you can catch up on everything faster then you think. After a 5 day hike I was able to jump right back into social media and work after 3 hours of good work.

May 30, 2025

Gratitude

Peers I'm grateful for:

Catalina Cox

Thank you for listening to me during the Tuesday sessions. I found your advice and your listening ear really helped me understand and get through the difficult situation that I was in.

September 11, 2025

Peers who have expressed gratitude for me:

Teo Esteban Oppenheimer

Maestro! Grande que eres a ver si hablamos estos dias!

October 31, 2025

Zeiad Ahmed

Hi Owen! We haven't interacted much, but I wanted to lyk that I always look forward to the questions you ask in Courageous Conversations! They're intuitive and genuinely help me think the lessons through, I'd say you've definitely mastered the lost art of question-asking ahahah!

October 19, 2025

Magical Moments

Light-kindling moments

Light-kindling moments

May 16, 2025

This may have been the biggest mistake yet of my trip but I still felt it important to include in my magical moments. When I was booking flights out of Bolivia I booked one from google flights from the La Paz airport. A few hours before I was meant to leave I found out that my previous flight was from La Paz Mexico and not La Paz Bolivia. This resulted in a very chaotic and difficult situation that resulted in me buying a next day flight. This ended up being much more expensive and I was extremely disappointed.

However later that night I found out that even if I made a huge mistake I was going to take full advantage of slightly more time in La Paz. I was staying with a family friend who welcomed me into her home and into her family. Luckily it ended up being her moms 86th birthday. That meant I got to meet the entire extended family and share many stories. It was so interesting to see how such a big family can interact and how they can celebrate one person. I was able to eat so much traditional food and hear stories from each family member. I learnt more in this one dinner then most people travelling Bolivia will ever understand. Beyond just the dinner it was also the famous night of the museums in La Paz. That meant that throughout the entire night every museum was open and there was music on every street corner. The streets were full of life and I was able to witness the diverse culture of Bolivia. This picture captured a typical Bolivian dance which was so beautiful and was the moment I forgave myself for making my flight mistake.

May 10, 2025

I had the amazing opportunity to visit my old roommates family in Bolivia. I was with his dad, his stepmom and his three step sisters. They lived in Oruro which is the fourth biggest city in Bolivia and certainly off the beaten path for travellers. Tourists when visiting Bolivia tend to stick to La Paz, Lake Titicaca and the salt flats. However I have learned the importance and impact of visiting cities that had never been visited. When visiting the city most people had never seen a foreigner in their lives and it was very special for them to share stories. The father also worked at a school which I got to visit and share opportunities with students such as UWC and the Flight School. The students were so passionate about learning and getting to know me. I made many friends and saw what life was like in school there. The older step sister also fully adopted me into her life. She introduced me to all of her friends and invited me to many different events. The mom also drove me around the entire city to find a suit for an upcoming wedding. The two younger sisters shared jokes and invited me to their school play and sports games. Although I was there for a very short time there were countless magical moments with this family. They opened their houses and hearts towards me and for the first time in a long time I felt part of the family. I wasn't a tourist and a bikepacker but I was just someone doing the daily activities. The most mundane activities like going to the market or going to a friend's birthday was incredibly impactful. I will always remember my new family and my new home.

May 7, 2025

I decided to start my journey in Bolivia by crossing the border from San Pedro de Atacama and Uyuni. This entailed many magical moments in nature where I got to see the biggest salt flat in the world. However this magical moment entails my adventures with my first day back in civilisation. When I arrived in the small town of Uyuni I had lots of time to kill with a new friend I made on my tour. We wandered around until I found a fruit market. Because Uyuni is so rural and far away to get contentious produce every so often there is a massive truck that drops off a lot of fruit. On this day it so happened to be bananas. I originally wanted to buy a few bananas, however the salesmen informed me the minimum amount was fifty bananas. I decided this would be the perfect opportunity to meet people so I decided to buy the bananas and use them as a conversation starter. This resulted in me being invited to the championship of the police force football teams. There was music, incredible food and many new local friends. They explained to me the dynamics of the teams and who I should cheer for. Every banana given felt very magical and brought a lot of smiles. I entered the town a tourist and I left a friend of many which felt very magical.

Apr 4, 2025

This is one of the moments of bike-packing that will stick with me throughout my life. I remember waking up after the coldest night of the trip. There was snow on my tent and the roads were slick. I had just had a few days of really hard biking and was extremely tired. I remembering arriving to my campsite late and not knowing what I was going to wake up to. I woke up with the sun that illuminated the snow capped mountains around me. I was surrounded as far as the eye could see with the most beuatiful landscape I had seen and was completely alone. It also helped that I had 800 meters of slow decent ahead of me and I could finally make some real distance. This moment was so special that I sat and was able to meditate for 45 minutes. I was so content with how I acted each day and had never been this present. It finally felt like the lessons that I learned in Thailand from the monk were working and I was able to put them into practice.

Mar 29, 2025

As the wind howled by I couldn't hear anything. No birds, no guanacos, no life. I couldn't hear my own voice and it felt like the wind was even blocking out my own thoughts. Not only could I not hear anything but there wasn't much to see either. The dessert was endless with nothing but dust and rocks. After days of dessert and not seeing any humans in 3 days and not speaking for 6 I noticed three figures in the distance. As I approached I had no idea how important these three people were going to be. They were three hitchhikers that made it to the penguin sanctuary and got stranded. I had no food or tent and there was certainly not going to be any cars that would pass. That day I decided to give them a life line and made them dinner. We found a shelter and spent a very cold night. We laughed throughout the night and these new friendships were well worth the rice and lentils I gave them.

The magic of this moment went well beyond my first encounter with these new friends because they were a huge part of my journey throughout two months. About a week later I was trying to get into a hostel after arriving very late from the ferry. While they said they would open I was not able to get in and I was stranded on a cold night in Punta Arenas. Luckily the three hitchhikers passed me and welcomed me into their hostel with a whole meal and more great stories.

Later that month the karma kept giving back and I met two out of the three hitchhikers at the best moment possible. On one of my hardest and coldest days in pelting rain I had a flat tire. I thought I could change it but all of my extra tubes were losing air and useless. After a day of walking my bike trying to get to the closest town I wandered into a campsite. Randomly I met one of the hitch hikers and he helped me change the tire and had all the right supplies to patch it. About a month later I encountered another one who ended up buying my bike. All of these chance encounters helped me and was a great reminder in the importance of helping those in need when possible.

Mar 14, 2025

The start of my adventure was one of the hardest weeks of my life. Immediately I was hit with extremely cold weather and a wind storm. I had to cross the peninsula of Tierra del Fuego before a ferry that took me to the mainland in a week. This entailed biking over 100 km each day on fully gravel roads. What I did not expect was headwinds that reached over 150 km an hour. What started as a hard adventure became impossible and dangerous. I would bike from 4 am to 8 pm every day and barely meet my quota for the day. This took all that fresh energy out of me and left me unmotivated and depleted. However, every time the howling wind would knock me over I would get back up and slowly make my way. All of a sudden I made it to the coast and to the only king penguin sanctuary in latin america. People travelled across the world to come to this singular destination. Others also paid extremely high tour fees to reach this location yet I could see it just by biking. This was an extremely big wake up call and a very important magical moment. I was able to witness these king penguins first hand and for the first time since I started to see the beauty of bike packing.

Feb 27, 2025

Going into my time in Patagonia I was certain that I wanted to complete certain tracks. I had already prepared the gear for my bike trip and I figured beforehand I could test it out on some overnight hikes. Many of the treks in Patagonia are full of people and completely overrun. On top of that at times there are insane camping fees and you must book spots months in advance. Wanting to go off the beaten path, Zane and Anna decide to attempt the Huemul circuit. This is a 4 day 3 night hike that circumnavigates the Huemul mountain. It is also the only way to walk on the Southern Patagonia icefield. There were however certain risks that came along with such an undertaking. Two river crossings in harness, steep ascents and descents with unmarked trails at points. Despite the known challenges we had an incredible weather window and decided to go for it. We also met two Dutch girls that joined us for the journey and gave us great company. Every moment of this hike was stunning and transformative. We all pushed each other as a group and were rewarded with incredible views. We were isolated and surrounded by the famous patagonian nature and finally slightly off the tourist path. I found it very special to complete this challenge with others and see parts of the world that were so untouched

May 7, 2025

This was me at the start of March about to embark on one of my biggest adventures yet. Earlier when I was in Brazil I encountered a bike that was being sold in the most southern part of the world, Ushuaia, Argentina. I decided to buy that bike with no experience and no plan. Once I arrived I was lucky to pick up the bike in great condition and with all the needed supplies to start bikepacking. White I knew I wanted to change the way I saw Patagonia. However, I was also terrified to start this journey Everyone I talked to extremely discouraged my journey and laid out the many risks that were involved. I learned before departing that going from south to north is extremely difficult because of some of the strongest headwinds in the world. I was also starting in late season and was warned about extremely cold temperatures and unfavorable weather. Feeling unmotivated and scared I still pushed on and prepared for departure day. I prepared much more food that was needed and bought extra supplies for cold weather. I was fresh and ready for an adventure. This moment right before departure was like no other. After being told none of my journey was possible I had the opportunity to prove everyone wrong. I had the opportunity to push myself the furthest in the stretch zone that I had ever been. I was about to embark on the bike packing journey from the end of the world up Patagonia!

Feb 13, 2025

After already meeting two other fellows I was super excited to meet Zane and Anna in Argentina. Anna was currently living in the city as well which was very special as she was able to show us her favorite spots and what life was like living there. She was working with a lot of different organisations that helped Russian immigrants adapt and live in Argentina. That meant we got private invites to different events across the city with the Russian immigrant communities. Although I was in Argentina I was able to try tons of different Russian cuisine and hear some Russian Music. This was a great way to get to know two new friends and I found it to be a very impactful part of my year. While I learned a lot about Anna’s life in Buenos Aires I also found a lot in common with both of them. I learned about Zanes' interests in public transport and karate. I also learned about Anna’s interests in writing and fencing. This whole experience in Buenos Aires was very majical and a great change of pace to traveling. I was able to do different activities then I would normally choose and explore the city in a completely new way. This friendship also lasted beyond the city and into the Patagonian mountains.

Jan 10, 2025

My expectations for Mexico City were very high and in every way they were still exceeded. I had never yet visited a city of this scale and I also felt like I had not really seen Mexico. I had been before to Cabo San Lucas which is a beach destination in Mexico however I always knew there was more to see. Mexico City has always intrigued me as it has such a rich history of Aztec and other indigenous populations as well as it being the current cultural hub of Mexico. Looking at the city from an eco tourism point of view it also has a lot to offer. As I learned from locals and prior research Mexico is trying to grow their tourism industry and diversify it from being more then just a beach destination. At this moment on January 10 I was in absolute awe of how much there was to offer and how much there was to learn. Just a quick trip from the city I was able to see real life pyramids and ruins of Ancient civilisations. If I didn't want to go so far I could see the ruins of Tenochtitlan the capital of the Aztec civilization right in the center. I was surrounded by more modern Mexican music and food and experienced it all. Through experiencing this city and especially these pyramids on this day I was inspired by how much visiting a place can teach you.