My Adventures to Date

My Backstory

I spent one year riding a bicycle through Africa back in 2013 and went on to take many more journeys on foot including some very long walks in Ireland and America. I try to use these trips to share meaningful stories  and often speak about fear and meaning in life. But let me tell you why I began taking these trips…

Derek Cullen Indoors

You’ve got to go back more than 15 years to really understand how a spiral of self-destruction – which ended in me walking out of my job one Monday morning – began and led to my now unconventional life path. My mother died in my early twenties and two years later, my father died of cancer. I was working in a bank and studying for stockbroking and marketing diplomas at night. After their passing, I felt very resentful about life and having to constantly deal with bad stuff. There wasn’t time to grieve the loss of my mother and then my father was gone. I lost interest in my career, and this led me down a path of self-destruction. I blamed life, everyone and everything around me and by the time I hit rock bottom – a dark, lonely and bleak place – I felt mentally and physically beaten. But this was also one of the first times that I had a kind word for myself.

One Monday morning at my workplace in Dublin, I was feeling so ‘tired of everything’ that I walked outside and stood next to River Liffey. I put my hands on the wall and stared down the river as tears ran down my cheeks. It was in that moment I heard a compassionate voice in my head which began asking some questions: “What is wrong with you? Why are doing this to yourself? It was you that made all those decisions, right? Yes, some bad things have happened but that’s life, Derek. Now what are you going to do about it?”

Derek Cullen

I quite my job that morning and walked home. I also made a pact with myself that by the time I walked home, I would have a plan to go some place away from distractions and try to figure out how to turn things around. But I also knew some sort of challenge was necessary, and I would need to “do something hard” in order to make some meaningful changes. I had watched a tv series in which Ewan McGregor and Charley Boorman travelled through Africa on motorbikes and thought to myself ‘That looked hard and interesting, maybe i could do that’ but I didn’t have a full license at the time and so in spite of having no past experience with such matters, I decided that I should travel through Africa on a bicycle instead.

The first few weeks were terrifying. I cried a lot, and I was lonely and, every day, I thought about quitting. But as the weeks and months went by, I began to see the world and my life in a very different way. I didn’t realise this at the time but the physical and mental nature of that journey was forcing me to undergo a major transformation. Another way to see this is that what happened on that trip wasn’t always what I wanted but often what I needed to experience in order to change the way I was thinking and feeling. In spite of the bad days and all the fear and anxiety, I just kept getting up every morning and going a little bit further and after doing this over and over for one year, I arrived at the Great Pyramids in Egypt. T.S Elliot once said “the man who gets on the train and reads a newspaper is not the same man that gets off the train” and with this in mind, I believe there was a very different person on that bicycle by the time I had cycled from Cape Town to Cairo.

I did take many more long-distance adventures on foot but in 2025, I decided to move home to Ireland in order to settle down. I sometimes organize adventure tours to exciting destinations and plan to resume public speaking in 2027.