How to be Happy: Lessons from Chris Guillebeau

Last summer, I went to Powell’s Bookstore in Portland to pick up a present for a friend. I got distracted by the best selling books on the ground floor of the store. One book that caught my eye was the New York Times best selling book “The $100 Startup” by Chris Guillebeau. In a rush and on a budget, I passed on the book.


A few weeks later, my colleagues talked about their experience at the World Domination Summit…the what? I knew nothing about this event. That name stayed top of mind. After a quick google search, I learned this event brings together hundreds of thought leaders and millennials determined to make the world a better place. Chris Guillebeau created this event.


Last month when I researched networking events in town, I stumbled upon the Oregon Entrepreneurs Network which brings together like minded entrepreneurs. Their next event featured Chris Guillebeau and his new book, “The Happiness of Pursuit.” Without hesitation, I signed up for the event.


When I walked into the event, Chris was lounging by the entrance. Casual, calm and composed, he mingled with the attendees. I felt at-ease in his presence. While he delivered his keynote, I questioned how someone so accomplished and driven exuded such calmness? Chris has yet to write a book answering my question. Chris Guillebeau shared 3 stories to inspire us to find happiness in our pursuits:




Chris shared the story of a woman who pursued a career in journalism. She earned a masters degree in journalism and became recognized in her industry over the years. She decided to take her side passion for photography and teach others through online courses. She made a photography 101 course to share with her friends on social media. Her friends enjoyed the course so much, she decided to make another photography course.


Soon enough, she built a collection of courses and her passion turned into a business with many followers buying her online photography courses. Within a year, she quit her job as a journalist and now produces online photography courses on a full-time basis.




Chris also shared a story about a man who thought he had a crazy idea. He wanted to walk across America. To fulfil his dream, he started walking west from Portland, Maine. The man recently broke up with his girlfriend and found himself frustrated when it rained during his walk across America. Why did he keep walking? This was his dream and he would have felt unfulfilled if he didn’t do it. In order to complete his adventure, all he had to do to was put one foot in front of the other. Seven months later, he arrived in San Francisco California and completed his walk across America.




One of the last stories Chris shared was about a woman who worked at General Motors for most of her career. Her and her colleagues worked their way up the corporate ladder. At the peak of the recession a few years ago, they called her department into an office to terminate their employment. They called this day Black Friday. Everyone started to panic as they rushed to edit their resumes and search for their next job opportunity.


The woman decided to take another route and follow her heart. She bought an RV and fulfilled her dream to travel the great U.S. Route 66. She traveled the country and interviewed many Americans along the way. She eventually realized how discontent she was at General Motors. This was the first time in many years she said “yes” to herself.


The Happiness of Pursuit


Ten and half years ago, Chris Guillebeau set a goal to visit every country in the world. In 2014, he completed his goal and published a book called the The Happiness of Pursuit. Chris aligns his talents as a writer and an entrepreneur to spread happiness with other mission driven dreamers. He values learning, experiences, and teaching others how to follow their dreams and change the world. He does not want to climb the corporate ladder, nor does he care about owning expensive possessions (I do, however, admire his beautiful scarf as displayed in our picture together). Chris is the essence of the new, millennial American dream.


How does Chris inspire others to be so great? He says the strongest skills he cultivated in last 17 years is confidence and self awareness. As you follow your dream, figure out what is holding you back. After you identify this, align your values and mission to conquer your dream with confidence and self awareness.