This weekend I found myself in the city of Lecce, where I met an extraordinary American—also our BnB host—that achieved his freedom in Italy, from working a 9 to 5.


Freedom is a key part of the American Dream. Originally, it meant being able to have economic mobility in a melting pot of opportunities. As an aspiring entrepreneur, however, it always meant working for myself and being able to invest in my family.


This combines the two concepts:

  • Having economic mobility, or the ease of growing one’s financial prosperity
  • The freedom that comes from working for yourself


If you really want to add the icing on the cake? Throw in a burning passion for whatever you’re pursuing as well. These three things in mind and you’ll have a life recipe that everyone will want a piece of.


A master of this recipe, and also New York Times featured sous-chef, as well as painter and architect, John Duggan, gave me the pleasure of speaking with him this week.


John is a Californian that got his architectural degree from Cal Poly San Luis Obispo in 1988. He moved here with his wife over two decades ago—whom he had met in Florence his last years of college—and proceeded to live a life that felt like it was almost out of a storybook.


The result has been a career of lifelong accomplishments and more importantly, an environment of creative freedom as a well-paid master of his craft, without the confines of a manager to answer to.


“A lot of it has been chance… Sticking to what I was good at… I started moonlighting at an architect’s office, 8 to 5 there and then from 5 to 8, 9, or 10 at night, I would start working for myself… At the end, I would start making more after work then at work and that kind of told me I was onto something.”


From the beginning of his career, even working at that studio prior to his degree, he knew he wanted something better.


He didn’t want to face the tedious initial years of an architectural career, stilting his creative capabilities, or worse, working for little to no pay on a glorified project.


Instead of freezing up as a deer in headlights, he took the initiative to perfect his craft. He did water color renderings for countless hours after he got off work. He saw the work of his competitors and knew he had the potential to be better than any of them.


And it paid off.


By the time, he graduated and landed a job at another architectural studio, he had the experience and fire to quit after one day of torture.


I consider this to be an entrepreneurial drive, as he took a risk that fateful day, that led him to have a career unlike most of his peers today. He could have failed or worse, he could have convinced himself he was going to fail before he even started.


As most of us realize but fail to do, sometimes just taking that first step despite all fear is worthwhile. John could have feared the life of a starving artist, but because he didn’t and diligently worked to refine his craft, he is living the rare life of a thriving artist.


Let this be a point that resonates. It is never too late to pursue something you’re passionate about. If you are driven enough to fight for what you believe in as John did, the results are inevitable.


This isn’t to say that success will come easy, as others often only see the tip of the iceberg. John worked after hours for years before he had the skill to break through normal limitations.


It takes time; it takes patience.


Being an independent artist, he had to work from home. This came with an enormous responsibility and self-discipline that most would find difficult.


You also run into issues as you would if you were an employee, except the only one to pass the blame onto, is the mirror.


“I see a problem… maybe it’s our design background or something… and there’s gotta be a solution here you know? For artwork… the speed is essential, you have to get in and out of projects or you don’t get better and you get bogged down… you get very confident and with years of experience you can see what’s not quite working.”


John attributed to much of his success to the adept level of problem solving that came with his creative discipline. In art, he always looked at how to get past obstacles, whether it be a new medium, or tight deadline.


He applied the same mentality to his life.


If his problem was being confined to spending the rest of his life working in an architectural studio, he saw the solution of becoming an independent artist. If he realized programming was replacing the water color renderings he grew to love, he switched to murals.


He has even taught in a cooking school as a translator. He is the Jack of all Trades, or rather, the John of all Trades.


He is a reminder that even the most daunting obstacles in life are able to be overcome. As an entrepreneur, unexpected things are inevitable. Whether it be unexpected competition or barriers to entry, as John says, there’s always a solution.


And I really needed to hear that.


Despite being open to the idea of breaking through barriers as John was and still is. Life can throw relentless curve balls that leave even the umpire disoriented. Ambition as with anything in life, isn’t perfect.


There are plateaus that I struggle with every day and I had to ask John how he overcame this as an up-and-coming independent artist.


“You get to be efficient. I’m a big fan of deadlines. The worst clients I’ve had say, ‘just do something in your free time’ Well I don’t paint in my free time. It’s nice when clients need this job and they need it yesterday, and those are the best… You find solutions to a problem because that’s the only way you can do it on time.”


John reinforces the idea that we need to have clear and concise goals. It is in the murkiness of vague goals that people forget what they’re working towards. When he sets out to finish a project he uses the technical side of architecture and meshes it with painting.


This allows for a very clear vision of what you want to accomplish.


Clear goals that have a deadline to them will be your motivational best friend.


“Follow your inner voice”


John is a believer in doing what you love. If you do what you love you’ll have the energy and ambition for it.


I hope his creative discipline helps you understand that there’s always a solution if you are willing to make the structured effort to break through life’s limitations.


Check out his work at:

Want a fantastic experience in Lecce? Here’s his BnB!