I’m not someone who would consider themselves much of a risk taker. I doubt close friends or family would disagree. As a general rule, I have always lived below my means, been a conciencious saver and investor and have tried to do the right thing. However, there have been a few pivotal moments in my life, some where I had a choice (quitting business school to follow a startup to D.C., or moving from D.C. to New York three years later) and others where I did not (leaving my home and all my friends to attend boarding school in another state), that could be considered risky. Not risky in the sense they were silly or unwise, but in the fact that they entailed stepping deep into the unknown. In the situations where I had a choice to make, I agonized over what the right decision might be. I made lists of pros and cons, asked friends and family for their opinions, took walks or long bike rides to clear my head. Ultimately, no doubt aided by all of this information gathering, I trusted my instinct and went with my gut. Once the decision was made, I committed myself wholeheartedly. Without exception, the positive impact to my life from each of these scenarios far exceeded anything I could have imagined. One of them even led to meeting my wife.

I am about to embark on another major life change, one that was not arrived at without a similar level of scrutiny or thought. My wife and I decided to leave New York to become "location independent” and will be moving to Taipei, Taiwan at the beginning of March and on to a new city in a new country at the end of each month. One of the true advantages to building a digital business is that the work can be done from anywhere and I intend to take full advantage of that fact. While living and working in Manhattan has been beneficial as it is the media ad ad tech capital of the world, the truth is that beyond initial meetings, the vast majority of business can be done via email, phone and video conference. Out of the dozen or so clients my business has at any given time, only one or two of them are based in New York, and even those are rarely in Manhattan.

I will have two singular goals while “traveling”. First, to experience what the world has to offer, especially within those cultures that are most foreign to me. Second, to build scalable and sustainable businesses that provide an unusual degree of freedom for the principals and employees. This means continuing to improve the day to day operations of 360ops, my existing company as well as launching new endeavors that solve a specific need. Most importantly, I will be more effective on the road than when I was based in New York. Anything less will be considered a failure.

I don’t know what this adventure will bring. There is risk involved and I certainly have moments of abject fear. For me and for many people, one of the biggest drivers of fear is the unknown. I am able to keep these demons at bay by focusing on all the positive outcomes that might happen. I could connect with like-minded entrepreneurs who I can bounce ideas off of or even work together on projects. We might meet life-long friends in the most unlikely of places. We hope to take advantage of our great fortune and give back through local volunteer opportunities. No matter what happens, my wife and I will share experiences that we will carry with us for the rest of our lives. Something I heard on a podcast in the past few weeks is “what would you do if you knew you could not fail?” This is an interesting way to frame any decision and is especially powerful when we stand on the precipice of the unknown. By keeping all those positive outcomes in the back of my mind, I am reminded that there really is no possibility of failure.