Blog Archives

A Two-Year Retrospective

A bit more than two years ago I sold all my stuff, rented my house, said my goodbyes and lit out for parts unknown. I was inspired to take a look back by a couple of events. The first is that a new friend, as he’s learned about what I’ve been doing he’s encouraged me to start writing again. The second was Dan Hough’s six-month retrospective of living by his own rules. Some good lessons in that piece.

So what is it that I’ve done over the past couple of years? In short I’ve lived on 3 continents, including Seoul, Mexico City, London, (and now NYC). Worked less than 1500 hours for pay, about the same for free, including advancing the I Am The Cavalry movement. Met dozens of great new people. Improved my career by taking only jobs that made me better. Read, researched, analyzed and honed new ideas and old. Collapsed a house of possessions I unquestioningly kept around me into what can fit in a couple of big backpacks…and even most of that is disposable. I’ve lived as my own master and couldn’t be happier about how it’s all come out.

But I recognize that I’m far from the norm. I’m the outlier. I work in a field that allows this kind of motility, pays well enough, and has enough offers for work that I could support myself financially. That isn’t true for everyone.

It is said that luck is when preparation meets opportunity. To take advantage of this kind of luck you must be both available and willing when the opportunity arises. When you are available you quickly find that the opportunities are everywhere.

I have a personality that lends itself to optimizing for opportunities that come up. In other words, I don’t set goals to achieve or things to attain I set ideals and behaviors to guide me.

To prepare myself I set a 5-year plan to learn skills and build my network. After a realization that I was only truly happy when I felt the freedom and self-determination of travel, I set about figuring out how to do that. The skills I had recently begun to develop were conducive to taking short-term work and working from anywhere. To get the kind of work I needed I’d need to build my skills and improve my connections to job opportunities. So I set about achieving that.

I took a new job, became more social and began publishing a blog. I sought, found and won a new job as a traveling consultant. I started going to security conferences, offering to speak at trade shows on behalf of my new company and organized get togethers of like minded folks. I wrote up my thoughts an published them, engaged with others and cultured dialogs on topics I was interested in. This boosted my skills, extended my reach, raised my credibility in the community and as a bonus it let me travel on others’ dime.

When the opportunity arose I took a new role in the same company on the business side. I was given the chance to work alongside my boss, helping to run and develop the consulting practice. This taught me valuable lessons that I wouldn’t have to figure out the hard way when out on my own. It was like a mentorship or apprenticeship program, learning and developing at full speed but with backup support and a safety net.

Finally it was time to go but a threshold of fear seemed to hold me back. One day I simply looked at the worst case scenario. If I failed and ran out of all my saved money I could borrow enough to get home, live with friends and family, get a new job in the same industry…probably making more than when I left and with a lot more wisdom. My worst case scenario was better than the life I was living!

So the decision was made and a date was set. I closed out projects, left my role better than is found it, trained my replacement at work.

And that gets me back to where we started. I sold all my stuff, rented my house, said my goodbyes and lit out for parts unknown. I left the known behind for the exciting. And I haven’t looked back. Except for this post.