How I got to where I am.
ASTORIA, NYC- Here it is: blog post #3,650. That’s a blog post a day for ten years. However, I can’t lay claim that title. The first post on this blog was published 18 years ago on April Fool’s Day, 2004, and is something that has been with me ever since.
I received this comment a few days ago from Richard and it shook me up a little:
I’ve been following you and your website(on and off) since I was 15 years old. I’m 34 now! I can’t for the life of me see how you’ve done nothing. Sure things slowed down because of covid but if you make as much as you say you make without busting yourself into the grave I think that’s a huge win. Who wouldn’t be proud of that?
Because of you and other sources I’m following a similar path and I thank you for giving me the awareness I needed.
For half of his life, Richard has been following this blog. That not only makes me feel incredibly grateful but made me realize that I’ve been doing this for a long time … and I began thinking about where all of this came from.
This blog began with a dream of being able to travel the world and writing about it. When I became aware of HoboTraveler and Andy Graham the dream shifted to being able to travel the world writing about it AND making money. Andy was the original digital nomad. He was the pioneer who first realized that blogging could make him enough money to travel. He was also the first one to share how he did it so that others could follow. Without that influence I’m not sure if I would have done this, and life would have looked very differently:
If I didn’t blog full time I wouldn’t have been able to travel like I did in the early days.
If I didn’t travel full time writing about it I wouldn’t have gotten my first book deal.
If I didn’t get my first book deal I wouldn’t have been invited to write for the South China Morning Post.
If I didn’t write for the SCMP I wouldn’t have gotten invited to write for Reuters.
If not for Reuters I wouldn’t have spent three years at Forbes.
If no Forbes then there would have been no bylines at The Guardian, Bloomsberg, The Diplomat; no films with the BBC, no working with Oscar-winning filmmakers, and probably no Real Life Cinema … what I’m doing now.
Fate is like a colossal set of dominos with an almost infinite number of pathways. One domino strikes another and leads you along the path you call your life.
How did I find HoboTraveler? A secretly half-deaf opera singer that I met in the North Country of NY State one day forwarded me one of his newsletters. It was that simple. If I didn’t start talking to her one day as she sat at the computer next to mine a college library my domino fall probably would have gone in a very different direction.
While I was already traveling at that point: I logged two journeys to South America, one to Europe, one to Japan, moved around the US, and was preparing to travel through the backwoods of Canada — seriously, that’s why I was in the North Country — I had not yet conceptualized how I was going to get to where I wanted to be. I wasn’t lost but I was still finding my way. Then I began getting these newsletters from this guy who was making enough money to travel the world by writing crazy shit. I wanted to do that too. So I got my first laptop — a giant brick of a Dell — and started swinging.
This was 2005, when blogging had just become a thing and the infrastructure had just appeared to support it. The internet was different then. There was no social media. No Facebook. No Twitter. No smartphones. No apps. There was only mainstream news and blogs. And a critical mass of people gravitated towards blogs … and that ecosystem quickly transformed from online diaries to a form of news in and of itself.
My first years of blogging full time were nothing less than exhilarating. I suddenly had a mission which gave a sense of purpose to my travels. Ever single day I would wake up and have something to do. I thought I was becoming a little disillusioned with travel at that time. I’d go way out there to where I wanted to be, feel that initial boost of excitement and then it would die off … I thought there was something wrong with me. The reality was that I was just bored. I wasn’t really doing anything other than traveling. I just didn’t have the impetus to push things deeper, to peer under the surface. It takes a little gumption to talk to strangers, to ask for interviews, to request permission to go to places that ordinary tourists are not allowed. Blogging gave me this impetus … it gave me a reason to have courage.
Travel blogging also wasn’t very easy back then — WIFI was sometimes difficult to find, worked horribly, and internet cafes became our offices — but something about this gave it appeal, as it wasn’t something that everyone was willing to do. You really had to earn each blog post back then …
And each blog post was a way to quantify and commodify experiences and knowledge. It was a way to accumulate what I did and learned and somehow make it seem tangible. It was a collection — each post gave me a feeling of accomplishment — and I’ve always been taken by the collector’s mentality, whether it be counting countries, sex partners, tattoos, coins, sports cards … The steady accumulation of numbers has always excited me, and watching the ticker of blog posts / traffic / earnings get higher and higher fed that fix better than almost anything else.
I was making pennies per day at that time — literally — but I was still making pennies traveling and writing. I knew that if I kept at it those pennies would turn into dollars and those dollars would turn into hundreds and those hundreds into thousands. It was a bit of a pipe dream, but one that I seem to have pulled off — I’ve probably made around $250,000 from this blog.
I’ve never really been adverse to molehill-to-mountain types of strategies (just read my recent post on dividend investing). Collector’s mentality, I suppose.
This was the first version of VagabondJourney.com in 2007. I remember being so proud of this homepage … but today I just have to laugh. I was young, and it showed, and this is the long-term value. VagabondJourney.com was my kid project — my kid project that I’m still working on today.
A couple of years later we were a little more sophisticated, pushing for a news-style information site. I actually kind of like the web 1.0 look. Websites don’t look like this anymore … probably for good reason.
By 2012, I was getting the hang of it. We were bringing in 7,000 unique visitors then and had a design that looked like a real site.
In 2016, we were back to being a blog and I was writing articles that could have been publishable in mainstream news outlets. This was around the time that I transitioned to being a journalist and began leaving this blog by the wayside a little.
In 2019, we landed on a design that we just kept. It’s simple, doesn’t tell its age, and is all about the words on the page. I was working full time as a journalist and was only blogging personal stories, thoughts, and anecdotes … a model of pure blogging like I do today.
When I look back on my history of blogging I kind of see it as the tendons and ligaments that hold everything else together. This was where I told the background story of what I was doing and thinking about, which is ultimately the real value of journaling: it tells the story of how you got to where you are that you’re liable to forget.
When I go back and read some of those old posts now I feel like a voyeur looking into someone else’s life … which is proverbially accurate. People change over time, and having these demarcators of what you were — these wayposts leading back to your origins — allows you to preserve the most valuable possession that anyone can have: memories.
It’s funny to think that all of this started on that day when I turned to stranger and had what seemed to be a completely innocuous conversation. Listen to your visitors, as you never know where it will lead.