15 Lessons from 15 Years of Blogging

Posted: 4/2/23 | April 2nd, 2023 Today is a big day. It marks fifteen years running this website. I posted my first blog entry in early April 2008, after spending over a month bugging friends I met in Vietnam for help with coding. Back then, in the days before WordPress, you had to hand-code everything, and I spent a lot of time figuring out how to move images around, design graphics, create links, and format the site. I started this blog as a way to get freelance writing gigs so I could afford to keep traveling. I just wanted to put off going corporate for as long as possible. I never thought I’d have a career in travel, but I guess after fifteen years doing so, this counts as a career. I’ve created books, courses, and tours, spoken at conferences, and am quoted in the media. So, I guess I’m kind of an expert in travel? That feels weird to say. Being a public figure is surreal to me, because, in so many ways, I’m still just a guy who wants to keep traveling. There’s so much of the world I want to see. Sure, I love the business of running a website. It’s a mental challenge I find fascinating. But, to me, it’s still just a way to satisfy my travel addiction and avoid having to work in an office (though, now that I have a team, it’s a more complicated way to avoid the office!). In the last fifteen years, I’ve seen the internet and travel content creation change dramatically. Digital nomads are no longer weird, and making money online isn’t odd. “You quit your job? Are you crazy?” isn’t something a lot of people say these days. There’s a lot of positive encouragement for this thing that was once considered so crazy that there must have been something wrong with you if you wanted to do it. As people are prone to do during milestones like this, I wanted to share some lessons I’ve learned as a grizzled old internet person (because people refer to me as “an OG digital creator” as if I’m 90!). 1. Most people succeed because of luck Someone’s video goes viral, and suddenly their bakery in Australia has more orders than they know what to do with. Some people get that lucky interview that opens the door to fame. Some people just meet that one right person at a conference. Of course, skill is needed to maintain that success, but a lot of times, luck and timing play a bigger role than people would like to admit. That’s not something you can control. Would I be where I am if I hadn’t started early with a focus on SEO? Probably not. I just happened to start at the right time. That’s not something I controlled. I got lucky. 2. Throw a lot of spaghetti against the wall I’ve had a lot of failed ideas — from apps to T-shirts to a conference to a hostel. Some of those ventures stuck for a while; others were immediate failures. Some came back years later (we do tours again!). I’m constantly trying new things and then discarding what doesn’t work. But all those things that didn’t work helped us do other things that did work. 3. No one reads blogs for personal updates anymore Back in the day, blogs were where you told stories and gave life updates. People had RSS feeds and left comments. Now, that happens mostly via email and social media. Yeah, some people will click over to your stories, and blogs are still useful for sharing service-based content, but the way people used to consume personal updates is dead. It probably won’t come back either. The kind of engagement blog comments used to generate is now found on social media. 4. Therefore, you have to be on social media You can’t be against social media. You have to be on it. I don’t believe you can run a personality-based website without using social media nowadays. You don’t need to be on every platform — join those that make you most comfortable — but you have to be on some. As I said, all social engagement happens there now. It’s where you connect and maintain a relationship with your readers. Your blog is just where you send them when they have questions. 5. You have to learn to make some video content I hate video. I love words. But video is the wave of the future, and you have to learn to produce it. I’ve already started doing more video and plan to do even more. If your blog has a face (you), that face has to be making video. It’s how young people consume media, and, if you want your message heard by them, you have to do it. 6. It’s important to always reinvent yourself Change is the only constant in life — and the internet changes at lightning speed. If you don’t constantly reinvent yourself, you are going to get left behind really fast. I know tons of online creators who never moved off their dying social media platform or changed their business model and is puttering along, grinding it out but never really growing. They didn’t adopt new strategies or get on new platforms. They didn’t follow their audience. And, as a result, while they make a living, it’s just a stressful grind of diminishing returns. You have to be willing to chang

15 Lessons from 15 Years of Blogging