It is hard to believe it has been six months since I left Corporate America (and yes, I’ve managed to keep my 'housekeeping' job at home for at least one more month). September felt symbolic because it officially connected where I’ve been with where I’m going. While I’m not exactly where I expected to be when I started this journey, I’ve found a rhythm that works: going full steam on Radio Chatter while supplementing it with freelance projects in the overlanding space. It turns out that piecing together a life of intentional experimentation might just be enough to make this whole experiment work.

August was a month (insert dramatic music). Between launching the Radio Chatter iOS app and ripping my truck apart for major upgrades just days before a two-week trip to Utah, the pace hasn't slowed down just because the acquisition deal did. From teaching at Overland Expo to watching my son head off to second grade after a 14-hour straight drive home, I’m realizing that this journey is less about finding one 'perfect' business and more about the excitement of building my own. Here is the data on month five and why the 'drawing board' is actually a pretty fun place to be.

When I told people I was leaving my engineering leadership job, the most common reaction was that it sounded a lot like 'that overlanding thing' I do. At first, the connection wasn't obvious, but the more I thought about it, the more it clicked. Overlanding is about self-sufficient travel where the journey is the destination (complete with the risks and gear to survive it). My career transition is no different—it is an expedition driven by curiosity, guided by values, and sustained by preparation.