It has been a busy two months since my last update, and the 'pie chart' era of my journey is officially over. Surprisingly, running just one business (Radio Chatter) is much harder to track because I’m wearing so many hats and bouncing between tasks. From using AI to manage 'context switching' to dealing with the inevitable trolls that appear once your marketing starts reaching the masses, I’m learning that building a product isn't for everyone. It turns out that when you build something for someone, you aren't building it for everyone (and I’m having a little too much fun responding to the critics).

I stumbled across an old email from the spring of 2024 where I told a mastermind group my goal was to 'Make my W2 Offroad.' At the time, leaving my job was just a pipe dream. Now, eight months into this journey, I’ve realized that even though I spent months exploring other paths (like business acquisition), I’ve landed exactly where I hoped to be. This month was about a deep dive into my time data, moving from a 'Company of One' mentality into a growth phase for Radio Chatter, and finally wrapping up my time with my career coach now that the clarity I sought has arrived.

Seven months into this journey and I’ve officially hit my version of 'Day 1.' Stolen from Jeff Bezos, this mindset shift means moving away from the broad exploration of the summer and doubling down on Radio Chatter with a structured plan. It has meant saying 'no' to some lucrative partnerships and consulting gigs that didn't align with my vision (which is a scary but liberating thing to do). I’m realizing that being in control of the execution—and how it fits into my family’s daily life—is worth more than just chasing the next big acquisition.

Six months ago, I left the corporate rat race with a plan that was part therapeutic, part side-hustle, and part business acquisition. My coach recently asked me what I’d tell the 'past version' of myself, and the shift in my response surprised us both. I might not be as far along financially as I expected, but I am miles ahead in clarity. From launching the Radio Chatter app to surviving a rigorous due diligence process that didn't end in a deal, I’ve realized that I’m no longer just 'exploring'—I’m building a life that is finally true to who I am.

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.

For a long time, I thought of my first business as just a 'silly card game' (a bit of a defense mechanism against the fear that a simple idea couldn't have true value). But after the high-stakes world of business acquisition fell through, my perspective on risk underwent a massive shift. I realized that without a massive loan draining our cash, the runway we’ve built is much longer than I thought. It turns out that 'silly' idea might actually be the most sustainable path forward, and I'm finally ready to stop calling it a side hustle and start calling it a business.

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.

Four months in and it is officially back to the drawing board (insert crowd gasps). After weeks of due diligence and narrowing it down to one local bank, we just couldn't find a financing plan that didn't involve over-leveraging our personal assets or becoming accidental landlords. It is a frustrating turn, but the data doesn't lie. While the acquisition path hit a snag, it has opened up a massive window for Radio Chatter and some upcoming overlanding expeditions. Here is how the 'failed' deal is actually shaping the next phase of this transition.

Three months in and the data is starting to tell a story (one that involves a lot more due diligence than I originally anticipated). While June felt different from May, my time allocation stayed surprisingly consistent, even as we moved into the heavy lifting of financial and operational deep dives for a potential acquisition. Between getting Apple’s approval for the Radio Chatter app and navigating the 'crazy' variables of bank underwriting, I am learning that this journey is less about a single leap and more about managing a dozen moving parts at once.

I’m 60 days into this journey, and the biggest surprise isn't how I’m spending my time, but how my energy is flowing. I had a plan (literally drawn out on paper) for how to balance personal projects and business acquisition, but the reality has looked much different. Between developing the Radio Chatter app and navigating the 'nerve-racking' possibility of my time no longer being my own if an acquisition happens, I’m learning to stop asking if I'm drifting and start asking if I'm building momentum. It turns out that quitting the job was just step one in designing a life that actually fits.