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).

When it comes to a career pivot, not all moves are created equal. I’ve found that the success of your transition usually comes down to two variables: your Role and your Industry. If you are trying to change both at once, you’re playing the game on 'hard mode.' Whether you are moving from project management to software development or jumping into a new field entirely, there is a specific 'backdoor' strategy involving team-level networking that can help you skip the HR black hole and get your foot in the door.

When you make a big life change, it sparks conversations with people who are wrestling with the same questions you once were. I recently caught up with an old friend who asked the question that stops most people in their tracks: 'Can I even do this?' The truth is that mini-retirements aren't a one-size-fits-all solution. Whether you need a short sabbatical to reset or a long-term bridge to entrepreneurship, the path only becomes clear once you define your 'why.' Here is the framework I use to determine the duration, the financial impact, and the level of risk for a season of intentional exploration.

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.

I remember telling my wife years ago that I don’t ever expect to just 'stop' working (I’m too much of a serial hobbyist for that). If you assume you'll always find ways to make some money, your path to retirement looks a lot different than the traditional 9-to-5 grind. This post is about why so many people in the FIRE community actually over-save, and how a mini-retirement can act as a bridge to a life that’s more about intentional experimentation and less about the rat race.

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.

One night at my son’s flag football game, I watched him walk to center field for the coin toss. He came back puzzled that his coach was happy they 'lost' the toss, but it reminded me of exactly where I was this summer. I was staring at a 50/50 chance between two life paths: the freedom to build and experiment on my own momentum, or the structured ownership of an existing business (with all the cash flow and tethered schedules that come with it). When the acquisition financing fell through, the coin finally landed, and the feeling that followed wasn't what I expected.

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.

It was 10:00 AM on a Monday, and I was running errands—exchanging my son’s clothes and grabbing Costco cold brew—all before a 1:00 PM client meeting. As I drove, I couldn’t help but wonder (with a genuine sense of bewilderment) how we ever managed this when we both had a 9-to-5. We’ve always split responsibilities 50/50, but the mental load of 'convenience' actually carries a heavy price. I’m realizing that the flexibility of this journey isn't just about business; it’s about finally having the bandwidth to handle the 'family stuff' that doesn't wait for the weekend.

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.

There is a lot of buzz out there about buying a business (thanks to the social media influencers who make it look like a weekend hobby), but I’m here to tell you it isn't all it’s cracked up to be. From the grueling timelines and the 'cash drain' of the search phase to the legal minefields of asset vs. stock sales, the acquisition journey is a mountain of work before you even get the keys. If you aren't prepared to build a team of experts or handle the anxiety of a deal falling through, you might want to stick to the W2 life.

“It must be nice to be able to afford to quit your job.” I’ve heard this more than once (and no, I didn’t win the lottery or flip a double middle finger to my boss on the way out). The truth is that this transition was a calculated move rooted in decades of discipline and a heavy dose of the FIRE movement. But even with a solid foundation, being in the 'search phase' means watching your cash slowly drain while you hunt for the right deal. Here is how we prepared for this leap and the scenario planning I’m doing now to make sure the math actually stays mathing.

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.

One of the biggest reasons I left corporate America was to escape bureaucracy and regain my creative freedom, so the last thing I wanted was another boss (even if that boss is a franchisor). Following the 'Venmo Challenge'—looking at where we already spend the most money—I set my sights on a local business I’ve respected for years. I sent the letter, braced for the 'no,' and actually got a response. It wasn't a deal, but it was a start. Here is what I learned from my first official strikeout in the world of business acquisition.

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.

I recently saw a post claiming that you shouldn’t buy a business if you haven’t built one from scratch (a pointed question about where your 'point of reference' comes from). As someone leaving corporate to do exactly that, it got me thinking. From my time as a process improvement engineer in healthcare to stepping into subject-matter-blind roles, I’ve learned that corporate life is a fertile training ground if you approach it with the right mindset. I might not be a 'starter' who loves a blank canvas, but I am a 'builder'—and there is a massive difference between the two.