The 5 Month Check-In

For those subscribed to my email list, thanks for continuing to check in. At the end of this post, I’m going to ask you for a favor: send this to someone you know who desires a change. Maybe they want to take that leap into entrepreneurship. Maybe they just need a break. Either way, think of that person.

So let’s get to what you came for: the August update (and 5-month check-in) from when I left Corporate America (insert dramatic music).

August was a month, let me tell you:

• Launched the Radio Chatter iOS mobile app
• Taught a class at Overland Expo Mountain West
• Ripped my truck apart for major upgrades a week before a two-week road trip to Utah
• Rented a pontoon and floated in a crystal-blue lake for a day in Idaho with friends
• Watched my son head off to second grade (after 14+ hours of straight driving to get home to send him off)

As much as each month feels different, this one really was. As part of guiding with Mountain State Overland (MSO) (we provide off-road/overland guide services out of West Virginia), we also are filming a multi-year trip across the US on the Trans America Trail. This is the 6th year overall and my second year joining the group. We picked up midway through Utah to get to Idaho for this season. You can check out Episode 1 of 3 from last year on YouTube. This trip will be posted in the Fall and Winter and will be included in future blog posts.

Before I get into details about this month, I want to take a detour to share a story on making time for side hustles and hobbies when you have a typical 9–5. This same approach can be used to create more flexibility in your schedule. Maybe you need more remote work, maybe you need time off.

Last year, in order to do this week-long trip, I needed more time off than I was allocated because it was just me (no family). Our normal vacation allotment was already spoken for with family vacations. So I had to get creative:

1. Negotiated vacation – At the beginning of the year, I asked my boss for an extra week. At my company, year 10 you got an extra week, but I was only at year 8. I asked for it to be pulled ahead and was even willing to forego a yearly pay increase to get it. Time was quickly becoming more important than money. HR wouldn’t go for it, but allowed a “handshake” agreement between my boss and I for an extra week that year, with the caveat that if I got a different boss the following year, it wouldn’t carry over. I took the deal.
2. Worked on the road – To stretch it out further, I arranged to work on my trip out to Colorado, doing normal hours Monday–Wednesday and driving in the evenings. I did this with two others and all of us worked off Starlink during the day. That saved me from burning extra vacation days on drive time.
3. Flex time with marketing – I coordinated with our marketing department to attend Overland Expo Mountain West for free if I worked the company booth for a few hours. Since I was already going to be in the area, it was a no-brainer for them to give me a free admission pass as part of their sponsorship. That counted as “flex time” and stretched my vacation further. Tangent to the tangent: I used this same approach to get in free this year to the event but instead, I signed up to be an instructor for a class which was a great experience. It got me in free and I got paid a nominal amount.

Moral of the story: you can’t get what you want without asking. The worst-case scenario is someone, like your boss or HR, says no. The key is building credibility first - being trustworthy, getting things done - so it’s minimal risk for them to say yes. Start small. Ask for a day or two. Or propose a blend of remote work with check-ins. Make it a win-win.

Now, back to the regularly scheduled program.

How my time broke down this month (August 2025):

Personal – Mostly prep for the MSO trip. Installing a recovery winch, a new air compressor, and a new shower system. Considering I was gone two weeks and spent over a week prepping, the 50%+ of time showing up here makes sense.

Radio Chatter – This increase was deliberate. We launched our iOS mobile app this month and are already getting enhancement requests (yes, we’ll add a back button!). I also increased outreach to wholesalers and secured more sponsorships/partnerships for events. Without advertising, Instagram remains our primary channel, and I’ve finally admitted that for a garden to grow, you need to water it. More on this to come in an upcoming post.

Project Exploration – Two parts. First, housekeeping. My coach reframed it for me: if I’m doing the cleaning, it’s money not leaving savings, so technically I’m “making money” and should be counted towards my project exploration (making money) time. My wife is hesitant to agree on this, mostly because I spread the cleaning over several days and can't seem to make the time to get it all done in a day like our housekeeper before. Rumor at the water cooler (our kitchen on her WFH days) is that if I don’t get it together in September, I’m fired.

Second, freelancing and new ideas. I offered to build a simple website for someone in the off-road/overland space to continue to build on my freelance skills in this arena. Although not a branch of Radio Chatter per se, I have some ideas on how to broaden the brand that I am considering. I also brainstormed new ideas during the long drive out west, both for Radio Chatter and my other project ideas. ChatGPT’s voice feature worked OK for this brainstorming, but spotty service lost a lot of my transcripts and I didn't know it until I got home to go back to reflect on the conversations. Per the angry people on the forums, this has been an issue for a while so proceed using this feature with caution. Still, I came up with an exciting new idea and even started developing a prototype at a HipCamp in the middle of nowhere. I’ll revisit it in mid-September.

Looking Ahead – September is mostly about wrapping up planning for Mountain State Overland’s Adventure X Fest, which has ramped up in the last few weeks as the last minute prep rears its head. I also expect to prep with my 7-year-old for teaching a class in October at Overland Expo East about long road trips with kids. As I put it in my class description: "Since this is Paul’s first presentation with a kid, it is likely to mirror that of your next road trip: smooth and engaging or a complete disaster. Join us for the ride; we are confident it will be memorable!" Lastly, Radio Chatter will continue to ramp up. As promised, I’ll dive into that in a future post about doing this decision vs the business acquisition piece.

To wrap this up – I had a challenge at the start of this post. Hopefully something here triggered a thought for a friend. Who do you know that’s looking for change? Forward this email to them. I want to help them on their journey.