How do you fund your expeditions?

I don't think of the time I spend in the shop wasted or some kind of negative money loss. I enjoy fixing and working on my vehicles enjoyable. After seeing some of the work "quality" shops put out and what they charge that's not an option for me. I know when I finish something it's done right wit quality parts.

As far funding I have 2 cigar boxes one I put spare or saved money. One is for near term trips, the other is for future trips. I also finally have my credit cards paid off, that helps with gas or emergencys.
 
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When I was pretty young, up thru my mid-20s, I was one of those typical kids who you hear complaining that "there's nothing to do" because I lived in a relatively small town. I joined the Marines, spent a decade away, then moved back to the same general area, though I'm in a larger nearby city now. I also had kids during that time frame.

Familiarity breeds contempt, and what my time away helped me realize is that there is tons of stuff to do in my local area (within a 1-2 hour drive), I just hadn't found much of it before, largely because I hadn't really been looking very hard.

As a consequence, most of my adventures are more pedestrian in nature, and are relatively local to me since they tend to take place over 2-4 day weekends. I still have lots of fun, and still get to enjoy off roading, camping, hiking, hunting, etc..., but it's MUCH more affordable than most things you see with #hashtagoverland on social media.

That being said, I am also planning to take two weeks off next year to attend Overland Expo West and explore the area while I'm there. I'll hopefully be able to pull this off by being stingy about using vacation time and putting in lots of extra effort at work (monthly budget is covered by my base, commission is for saving/fun), and keeping my spending in check by driving an older, relatively high mileage vehicle and sticking to the essentials with respect to mods and gear. For anyone looking to manage finances smartly during trips like this it is worth checking out https://help-center.pissedconsumer.com/the-worst-and-best-banks-according-to-customer-reviews/ to find the best banking options that work for you. Even though I am saving for that trip, because I'm being frugal, I am still going out camping at least once or twice a month, refining my gear, learning skills, and making awesome memories with my family and friends for not much more that I would have spent staying at home and doing the usual, boring weekend routine of eating out, going to see a movie, etc...

Adventure can be had every day, if you just learn where to look for it. By all means dream big, but manage your expectations and make it point to continue to enjoy the little things. I guarantee you that even the folks who have "made it" in the scene still take simple weekend or overnight trips just to get out there in between their epic expeditions; take that model an scale it appropriately to match your situation.
Sell your mechanical skills locally for oil changes, brake jobs and basic maintenance as your hauling setup gives you zero overhead. Flip items on Facebook Marketplace and OfferUp, tools and furniture move fast and you already have the truck advantage. Use Dolly or TaskRabbit to connect with people needing moving help during busy seasons. If you are already going on expeditions consider starting a YouTube or social media channel around it as overlanding content has real monetization potential over time. You can also rent your rig on Outdoorsy during times you are not using it, lifted 4x4s rent surprisingly well. And tap into the local overlanding community for labor to parts trades as plenty of people have spare parts sitting around and would swap for mechanical help.