Life is hard for everyone, and we all face the consequences of our choices in one way or another. In our case, much of our struggle has come from intentionally choosing discomfort over convenience for about a decade. Not having running water or heat for years at a time is tough. Living in multiple construction zones encompassed by constant dust is hard. Doing concrete work in over 100 degree heat and coming home to no actual shower sucks. Having over a million dollars in debt is scary when you don’t come from money and don’t have the built-in generational understanding that this is how wealth is built through real estate. Waiting until your mid-to-late 30s to have kids is a gamble and is tough on your parents who are eager to become grandparents.
These are all choices that Kelsey and I make in our shared pursuit of freedom and our version of living it right. Do we know we’ll get the results we want at the end of it? Heck no but we’re taking the information we have now and doing the best we can with it.
Choices are about optimizing one thing and sacrificing another. We are all making educated guesses at best. A favorite book of mine about making life’s hardest decisions is Annie Duke’s Thinking in Bets: Making Smarter Decisions When You Don't Have All The Facts. It’s a game-changer for decision making under a cloud of uncertainty and extracts most of the genius of understanding the game of poker. I called poker my job for 4 years when I was playing full-time and it structurally altered how I think about everything. Thinking in bets allow us to really figure out what matters most to us by essentially betting on it. What are you willing to sacrifice to gain what you want?
10 years ago I was worth 1,000,000x less than I am now but I was living a life of luxury compared to how I live today. I had no concept of delayed gratification and took whatever earnings I made in my late teens and early twenties then dumped it straight into the hedonic slot machine of America. Out of it came a fancy 40th Anniversary edition 370z sports car and a cozy 2-bedroom apartment in the hottest neighborhood in Tampa.
Nowadays you could argue we are delaying gratification too much. However, the weird thing is we’re both still very happy living like broke college kids regardless of our net worth on paper. This is mostly due to seeing the results of a choice we made 7 years ago to stop doing YouTube full-time, sell the boat and buy property of our own. We were both 27 years old at the time and it was a pre-Covid world. We had no clue property values would explode the following few years because the U.S. dollar was devalued at a gangbusters clip. Now we look back fondly at the very impulsive decision to sell our fully refit 35' Hallberg-Rassy and buy our downsized, much cheaper 22' Falmouth Cutter and invest the difference in value-add real estate in 2019.
Did we miss out on seeing more of the world in our 20s? Absolutely. Did we quit YouTube at 95,000+ subscribers and miss out on hitting the milestone of 100k? You betcha. This was all a trade we were willing to make at the time and are happy with the results.
That impulse decision at 27 years old was rooted in wanting to pursue financial freedom and wealth instead of continuing to chase status and location independence like we were on YouTube. Nowadays I feel the pull to get back on the tube and get back to growing our community. Some of the connections we made while sharing our lives online has formed the basis of beautiful relationships and mentorship that forever changed our trajectory in life. Going back to YouTube full-time would be trading our currently coveted privacy for a community that gets us better than we do. It is also taking time away from our growing real estate business which will ultimately suffer the consequences of this decision. Every choice is a trade.
I do not have the answers. I never will. I only have the bets I’m willing to make now and my best guess at the potential results in the future. I like to think in the form of a best case, worst case and most likely case. From there I can try to mitigate the downsides as best I can. Eventually abandoning comfort will manifest itself in a different form than physically abandoning comfort like we currently are and more mentally abandoning it. An example I mentioned earlier would be giving up some privacy in exchange for status and community on YouTube again. Ultimately delaying gratification and trading short-term discomfort for long-term freedom is a trade I’ll take everyday of the week - for now. Don’t take my word for it, take Naval’s: