Oct 21
37m 13s
In 2023, we stretched to upgrade into a larger home we didn't need. Three years later, I sat down with my wife to talk through the whole experience and answer the question everyone keeps asking us: was it worth it?
The short version is that we found a unicorn. A home on a large lot at a relatively low price point, fully remodeled and landscaped, with a view of the Golden Gate Bridge. In 24 years of hunting for property in San Francisco, I'd never seen anything like it at that price. So we had to buy it, even though it meant selling a chunk of stocks and bonds and blowing up our passive income.
In this episode, my wife and I get honest about both sides. The joy of watching our kids run around an enclosed front yard with zero fear of traffic. The peace of finally being off the property ladder. And the part that still stings: the $1 million to $1.5 million in stock gains we likely gave up by turning investments into a house we live in every single day.
If you're sitting on big gains and tempted to upgrade into more home than you need, this one is for you.
Read the full written breakdown, including our three-year maintenance costs and my checklist for anyone planning to upgrade into a home they don't need: Whether Upgrading To A Home You Don't Need Is Worth It.
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