Dear Dave: My husband and I are completely debt-free. He makes about $100,000 a year with great benefits, plus we have $80,000 in savings. The problem is he hates his job. He wants to try something else, but he's not sure where his passion lies. When is it OK to pull the plug?
In a situation like this, I think you need to combine the desire to do something you love with enough wisdom that won't leave your family in jeopardy. In other words, let's run to something, not from something.
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I'd suggest that he grab some of Dan Miller's books, like 48 Days to the Work You Love and No More Mondays, and begin a process of reading, studying, and thinking about what he really loves to do. Then, figure out a way to monetize that idea. You're more creative and passionate when you love what you're doing, and with the right plan in place you'll make more money, too!
Now, doing this will probably result in a temporary pay cut. But even if he goes from making $100,000 to $50,000 that first year, you guys can adjust your lifestyle and still live comfortably. You can get by on way less than a hundred grand, and if needed, you can live for a little while off bits and pieces of that big pile of cash you've got in savings.
I can't imagine spending my entire life doing something I hate. If every Monday morning looks and feels like you're having a root canal, then it's time to find something else. Just make sure you've got a plan, and be smart about it!