If you are a decent programmer, you should be able to find some sort of satisfactory-paying work even with the "gap" you describe. And if you truly have 5-10 years of savings, you have more than enough cushion to try working for yourself for a year. Try to retain some discipline as you go. If after a year or two you're not able to make anything work, consider looking for a boss again.
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If you are a decent programmer, you should be able to find some sort of satisfactory-paying work even with the "gap" you describe. And if you truly have 5-10 years of savings, you have more than enough cushion to try working for yourself for a year. Try to retain some discipline as you go. If after a year or two you're not able to make anything work, consider looking for a boss again.