re: 40K to start working for yourself-WWYD?

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Experience with insurance has been on the consumer commercial side, not selling. More knowledgeable about real estate than anything (although that might not be saying much). Have had some success with a couple investment properties, and I know the market, just have to learn the actual hard parts-contracts/deeds/etc....

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Well - real estate or insurance, you're not just going to jump out with your own agency - you're going to go to work for someone else - at first. Now, being on commission, that $40k may provide some cushion, but we're already talking about living on the spouse's income for 18 months. There should be little to no overhead in working as a realtor or insurance agent for someone else.

Certainly $40k isn't going to buy someone out of their agency or realty - at least not one worth buying.