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This resonates with me. Like you, I'm risk-averse but I still have hopes to create my own company one day. It'll start as a side project and then if I get enough traction, perhaps it'll be enough to convince me to take the leap.

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My experience taught me that moonlighting is hard. If you are really convinced it's gonna work, try taking vacation or sabbatical leave for a month or so (if you can) and work full time, ship the damn thing, advertise the hell out of it, and start counting the money / since your life doesn't depend on it, you need some gratification to keep going.

This exactly. If you are committed to your project full time, then it's a lifestyle business and not the type of startup referenced here. Lifestyle businesses are great, but I've only met a handful of people who have had their life changed from a lifestyle business. If you are passionate about something, why won't you leap?

I'm mid 30s, married and kids and bills to pay, but I am still making the jump because I'm incredibly passionate about my idea.

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