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I didn't mention it in the post, but this was more so coming from an angle of preparing for money running out. How much runway is enough knowing that if I fail there will be some amount of lead time to find a new gig and if that new gig will pay similarly to what I am making now.

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That will depend on things you won't know until you start.

How much do you start with, what's your burn rate, how long until you get revenue, are you bootstrapping/funding, your personal cost of living, etc.

Running a business involves risk. Risk to your comfort, your mental health, physical health, financial health, etc. Closing a business is the end of all of that, not the start.

Why do you want to scratch that entrepreneurial itch?

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