Spend some time planning. Then spend a lot more time doing. If you're unsure, do something -- and then react appropriately.
It's easy to think and plan and evaluate yourself out of ever starting a side hustle. See starting a side business as the grand experiment it is. Never forget that the fun is in the doing -- not the thinking.
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"There's no money in poetry, but then there's no poetry in money, either." ~ Robert Graves
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Measure the total amount of time you invest each year to earn money. It includes the time you spend to commute to and from work, and time spent working on a side hustle or dropping your kids at daycare.
If you're unsure how much time you spend working, use 2,500 hours per year as a starting...
Go out and try to make more money. Start by optimizing your full-time job and starting a side hustle.
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