Back in 2008, I quit my 2-month old corporate job (and ultimately, career) to pursue WooThemes full-time. This was just as a worldwide recession hit and everyone was clawing to their existing jobs like there was no tomorrow.
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The World Rewards Courageous Decisions
Being courageous isn't about the risks you take (or don't take for that matter). Being courageous is about putting yourself in situations that are beyond your comfort zone.
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How to Take a Holiday
I don't know about you, but I'm incredibly bad at taking time off and just switching off (from work). Which means I'm equally bad at taking a proper holiday.
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Startups & Faster Learning
Regardless of whether you are bootstrapped or have a nice, comfortable war chest from fundraising, every day that you have unvalidated assumptions and you're not learning, is a day that costs you money.
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When to Worry About Competition
If you can't build an MVP or if it'll cost you loads of cash to build a product that'll allow you to capture enough of the market share to get that initial traction.