Over the next three posts I’ll cover my experience addressing the following cascading questions of starting up again: Whether to start a new startup When to start that startup What that startup will be Spending time deciding whether to start a new startup sometimes felt counterproductive. The decision could always be reversed. There was a risk of placing too much pressure on it; of chasing an illusory certainty. And consequently never getting going in the first place. On the other hand, as that startup progressed there would only be more commitments - customers, co-founders, team members and investors. There would be the inevitable and frequent low points when prospects look bleak - ample ammunition to question whether it was right to start in the first place. Comprehensively considering, without procrastinating, whether starting a startup was the right decision could only be of benefit to my future self. The confidence and peace of mind it provides is an invaluable asset on the entrepreneurial balance sheet.