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This post definitely resonates with me - throughout my career I've noticed my outlook shift from 'We'll definitely deliver what this customer wants in 6 months!', through 'The problem is always lack of planning at the outset - that's why we're late or we don't meet expectations', and finally to 'Don't think too many steps ahead, nobody really knows where this is going to end up'. Admittedly, different projects require different strategies for planning, risk assessment etc - but on the whole I feel that regularly re-assessing where you and where you're going is the best way to deliver something everyone is happy with.

I've found that letting go of 'needing to know everything up front' was probably the most liberating development - but it definitely required unlearning a lot of advice I'd received early in my career. Planning ahead is obviously beneficial, but you need to know where to draw the line, commit to building something, and then standing back and seeing how it fits. Rinse, repeat!

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Wow thank you for that deep share, Tom! Would love to follow up. I sent you a DM on Linkedin.

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