Imagine your future self

‘When I make a decision, I don't think about how it’s going to feel right now. I think about how it’s going to feel later: in the moment of the thing and also up to a year later. How will I look back on that time? Will I regret the decision? Looking forward to things is exciting but looking back on things tells us more of the truth.’ 

Use the past to guide you

‘You've got to know yourself. I've begun to realise that I don't want to do long-distance events. So I try to think about previous moments I’ve had and take inventory of those things to remind myself: do I want to do that again?’

Estimate your future capabilities

‘In the short term, there might be this pop of endorphins where you get excited. But what are the implications of this decision? What obligations are you sending yourself down the road? Is that going to be hard to maintain? It might be guesswork, but it’s really helpful.’

Evaluate your decisions holistically

‘I evaluate everything by asking: would I want to do that again? Whether it was worth making particular investments is something you won’t know until you do it, but even if it doesn’t pan out, you can still evaluate the pleasure of doing it. I try not to judge everything in terms of return – it's devoid of soul. You've really got to look at angles and the degrees that matter to you – and not just an objective set of yeses or nos.’

Show your working

‘Explain yourself and show your work. Say you decide not to implement a feature that your employees wanted you to make. As long as you explain the thought process, not everyone will be thrilled about it, but at least people will know where you’re coming from. Otherwise they tend to fill in that vacuum with bad news or conjecture, something that's not true. Then you're battling that.

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