The Weekly Resolve Email 40 – Are You Prepared?

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Hey, Darren here.

You’re receiving this email because you signed up to The Weekly Resolve, a weekly email about making better decisions. Thank you for being here. If you enjoy the email, please forward it to a lucky friend. And if this email was forwarded to you, get your own.📩


Hi, decision-makers,

Steve Jobs once said: “You can’t connect the dots looking forward; you can only connect them looking backwards.”

The line is one spoken by Steve at his commencement address at Stanford on the 14th of June 2005. The speech was significant because the story of the dots offers a crucial lesson. You can’t connect the dots looking forward.

But what does it mean?

No one knows what’s around the corner.

The worst story we tell ourselves is the one where we tell ourselves we are in control of our futures. Often, we can’t help it. Our intuition, driven by our cognitive biases allows us to believe in luck. As Feynman says, you must not fool yourself and you are the easiest person to fool. But we do fool ourselves – frequently too.

We can’t predict the future; we can only prepare for it.

Only with the power of hindsight can we connect the dots. After saying you can’t connect the dots looking forward, Steve offered another line; “You have to trust the dots will somehow connect in the future.”

You can’t foresee the future; all you can do is prepare yourself for it.

It is a leap of faith to trust that the life you want will somehow connect itself through the dots along the way. Some don’t prepare. They drift, letting the river of serendipity take them wherever it wants to flow.

Accepting the randomness and uncertainty gives you an alternative perspective.

It makes sense to prepare; to be ready for the challenge of uncertainty. Decisions become less certain, choices are broader rather than narrower, because the game is to be ready for whatever life gives us. Maybe Baden Powell was right with the scout’s motto – “Be prepared.”

If you’re prepared; you’re ready to live your life and join the dots up.

Luck requires preparation

Image Credit: Janis Ozolins

As Janis so wonderfully captures, these are the two ways we tend to live our lives.

The first is the drifter, the one who ‘hopes’ everything will be alright. The second one, well that would have been Steve Jobs. He built his skills, preparing for life and so was able to capitalise on his ‘luck’.

He was able to connect the dots, will you?


New For You

Reflective Decision-Making: Decisions tend to be better when we take the time to reflect on them – before we make them. The best decision-makers reflect – and so should you. Read the full article here.


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Make great decisions!

Darren Matthews

Founder, The Resolve Blog

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