The way I see it:
Looks like it's widely assumed that the secret of success lies in deciding what to do, then making a plan for it and doing it. The problem is that it rarely works that way.

The PLANNING part is the easy one, at least the most consistent, but the DOING part is where it gets tricky. When you are trying to implement your plan, it either gets altered with interruptions and unpredictable circumstances or it starts to feel constraining, outdated, as if you were being forced to carry out an obsolete agenda that doesn't represent you any more.

If so, shall we forget about planning and go with the flow and do whatever feels right in the moment?

Not so fast my friend.

As Oliver Buckerman states in his just released book Four Thousand Weeks, the secret relies in the way we see a plan. A plan is just "an expression of your current thoughts about how you’d like to deploy your modest influence over the future. The future, of course, is under no obligation to comply."
 
Relating to a plan that way it's extremely liberating and inclusive, as it allows you to making your plans and at the same time fully expect to change them, often, as events unfold.

Easier to say than to do. How can we possibly surrender to the unpredictable and unexpected?

There is a response to that.....having confidence; "the confidence that when unpredictable events occur, you could expect to have the physical and psychological resources to handle them."

That is to say, we'll cross that bridge when we come to it. When else can you cross a bridge, except when you come to it?
Compilation:

In the world of "personal productivity", there's no principle more widely agreed upon than the importance of planning out your day – and preferably your week and your year as well. Sure, there are those other kind of people – the ones who sail spontaneously through life, doing whatever feels right in the moment. But to the average time-management guru they are alien creatures, and they probably don't accomplish very much. No: the secret of success lies in deciding what to do, then making a plan for when you'll do it.

The trouble is that it never quite seems to work. The planning part is fair enough, but the doing part runs into one of two problems. Either interruptions and shifting circumstances make it impossible to stick to your plan. Or you do stick to the plan, but it starts to feel stale and constraining, as if Present-Moment You were being forced, against your will, to carry out the obsolete agenda of Past You. At which point you contemplate throwing in the towel, and may question the underlying principle. Does it really make sense to plan life out so rigorously? Mightn't it be better to just go with the flow, doing what felt right at each moment?

It's a trick question, though. Unless you're being physically forced to act, you always are doing whatever feels right in every moment, in any case. Even the most obsessive planners (and believe me, I've been there) are still deciding, moment by moment, what to do. It's just that the specific decision they're making, for now, is to keep on following the plan.

What we forget, whenever we imagine planning to involve anything more than this, is that "a plan is just a thought", as the meditation teacher Joseph Goldstein says. Or to quote, umm, myself, in Four Thousand Weeks:

We treat our plans as though they are a lasso, thrown from the present around the future, in order to bring it under our command. But all a plan is – all it could ever possibly be – is a present-moment statement of intent. It’s an expression of your current thoughts about how you’d like to deploy your modest influence over the future. The future, of course, is under no obligation to comply.

If you can begin to relate to planning in this more loosely-held, less strenuous fashion, you'll find you get the best of both worlds: you get to formulate plans for your future, so as to maximise the likelihood of accomplishing your most cherished goals – but without the feeling of being imprisoned by them, or the stress of trying to force reality to comply with them. On one hand, you make your plans; on the other, you fully expect to change them, often, as events unfold.

Living like this isn't an alternative to living in the moment. It's a way of living in the moment.

And yet there's something deep within many of us – the recovering-perfectionist, anxiety-prone ones, anyway – that wants to think of planning in a far more absolutist way than this. We imagine that our plans for the future have to be formulated exactly right, here in the present, because we won't be able to revise them later, or because it would be humiliating to have to do so. And we hate the idea of saying, about some future possibility that's worrying us, that we'll cross that bridge when we come to it.

A wise older friend once put it like this: imagine you were a member of a prehistoric tribe, setting out on a multi-day hunting expedition into the unknown. You couldn't possibly have felt confident, if "confident" means feeling sure of how things will unfold. But there's a kind of confidence you could have felt: the confidence that when unpredictable events did occur, you could expect to have the physical and psychological resources to handle them.

You can't ever be sure the future will go the way you want. But you can usually (if admittedly not always) be sure that when it fails to go the way you want, you'll have the wherewithal to cope.

I'm pondering such matters at the moment because later today I'm flying to England to join my partner and son in the North York Moors, where we'll be living for her academic sabbatical year. (Editorial note: I'm here now!) I can't wait. But at the same time the old anxiety is bubbling up. What if there's a problem with the house we're renting? What if the school my son is due to attend isn't as wonderful as it looks? What if this turns out to have been a terrible time to move from the US to the UK, Covid-wise? Etcetera, etcetera, etcetera.

And of course the answer in every case – though apparently I need to keep relearning this lesson, again and again – is that we'll cross that bridge when we come to it. We'll figure it out then, based on what's actually happening then, drawing on the internal and external resources we'll have access to then.

After all, when you stop to think about it, there isn't really much of an alternative. When else can you cross a bridge, except when you come to it?

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