Planning is not all it’s cracked up to be.
It feels like we’re capturing the facts on paper, manouvering them into the right order, and surgically removing what’s irrelevant or impractical.
We’re taking unbiased stock of reality, then moulding it to our will. Aligning resources and channeling our efforts to reach the outcomes we desire.
But things are not what they seem.
Yes, there is merit to planning in this way. But delivering our desired outcomes is actually the smaller effect of planning — its main impact on us is to act as a comfort blanket.
Planning the future allows us to envisage it happening that way. More, it allows us to banish all thoughts of other possibilities to the back of our minds. Because we’ve said we intend to make it so we now believe that it will be so. Through that act of imagination we instantly take all the other undesirable futures off the table.
This does two things.
The first one is the most obvious. It gives us hope. We’re going to get what we want (yay!). And all the bad things we don’t want are going to be avoided (double yay!).
But I suspect that this is actually the smaller of the “comfort blanket benefits” that we get.
You see, it’s not just about getting what we want — but about banishing the unsettling feeling of ever-present uncertainty. The awful torture of not knowing what’s going to happen.
So even if our plans don’t direct us to the outcome of our deepest inner desires, they still provide a life raft to cling to in the raging ocean of uncertainty that is life.
They tell us “here’s where we’re going”. You don’t need to worry about all the possibilities. You can relax and get swept along a known path.
Once we acknowledge this we get to ask : “Is it such a bad thing?”
Planning feels like engaging in the eminently reasonable act of accepting reality, but — in another sense — it’s actually fighting it. We may have identified the most probable outcomes. But, whether we’re aware of it or not, we’re still trying to trick ourselves into thinking those outcomes are now certain.
Outcomes are NEVER certain. One of the few things you can be sure of in life is that you’ll never be released from a state of uncertainty.
Trying to make things certain is a futile fight — the only reasonable choice is not to seek certainty, but learn to dance with uncertainty instead.
This isn’t to say you shouldn’t make plans. Just be aware of the false certainty you’re creating when you do so. The danger comes when you accept the false certainty you’ve manufactured (through planning) as real. This leaves you unready to deal with other outcomes.
Now, there’s no law that says you must be acknowledging and engaging with reality 100% of the time.
If, at any given moment, staring down the barrel of reality turns you into gibbering mess — incapable of doing what’s needed to move you forward — then it can make sense to sidestep reality for a bit and take a perspective you can work with instead.
In this case, the end can justify the means. Sometimes you need to take the perspectives that Derek Sivers calls Useful, Not True.
But don’t retreat into this all the time. Confront reality head on occasionally.
And recognise what the act of planning is accomplishing for you in these situations. That it’s not really aiming at better results — merely getting rid of the discomfort we feel with uncertainty.
I’ve been reflecting on one of my own recent planning sessions as an example:
_[I’ve always been a compulsive plan-maker. But it’s only really now that I’m starting to ask myself whether this might actually be counterproductive. Hence my writing this essay…]_
I was planning out the specifics of some work tasks that have been top of my mind for a while. So I was already pretty clear on what needed doing.
Were the resulting plans helpful in deciding exactly what to do and when? — I think partly yes (but I’d have managed just fine without them).
Were they also about soothing my anxiety by reducing the perceived uncertainty about how the coming days and weeks would play out? — Undoubtedly yes!
As long as I’m aware of this, then my planning can be useful — or, at least, not actively harmful.
But when I lose sight of it I fall into spending loads of time planning simply to try and reduce my discomfort. To help me feel safe.
But, of course, my plans can never actually deliver that safety and certainty I’m after… They’re a false comfort and a waste of time in that sense. As long as I’m not so anxious that it stops me functioning effectively my best approach is not to plan, but to embrace the uncertainty and take decisive actions anyway.