To plan or not to plan? That is the question.

Planning out a project can give you a sense of direction and purpose. It can make it easier to stay motivated and ride out the hard times — all you have to do is stick to the plan. It can help you overcome doubts and provide you with some confidence that your goals are actually achievable.

But planning can have its drawbacks. When each step on a journey is clearly mapped out, you lose the option of wandering off the path. I was reminded of the importance of spontaneity a couple of months ago in Thailand — having an open agenda meant I could wander way off my intended path.

In my post from Thailand I talked about how Nassim Taleb points out in his book The Black Swan that many of life’s opportunities emerge through serendipity (chance encounters) — to grab them, you have to be prepared to act spontaneously.

Grabbing opportunities might mean taking the time to talk to somebody new. If that person isn’t part of your plan, it could be easy to convince yourself that talking to them is a waste of time. When you’re totally focused on plans, goals and desired outcomes it can be easy to ignore the unexpected opportunities along the way.

Travel is awesome for meeting new people, especially people with very different backgrounds to you. Planning can also throw a spanner in the works here — if you’re rushing to your next pre-planned stop, you’ll feel far too rushed to take the time to speak to that random person who takes a seat next to you.


So what’s the answer?

Last year I wrote a guest post for Anna Lundberg on balancing routine and novelty. I talked about having too restrictive a routine (too much planning) and the flip-side — having no routine and feeling a little aimless.

In that post I talked about setting some goals that ensure that you keep a good balance between routine and novelty — goals based around travelling or trying new things. If your goals are only based around ‘work’ projects, work can suddenly seem more important than anything else — having non-work goals can help keep things balanced.

It might seem a little crazy that you need to remind yourself to travel and do the things you love. But that’s the effect that setting goals can have — everything that’s related to a goal becomes super important whilst everything else fades into the background.

As Oliver Burkeman points out in his article criticising time management routines, work can expand to fill all our available time. We feel pressured to meet society’s vague definition of success, meaning that any moment spent doing something ‘unproductive’ suddenly feels like time wasted. We set goals that require us to work harder and harder, planning out more and more of our time.

Buddhist teachings talk a lot about the dangers of grasping for things that are out of our reach. Goals are a form of grasping — that much is clear to me. If you’re totally focused on goals, you’re always striving for something more and you’re rarely appreciating the present moment. If you have a strict plan in place, you’re always grasping after the next achievement that your plan presents to you. Living this way 24/7 means risking the loss of all the joy of life.

I think that’s where the problem lies — planning 24/7. There’s a balance to be found — goals certainly can be beneficial — but that balance isn’t always easy to find. It can be tough to trust yourself to get things done – planning creates a kind of external source of pressure to stick to the right path.

You can only really figure out what level of planning make sense for you through experimentation. Make a plan, work through it and then reflect on how it worked for you.

To make it easier, here are three things to look out for:

  1. Rushing. Rushing kills quality and it kills enjoyment. If you’re rushing, you’re either planning too intensely or not leaving yourself enough time.
  2. Spontaneity. If you find yourself too busy or rushed to think about anything outside of your plan, something is wrong. Opportunities require spontaneity – don’t plan so much that you can’t grab them.
  3. Trust. If you feel unable to trust yourself to get anything done without a plan, you’re probably not giving yourself enough credit. Doing things simply because you want can often work better than following a strict plan – I talked about this in my post on extrinsic vs intrinsic motivation. Make room for trusting yourself to just get things done, then reflect back on whether you actually did them (and if not, how come). You’ll figure out a lot about what motivates you.


If you’ve got your own ideas or experiences, I’d love to hear about them in the comments!

Also published on Medium.

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