Plan if you must, but please don't make me do it

Being spontaneous in Athens, Greece with my meticulously packed little bag, October 2016.

When packing for an international trip, I am committed to traveling as light as possible.

This takes a lot of work. I have to choose my most versatile clothing, select the tiniest toiletries, and forgo some conveniences. The key question is not, “Is there a chance I’ll need it?” but “Can I live without it?”

Then, the clothes get packed in a compression bag and slide into a small messenger bag along with everything else. I have lived happily this way for three weeks at a time and could probably make it much longer. Traveling with so little does require doing a bit of awkward laundry, but it is worth it to be able to hop off of a plane or train and do whatever you want without having to worry about your bags.

In other words, I do this advance planning so that I don’t have to plan anything else after that.

And other than international trips, I plan very little.

Instead, I prepare.

Perhaps it comes from the decade-plus that I spent teaching private music lessons, in which the direction of the lesson is entirely dependent on the student’s interests and skills in that moment. A plan is counterproductive.

And yet, preparation is essential. I always had a shelf full of music books to offer based on whatever the next step turned out to be. I had stickers. I had snacks. I was ready to teach the material in six different ways, depending on the student’s needs.

This has carried through to much of my teaching and leadership work. I tend not to plan most of my lessons, meetings, and speaking engagements. However, I prepare intensely. That way, when the moment arrives, I am ready for things to go in any direction.

Making a plan (and worse, following one) gives me a feeling of tightness and restriction. I will procrastinate if I feel like I’m supposed to make a plan. I may be willing to travel with only one pair of shoes, but I find it a lot harder to let go of ideas that might be useful and narrow things down ahead of time!

So I over-invest. I go deep into a subject and learn as much as I can — much more than I need to know to carry out the task. Ideally, I do this without a deadline, before there’s even a specific need for the knowledge or skills I’m developing. Then, when it’s time to deliver, I can take all the ingredients and whip something up without a recipe.

I’m sure this approach probably sounds outrageous or even horrifying to some people. I know it wouldn’t work for everyone. But most of the time, it works very well for me. I’ve optimized my work life to accommodate my preferences in this regard — I’m not coordinating a dozen specialists in a separation surgery for infant conjoined twins. I respect the fact that there are lots of situations in life when winging it does not fly.

No, I’m not trying to convince anyone to do it my weird way. Rather, by offering an alternative to the agreed-upon way that you’re supposed to do things (similar to the habits-vs-goals conversation), I’m hoping to at least start a conversation — and at best, help someone who might really benefit. If “there must be a plan” is a basic truth of life that you’ve never questioned, see how it feels to try on a different viewpoint. It might be just the thing you need in order to release yourself from a lifestyle that isn’t working for you.

On the other hand, if you are a die-hard planner who thinks I’m totally nuts, you may still find a benefit (for instance, relief from anxiety) in shifting your focus from planning to preparation. You may discover where the holes are — for instance, where there’s a question you hope the opposing counsel won’t ask you. Or you may discover that you’re very well-prepared, and your detailed plan is backed up by a solid foundation.

Being prepared offers a sense of freedom from worry and stress. For some, part of being prepared is having that tightly structured plan. For me — and I don’t think I’m alone — the sense of flexibility balances out the challenge of having to improvise and adapt. In fact, that’s my favorite thing about international travel — the opportunity for that spontaneity! And it’s kind of fun in the classroom, too.

What do you think? Are you a planner, a preparer, or both? What are the challenges of each of these approaches, as you see them? I would love to hear your thoughts in the comments.