To truly have a vacation means to enjoy it spontaneously. I realized that just after I realized that I never really had a vacation — most of my time off in the past has been taken getting things crossed off lists and being part of others’ time off.

As I am deciding to take a week off in the Summer to go to Italy, I am tempted to do exactly that: be spontaneous. Wake up, and decide on the fly what I feel like. I think, in addition to being a true vacation, it will also be a higher quality one: because I will be able cater to my feelings and desires as they happen, rather than make plans ahead of time irrespective of how I will feel on a particular day. Do I really want to see the Coliseum today? Why decide sooner than today.

That inability to be spontaneous manifests itself in other ways. For example, while a lot of my friends did, I didn’t enjoy Avatar. A lot of my friends enjoyed the way it drew them in, gave them a feeling of high, so to speak. I sought some higher purpose, a meaning, or an aesthetic, and got neither. I think if I were spontaneous, I would be able to connect to the natural desire of the human mind to be taken to places.

How does one become spontaneous? Ha. (It’s not like there’s a 12-point plan to being spontaneous–I am constantly shocked by how many people make money out of people who don’t understand the irony in this). I think, at least for me, the key to this is to first let go of my desire to control things (yes, I am a huge control freak). This means doing things which I’m not comfortable with (there’s a difference between comfort and what–for a lack of a better word–I’ll call synchronicity that comes from doing things spontaneously). Like go ride a motorbike with my friend in Thailand without a map or purpose, and even though neither of us ever rode one (unsurprisingly, this ended up being the highlight of our stay on this island).

Another thing I have to do is to mitigate risks that don’t directly affect spontaneity. For example, I will read about Italy a lot before going there, because it’s hard to be spontaneous if you don’t have options (and nothing paralyses me more than having to make a decision without knowing what options there are). But I will not ask myself what I would like to do. While it may seem trite, there is something incredibly liberating about waking up and deciding, randomly and on the fly, that I want to do X.

Overthinking it is also an obstacle to spontaneity. I will try to think as little about my vacation as possible. Sure, it will be painful (this is one exception to my rule about ordering things to do), but the effect will be beautiful: here I will be, in Italy, having to rely entirely on what I feel like, what I’ve read, and what I see (my guess on why I’m not spontaneous has to do with the fact that I haven’t really been forced or encouraged to express opinions or preferences until late in life).