Many mistakes I regret are mistimings, not mishaps; it was a constant delay until I felt "ready".

The strange bit is, waiting feels like the responsible choice most of the time. I hadn't hit reply or done anything I couldn't undo, so it felt like taking care and deliberating over my options. I could have a good conversation, yet the follow up would be something I needed to get right rather than the natural continuation. An application could have a deadline, yet I'd treat starting it as something I needed preparation for.

The problem though, is waiting changes the activity subtly. Something which would be light and easy early on, gets heavier and more consequential the longer it sits. By the time I felt "ready", a lot of what the action was worth disappeared. These delayed actions function like holding cash. The longer you hold, the less useful they became.

The follow-up

I cold-DM'd a founder about a possible internship one time, which to my surprise, he replied to. We had a chat about it, and at the end he said he'd reach out afterwards. I took this as a legitimate excuse to wait it out, since I supposedly didn't have to send any awkward follow-up messages.

After a few days, there was no reply, but I still kept myself waiting. My deliberation was that I would look impatient, or distrustful of his word, so not sending a message felt like the careful option.

But the longer the silence went, the harder it was to muster up any message from my end. Now, I had to explain the long gap, reintroduce myself etc., instead of asking for a simple update. So, I continued waiting, holding onto the same reason as before.

Nothing happened in the end. It was so strange, I hadn't decided against it, but I kept choosing the polite option in my mind, that I had just waited the opportunity out. It seems obvious now that I should've followed up as soon as I thought about it, but it's more damning how easy and responsible it felt just to let things play by.

Why we wait

Waiting is easy because it doesn't require a decision. That's why it becomes the decision. There's no energy barrier and so it's the default that our brain goes to. This default usually shows up in two ways.

Small things tend to be put off because of their triviality. The smaller they are, the more unnoticeable they become and the more that clump up. The more annoying part as well, is that despite their perceivably small cost of work to do, each actionable item has the fixed cost associated with getting into the mindset, context switching to it, and physically going around. So it's not as if stacking small tasks into one clump will make it easier, it just means you have more small tasks to rush around and do.

Think about a list of reminders like: do laundry, reply to email about tutoring, throwing away the trash. All relatively minute things, yet they clump up as you put them off, and then it becomes a constant nag on your mind.

The only exception is if you're in the middle of a much more important task, and the cost of switching is much higher than the cost of saving a small task for later. Then, obviously you create a reminder to do the much smaller task later. But convincing yourself otherwise when you don't have that much more important task is just putting you off.

By contrast, large things get put off because they seem too important to start yet. They have a large activation energy. It's simple to say you're being thorough and waiting until you're "prepared". The underlying mechanism is simply innate: large things appear hard and scary, so we put them off with these preparedness excuses. Thoroughness is simply a facade for avoiding action.

Unfortunately, larger items have much huger costs associated with them, tautologically. Put one off and the cost compounds: either the potency of your actions slowly degrades, or they need to be rushed later.

The more intriguing part though, is that these aren't necessarily split cleanly, there can be quite a lot of overlap and drift. Messaging the founder was a small task (a short message), but it was the facade for a larger activity: the internship opportunity that I wanted to "handle properly". This made it easier to convince myself it was too trivial to interrupt my current work, yet too important to rush through.

Either way, waiting doesn't have to present a case for itself, which is why it wins over your mind. The consequences are hard for us to internalise, since they are more abstract annoyances rather than physical punishments.

In the end, the careful waits cost me most, yet they were so disguised, and that's what makes them most dangerous.