Maybe it’s just me, but making decisions, especially of the administrative sort, such as retirement plan, insurance, major purchases, etc., is really taxing.

I don’t think I’m that unusual in this regard.

What’s interesting about this is that, while obviously complexity and choice/information overload is a factor, it can’t be the ONLY thing that makes such decisions hard.

There are plenty of other domains, like writing, or programming, that in some sense are equally or more hard/complex, and yet these are not nearly as taxing and do not invite nearly as much procrastination, at least not once you’ve gotten some experience with them.

One possible reason is that these kinds of decisions aren’t something you do over and over again under the same circumstances, so you don’t practice or acclimate much.

As best as I can tell from my own navel gazing on the topic, the main reason is something else. I think it’s the fact that it’s easy to imagine (and exaggerate) the consequences of a less-than-optimal decision.

How I’ve started to deal with my tendency to put off decisions is, when I realize I’m doing it, to imagine myself after having just made the decision, as if I made it soon.

Specifically, I imagine the relief I ALWAYS feel when it’s been done, and how I rarely feel the temptation to second guess myself – and how I can’t even remember regretting the results of making a particular headache-inducing administrative decision.

In fact, the only thing I remember regretting as I think about it right now is PUTTING off decisions – this has cost me plenty of time and annoyance and even occasionally some money.

So, after imagining what it would be like making the decision now, I then imagine myself having finally made the decision after putting it off – and how much more it cost me in terms of time spent dreading the process or even, in some cases, money.

By doing this, I enlist my emotions to push me harder away from the state of putting it off and pushing me toward the state of just doing it.

It hasn’t made me an executive genius yet, by any means, but it’s definitely cut down on my procrastination.

Imagination is often spoken of because of its role in creativity, but I think most underestimate its role in motivation – even if it’s strategically imagining a negative outcome in order to push you away from a bad behavior.

I’m not here to tell you to embrace your inner child – or your inner optimist for that matter, assuming you have one or both. Think of it as embracing your inner pessimist and your inner optimist, and arranging them such that running from the former and towards the latter causes you to plow through that thing you’ve been putting off.

The metaphor is a bit stretched, but it worked for me.

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