Making good choices is hard. In fact, there’s only one thing I hate more than not having any choice, and that’s having to make one at all.

I feel trapped when I have too few options, and overwhelmed when I have too many.

Why are choices so difficult?

Easy Choices Aren’t Choices at All

If I imagine a choice, I usually picture two options: one good, one bad. But this is a childish impression of what choices even are. A choice with an obvious right answer is no choice at all.

In real life, we almost always have incomplete information. It’s generally impossible to know in advance whether a particular option will end up ‘good’ or ‘bad’.

And then there’s the difficulty of applying simple labels like ‘good’ or ‘bad’ to complex sets of potential outcomes. If I win the International Quiz Championships, but lose my leg in the process*, would that count as a good outcome?

* I have no idea how this outcome would come about, exactly. Probably best not to speculate.

In the real world, since we lack a crystal ball, we’re forced to guess a likely outcome using only the best information we have at the time.

But that’s okay. Every choice we’ve ever made has been this way. Incomplete information is only a problem if we get hung up on it and refuse to act.

Good/Bad is Easy; it’s Good/Good that’s Hard

Even better, in real life most of our difficult choices aren’t between a good option and a hidden bad one. In practice, we mostly get stuck choosing between multiple good options.

(Occasionally, we’re unlucky, and get faced with a choice between only bad options, so we have to find the least-worst. But most of our life choices and daily choices aren’t like that.)

“Do I order the burger, or the steak?” is more difficult than “Do I order the burger, or a punch in the face?”

This sounds great, but choices between multiple goods are hard. In case you’re not convinced, consider that “Do I order the burger, or the steak?” is more difficult than “Do I order the burger, or a punch in the face?” When we’re making a big decision**, if all options are good, how do we pick the most goodest?

** I don’t mean to imply that ‘what to have for lunch’ is a small decision, of course!

The next best thing to a crystal ball is a combination of head and heart.

Use Your Head

In theory, our brains are rational decision making computers which weigh up pros and cons and present us with the best possible option.

In practice, anyone who has actually lived as a human learns quickly that our brains are as distractible as the dog from Up and trying to keep them on task to perform rational analysis feels like juggling springs on an inflatable unicycle.

Worse still, when making a big decision, we have to rationally weigh up things that can’t possibly be measured. If we’re considering a new job, how is it possible to measure the value of a 20-minute-longer commute against an increase in networking opportunities?

If you want to be really rational, you can assign each a point value. Perhaps a 20 minute increase in commuting time is worth negative ten points, but the networking opportunities are only plus two points. We could do this for every pro/con and see which comes out ahead.

Unless the decision is massive, we probably don’t need to spend hours assigning points to every potential outcome. But taking a few minutes to consciously consider pros and cons helps to inform the process. I find that dashing off a quick list in each of these areas usually sparks insight into what are the most important considerations in this case:

• Long-term benefits / costs

• Short-term benefits / costs

• Physical benefits / costs

• Emotional benefits / costs

• Time benefits / costs

• Financial benefits / costs

• Personal satisfaction , ambitions, bucket lists, etc

But Also Use Your Heart

Usually, for me, a fully rational process doesn’t lead to a clear outcome.

Or perhaps the clear outcome just feels wrong. I’ve learned it’s worth paying attention to this feeling.

You may naturally tend to being more rational or more instinctual. In each case, it helps to be aware of this tendency and to ensure the other side is allowed to inform the process.

My tendency is towards over-rationality: making decisions which on paper seem to be the best, and overridden my instincts in the process, and it has generally cost me. Several times I’ve taken on jobs or projects that rationally seemed like a good idea but required me to go against my gut, and each time I’ve come to regret it.

I’m now learning to trust my gut more – but without flipping to the other extreme.

Similarly, those of us who tend to fly purely by instinct might benefit from a little more use of the head – is there a great option that you’re missing by just listening purely to your gut?

Take the Pressure Off to Be Perfect

Lastly, remember that you can’t control the entire universe. All we can do is our best.

Remember that the whole problem is often that both options are good.

Perhaps one option will get us to our goal faster, but as long as each option moves us towards one of our goals, it doesn’t matter which we pick. Some progress is always better than none.