How To Make Decisions When Faced With a Dilemma

What a Dilemma is Not

Imagine you have two choices to make where Option A is that you get get the job of your dreams and Option B is that you end up with a job you’d hate.

This is not a dilemma.

You have one good choice and one bad choice so it’s easy to choose Option A in this situation.

Now let’s continue with this scenario. Imagine that you have three options:

  • Option A: Job of your dreams, paying you 10% more than what you currently make
  • Option B: Job you’d really like, paying you 30% more than what you currently make
  • Option C: Stay at your current job which you really like and keep the same pay

This isn’t really a dilemma either.

It’s all good options to choose from so it doesn’t really matter which decision you make. The only thing you need to do is make a decision in a timely fashion.

If you go, you’ll probably end up working somewhere you’d really like and get more pay (win!). If you stay, you’ll keep the job you like and that will turn out just fine also.

So then, what makes a dilemma, a dilemma?

A dilemma is when you must make a decision with only bad options to choose from.

For example, imagine that after a boat crash you’re on a life raft that you can only fit one extra person. If you get off the life raft, it’ll float away and no one will be saved. You spot your spouse and kid in the water where they too have survived the boat crash. You paddle over there to them but you can only take one of them with you.

Which one do you take?

That’s a dilemma.

For many people, this would be an impossible decision. So what are some rational ways to consider decision making in a scenario like this?

Here are some strategies to consider:

  1. Choose the least bad option. When faced with choosing between two bad options, choose the one that is “least” bad or causes the least amount of harm. (e.g. having a broken arm vs. a broken back, wearing a mask vs. catching COVID, missing a deadline vs. delivering an incomplete product, etc.)
  2. Choose the option that presents the best long-term outcome. Try thinking long-term. If given a 10 year or more time horizon, which decision do you think you’d be happiest with? (e.g. walking away from the business today vs. being in an unhappy/unfruitful partnership, paying rent vs. the cable bill, taking the $10k loss now on an investment vs. potentially losing $100k later, etc.)
  3. Make a quick decision. If it’s between Option 1 and 2, decide to always choose Option 1. When faced with a dilemma where you cannot determine the least bad option or the one with the best potential long-term outcome, the best option then is to make a quick decision. Coming to a quick decision presents you the opportunity to recover from it sooner. The key is to determine which option you’ll choose BEFORE you end up in a dilemma. This is another way to use pre-decisioning. Use whatever criteria you like, just be consistent with it.

Decision making when faced with a dilemma ultimately comes down to reducing harm, optimizing for long-term outcomes, and speed. All of these factors can help frame the decision to be made.

Also, if in doubt, just choose an option quickly and trust your ability to recover.


P.S. For the record, me and my wife talked about the boat situation, we both would want the other to always save our child.

P.P.S. Aloha, from Hawaii! Been here the past few days to recharge.