How do you make a difficult decision when both options are good?

You have been going back and forth on this for months.

Not idly. You have done the work. You have talked to the people worth talking to, you have run the numbers, you have made the list with the two columns, and you have made it more than once because the first version did not settle anything. Some mornings you wake up certain. By the afternoon it has moved again.

And underneath all of it is a quieter worry, which is that a person with better judgment would have decided by now.

Let me offer you a different explanation.

How do you make a difficult decision?

A decision stays hard when the options are genuinely comparable and neither one is better. Philosopher Ruth Chang calls this being "on a par". No further analysis breaks that tie, because there is no missing fact left to find. What settles it is committing to one option and creating a reason, rather than waiting to discover one.

Why the pros and cons list didn't work

Every decision tool you have tried assumes the same thing: that one option is better, and the job is to find out which.

Weighted scoring assumes it. The 10-10-10 rule assumes it. Sleeping on it assumes it. They are all instruments for detecting a difference that is already there.

Ruth Chang has spent her career on precisely this problem, and her argument is that the hardest choices are not hard because of ignorance. They are hard because the alternatives are on a par: genuinely comparable, and yet neither better, nor worse, nor exactly equal (Chang, Hard Choices, Journal of the American Philosophical Association, 2017).

That last part is worth being careful about. On a par does not mean the options cannot be compared. You can compare them fine. It also does not mean they are exactly equal, which would at least let you flip a coin with a clear conscience. It means neither one comes out ahead, and no amount of further looking is going to change that.

Which means your list was never going to work. You have been running a tie-breaking procedure on something that does not have a tie-breaker in it.

The months of going back and forth are not evidence of weak judgment. They are evidence that your judgment is working correctly on a genuinely close call.

Why am I so indecisive?

Probably you are not, in general. But there is a habit that makes this worse, and it has a name.

Psychologists distinguish between people who search exhaustively for the best possible option and people who stop once they find one that is good enough. Barry Schwartz and colleagues found that the exhaustive searchers report more regret and lower life satisfaction (Schwartz et al., Journal of Personality and Social Psychology, 2002, US and Canadian samples).

The sharper study followed 548 graduating students into the job market. The ones who searched hardest for the best job ended up with starting salaries about 20% higher than those who stopped at good enough. They were also less satisfied with the job they took and reported more negative feeling about the whole thing (Iyengar, Wells and Schwartz, Psychological Science, 2006, North American sample). That study measured the tendency rather than assigning it, so read it as a strong pattern rather than proof of cause.

Sit with the shape of that. Better outcome. Worse experience of it.

You may also have heard the famous jam study, where shoppers offered six varieties bought more often than shoppers offered twenty-four (Iyengar and Lepper, Journal of Personality and Social Psychology, 2000, US research). It is a good story and I am not going to lean on it, because a direct replication found no effect and a later analysis pooling fifty experiments found the average effect was close to zero (Scheibehenne, Greifeneder and Todd, Journal of Consumer Research, 2010). More options do not reliably ruin decisions. They also do not reliably help. The list that keeps growing is not making this easier either way.

The cost of keeping the door open

Here is the finding that changed how I think about this.

People are reliably bad at predicting how strongly, and for how long, they will feel about an outcome once it has happened (Wilson and Gilbert, Current Directions in Psychological Science, 2005, US research). Which means the simulation you keep running, imagining yourself into each option to see which one feels right, is being run on faulty equipment. That is why the tenth run tells you nothing the first did not.

Then there is this. In one experiment, people chose between two photographs. Some were told the choice was final. Others were told they could swap it later if they wanted. The people whose choice was closed grew to like what they had chosen noticeably more over the following days. The people who kept the option to change did not (Gilbert and Ebert, Journal of Personality and Social Psychology, 2002, US research).

The people in the experiment did not predict that about themselves.

Keeping your options open does not just fail to help. It can quietly prevent the settling that only happens after the door closes.

So part of what you are experiencing as an unresolved decision is actually the experience of an open door. The discomfort is not telling you that you have not thought hard enough. It is what an unclosed choice feels like.

What to ask instead

If the tie cannot be broken by looking harder, then the question has to change shape.

Not: which option is better. There is no answer to that one, which is why you have not found it.

Instead: which of these can I put my whole weight behind?

That is not a softer question. It is a harder one, because it stops being about the options and starts being about you. Chang's account is that when reasons run out, you can create one, by committing your agency to something about one of the paths and becoming the person who chose it. She also allows a second honest possibility, which is drifting, letting circumstance decide. That is a real option. It is just worth doing on purpose rather than by default, and after enough months of going back and forth, drifting is often what is already happening.

Two things I would actually do this week.

Notice which option you have quietly stopped researching. Then ask yourself the honest question about it: did you stop because it was settled, or because something in you had already settled it and has not told you yet.

And try saying the decision out loud to one person as though it were already made. Not asking. Telling. "I'm taking the job." Then pay attention to what happens in the second afterward. Not as a verdict, and not as a gut feeling to obey. Just as one more piece of information, from the one instrument you have not used yet.

If what you are calling a decision turns out to be something vaguer than that, this is closer to it. And if you are not yet sure what the options even are, start here instead.

The choice will not get easier. It was never going to. But it can get finished, and finished is the thing you actually want.

Sources

Chang, R., Hard Choices, Journal of the American Philosophical Association, 2017, and The Possibility of Parity, Ethics, 2002. Schwartz, B., et al., Maximizing Versus Satisficing, Journal of Personality and Social Psychology, 2002. Iyengar, S. S., Wells, R. E., and Schwartz, B., Doing Better but Feeling Worse, Psychological Science, 2006. Iyengar, S. S., and Lepper, M. R., When Choice is Demotivating, Journal of Personality and Social Psychology, 2000. Scheibehenne, B., Greifeneder, R., and Todd, P. M., Can There Ever Be Too Many Options?, Journal of Consumer Research, 2010. Wilson, T. D., and Gilbert, D. T., Affective Forecasting: Knowing What to Want, Current Directions in Psychological Science, 2005. Gilbert, D. T., and Ebert, J. E. J., Decisions and Revisions, Journal of Personality and Social Psychology, 2002.