Most of your identity is the culmination of the choices you’ve made. You choose all day every day. Many people have trouble making big choices, for some choosing is even debilitating. If you do, you’re holding yourself back from living your life more fully.
I used to dwell on decisions too. In my second year of business school I saw many of my classmates dwelling on choices between different job offers, unable to choose between Goldman and McKinsey. While most of the world would imagine it simple to choose among six-figure offers from prestigious firms, people choose for their reasons, not anyone else’s. Still, I saw their self-fabricated conundrums as pathetic and pitiful. They seemed like an emotional version of physical compulsive hoarders—people who save stuff others consider junk. You see the disaster they’re making of their lives, see similar tendencies in yourself, decide your life will improve if you handle them, and act.
My result: a choosing algorithm to act and a few mental models to support the action.

Beliefs

Belief 1: Choosing is fundamentally emotional

People try to reason through choices, thinking emotions get in the way of reason, which they imagine would lead them to their best choice. I suggest seeing it the opposite way—that whatever our reason tells us, the final choice remains a gut choice, only partly informed by reason.
Our values are based in our emotions. Our worries about wrong choices or lost options are based in the emotions we’d feel after. Emotions are at the foundation of every part of choosing.
Think of it this way: all animals have to choose among options, not just humans. Dogs choose. Cats choose. Mice choose. They can’t reason anything like we do, yet they do fine. Reason informs how you choose, but your rationality doesn’t choose, nor does it bring you reward or punishment based on the results. Your emotional system does.

Belief 2: You can never know everything you wish you could for a choice

This belief speaks for itself. People seem to disbelieve it while choosing, acting as if waiting, studying, or analyzing will make a choice clearer.

Belief 3: You can second-guess any choice, so fearing you might second-guess one shouldn’t affect the process

Do you fear you might second-guess yourself after choosing? This belief keeps you from that fear by pointing out you could second-guess any other choice too.

Belief 4: You can only choose based on what you know when choosing.

Do you fear you might find out relevant information after choosing? This belief keeps you from regret by reminding you you chose as best you could based on your knowledge at the time. If you learned more later, you don’t have to feel bad about a choice before you knew.

Belief 5: The hard part of choosing isn’t deciding what you like, it’s getting rid of things you like almost as much.

Read the two-part post from this link, with graphs, for more background. If the choice forces you to pick one, realize you can’t avoid losing the others. Waiting to choose won’t help.

Belief 6: My skiing / surfing analogy

These posts—“How to decide among close options” and “A belief to choose without getting mired in indecision“—describe this model. Read them.

Actions

Step 1: If the choice is obvious, choose and live your life

If one option stands above the rest, choose it and move on.
Some people have trouble even here. They wonder if their decision might change later if they find new information.

Step 2: If the choice isn’t obvious, eliminate as many of the worst options as you can

Get rid of the options you don’t like.

Step 3: Change your question from “Which is best?” to “How do I want to live my life—by letting things happen to me or actively deciding for myself?”

How you frame the act of choosing affects how you handle the challenge. I stop comparing the options and I think about the value of choosing to my life. I never want to be like those classmates dwelling on their issues, complaining to each other how hard their choices are. Imagine a compulsive hoarder’s apartment with years of newspapers and beds so covered with crap they can’t sleep in them. You’re doing that to your mind when you try to keep your options open.
You can’t change that you can’t tell what will happen after you choose and no matter how much information you have, you’ll never have all of it. No matter how much you get, you can always get more.

Step 4: Once you choose, live your life the best you can

By contrast, once you choose and the options you eliminated are gone, the best thing you can do is live your life as best you can with the choice made.

Step 5: If feelings of regret start to surface, remember you chose as best you could when you did and keep living as best you can

Nothing keeps you from regret like moving forward. You can’t change the past. You can learn from the past, but dwelling in it doesn’t help you learn. In the meantime, you can act in the present to improve your future.

Notes

Every situation is different so you have to adjust the algorithm every time. I’m not suggesting you choose fast every time. You can always choose to wait.

Summary

If you haven’t mastered choosing without regret, you have a problem in your life.