Ideas for making difficult decisions

Sometimes there is that little or big decision that just drives you mad, right? Well, here is a braindump that might help you (or me :-) ) when you're facing a decision that is hard to make because it's not clear what consequences it has, because of emotional involvement, because it's something you cannot now but have to decide anyway, and so forth. It consists of questions, ideas, tips and things to do. When taking a decision, you can just go through this several times and think about what jumps into your eyes. Or, of course, you can go to your favorite AI, describe the problem, what you think and feel about it, and then give it this list and ask it to grill you. :-)

If you have more ideas on that topic - please make sure to contact me!

I'll be assuming that the decision has a number of opinions where you have to choose one, and that it has implications on the future.

Put it into perspective

First and foremost: be grateful you can make that decision. Turn it into a fun project. Write a blog about it.
How important is the decision? Assign a measure, perhaps in terms of money, time, effort.
Assign an amount of time you want to spend on that decision. Make sure you actually do that, instead of just mulling over it in the back of your head. Calculate a hourly rate for the time to put it into perspective.
If it is very important and irreversible, vow to follow this process completely before doing anything.
Make a deadline and track how much time you actually focused on the decision. Make sure you really do something.
Is that really one decision or several different, or can be done in several steps?
Ask as many people as possible, close and not so close, (and AI :-) ) about it.

Collect the options

Write down the options you have.
- What are the implications?
- Write down the reasons for / against each of them.
- How reversible are they?
Are there options that leave many other (later) options open, or block many other options?
What is the cost of not making the decision? (Is that an explicit option?)

Future scenarios

Collect future scenarios that have implications for the quality of the options, or are affected by the options.
- Assign a "felt probability" to the scenarios.
- What qualities have those options in the different scenarios?
- Are there some where you would be proud of your decision?
- Are there some where an option creates a dead end, troublesome situation, or something you cannot live with?
- Does an option enable certain things you could do then, or block you from doing certain things?

Connect to your future self

Imagine yourself vividly in the future for each of the scenarios and for each of the options.
- How do you feel about that option in that scenario? Proud? Uncomfortable?
- Imagine you looking back to today and telling a story about why you made that decision. Note your feelings.

Check out your emotional involvement

Is there something that triggers you emotionally wrt. one of the options? Find out why.
- Is that wholesome or just an irrational leftover of your past?
- Can you modify options to avoid that trigger?
- For removing an unwanted bias imagine vividly the advantages of the unwanted option, invent a story to sell it to yourself.
- Turn it around: imagine vividly the disadvantages of the option you are emotionally attached to, invent a story to make it look bad.
- Imagine another person comes with the same problem to you and asks for advice. What would you tell them?
Do you want to protect something that does not need protection (anymore)? Can you let go of that?
Make sure you keep going a bit each day. If you're stuck talk about that to someone, or to an AI, or write about it.
What are the deeper reasons? If something is really hard to decide that's possibly because of some deeper reason that doesn't have to do with the decision itself, but with something else.
What impact has the fear of making the wrong decision on you? Is it possible that you're tending to the opposite of what you actually want, because of the fear of making the wrong decision?

Values

What values do you have that are relevant for the decision? Which of the options agree with them the most?
Which of the options are more open, upright, or more based on fear?

Stories

Tell stories about the options. Invent for each option a good story that sells it to you, and a bad story that makes it look bad. Which of the options has the best good story and the worst bad story?

Random questions

Did you have moments of intuitive clarity about the decision? What did you feel / think then? What did you think then?
Is there an option that just seems "the right thing to do"?
Do I have biases with regard to that kind of decision?
Do I have tendencies dealing with past decisions? (You might feel particularily proud of certain things, you might tend to certain regrets, even remorse.)
How does the decision affect others?
Can the decision be done as an experiment, changing course later if appropriate?
What is unique in this situation and about me in this situation and how can I turn that to my advantage?
Is there a greater context this plays a role in?
Minimize maximum regret: Which option would I regret the least if it turned out to be the wrong one?
Is it possible to share the decision with others?
Is it possible to change the decision so that it is easier?
Did something happen in the last time that felt like a sign? (Might your subconsciousness pointing out something.)
Is there a bigger context for the decision that needs considering first?
Does the decision have the potential to be a "The Situation Is Hopeless, but Not Serious" (by Paul Watzlawick) style self-trap to make you unhappy?
What type of decision maker are you? What impact does that have?

Use AI

Besides talking to other people, of course, I think that using AI is usually a great idea because AI has different biases than you and your peers and also isn't as dedicated to make you happy as your friends are. AI is creative in a different way than people, so it will give you other ideas than your peers. It has infinite patience. So you can try to look at the problem from many different angles. So talk to an AI! Some specific ideas about that:

If any of the tasks here feels too mentally or emotionally draining for you, ask the AI to do it, and improve the results if they do not fit. That's certainly better than not doing it at all.
Describe your thoughts (e.g. about all the topics above) and then ask the AI to give you a number of ideas about what you forgot.
Have it list more options you have.
Have it simulate some situations you might be in because the specific option you choose.
Ask it for more questions to ask yourself.
Have it summarize your points.
Play roles:
- simulate other persons / you in the future
Have it do parts that troublesome for you
Ask it how it can support you in this regard.
Maybe abuse it to take some responsibility you do not want.
Have it review your progress in making the decision.
Make a log about your decision process, and ask the AI to review it and give you feedback on what you missed and your timing.

And so on. For some of the topics you can make a dedicated ChatGPT chat and talk about them again and again. An interesting technique is to talk ant talk again with fresh chats, while collecting the insights you get in a document, and then feed that document to a new chat and start again. Make a document with links to each chat.

If you like - you can try out a Decision Dialogue GPT that I fed with the thoughts above. So, have fun with that! :-)