The problem with most goal-driven plans is that most goals are fake, and so are most plans. One way to fix this is to fantasize.
There are lots of domains where someone is trying to plan for success, but instead of having a clear compelling objective in mind, they have a vague sense that something's not right yet, plus some made up goal that sounds good.
Sometimes the mind censors out goals or plans for achieving them, on account of your first idea being impossible, improbable, wrong to want, or you just don't know how to get it. Often one can route around this by explicitly fantasizing. In my experience, once there's a fantasy version, it often becomes pretty obvious what the real-world analogue is, and it feels awesome, way more motivating than "shoulds".
To get more clarity on a goal, it helps to flesh out a vivid fantasy picture of what you want. To come up with better plans, it helps to start with such a goal and backwards-chain to a plan.
Here are some ways to get started.
Backwards-chaining: how to fantasize a path to your goal
Making your own luck
Prompt: What lucky event would give you the thing you want? What causes such events to happen? Can you influence that process?
Example: A friend was complaining that most of their good business opportunities came from fluke events. I asked them, what would have to happen to produce more of these fluke events? They responded, that they’d have to have more chance conversations with people who had relevant business problems. And it was immediately obvious to them that they could do something to increase the rate at which such conversations occur, by going to more events for businesspeople and talking with them about their problems.
Laziness (or, problem easification)
Prompt: What if the problem turned out to be easy? What lucky event would make it already solved? Then figure out whether you can make that happen.
This sort of thing often leads to a simple potential solution like “Google it,” or “ask a friend for a favor”.
Example: A friend was trying to figure out how to get themselves to practice the guitar more when they got home instead of just going straight to sleep. It turned out that if, when they got home to their room, the guitar was near at hand and they heard music that they wanted to play, they felt that it would be easy to get themselves to play. But getting the music to play seemed difficult - would they need to set up some sort of automatic switch to start it when they opened the door? Would they need set up a button and the habit of pressing it when they got home?
So I asked - what would make this trivially easy? And the answer came - if the music were already on. They didn’t need to set up any system beyond just leaving the music on repeat when they left for work in the morning.
Example: In talking with people about career decisions, often they'll be planning to go to school to qualify themselves for a career. Generally they've neglected the step of directly trying to get the job they want, or talking with people who have it to find out what, if anything, their qualification gap actually is.
Example: My original plan for the Effective Altruism Society of DC was to first build up the membership so we had a large group, and then find people in this group committed enough to work on a project together. But then I realized that this would be easier if I already had enough people to do this. I asked - and I did - and that's how we got started on doing independent cost-benefit analyses of regulations. I left DC, but with nearly no additional effort on my part, Matt Gentzel continued this work and turned it into a more formal project, EA Policy Analytics.
Fantasizing: how to connect with your goals
Set the scene
Prompt: Come up with a literal fantasy version of the thing you want. You're allowed to have floating cities, or dragons, or magic powers. You don’t have to, though. You’re also allowed an extremely large budget, etc.
Example: I spent a few minutes fantasizing about the ideal apartment I’d have, and one of the items it ended up including was a giant stained-glass window with a Mondrian-like pattern. So when I started figuring out how to decorate my room, I bought window film that mimics this effect.
Greed (or, uninhibitedly listing all the desiderata)
Prompt: List out all the attributes you want, don't worry about which ones are more important or whether you can get them all.
Example: A couple of years ago I was trying to think through various potential next career moves, and it felt hard to compare them, partly because it didn’t feel like my criteria were real. So I decided to make a list of everything I wanted in a job, regardless of how achievable it was.
The first thing I came up with was that it should make me a billionaire, because that seemed so obviously better than that not happening. Then I kept asking myself “what else?” until the list felt like everything I wanted. I listed out some other things, like strong positive impact on the world, lets me have and enjoy nice things, strongly compatible with spending time with my friends, work I’d be interested in talking and thinking about with friends and colleagues. By the time I was done with the list, it was obvious that being a billionaire was clearly the most difficult item on the list - and also, not very valuable to me if I could have all the other things. So I was able to confidently take it off the list - and the remaining set of things felt very achievable.
Envy (or, finding an exemplar)
Prompt: Is there someone you know or have heard of, who has the thing you wish you had? Is there a character in an existing fictional story who seems to have the thing?
Example: Miranda has a good example of using the fictional envy criterion to notice something she deeply wanted:
It wasn’t until this August that I convinced myself that this wasn’t a failure in my rationality, but rather a difference in my basic drives. It’s around then, in the aftermath of the 2014 CFAR alumni reunion, that I wrote the following post.
I don’t believe in life-changing insights (that happen to me), but I think I’ve had one–it’s been two weeks and I’m still thinking about it, thus it seems fairly safe to say I did.
At a CFAR Monday test session, Anna was talking about the idea of having an “aura of destiny”–it’s hard to fully convey what she meant and I’m not sure I get it fully, but something like seeing yourself as you’ll be in 25 years once you’ve saved the world and accomplished a ton of awesome things. She added that your aura of destiny had to be in line with your sense of personal aesthetic, to feel “you.”
I mentioned to Kenzi that I felt stuck on this because I was pretty sure that the combination of ambition and being the locus of control that “aura of destiny” conveyed to me was against my sense of personal aesthetic.
Kenzi said, approximately [I don’t remember her exact words]: “What if your aura of destiny didn’t have to be those things? What if you could be like…Samwise, from Lord of the Rings? You’re competent, but most importantly, you’re *loyal* to Frodo. You’re the reason that the hero succeeds.” [...]
So. I’m Samwise. If you earn my loyalty, by convincing me that what you’re working on is valuable and that you’re the person who should be doing it, I’ll stick by you whatever it takes, and I’ll *make sure* you succeed. I don’t have a Frodo right now. But I’m looking for one.
[...] I’d like to live in a world where an aspiring Samwise can find role models; where he sees awesome, successful people and can say, “yes, I want to grow up to be that.”
Maybe I can’t have that world right away. But at least I know what I’m reaching for. I have a name for it. And I have a Frodo–Ruby and I are going to be working together from here on out. I have a reason not to walk away.
Prompt: If you could write any story you want and it would happen to you, what would you like to happen? Start the story as late as possible, and go from there. Don’t go sequentially, just tell the parts of the story that have to happen.
Example: One morning, about a year ago, I was feeling pretty sad, so I asked myself what would be a story for something that could happen that day, that would cheer me up. It seemed to me like doing a badly needed favor for a friend would be a great way to spend the day. Someone would call me up and say, “Ben, I need your help on this,” and then I’d rush out of the house to go take care of the thing. After that, I’d have momentum, plus a sense of value and accomplishment, and it would be easier for me to go on with my day.
So after a bit of backwards-chaining I posted the following on Facebook:
Is there anything you would like from me today? Don't limit yourself to things you think I'm likely to want to do. Not guaranteeing I'll say yes, but I'll try to make you glad you asked.
People responded, and I did a few things, and then I felt a bit better. It wasn’t quite what I’d hoped for, but it was a lot better than nothing.