Things I've learned about making decisions

some tips and tricks

A friend recently texted me about how she’s not happy in New York, and she’s not sure what to do about it. She tells herself that it’s because she’s been spending too much time at work and not reaching out to people enough to make social plans. But then she wonders if this is just cope, and actually, New York is not the right place for her, and she should move to San Francisco instead.

This is the question at the heart of much of our turmoil: am I making up rationalizations for why I should do this thing (e.g. move to a new city), or should I actually do it? Is my mind giving me excuses or is my mind giving me the truth?

The unfortunate reality of it is that there is no formula for figuring out the answer to this question in all cases. Our mind is a genius at making up excuses and rationalizing things when it wants us to believe something, so you generally can’t figure out the answer by thinking through the excuses themselves.

One of my main heuristics for this question is: Which way do you lean when you’re most happy and most confident in yourself? I recently made the decision to move to San Francisco myself, which has felt like a big and scary decision for a while, and some days I wonder if I’m just deceiving myself with the fantasy that life will be “better” in another city. But when I feel this doubt, I generally I go back to the moment where the decision felt clear: I was having an absolute blast there, and I thought to myself, yea, I actually really want to try this city, and anything else I say to myself is just cope for fear of making a life change.

Another thing I’ve realized is that you will never be totally sure. So it’s better to just give one path a try than to wait until you’re 100% confident in what the right decision is. It’s always tempting to wait so you can collect more information, but the more you wait, the more the situation in front of you continues to change (e.g. job prospects change, or some friends move from one place to another), and so you’re once again “behind” on having all the information you need. Also, there are some bits of information you only get once you actually choose one path or the other, and usually those are the most salient pieces of information (e.g. having a sense of what your actual social life would look in a city will only become apparent once you’re living there), so you will never have all the information you need.

Which way do you lean when you’re most confident? Or perhaps right after you’ve prayed, or had a really long, cathartic meditation? What do you feel when you’re most curious? Generally my motto is to follow curiosity and excitement, rather than fear. Of course, this motto is a corrective for what is, in my case, an underlying tendency to avoid risk. Maybe you’re the opposite and tend to lunge yourself into things fearlessly, causing needless strife for yourself—in which case, your motto should be “measure twice before cutting once.” In my experience, though, very few people are like this, and most people are too risk-averse, too averse to change, too constrained by their fears.

Generally, don’t spend too much time thinking about decisions. Now, this is hard to implement if you’re neurotic. One corrective for this is to lower the stakes of any decision, even a big one: you’re already doing fine, and you will not find heaven on the other side of your big decision. For the most part life looks the same, whether you take this job or that job, whether you live on this coast or that coast. No, I really mean that: it’s still you living that life, with all your neuroses and tendencies to doubt your decisions and your insistence on overweighing external factors on your quality of life. You’re the one that’s gonna be living in that other city or working that other career—you, the one who’s always wondering whether some other path would have been the right one—so you’ll still wonder now and then whether you’ve made the right decision. The life change is not gonna resolve all your insecurities.

There’s a deeper question here, which is: who are we, and how much of who we are is dictated by our environment? How much of our happiness is dictated by our circumstances? I don’t think there is a general answer to this question that will be useful for everyone. Of course, the happiest person on earth will probably be fairly miserable in a torture chamber, and the most neurotic person on earth will probably be pretty relaxed living in a luxurious communal home with loving friends and a bunch of cute dogs and cats. But my personal heuristic is to remember that I will overestimate how much my environment influences my happiness, and that wherever I go, I will carry the baggage of all my memories, personality traits and bad habits. And this is fine, because it also means that wherever I am, I am free to choose in any moment to let go of all my memories and personality traits and bad habits and instead respond to this moment with true presence, taking it in as the shining, novel, brilliant ray of experience that it is. I’ve found, for example, that sitting for eight hours a day quietly with my eyes closed and only eating two meals and not talking to anyone and having pretty much nothing else to do the entire day actually substantially increases my subjective quality of life (i.e., meditation retreats), and so I hesitate to hold any strong assumptions that I need some specific external factors to “truly be happy.” Remember how I said our brain is endlessly creative at coming up with excuses? It’s also endlessly creative at adapting to new environments.

Of course, your environment does have some influence on you. If you have nice art installed on your wall and a big window that lets in sunlight, you’ll have a slightly larger number of moments in the day where you go, “ah, beautiful.” If you live with good friends, you will feel substantially more relaxed when entering your home than if you live with strangers. If the weather is not too hot and not too cold outside, you’ll be more inclined to take long walks, which are likely to make you feel more energized and alive. But still, what I’ve found is that even with all these environmental supports, it’s possible to be utterly miserable, and it’s also possibly to be totally thrilled, and that’s just how this little brain of ours rolls. Your brain might operate differently—I know at least one person whose wellbeing is perfectly correlated with the amount of sunlight in his room, and I simply can’t relate to this, as someone who happily lived for two and a half years in rooms that never got direct sunlight.

The main thing I’ve learned about decisions is that you can never really know the right answer. We often ask ourselves whether we “should” be doing X or Y, and sometimes these should’s aren’t even about the specific decision itself (“should I live in New York or San Francisco”), but about the meta-factors relating to the decision, like “I want to go with the flow but I feel like I should have a longer-term plan.” Who said that you should have a longer-term plan? Who said that you should make decisions based on a spreadsheet versus a coin flip? The funny thing is that if you inspect a lot of your feelings that you “should” do this or that, you find that underneath them is fear and shame, not anything having to do with moral duty, which is ostensibly what the word “should” was originally about. Ultimately our tendency to ask what we “should” be doing stems from a desire to abdicate responsibility for our life and to have some external authority tell us what to do. And listen, I get it—for most of history we did have an authority tell us what to do (perhaps our parents, or our tribe, or our religious customs), and it just happens that today none of those influences have as much authority as they used to, and so we’re left with figuring out all the “shoulds” for ourselves, as individuals. My ask is that you face this reality head on, with poise, and recognize that at this particular time in your life and in history, you are responsible for deciding what matters. Sometimes a life decision is just a matter of taste, and other times the decision has actual moral import. Either way, embrace it and just choose.

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Thanks to Susie for feedback on earlier drafts.