How I Make Difficult Decisions

There’s a decision I’ve been sitting on for the past couple months, which involved making a big change in my life. On one hand I felt like my mind was pretty clear on what I wanted to do, but at the other hand, I kept agonizing over the decision. Back and forth and back and forth. I had all the information, or did I? Every time I came to the brink of making a decision, I made up some excuse for waiting longer. Maybe if I thought about the choice for a little bit longer, I would come to a point where everything seemed crystal clear, and I could jump forward without any regrets. But, strangely, that never seemed to happen.

I feel like I spend a lot of my life in the limbo between seeing decisions and making them. The process starts when I find an important decision looming on the horizon. Do I leave my job for another opportunity? Do I take that new job that’s being offered versus remaining a free agent? Do I go to graduate school? Do I end a relationship that has some good qualities, but that isn’t working out in some way? Do I move cross-country for the promise of a new future? Do I commit to a new activity that will take a large amount of time or attention? At any point in time, at least one major decision always stands in front of me (and the same may be true for you).

There are two major types of decisions in life - the ones that have straightforward answers, and the ones that don’t. A decision with an easy answer will have a single clear upside, and any downsides will feel small and manageable. I’m pretty good with those decisions - I look both ways (sometimes a little too quickly) and then jump (sometimes in the wrong direction). The decisions that tend to trip me up are the ones that don’t have an easy cost-benefit analysis. In making a hard decision, I have to give something up, often in exchange for the possibility of a future payoff. For example, “I’m going to leave my job that pays a lot of money in order to start a new company.” Actually, the previous has been a remarkably easy decision at various points in my life, but it all depends on the circumstances.

The primary tool for decision-making is rational analysis, i.e. “choice X is better than choice Y because of information Z.” The problem is that, with a difficult decision, rational analysis probably breaks down. Choice X and choice Y seem equivalent in some major respect. So I’m not going to reason it out with the information I currently have. Which leads to a few other tactics, namely waiting it out or consulting outside sources.

My usual response when I have a hard decision is to sit on it for a while. At first, it appears that things will get clearer as time elapses, but in many cases they don’t. I get more and more information as I wait it out, but that information is often conflicting, and falls on both sides of the decision. Experience tells me that obsessing about a decision for twice as long will make me about 10% more clear than I was before. And the return diminishes over time. So, if I’m 50% clear on something after 3 days of deliberation, maybe I’ll be 55% after 6 days, and 60% clear after 12 days.

The conclusion is that it makes sense to give myself a reasonable but firm deadline to make decisions. Putting a hard deadline on it tends to work best, since soft deadlines can always be pushed off for later. So, it’s better to make it such that the decision gets automatically made on some particular date if it isn’t made by then. At the very least, that keeps me from obsessing about it ad infinitum. And, if it’s a hard decision, there’s a good chance that either opportunity 

Another common strategy is to ask others for advice (either human or spirit-based advisors). I have a few trusted advisors who seem to make suggestions based (mostly) on my interests. When I have a difficult decision, I usually consult one or more of them before putting anything in stone. But, in general, you have to consider a person's self-interest when asking him for advice. You can’t expect someone to give you advice that contradicts his own self-interest in favor of your own (although, you could make the argument that doing things in others’ best interest will yield a long-term positive effect for you). So, you would never (for example) want to rely on the advice of someone involved with the decision, or whom its effects might impact. Unfortunately, there are many decisions that will probably involve just about everyone in your life (if only peripherally), so it’s better to use other people as a sounding board rather than an oracle.

In the end, it’s important to trust your own gut. There are as many neurons embedded in your stomach lining as there are in your spinal cord, and although that may not actually mean anything to you, it sounds pretty important to me. Regardless, I’ve learned over time that my gut is pretty good at staying in tune with what I really want. So, when I get a feeling in my stomach, that probably means something important is underfoot. For some reason, a negative gut result is probably more accurate than a positive one. If something doesn’t feel right in my gut, then it probably isn’t good for me. However, if it feels good, then I may or may not have all of the relevant information to make an informed decision. I’ve made less than 100% sound decisions because they felt right in my gut, and usually I could attribute this to incomplete information. So, there’s some combination of gut feeling and rational analysis is required.

So, after much reflection, I finally decided to make a decision. I jumped, without knowing what lay on the other end. It felt kind of like jumping off the high dive after spending a long time with my toes hanging over the edge (you know that tingly achy feel). Was there anything worthwhile at the bottom of that pool, or was there just self-doubt? Regardless, with the decision made, I can move into 2014 without looking back (too much).

Happy New Years!