Three Things #20: June 5, 2022
On making difficult decisions successfully
I’ve been struggling with some big personal and professional decisions recently. Hence, this week I’m going to write about the process I use to make difficult decisions. I hope it’s helpful.
Thing #1: Start With Values
Values aren’t particularly sexy and in my experience they tend not to get a lot of attention. There was no class in high school, or even in university, on how to discover one’s values and construct a value system around them. And religions are more likely to impose their prescribed values on you than to help you reflect and discover your own. Yet knowing your values is absolutely essential to happiness and success. This has always been true, and I suspect it’s even more true today given the way modern society seems to be losing its grip on reality. Once you’ve taken the time to understand and reflect on your values, they become the bedrock of your personality and sense of identity. They’re especially useful in times of stress, challenge, and conflict, and when you need to make a hard decision. Without knowing your values, you’re really in the dark dealing with these difficult situations because you have no foundation upon which to base your decision or actions.
The starting point is asking yourself big questions like, What matters most to you in the world, and in your life? What motivates you? What makes you feel excited to get out of bed in the morning? What brings you the most joy? What would you die for?
Many people will immediately think of things like love, kindness, generosity, freedom, and creativity. But there are probably many other things you value. Some of my other values are curiosity, integrity, excellence, gratitude, and patience. There’s no specific, optimal number of values, but based on personal experience I suggest you try to choose between five and ten (less than this feels incomplete, and more than this is unmanageable). Choosing your values is more of an art than a science, but as you read descriptions of the things lots of people tend to value (here’s a good starting list), some will inevitably speak to you more strongly based on your own life experiences.
It’s also helpful to try to rank your values: in other words, rather than a list of values, what you really want is a value system, so that when you’re inevitably faced with the choice between two actions that represent two different values, you don’t get stuck. One of my highest values is freedom. If faced with the choice between, say, excellence and freedom—e.g., considering a role that would give me the opportunity to do great work, but that would require me to sacrifice a lot of personal freedom—then I will always err on the side of freedom. It’s really, really helpful to reflect on these values and how they relate to each other, and pre-commit to your value system ahead of time so that, in the heat of the moment, seemingly difficult decisions can become much easier.
Reflecting on your value system is literally one of the single most valuable things you can do in your life. And it’s something you should do periodically, because while your values don’t change radically, they do evolve over time. I do an annual self-reflection and review process at the end of each year, and reviewing my values and how they and their relative weights have shifted is an important part of the process—and an important part of updating my understanding of myself and who I am, and how that has evolved over time.
When I have to make a difficult decision, I begin by spending some time reflecting on my values. I re-read the list, spend some time thinking about each one, and just sit with them. I consider why I chose that value in the first place: what was the formative thought or experience that led me to value that above all else? Often, this is enough by itself to make the decision: it will be made for you because it’s clear which path is most in line with your values.
Thing #2: Weigh the Pros and Cons
Whereas the previous stage is more open-ended and reflective, the next stage is more rigorous and methodical. If reflecting on and weighing your values doesn’t quite get you across the finish line, the logical next step is to rigorously weigh the pros and cons of each option.
I like to do this the boring, old-fashioned way. Take a big sheet of paper, draw a line down the middle, and list the pros and cons of choice A on the left, and the pros and cons of choice B on the right. If you’re quantitatively minded, you might try assigning weights: something that’s a small potential benefit might get a +1, whereas something that’s a huge negative might get a -3 or even a -5. (Of course, this assumes you’re choosing between two options. If there are more than two, the same logic still applies, or you might try pairing options against each other.)
A good strategy is as follows: start by listing all the pros for choice A. Brainstorm and write down as many as you can. Next, go over the list and write down a “response” for each for B. In many cases, B may have the same benefit, so you can give it the same score. Or, B may have a greater or lesser benefit, or even a con. Next, brainstorm again and list additional pros of choice B that weren’t already covered, and repeat the process of “responding” to each one for choice A. Finally, repeat this entire process for the cons. At the end of this process, tally the number (or weight) of pros and cons of each column. While the actual score should be informative, what’s probably even more important is how you feel about it. If A has a much higher score than B, but that somehow nevertheless feels wrong to you, that’s a sign that your heart is telling you B is the better choice! (Exactly how much weight you choose to assign to the rational, quantitative score vs. the “gut feeling” is up to you.)
Note that, with this strategy, you can stay as high level or go as deep as you like. For a really tough decision I often try to be thorough and do a breadth-first search and build a tree of consequences, going two or three layers deep and trying to really think through the second- and third-order consequences of each choice. Obviously you don’t have to be so thorough for this exercise to be useful; by the time you get to second- and third-order consequences, you’re speculating anyway. (As a result you may also want to assign lower weights to these higher-order consequences!)
One more piece of advice. Novel ideas, and resolve in response to tough decisions, rarely emerge from a vacuum. They tend rather to emerge through processes like meditation, dialogue, and reading. Personally I find that sitting down, putting on my thinking cap, and just trying to intentionally make a decision tends not to work very well. What works better is putting some distance between myself and the problem. Spending time in nature tends to be especially effective. Go for a walk, a run, or a hike. Go swimming or climbing or skiing, whatever floats your boat. Let nature talk to you for a little while. Answers to difficult problems often tend to emerge this way, when you approach your problem from a different angle. Don’t be surprised if the resolve you need to make a decision suddenly appears, unbidden, inside of you somewhere.
Thing #3: Decide and Get On With It
If I had to give just one piece of advice about making decisions, it would be this: what you decide is much less important than simply deciding with confidence and boldly moving forward.
It’s very easy to get stuck in analysis paralysis when trying to make a hard decision. It often feels like the perfect solution is just around the corner: by doing just a little more analysis, giving yourself one more day to think about it, or asking one more person for advice, you’ll magically find it. But the truth is that, as with so many things in life, there is no one, perfect solution to any hard choice or decision. There are always many possible solutions. If you pick a reasonable one and feel confident about it, you will do just fine.
This is especially true if you’ve followed the above advice. If you’ve reflected on your values, done some analysis, and there still isn’t a clear winner, that’s a strong sign that it doesn’t actually matter which you choose. And there isn’t that much more that you can do, anyway, other than make a decision and move on.
This is true for at least two reasons. One, we actually create our own luck and our own fate through force of will (hence the need for confidence). Two, almost no decision is one you make for life. You can always reevaluate, sometimes much sooner than you think. I know how enticing it can feel when you’re presented with an opportunity, and you don’t know if and when such an opportunity will arise again later. But they always do. Opportunity is always part luck, part hard work and preparation. If you keep working hard, putting yourself in the right place, and preparing to seize the opportunity when it arises, there will always be exciting future opportunities.
When you just can’t make up your mind, flip a coin. Before the coin has landed, you’ll know in your heart which path you want to choose.
One more thing: the moment the decision has been made, you’ll feel as if a weight has been lifted from your shoulders. It feels extremely liberating, like you’re finally free to move on, get back to work, and do great things.
So: take a breath. Close your eyes. Pick, randomly if you must, and get on with your life. Enjoy the feeling of liberation. Move onto the next challenge. And reevaluate in a few months. You’ll do great and you’ll be just fine!