The ‘Difficult But Right’ Strategy

For those on board with doing things right…
For those struggling through a difficult time…

Here are a few elements of a strategy that I use. Things that will always be on the right side of being right, even when things get difficult.

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Avoid breaking my word. I know that in a competitive market, if there are two equally-qualified people in the running, the one with a track record of integrity will get the role. If not, it’s not a place that rewards keeping one’s word, and so it’s not a good place to work anyway.

Produce scary-important work. Out of all the projects I can choose to put my efforts in, there’s a type of project that has higher value in my eyes. If the project produces a dual feeling of fear and aspiration, of making me scared and of it feeling sacred, that project qualifies as ‘scary-important’, and it’s a better project to work on. Few people choose ‘scary-important’ work on purpose, especially when times are difficult.

Invest in things I can’t measure. If I spend all of my time chasing things that can be measured, I might optimize my way into a dead-end. But if I spend some of my time investing in activities for which I don’t understand the reward, I might avoid trouble or get nice surprises when things get tough. I might also avoid regret in the long term, especially around relationships.

Upgrade the relationships I keep. Not all relationships are worth the effort, but the relationships I do invest in are worth being upgraded. The upgrade goes as follows: from dependence to independence, and from independence to giving. Upgrade casting of blame to owning the responsibility, and then upgrade a focus on self to a focus on the welfare of the group.

See constraints as gifts. Most people will want to remove constraints, and seek freedom. Constraints are everywhere, and when they come up, they might as well be seen as gifts for my creativity. A constraint lets me purify my priorities, helps me make better choices when doing design, and teaches me something new about myself.

Expose my risk. My idealism better be useful. There’s no shortage of people with good intentions who are protected from the bad consequences of what they preach. I should aim to get those consequences, if only to make sure my idealism has a healthy contact with reality.

Avoid selling when the person isn’t in motion. People don’t want to make progress until they’ve decided it’s time. When they set themselves in motion, they will be open to new information, they will be making trade-off decisions, they will reacting to an urgency. Selling is about helping people make progress, selling the right kind of help at the right moment.

Only keep a small stack of beliefs. Because the mind is a belief-creation and a worldview-creation machine, I can easily operate on some false conclusions. When there’s a critical moment of decision, and the mind wants to keep a tight hold on some beliefs, it’s the almost always the right move to do the following: pause, inspect the convictions coloring my view of the world, and proceed with what is true. “What am I so convinced of? Maybe these two things can be true at the same time.”

Imagine the end. “Before the end of this conversation… before the end of the month… by the time I can say I’ll have…” Every situation is made better when you time-travel to the end and work your way back to how you got there. Not everything that’s important can be written as a to-do, but all of what’s important can be written in the future-perfect tense. “By the end of my conversation with my spouse, she’ll have felt listened to.”

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There’s no guarantee that these rules will avoid every difficult situation. But in my sense, if I want to avoid regret, I won’t make a mistake if I follow them.