optimize, How Hard Decisions Become Easy Choices

optimize, How Hard Decisions Become Easy Choices

I want to take this at face value and start categorizing people in these two camps. But I can’t. It’s not that neat and clean. The truth is that no one is wholly a simplifier or wholly an optimize. We are both. We each possess the ability and desire to simplify in some situations and optimize in others. We regularly teeter between the two poles.

When are we simplifiers?

We simplify when we work with the familiar. We optimize when we work with something new. Look no further than the way a new hire behaves in their first week on the job. They tend to optimize, doing everything the best the can, staying on high alert for every suggestion, request, or need. Over time, this changes. The new hire becomes an experienced veteran who can see through the noise and pick out the two or three things that need to be tended, leaving out the rest, to deliver something “good enough.”

So familiarity … that’s one determining factor.

Another is the number of priorities we try to manage. We often simplify when we have just a few priorities. We optimize when we have many. Want to eat something? Well, if your priority is something cheap and salty, the choices are pretty easy. But if you want something that tastes good, is healthy, sustains the planet, contains no artificial ingredients or GMOs, and is locally-sourced, then you will have a harder time. That’s a lot of priorities. It isn’t simple. It’s optimized.

And it makes us neurotic. This is the horrible effect of managing multiple priorities. It implies multiple needs. Which lead to multiple demands. Which result in multiple sources of stress.

Demand Is The Engine Of Stress

The National Institute of Mental Health offers the clearest definition of stress:

Stress is how the body and brain respond to any demand.

This explains why high-end restaurants stress me out. Despite the elegant setting, the warm atmosphere, the wonderful service, I feel anxious every time. Why? It’s the demands I place on myself. I want to (a) have a good time, but (b) not look like an idiot, and (c) order what I want, but (d) not order too much, and (e) act like I’ve been there a million times.

These self-imposed, conflicting demands are impossible to satisfy. And that’s just one small example. But if you toggle the switch to simplification, and go with a single priority (have a good time), the stress reduces greatly. And often just melts away.

So how do you relieve stress? Yes, exercise helps. Sleep does wonders. Relaxation, too. But those are treatments of symptoms. The innermost cure for stress is a simplification. Reduce the demands you choose to satisfy and you will reduce the stress you feel. Keep the main thing the main thing.

It makes the stress manageable. You’ll find it makes decisions easier, too. Especially when you combine it with one excellent principle for decision-making.

Binary Beauty

Derek Sivers has offered a lot of great wisdom through the years and his most popular guidance is found in the book Anything You WantIt reads as follows:

If you’re not saying, “Hell yeah!” about something, say no.

Simple, right? Indeed. In fact, this is how you transform the hard decisions of life into easy choices. It’s simple, beautiful, and oh-so-accurate.

But as Derek himself would say, simply doesn’t mean easy. What do you do when nothing ever feels like a “hell yeah?”

The short answer is you do nothing. Nothing major, anyway. Instead, you continue searching, experimenting, taking small bets, and humming the U2 song, “I Still Haven’t Found What I’m Looking For.”

See? It’s so simple. And incredibly hard. Because the plain truth is that saying no to most things will feel suboptimal in the moment. And because we are both simplifies and optimize, this feeling will spark a war within us.

Conflicting Advice

Recall the old expression: A bird in the hand is better than two in the bush.

Or the other expression: Don’t let perfect be the enemy of good.

Or the other expression: Don’t wait for the perfect moment. Take the moment and make it perfect.

Or the other expression: Nothing is more expensive than a missed opportunity.

I could go on and on. If you are looking to say no to something, these and countless other adages can and will be used against you in the court of choice. Because these bits of wisdom strongly compel us to say yes to everything. If applied on a certain level, these bits of wisdom run counter to “Hell yeah or no.”

Our heart can tell us one thing. Our head can tell us another. And both have plenty of timeless wisdom at their disposal. How can we pick sides?

Head Versus Heart

I’ve made a lot of big decisions. Some by saying “hell yeah” and some by ignoring Derek’s wisdom. To my peril. In every instance where I’ve violated the rule, it’s because I’ve considered the opportunity, felt the tepid interest in my heart, drifted immediately to say “NO,” and then recognized that feeling of loss.

Because when you say no to something, you lose the chance to find out what might have been.

That feeling of loss is something we all hate. So loss aversion, as a bias, kicks in. That bias sends a bat-signal to our rational mind. The rational mind then grabs its tattered cape and pocket protector, takes to the skies, quickly swoops in with charts and graphs in-hand, and starts shouting at your heart. “Don’t say no! This opportunity is 10% better than what you have today! That’s marginal gain! There’s nothing else on the table! Don’t wait for the perfect moment! Bias to the action! YOLO!”

Thus the battle of head and heart begins. I can tell when it happens because the time horizon for a decision stretches out quickly. Obvious answers get lost in new countervailing evidence. Sub-priorities by the dozen rise up in mutinous anger to overwhelm the Top Priority. Then I get lost. I go back and forth, talk to others, and basically use the time to wear down my instincts. Rationality claims victory and I then say “Okay.”

Not “hell yeah.”


Then I do it. Whatever it is. And it’s fine. But because it isn’t a “hell yeah,” it gets tedious as well. Tinged with soft regret. Eventually, I let go of regret. I move on. But that’s a lot of work to say yes to something that was going to be a “no.”

Maybe it’s just me. Have you experienced anything like this?

Priorities — There Can Only Be One. Okay, Three.

This battle between the head and heart is a shift from simplifying to optimizing.

In the instances where I’ve abandoned the “hell yeah” principle, I’ve used rational processes and multiple sub-priorities to override my instinctual “No” with a classic adult “Yes.” Not because it’s natural. It isn’t natural. Instead, because it’s difficult. And we often think that BIG DECISIONS must require difficult thinking.

This is true. Many big decisions require difficult thinking. But I’ve often confused “difficult thinking” to mean rational thinking. As in, “Gee, that’s a great opportunity. I need to think about it. Give me five weeks and I’ll get back to you after I’ve weighed every pro and con under the sun.”

That triggers overthinking, a problem studied and solved in the review of Algorithms to Live By. And any mention of overthinking requires me to recall the beautiful passage from the 1710 Japanese classic, Hagakure, The Book of Samurai:

Lord Takanobu said, “If discrimination is long, it will spoil.” Lord Naoshige said, “When matters are done leisurely, seven out of ten will turn out badly. A warrior is a person who does things quickly.”

Which is to say that making big decisions can be a difficult process. But it mustn’t be a lengthy one.

It should be a discipline that makes big decisions difficult. Not time. As highlighted in the review of Greg McKeown’s Essentialism:

Yes, it takes discipline to apply tough criteria. But failing to do so carries a higher cost.

Derek Sivers’ “Hell yeah or no” is the toughest criteria of all.

If you’re an optimizer.

So don’t be an optimize. Don’t try to solve for multiple priorities. Or if you do, stack them. Make a pyramid. One priority must be at the top. Always.

Indeed, it already is. It’s called Happiness. In reviewing Daniel Gilbert’s brilliant book, Stumbling On HappinessI finally accepted the truth that even the most rational person is still just a heat-sinking missile in search of joy. Call it contentment. Call it tranquility. It’s all the same.

So from that single top-most priority, which we all share, figure out the next two priorities that lie adjacent-but-underneath. One might be personal growth. The other might be independence. optimize Or community. Or risk. Or art. I don’t know. But when you figure it out, you have a trifecta. That is all that you need to become a simplifier. In fact, it’s imperative to have nothing more.

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