From Shane Parrish’s Decision Making Course

Anticipate the Future.

The Automatic Behavior: Anticipate the future and plan for obstacles.

Wouldn’t it be nice if we could create a telescope into the future so we can anticipate what problems and opportunities might arise as a result of the decisions we make today?

One of the ways we can make the hindsight of our future selves the foresight of our current selves is to use thought experiments.

Basically, thought experiments allow us to time travel and understand how our choices today impact our future reality.

A study conducted in 1989 performed by Deborah Mitchell, J. Edward Russo, and Nancy Pennington found that imagining that an event has already occurred increases our ability to correctly identify reasons for future outcomes by 30%.

First, we’ll talk about arriving at the positive future, and next avoiding the negative one.

Forecasting is what we do when we anticipate what will happen. We’re predicting the future. But when we think in this “forward” direction, we’re more prone to falling prey to overconfidence.

We tend to overestimate what our return on investment will be (whether financially or even in terms of happiness), and we underestimate the amount of work it will take.

A much more effective technique is to work backwards. When we imagine we’ve already arrived at success — we can then “backcast” into the past and see more clearly what it took to get to this ideal outcome.

Working backwards allows us to reverse engineer the amount of effort something takes and overcome overconfidence bias. It also allows us to turn a murky goal into specificity, and transform our insights into action. Finally, it helps us identify what might derail our efforts. And therefore backcasting gives us the opportunity to anticipate and address roadblocks before they arise.

You can think of it this way, forecasting is standing at basecamp and looking to the summit and anticipating the route you’re going to take. You see where you want to go, and you can see a few hundred feet in front of you but you can’t see more. Backcasting is the opposite. It is looking from from the summit to basecamp, and identifying the exact path you took to get there.

A backcasting thought experiment. She says: “We imagine we’ve already achieved a positive outcome, holding up a newspaper with the headline “We Achieved Our Goal!” Then we think about how we got there.”

  • Regarding the decision you’re trying to make, write out what your ideal future is. What is it you want to achieve? Think of the positive outcome that’s worthy of headline news. If you need help, check out the skill “the most important thing.”

  • Take some time to place yourself in that ideal future. The goal is to work backwards. To do that, you need to mentally elaborate on what your ideal future is like. What makes it ideal? What does your life look like? Describe a day in that ideal future in as much detail as you can.

  • Once you’ve got a clear idea in mind, ask yourself: What did I do in order to arrive here? In other words, what behaviors, decisions, and actions did you have to take in order to get to where you are now (in your ideal future)?

  • When you’re doing this exercise, watch out for the tendency to slip into what you “have to do” to get from where you are now to where you want to be. So instead of “I’ll have to talk to this person, and get this information”, frame it as “In order to get to success, I talked to this person and got that information”. Keep focused on what you DID do. The shift is subtle, but it changes responses from things that are often outside of our control or ambiguous, to things we have direct control over.

  • If you’re struggling, slow down and break the path down into tiny steps. If you think back to the analogy of standing on a summit and looking back to basecamp, the first part of the path you want to identify is the last step you took to get on the summit. You don’t look all the way to basecamp. You look down at the rock and snow just below the summit ledge and as yourself, “what was the last step I took that got me on the summit?” Once you identify that step, you go to the one before that, and so on, until you’re back at basecamp. Apply the same thinking to your decision.

Now that you have your path, come back to the present and write down the following:

  • When you’re three quarters of the way there, what are sign you’re on the right track to get to your ideal future?

  • What are the sign at the halfway point that you’re on the right track? When in time will that halfway point be? What are the sign you can measure?

  • Finally, what are sign in the near future that you’re headed on this path? What will you have done, or not done, that means you’re on track for the best case scenario?

Okay, now, let’s talk about imagining our worst case futures — so we can avoid arriving there.

Gabriele Oettingen, who specializes in researching motivation, has found that positive thinking and daydreaming about what things will be like when we reach a goal actually results in little progress towards our goals. Elaborating only on what life will be like without thinking about how hard it will be to get there, can actually hurt us because we’re not preparing for the inevitable pitfalls and obstacles.

Her research over the past 20+ years backs this up in a myriad of contexts. Fantasizing about what we do want is helpful, but only when paired with imagining what will also get in the way.

Anticipating obstacles allows us to avoid them and if we can’t, we at least have a plan for what we’ll do when they’re encountered. In other words, she encourages people to be “negative” and think about what won’t work and how to deal with what won’t work.

In business circles anticipating what won’t work is often called a premortem.

A postmortem happens after the fact, and tells us what the cause of death was. A premortem tells us why a project, idea, or decision will fail — before it fails. So we can try to prevent failure.

So now, instead of your ideal future, imagine you’ve arrived at your worst case scenario. The decision you’ve made has turned out terribly.

Just like the headline in the previous exercise touted something incredible, the headline now reads your worst fear.

  • Regarding the decision you’re trying to make, write out what is the worst case scenario. The outcome that makes headlines.

  • Then, think back at how you’ve arrived at the worst case scenario.

  • Exactly like in the positive scenario, you want to break the steps down as small as you can.

    For example, if your worst case scenario is that everyone hates your new product, you could start with imagining a consumer writing a review saying they will never buy it again. What happened in the moment before that? Maybe they were frustrated. Why were they frustrated? The product didn’t deliver. How? Was it too hard to use? Did it break? Were they not the right target consumer?

    Keep working backwards. What was the marketing that got them to buy it? Or which part broke? Where was that sourced? Maybe the directions weren’t clear? As you can see, when you start with results, you are then able to explore and identify all their potential causes, going all the way back to the decision you are now facing.

Now that you’ve identified your path from hell, come back to the present and ask yourself:

  • What are signs at the halfway point that you’re on the wrong track? (Signs you can measure?)

  • What are signs in the near future that you are headed down the wrong path?

  • What will you have done, or not done, that means you’re on track for the worst case scenario?

Second Order Thinking

We often miss opportunities when we don’t ask the question “And then what might happen?”

And we often miss inevitable problems when we don’t ask “What are the potential consequences?”

As part of our decision making process, let’s zoom out and look at how our opportunities might meet our objectives not just in the short term- but in the long-term as well.

Here’s what’s great about using backcasting from a positive and a negative future, and thinking about second order consequences to map your opportunities in time:

  • You learn exactly what information you need to gather in order to choose a path.

  • You turn amorphous goals into actionable steps.

  • You learn the worst case scenarios, so you can avoid them. And when you know the worst case scenario, you can plan on how to protect yourself from it.

How can I apply this Professionally?

  • Backcasting from your ideal to identify what choices you need to make today to get there is relevant in many professional situations. Here are a few:

  • If you are developing a new product, work backward from the end-user experience.

  • If you are trying to change company culture, work backward from a dynamic, rewarding environment.

  • If you want your company to still be around in 50 years, work backward from the annual report that comes out 50 years from now.

  • Second order thinking has many uses in our professional lives, It helps us avoid the pitfalls associated with just imagining the good, instead of also anticipating the bad.

  • If you’re adopting new software to solve a problem with your current software, can you anticipate the problems the new software might create?

  • We tend to imagine the good things about promotions, but not the bad. If you get that promotion you want, what does the world look like? Do you have as much control of your time as you do now? Will you have to deal with politics?

  • Second order thinking is particular important for hard decisions. If you cut a product, you need to work through what that means for the customers, the team, the offering, the business and so much more.

  • If you let go of an employee, what does that mean not only to them, but their co-workers, customers, etc.

How can I Apply this Personally?

  • When you have career goals, backcast from the future dream scenario to figure out what you need to do to get there. Say you want to leave your current high-stress job and do something creative. First you backcast from what that creative effort looks like.

    Will you have to take a paycut? Will you need to develop some new contacts in different fields? Then you imagine what the rest of your life has to look like in order for you to pursue that creative endeavor. Maybe your mortgage needs to paid off in order for you to take that paycut. Through backcasting, you learn that you need to be making certain financial decisions now in order to get on the path leading to that career change.

  • Backcasting is great for helping you let go of the small irritations that don’e really matter in the long run. If you have kids, imagine what you want your relationship with them to look like in 30 years.

    As you work backwards exploring what you need to do to get there, you’ll likely realize that your efforts are better spent on things like building trust versus fighting with them about cutting their hair.

  • Second order thinking helps put your choices in the context of the long run. A common area where second order thinking has immense value is health. Skipping sleep or exercise today, versus good blood pressure and low stress twenty years from now.

    When you’re reaching for that doughnut, instead of negative thoughts that make you feel guilty, you can just ask yourself, if I make this choice, what are the consequences? Sometimes you want to live with them, and sometimes you don’t.

  • Second order thinking is great for identifying the win-win in relationships. Taking advantage of someone today means you are unlikely to have them in your life tomorrow. When you imagine what the consequences will be of how you treat people, you can make choices now that create a network of positive reciprocal relationships that you can rely on the rest of your life.

You’re Ready to Move on to the Next Lesson When the Following are Complete:

  • I’ve completed the backcasting from a positive future exercise.
  • I’ve completed the backcasting from a negative future exercise.
  • I’ve written our second order consequences for three options I’m considering.
  • I have a list of information I need to gather.

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