7 steps to make difficult decisions more clear - THINKERS Notebook

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7 steps to make difficult decisions more clear

Spencer Greenberg is a thoughtful person.

At his personal website, Optimize Everything, he has nearly 100 essays exploring topics like decision making, habits, rational thinking, emotions, and more.

And if you go to the website for one of the companies he founded, Clearer Thinking, you'll find courses and quizzes that will help you become more rational in your thinking.

Spencer also recently gave a TEDx talk on how to know when to use your gut for a decision and when to be more reflective. 

Basically, Spencer has dedicated his life to helping people think better and make more optimal decisions.

That's our kind of guy.

Which is why we invited him to join us inside of the THINKERS Workshop for our guest lecture series. Check out the details below, because you're invited.

Before we get to that, I want to summarize Spencer's main points from an essay he wrote called Making Really Hard Decisions.

We all face difficult decisions from time to time, and it can be helpful to have a toolkit of strategies we can rely on to make sure we're approaching the decision in the right away.

Here are the seven strategies that Spencer recommends ... then I'll reveal which one really opened my eyes and that I will be adopting for my next difficult decision:

  1. Think about the advice you would give a friend. "Sometimes it is helpful to forget for a moment that it is your own life you are deciding about. This method helps us detach ourselves from the emotions of the situation, which can sometimes prevent us from making the right choice."
  2. List the pros and cons. "Keep in mind that when you come up with the pros and cons of multiple options, you need to have a baseline option to compare against, and this baseline needs to be the same for each of the options."
  3. Do a full cost-benefit analysis. "If you want a formal procedure for making a really tough decision, try this one. Again come up with a list of pros and cons for each option, but this time also come up with three numbers for each of these pros and cons."
  4. Gather data about others who have made the same choices. "It’s important to do this research when possible,  and not overestimate how special or unique your situation is. If things almost always go badly for people that select a certain choice, then they’ll most likely go badly if you make that choice as well."
  5. Visualize the options. "Make sure these visualizations cover both the good and bad aspects of each choice. Spend more time focussing on the aspects of the options that will occur the most, since these tend to have a much greater impact on how good or bad a situation is overall."
  6. Persuade yourself with an essay. "This writing process can help you flesh out your thoughts, analyze the situation more completely, and discover more about how you feel about the various options."
  7. Poll good decision makers. "Think of three or four people who are unusually good decision makers, and unusually careful at thinking through challenging problems. Now, explain to each of them the details of your situation, and ask what they think you should do in the circumstance."

Which of these seven strategies jumps out to you as the one you'll lean on for your next big decision?

For me, #6 really stood out.

I've written before about the clarifying effect of sitting down and writing. It's one of the main reasons I enjoy writing this newsletter each week, because the act of researching and writing it helps me understand and absorb the concepts. It's also one of the reasons why I've adopted Brian Schultz's habit of journaling for 15 minutes every evening. 

But I've never applied this practice to decision making in the way Spencer prescribes, which is to actually write a 400-word essay arguing for one side of the decision ... and then write a 400-word essay arguing for the other side. I can easily imagine how much clearer the decision would be afterwards. 

Which of Spencer's seven strategies stands out the most to you? Will you commit to adopting it for your next difficult decision? (Hit reply on this email and let me know.)

There is much more in Spencer's article than just these seven strategies. He begins the piece with four traps that are all too easy to fall into when we are faced with a difficult decision. I'll let you read those on your own.

Read: Making Really Difficult Decisions (Spencer Greenberg)

Below, you will find three other resources to help you make difficult decisions.

But first, a quick couple of notes about next week's new webinar with Spencer (plus our first Book Club!) inside the THINKERS Workshop ...


This Week in the THINKERS Workshop


On Tuesday, July 7th, we are hosting the first edition of the THINKERS Book Club.

We will be discussing Orbiting the Giant Hairball by Gordon MacKenzie, a book that was recommended by a member of the THINKERS Workshop during our first virtual happy hour a few months back.

If you want a unique, engaging, story-based manual for how to maintain your individualism and creativity in a corporate environment, this books is for you.

Then, on Thursday, July 9th, Spencer Greenberg will join us for a webinar to discuss how to avoid common thinking traps that lead to bad decisions.

We'll discuss probabilistic thinking, cognitive biases, and how to know when to use your gut to make a decision ... plus plenty more.

We hope you'll join us for these two events. If you can't make it live, replays will be posted afterwards.


The THINKERS Workshop costs $99.99 per year (or $9.99 per month) to be a member. If you own a THINKERS Notebook, then you get in free. If you haven't activated your free account, just reply to this email and let me know so I can send you the special link.
Now on to this week's links ...

Yes, you can practice getting better at making decisions


If you’re chronically indecisive, build that decision-making muscle by starting small. Give yourself 30 seconds to decide what you’ll have for dinner, what movie to watch, or whether you want to go out tonight. Follow through on that decision. Repeat. Then work up to bigger things.

Does this give you anxiety? Ask yourself what the worst-case scenario is if you pick wrong. In other words, if you choose a movie that isn’t great, you can turn it off or choose a different movie the next time. If your lunch is lackluster, have something different for dinner. Making small decisions in a timely fashion will help train your brain to think through questions more quickly.

Watch: 4 Steps That'll Help You Cut Through the BS and Make a Hard Decision Faster (The Muse)

Rules can help you eliminate the waste of unnecessary worry


These two techniques — habits and if/then — can help streamline many typical, routine choices we face in our lives.

What we haven’t solved for are the larger more strategic decisions that aren’t habitual and can’t be predicted.

I discovered a simple solution to making challenging choices more efficiently at an offsite last week with the CEO and senior leadership team of a high tech company.

Read: 3 Timeless Rules for Making Tough Decisions (Harvard Business Review)

Seek out the wisdom of experts


Who can you ask for book recommendations on decision making? At Re:Think Decision Making, I asked a crowd that one former ivy league professor called “the best public crowd he’s ever seen” what they would recommend reading. These people are paid to make decisions for a living and want to find every edge they can.

So when I asked them what books on decision making influenced them, you can bet they had a lot to say.
Quote(s) of the week

“It is not hard to make decisions when you know what your values are.”

-- Roy Disney