A member of the Thinking Lab asked me for advice on how to decide whether to join a small startup or stay with his very successful, stable, lucrative job at a large company. Let’s call him Max. Max had done a lot of thinking about his choice, but he still had some nagging doubts. People had been saying he needed to make a “leap of faith” to join the startup, but he wanted a firmer basis for his decision. I would, too.

There is an objective problem in making such a high stakes decision. You simply do not know how the future will unfold — and it has significant implications. If the startup succeeds, Max could become extremely wealthy. If it fails, he could use up all of his savings and put his family’s security at risk.

Some people claim that the “rational” method for making difficult decisions is to assign probabilities for costs and payoffs of various outcomes, and then calculate the overall expected value for each option. The option with the biggest expected value is supposed to be the one to choose.

I disagree that this is a rational approach to a decision that is inherently uncertain. First, the probabilities for the different outcomes are guesses. Second, the costs and payoffs for the different outcomes are guesses. Third, this method necessarily reflects your preconceptions of the risks and rewards. It amplifies any subjectivity in your decision-making process. It does nothing to help you expand the context of considerations so that you see as far as possible, understand the risks and rewards as clearly as possible, and make the decision as objectively as possible.

In contrast, a rational approach helps you be more objective. It helps you to activate and hold the full context for the decision. That context includes known facts, important values, and areas of risk. Once these are clear, you can make a judgment call based on all of that information.

The concrete method I teach for getting this clarity is called “Decision Cards.” Roughly speaking, you create a card for each option, putting positives on one side, negatives on the other. Then you systematically examine all of the negatives to translate them into equivalent positives for the other options. There’s a bit more to it than that, but the effect is that you reconceive the decision entirely in terms of values, and then you can choose your direction while “holding all of the values with care.”

For most decisions, you simply write down positives and negatives off the top of your head. However, in a high stakes case like deciding whether or not to join a startup, I recommend additional steps for due diligence. There are so many long-range implications of the choice that it’s difficult to come up with them all off the top of your head. You need some way to bring more of what you know to bear.

My method takes off from the “pre-mortem” developed by Gary Klein for planning. In his method, you imagine that your plan results in a total fiasco. Then you reflect on how that could have happened, and make contingency plans to try to avoid it. What I love about the “pre-mortem” is that it uses your imagination to visualize possible outcomes, which gives you concrete scenarios to explore. It gives you something useful to think about.

So here’s my adaptation for high stakes decisions: Do some “awfulizing” about what might happen, and then give yourself an “empathy bath” for all of those awful potentialities to get fully clear on the values at stake. Then you can continue with the usual decision-making process.

Let me just walk through how Max might come up with these awful scenarios and investigate them to help him make a solid decision.

First, he’d imagine that he went with the startup, but it was a disaster — it struggled or went bankrupt. Here are some of the awful consequences he might imagine:

• This would radically reduce his savings at a critical point in his career that would make it hard for him to educate his children and live a comfortable retirement.
• He might never again get as good a job as he has now.
• The failure could result in ill-will between him and his partners, meaning he’d lose longtime friends.
• The failure would create terrible strain on his marriage and family, because he would have been working insane hours to try to save the company. He might become estranged from his wife or children.

On the other hand, he’d also need to awfulize what might happen if he stayed at the big company and the startup succeeded. Here are some more awful consequences he might imagine:

• He might feel lousy about having been afraid to try it.
• He might feel bored and a little burned out with the same old job.
• He might work just as hard to do well, with the same negative effect on his marriage and family, but with no offsetting personal meaning
• He might see himself as a person who had even less of a “startup personality,” so he was even less ready to seize the next opportunity, thereby sabotaging a major life goal

Now, mind you, I just made these up knowing little about Max’s real concerns. But we’ve all had these kinds of negative thoughts. The negative thoughts that occur to you easily reflect your latent concerns. These are a very important source of information, worthy of further investigation.

This is a bit contrarian. You may believe you should eliminate your negative self-talk. Indeed, the cognitive therapy school of psychology specifically teaches people to catch and correct these kinds of exaggerated negative thoughts — that’s where I got the term “awfulizing” from. Let’s face it: these thoughts are exaggerated, overly negative, and totally depressing. If you believe them, you’d never do anything. You’d be totally paralyzed.

And yet, they are leads to deep rational values. Your deep rational values.

These are emotionally charged thoughts. Where there are emotionally charged thoughts, there are deep values at stake — values that you may not be aware of, but which are important enough to have triggered confusing, contradictory emotions that are strong enough to paralyze you.

So, although I agree that it’s important not to get lost in negative thoughts, it is also important not to fear them or feel you need to get rid of them. There are no unthinkable thoughts. Rather, I believe the best approach is to get very curious about them, and what underlying values they reflect.

The path from experiencing negative, destructive thoughts to identifying deep rational values goes through introspection. In particular, I recommend the method I call the “empathy bath.” When you give yourself an “empathy bath,” you systematically explore 8 families of emotions — both positive and negative versions, for 16 emotions total. For each emotion, you ask yourself why you might be feeling it in relation to the decision.

For example, one of the families is despair/hope. Based on the awfulizing I imagined above, Max might feel despair, because it seems like no matter what he does, his family life could suffer. On the other hand, he might feel hope, that knowing that’s a risk will help him plan to avoid it.

Awfulizing triggers a lot of emotions; the empathy bath clarifies them.

The last step of the empathy bath is particularly important when you are making long-range decisions: identify the deep rational values that underlie every affect-laden or evaluative statement in the preceding work. The shortlist of deep rational values is available in the OFNR Quick Reference Sheet.

For example, Max’s concern about the family reveals a need for connection with them, and perhaps balance. His concern about boredom reveals a need for intellectual stimulation. His concerns about money reveals a desire to cherish and support his family.

The final step is particularly important, because naming the deep rational values clarifies the full context for the decision. Whenever you have an ambitious goal, you will face conflict at times. Pursuing one value will necessarily mean that other values get less time and attention. The constructive way to deal with conflict is to get crystal clear on all of the values at stake, and then choose the top value — the priority. The priority is not the only thing you do — it’s the most important. The priority is the one that gets the first call on your time and attention — but not all of your time and attention. When you know your priority, you can use that clarity to help allocate your energy to your other values.

When you make a decision based on top values, you can’t go wrong. Either it all works out, and you succeed. Or, you discover that the path you thought was the path to your top value was mistaken in some way — and you can correct your course. In either case, you stay focused on positives, not fears or regrets.

This is a short essay on a huge topic. I include references to the specific tactics I mention for further reading.

The bottom line: If you face a high stakes decision, take some time to get clear on all of the deep rational values at stake. Once you are clear on them, you will be able to choose a direction with confidence that you are pursuing what matters most to you.