The Anatomy of a Good, Tough Decision by Being Oneself

(7 minute read)



I. Introduction

One strong impression sticks with me above others from my law school days.

I would read a monumental Supreme Court Decision—one of these hotly debated 5-4 decisions. It would be something of great import to the nation.

I would read the majority decision. I would think, whoa, thank god. Hot damn. They got that one right. They nailed it! (I almost feel like Napoleon Dynamite when I say that last part.)

Then I would read the dissenting opinion. I would then fill with doubt. I would no longer be so sure.

These were the brightest legal minds our nation could offer. They could dive into the nuances and legal intricacies and swim gracefully. They could see far-reaching practical implications. They could identify deep ethical and moral considerations. Of course there were brilliant arguments on both sides of such crucial issues.

And this is in many respects like every important decision we face. We do not have 9 judges deliberating on our options. Yet our minds can create brilliant reasoning to back each possible alternative.

For many, this can be a daunting challenge. It can be easy to freeze in the headlights with indecision. It’s pretty common.

A tough decision is the type that has a huge bearing on the quality of our lives. It calls on our power of contemplation, self-reflection, soul-searching.

I present a framework here for working through a Good, Tough Decision (GTD). I provide simple, concrete examples as we go along.

As always, I aim to add texture to self-reflection. I don’t offer a set of rules to avoid self-reflection.


II. Start from the Inside Out

Before we get to the step-by-step, let’s start with the biggest key. Attitude is more important than what we decide. Attitude is about process. Process is in our control, outcome is not.

Navigating life means no fool-proof plans. Living with increasing maturity means embracing uncertainty. Bringing our utmost to the process is the best we can do. It's rewarding. We can look back with self-acceptance and minimal regret if we approach the process with care.

But we typically place much more attention in the what than the how and why.

We sometimes neglect to see that the what is the most superficial aspect of the decision. The decision is best served when we dig deeper, into our core. Deciding who you choose to be relative to any particular situation is an act of self-creation. It’s an act of declaration to yourself, to others, to life, to the universe. Its best when it comes from the Inside Out. An Inside Out decision is much more satisfying and effective than an Outside In approach.

An Outside-In approach complicates the process. It focuses on the what. It elevates superficial appearances above our natural inclination. Our ideas of who we are supposed to be and how we want to appear get in the way of what we actually feel and want. The fight between who we are supposed to be and who we actually are brings on self-judgment and labels. It emerges from limiting beliefs.

Let’s try a simple example to illustrate. Let's say we hold the belief that it’s cool to be the type of person who says “yes” to things. We believe saying yes is taking a plunge and being open to life. This can be at best a half truth. It can’t apply 100% of the time. Life is too vast to simplify and generalize like that. It doesn’t pay to make this a rigid rule, harden it into a “final solution” that applies regardless of context.

We give away our power to discern what is actually right for us when we try to live up to a final solution, a set way of being.  Context rules.

Saying no to someone or something can be in fact the strongest way to say yes to ourselves. So, the bias of saying yes interferes with who we actually want to be relative to this situation. It’s a superimposed dogma that we have not yet challenged. It influences and limits us unconsciously. It creates a disturbance in the decision making process. It creates the feeling that there are more than two sides inside you. The challenge is realizing which internal voice feels more core. What is the "should" here and what is YOU?

Our challenge is to identify what the noise is and cut through it. We want to give ourselves permission to accept what we actually want. We want to validate our own experience. This means that we are “allowed” to want what we actually want, instead of what others around us think we should want.

When we honor our actual inclination rather than a pre-defined notion of who we are supposed to be, we relax. How many times have we heard the advice to be ourselves? It often is difficult. It’s our formidable idealized self-concept and vanity that get in the way, never other people. I honor the challenge we face in this.


III. GTD Framework

The challenge calls on us to proceed with self-awareness, self-responsibility, and self-trust. What do those qualities look like in practical terms?

These qualities mean recognizing no option will create pure advantage only. If it’s a tough decision, there will be some downside to any course of action. There is a price to be paid. We often don’t want to embrace or hear that. We sometimes get lost wishing for life to be different than how it's showing up in the moment. It can take the edge off for a sec, but it’s in the end pointless and unconstructive.

Determining what we want given the circumstances and the downsides is an act of maturity. Like the judges, "5-4" type decisions mean not all parts of ourselves will be thrilled.

Here's a guiding principle. Our core/heart/intuition provides our most effective, powerful, satisfying decisions. Our reasoning power will understand and follow our heart after we feel into our best option.  Yet, when we can’t feel our best option, we need to use our power of reason to make the decision.

The steps below can support our reasoning process when it is not clear what our heart wants.


Step 1: Hear yourself think.

When it's hazy, we don’t have access to feeling into the options with sufficient clarity.

Let each alternative speak out its strongest argument. Listen to each side of yourself from a place of spaciousness and objectivity. Try to listen for what resonates with you most. See what sounds like appearance-based concerns. Try to detect what your core actually wants.


Step 2: Speak it out with a good friend.

If you speak it out loud to a friend, can you feel something new as you speak? Or can they reflect what it sounds like you actually want? Sometimes it’s not so much hazy as rather we aren’t willing to accept the downside of our preferred choice.

It’s rare that there isn’t at least a 55/45 inclination one way. The challenge in this case can be more about willingness to follow through. We may have sufficient clarity for a 5-4 decision but be in denial about the downside, the price to be paid.

Don't take your friend's reflection back as the absolute truth either.  That can be an easy way out.  See what you learn and what resonates with you.  

You may already have your GTD if you can feel that inclination and are willing to maturely accept the price.

In steps 1 + 2, we have been seeing if we could discern the voice emitting from the core. The following steps tap further into our power of reason in the absence of that.


Step 3: Dropping the RIGHT decision.

Unhealthy attachment to finding the RIGHT decision brings complication. The practical consequence is placing undue pressure on ourselves and creating unnecessary stress. Often this attitude connects to our fear of uncertainty and our fear of making a mistake.

It’s worth reminding your fear that you are strong enough to handle whatever comes of this decision. You have been in challenging situations before and you came out fine. And you always learned something. What happens when we let go of the idea of one right decision? We can navigate with more calm and tranquility.


Step 4: Shifting towards curiosity and experimentation.

A great remedy for this type of block is taking the attitude of a scientist conducting an experiment. Gandhi titled his autobiography the Story of My Experiments with Truth. True science can happen in our own lives, from the intentional willingness to learn from experience.

We can’t possibly know how something is going to turn out. What is the more interesting experiment to conduct? This means shifting one’s attitude towards curiosity about possibilities. That's more practical than the attitude that this is some sort of, say, final exam.

Here are some questions that can feed the inner scientist. Perhaps not all will be directly relevant to your situation. The point is to move back to your center, be as mindful as possible, and take an action that you can be proud of.

Giving one's best is a tastier recipe for the well-lived life than dependence on things turning out as we insist.


  • In what ways is this challenging decision actually something positive? (There are always some.)
  • What have you done in this type of situation before? How has that turned out?
  • What further information could have a bearing?
  • What is your hypothesis about each course of action?
  • What steps are in your power to prevent and limit the downsides?
  • What options would you have to address worse-case scenarios?
  • What decision gives you the best chance to learn something interesting?
  • What personal values are most important to express in making this decision?

All along the way, we are still listening for clues from our intuition.  Yet we may not know what our core wants.  If that's the case, then we simply pull the trigger based on the best our inquiry and reason can bring us.  Maybe we sleep on it one more night.  But we don't allow the indecision to linger indefinitely.  Investing in process can also become distorted if taken too far.   


Step 5: Double-check.

Even when the decision approaches clarity, it can help to entertain and double check the other option(s). This means letting the dissenting opinion speak out its most stellar argument. Hearing out the dissenting opinion can offer possibilities to strengthen the course of action. Sometimes there is a valid consideration easily addressed. 

But sometimes the dissenting opinion gets personal at this stage, bringing self-harshness. It is good to be aware and prepared. When this tone emerges, it’s usually based on rigid ideas of what is right and wrong. It wants to create labels that you are not living up to and demean you for that. It neglects to see the nuances of the situation. It definitely works against your own self-acceptance. It can be very insistent and persuasive.

If you stand firm after hearing out the noise, your conviction and resolve strengthen. It also means that you can look on the decision knowing you did it as consciously as possible.

This also gives us insight into the part of ourselves that is actively working against us. These observations can be precious because we know what it sounds like and how it operates.

This is all part of bringing our utmost to the decision-making process.


IV. Conclusion

Step 6: Aftermath.

It will never be possible to know what the other alternative(s) would have yielded. In the classic Choose Your Own Adventure books, you could retrace steps and discover where the other trails led. Life doesn’t afford that opportunity.

In the aftermath, the dissenting opinion may not let go. It may be bitter and try to pick moments to launch into doubt, regret, or attack. When you followed what you actually wanted and gave the utmost of yourself to the process, remember not to jump on that train. Simply don’t feed it without needing to fight and resist it either.

We will always have the comfort or burden of knowing how much or little we invested ourselves in the process. The better our process, the more readily we will live with the outcome. I wish you  well with your GTDs.