2 Ways to Make a Really Tough Call – Opening to Wisdom

We all face times where we go back and forth on a difficult decision that we have:  Do you accept the job offer? Do you let somebody go? Do you hire person X or person Y? Do you raise a tough issue with your partner, or when you pick your battles, is this one not worth fighting? How do you know?  Before you go further:  Think of the toughest decision that’s running through your mind, and then….

I’d suggest two complementary paths:  Knowledge and Wisdom. 

The Knowledge Method is likely familiar to you, but you may not have done it this time, or you may have rushed through it. I encourage you to use it now with the toughest decision you face.

The Wisdom path which I write about below the Knowledge path is IMHO (in my humble opinion) powerful new stuff, but let me warn you that it will take longer, because it involves major paradigm shifts and some time to do it right.  I would encourage you read on to the Wisdom path if you have time now and an issue you really want to tackle.  But you may choose to print and/or save it to test it out when you have time and mental space to do it.  It’s powerful to do yourself, or with someone else – helping them or you to find wisdom in a tough spot.  So, first the easy and helpful knowledge path:

Knowledge . . . 4 steps

  1. On a sheet of paper make two columns with your basic choices at the top. They might be Yes or No, or Hire X or Hire Y, or Raise-the-Issue or Suck-it-up and let-it-go).
  2. Exhaustively list all of the things in each column that support that decision.
  3. Decide which of those pro’s and con’s are really salient, truly important to your core values. Of all the things you’ve listed, some will seem minor, while others will appear to matter greatly. Circle the important!
  4. Make your best choice. Yay. Know your best choice is your best choice. Do it. Move on.

And here’s the deeply promising path of…


  1. Identify the two choices and put them at the top of two columns.
  2. Take each choice and in the top part of that column respond to this question:  “What about this choice strongly aligns with my core principles?” Or as I would ask, “In what way would making this choice be me ‘leading with my best self?'” Let that stand, drawing a line below it.
  3. If your decision feels clear, then you will only seek wisdom about that choice by asking this question.  If your decision does not feel clear, then you will repeat the following steps with the questions that follow:
  4. “What voices in me are resisting this decision?”  Give them names.  Here are some examples of important inner voices that many of us have:  The Pleaser. The Logician. The Skeptic. The Imposter. The Fearful One. The Inner Critic. My Spouse’s Voice in me (or Mom’s Voice, Dad’s, boss’, pastor’s, etc.).
  5. Identify the one voice, or the very strongest voices that seem to be resisting.  Name and list them.
  6. Step away from those voices and any anxiousness they cause you and instead, identify with Your Best Self. This is Wisdom. This is your inner Solomon. This is the Good Judge. I call this the Caring Curious Listener (CCL, for short). I imagine my mentor-friends, Fr. Canfield or Rebecca Parker, as my CCL, because they are the best listeners I have ever known. They listen equally with their heads to “get it” and their hearts to “get me.”
  7. Now write a dialogue, where one character is CCL and the other is the strongest resisting voice. You will alternately be the Caring Curious Listener (CCL) — whose job is NOT to resolve your dilemma, but simply to impartially and empathetically listen.  The CCL asks open, non-judgmental questions with that resisting voice. And then let that voice answer CCL’s questions — as if it is not you but is just that particular Voice given full freedom to share his/her point of view.  So, a dialogue about a hard choice might look like this:

CCL:  Is this the Imposter?

Imposter (Imp):  Yes.

CCL: You don’t like the idea of Dan (referring to myself in the 3rd person) deciding to do X. Is that right?

Imp: Yes. (the Imposter might continue, or CCL might need to ask, “Why?” and the Imposter would continue):  Because he’s never faced a decision like this. He’s acting cool, but deep down he has no idea if he should do that, if it will work at all.

CCL: Why do you think he has no idea?  What do you think he’s missing? (CCL is not judging or arguing, but is just trying to understand Imposter better)

Imp:  He’s never faced a decision that involved so much money. He’s not that great at numbers. He nods in meetings like he gets it, but you and I know he’s not sure he’s fully tracking.

CCL: And so that worries you? (Note how CCL is asking Imposter to continue and is not, is never arguing.)

Imp:  Hell yes! If his boss knew that he doesn’t know, or if he makes this decision and his boss finds out…God help us all!

CCL: Got it. That’s unnerving. (Notice how CCL empathizes. He gets “it” and he gets the Imposter.)

CCL might ask more, for instance, “Has Dan gone out on a limb before, and made you feel like the Imposter?” But at some point, he will move towards (some variation on) this next question:

CCL:  I get that you’re not sure Dan knows what the hell he’s doing. What could he do that would make you feel better about his making this decision?

Imp:  I don’t know.  Maybe run it past his friend Fred who’s got so much financial experience. Or maybe take a smaller step before he commits to this full-blown strategy.

CCL:  Got it. Those things might make sense. (End dialogue, but CCL might go back to another Voice of resistance and repeat the process.)

The point of this dialogue is…what?  That we know!  If we listen to ourselves — especially to our inner critic(s) – we can understand why the decision is so hard for us.  Hard decisions are personal and emotional, not just logical. A part, or many, of ourselves is emotionally involved.  It’s why we say “I feel conflicted.” There is inner conflict, a battle of sorts playing beneath our arguments and our conscious minds.  In this case, the Imposter (a genuine part of Dan/me and most of us) fears repercussions, being revealed, being laughed at, possibly being fired.

Dan’s Best Self may decide, “yep, there’s just some risk” and plow ahead.  However, like a good boss or good parent or good politician who has heard from a disgruntled or fearful follower, Dan would be well advised to explain to the other (in this case, the Imposter) that he’s heard the pushback, but feels it’s important to move forward, taking the risk.

Of course, as you can see from this example, the conflict is not just emotional, for the Imposter actually does have substantive points to make.  So more likely Dan will not just grit his teeth about his shaky financial acumen and push ahead willy nilly, but instead, thanks to Imposter’s help Dan may see ways to mitigate the risk, e.g., talking to Fred, whom the Imposter suggested.  So, Dan is not only lowering his inner ambivalence and conflict, but also strategizing on the outer realities, finding a way to push forward without putting himself at some extreme risk.

I have found this method of dialogue enormously helpful to myself and have used it with many clients.  They may journal a dialogue for us, or I may play the Caring Curious Listener, isolating their dissenting voices, so they can be more at peace with themselves and they can capture their inner wisdom.

I’d love to hear your experience at accessing your deep inner wisdom as you

Lead with your best self!


  • This, as always, arrived at the perfect time. I am printing and framing it. I hope you don’t mind. Thanks, Dan. Keep LWYBS!

  • Sherry,
    Please hear this in the voice of Moe from the 3 Stooges: “Whaddyou, some kinda wise guy?”
    Seriously, thanks for the generous and kind words. I’m glad you found value!

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