Questions to Ask Yourself When Making Difficult Decisions

Below are a list of questions that I have found helpful when making difficult decisions. The contrast in my mind is between this, what I believe to be, helpful list and that of the unhelpful but more common list of questions that we ask our selves such as: "What will make me the happiest?", "What's the right thing to do?", "What does God want me to do?". Here's my list of helpful questions to ask yourself when making a tough decision:

What choice will I regret more not doing?

Over the years, this question has been the most helpful.  The source of its power is that it accomplishes several things. First, it gets you out the moment and into a hypothetical future scenario where you're looking back at your life from a much more objective position than you are in the present, decision-tense moment.  Secondly, it attunes you to your conscience and in a way that is much more in line with how our brain actually works.  Studies have shown that people regret losses and not doing things far more than they regret mistake decisions or things they've done.  In a clinical setting you can set up scenarios where you give people ten bucks or you can give them forty and then take away twenty.  Which do you think people would be more grateful for?  A small gain or a big gain accompanied by a loss?  People hate loss.  We hate missed opportunities, almost successes, relationships that could have been, jobs that nearly were ours.  

I read an article once written by a hospice worker that stated that when death bed patients look back on  their lives they hardly ever regret things that they've done at the end of their life.  They regret the things left undone.  They regret not loving their family more, not smelling the roses, not taking risks, not going out on a limb, not trying new things, not giving more. So, the next time you're making a tough decision, what choice will you regret more not doing?  A day may come when you're thankful you answered that question.

What choice is more adventuresome?

Life's an adventure.  Your either living an exciting adventure or a boring adventure.  Get off the damn couch.

What makes me feel most alive?

Howard Thurman once said,

“Don’t ask what the world needs. Ask what makes you come alive, and go do it. Because what the world needs is people who have come alive.”

What will I be most proud of doing?

I'm a firm believer that there is good pride (and certainly bad, too).  Good pride says, "I deserve better than to compromise.  I'm worth more than that."  Good pride isn't about comparing yourself with other people.  It's about comparing yourself with 'sin' and saying that you deserve better.

What fits with the narrative/story I want to write with my life?

This question, as the first did, gets you to take a healthy future reverse perspective, but it also gets you to think from an other's perspective.  If a hypothetical other were to read/watch my life, would it make a good story?  What would they think of my character?  Did I live according to my values?  Did I try and try and try and try?  Did I love well?  Think backwards, think outside of yourself.

What is the most fulfilling?

First off, I love the world 'fulfilling'.  I love its imagery--fill so full that your life is brimming over and spilling its abundance and wealth.  And I love how much better it is at capturing that than other synonyms--it's such a better word than happy (sounds like a painted on smile for a photograph) or joy (a little to saccharin for me).  Fulfillment is about feeling good way, way, way, way deeper than superficial happiness can ever reach.  It's about living according your conscience.  It's about making a difference.  It's about giving and loving well.  Fulfillment sleeps easy at night.

In my mind it's entirely possible to live a fulfilling life and not be happy.  I think of a single parent I know.  She works a ridiculous amount of hours at minimum wage; takes care of two kids and an ailing elderly mother; and pours her heart out for students at a church I used to go to.  I can tell by the way she loves people, talks about her job and the way she worships her God that she finds fulfillment in what she does even though her life is often very painful and difficult.  Life is tough, happiness is distant, but she is living life damn well and it's because she's living for fulfillment.

What will bring the most balance to my life? 

It's all about balance.  Between work, social, romance, pastimes, being tough, being soft, working, resting, breathing in, breathing out.  Answer this question and you'll be living rightly.

To which side do I err?

Instead of thinking in terms of actions (Do I do this, or do that?), think in terms of values (Which is more important?).  Recent examples in my life: Question: Should I go out with friends or study more?  To which direction should I err? Answer: err on the side of relationships. Question: Should I donate to this organization even though my budget is tight?  Which choice is better to err on the side of caution with?  Answer: err on the side of generosity and helping others.Question: Should I reach out to this estranged friend or not? Answer: err on the side of building potential relationships.  Values clarify and this question can help suss them out.

I recently realized that I should do a blog on this when it struck me how often I revisit this list of questions I had put together on a Google doc.  I hope they help you as much as they have helped me.  Best of luck with your next difficult decision.  :)