The Art of Making Hard Choices


Many years ago someone asked me in a job interview what I want to have happen upon my death.

I told the interviewer that I wanted the devil to call G-d and say “you better take him, because we can’t handle him.”

What I learned that day was the guy behind the desk was a man of significant faith and he thought it was inappropriate for me to speak about the devil in such cavalier terms.

Since I realized it was unlikely I would be offered a position and was certain I didn’t want to work for him I added my standard question/answer about why the devil went down to Georgia and not LA.

That didn’t go over very well either but I was ok because I knew beyond a shadow of a doubt I didn’t want to work there.

Life is always easier when the choices we have to make are easy but ease isn’t always available because life is filled with big decisions that are made harder because you can’t determine which decision is the best to make.

The Art of Making Hard Choices

Many years ago my family and I went on a day trip with my in-laws.

Since we had a Honda Odyssey that would seat everyone we figured it made sense to all travel in one car. It was a nice idea that lasted for all of 20 minutes.


Because my in-laws managed to find  a way to make me so angry with them I drove them back to their house and told them to get out of the car.

As you might imagine my wife and children were not happy and the ride down South was ugly. I was the only one who wasn’t crying and if I told you I didn’t second guess my decision I would be lying because I did.

But it didn’t happen in a complete vacuum.

Five minutes before I decided they had to go I pretended to have a bathroom emergency and pulled over at a gas station so that I could try to calm down.

I remember the moment vividly because I called my dad and said I had a question for him.

He asked me what I needed and then I shared my side and said, “I need your best advice.”

Dad laughed and told me that he couldn’t tell me what to do.

“This is your decision and I have confidence you’ll figure it out.”

“Dad, there is an art to making hard choices. I was really hoping you had figured it out and could help me.”

“Jack, try not to splash paint in your mother-in-law’s eye while you are painting and remember sometimes the best precedent you set is the one you don’t take. But don’t forget to establish clear boundaries either.”

He was laughing as he hung up the phone but I understood why and I made the best decision I could which is why they got kicked out of the car.

A Father’s Advice & A Man’s Choice

Why did I think about that story today?

Because I am in the midst of this transition I keep talking about and it is filled with some decisions that are more challenging in nature than whether to wear black or blue slacks.

And because last night my son asked me for some advice about a few things and I realized I couldn’t give him the kind of black and white answer he was looking for because sometimes it doesn’t exist.

But it didn’t stop me from thinking about what sort of advice and counsel I should give him. That Emerson quote above came because it fit my search for answers about hard choices.

“It is a reminder that the big things we try to do/achieve start with small steps and or gestures.

How Can I Make Better Choices?

The 17 long time readers know I don’t carry many regrets around with me.

That’s because I see little upside beating myself up about what I could have done. Doesn’t mean that the few regrets that I have aren’t substantial because they tend to be huge.

Those are the ones where I sometimes shake my head and wonder why I didn’t make a better choice. But I also know that some of that regret comes with the benefit of hindsight.

I can see what happened and pretend that if I had gone the other way it would have been better for me.

But even though I don’t spend much time wondering and worrying about what I could have done I still like to think about ways to make smarter/better choices.

Remember I am the dad who talks to his kids about working smarter and not harder whenever we can.

And that is how I came across a TED talk Ruth Chang gave about How To Make Hard Choices.

I thought it was interesting which is why I embedded it into the post and am sharing the excerpt below with you.

“So when we face hard choices, we shouldn’t beat our head against a wall trying to figure out which alternative is better. There is no best alternative. Instead of looking for reasons out there, we should be looking for reasons in here: Who am I to be? You might decide to be a pink sock-wearing, cereal-loving, country-living banker, and I might decide to be a black sock-wearing, urban, donut-loving artist. What we do in hard choices is very much up to each of us.”Ruth Chang: How to make hard choices

I like the idea of using hard choices as another tool to identify who we are and who we want to be.

How about you?

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  1. Mitch Mitchell April 24, 2015 at 9:40 am

    You know what the secret is to making hard choices? Listening to your own intuition, which is what you did with your mother-in-law. Now, at least half the time you’ll have the option of doing research or getting the opinion of others but that means half the time you don’t. Most people just react to a situation without giving it any thought and that’s what leads to big problems. Instead, if most people took at least a minute, thought things through, then went with their intuition, it often ends up being the best decision for them… if not everyone else.

    At least that’s how I see it. 🙂

    • Jack April 24, 2015 at 10:55 am

      Hi Mitch,

      I used to be hesitant about relying upon my intuition because I wanted to make decisions about things based on rational thought. But as I have gotten older I have learned to rely upon it and found it frequently has been very helpful in making choices that make me happy.

      [image: –]

      Jack B.
      [image: http://]

      “When you’re in jail, a good friend will be trying to bail you out. A best friend will be in the cell next to you saying, ‘Damn, that was fun’.” —

      • Cathy April 25, 2015 at 11:24 am

        I agree with you both, Mitch and Jack. Impulsive decisions are rarely good ones, and unless it’s a life or death situation, there is always time to reflect a bit, then make a decision, whether it is intuitive or just by process of elimination.

  2. Cathy April 22, 2015 at 4:57 pm

    Enjoyed the clip but about 2/3 of the way through it stalled. I got enough of it to get the gist. I can’t remember having a lot of hard choices in life, but as with so many people, I have had regrets. I tend to chew on them for a while, then let them go, although some of the heavier ones return for a visit to perch on my shoulders occasionally.

    My in laws were jewels and we got along great. I have had difficulties with other people in my life though, and had to deal with things the best way I could. Funny, but the older I get, the blunter I get and the less I care what others think of me. I wouldn’t call it wisdom, just an I don’t care attitude.

    Enjoyed this and it sure resonated with me.

    • Jack April 22, 2015 at 5:43 pm

      When people tell me they don’t have any regrets I almost always wonder if they are drunk, high or lying.

      It is just part of life to wonder what could have been or would have happened if we chose a different path.

      I understand getting blunter as we age because I certainly see that happening with me too.

      • cathyjonest April 23, 2015 at 1:04 am

        I agree Jack. I don’t think there’s a person alive who wouldn’t change a thing or two at the least. I often wonder what direction my life would have taken with other choices. Not that I dwell on it, more out of curiosity at this point (I’m 62and curiosity isn’t dead yet!).

  3. Jack April 21, 2015 at 2:59 pm

    This is a test comment using the new Postmatic comment by email system.

  4. Gary Mathews April 21, 2015 at 4:26 am

    I had a similar episode with my ex in-laws once, I ended up walking two miles home just to get away from them they had me so stressed.

  5. Larry April 20, 2015 at 6:56 pm

    Interesting thought about hard choices there.
    I can’t believe you kicked your in-laws out. Your wife must have been pissed! You have guts!

    • Jack April 21, 2015 at 12:22 pm

      She was and I do. But the reality at that time was I could not conceive of spending two hours in the car both ways with them.

      There was no way terrible things wouldn’t have been said so ‘exile’ from the car was the lesser of two evils.

  6. Janine Huldie April 20, 2015 at 5:07 pm

    Definitely going to watch this Ted talk no, because as you know I have only a few regrets like you, but that are pretty substantial also indeed. And yet decision making on the whole has never been very easy for me. So I could use all the help I can get!

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