On Big Decisions

Asking The Right Questions To Get What Where Who You Want?

Over christmas time last month, I sat down to watch a movie with my brother.  I flipped around the channels and landed on Family Man.  It’s not a great movie – I swear I don’t like romance comedy dramas – but there wasn’t much else on, and we were both in that “gotta watch a movie” mood.

Early in the movie, the audience is made aware of a decision earlier in Jack’s life.  He had been dating Kate when he was younger and had the chance to move to Europe.  He knew that leaving Kate would end their romance, but he left anyways and 20 years later he’s a super rich wall street dude who has everything money can buy.  He mysteriously wakes up one morning to find himself married to Kate with 2 kids, a job selling tires, and a small house in New Jersey.  He get’s a glimpse at what life would’ve been like if he hadn’t have gotten on that plane 20 years earlier – if he made a different choice.

Initially he’s confused and angry and wants his Ferrari and Armani suits back.  Eventually, he finds that he likes this new, simple, low stress life better than the old.  However, he can’t keep it as it was just a glimpse/gift from an angel or something like that.  When he wakes up as the wall street guy again, he goes and finds Kate and true love and happily ever after.  Truly a heartwarming story.

Anyways… this got me thinking about big decisions and regret.

Some decisions in life are easy.

You can take a week vacation to the Florida Keys or you can get a colonoscopy.  Pick one.

The important, hard decisions are the ones we stress over.

Should I take this job offer in New York, or stay in San Francisco?  Should we buy this house, or rent the one a few blocks over?

Those are the one’s I’m after.

Several months ago I had to make a big decision.

Quit a job that I liked, and leave a place I’d loved and called home for over two years, Jackson Wyoming.

Or, continue at a job that had a ceiling approaching, and stay in a town where I preferred to have a beer and ski rather than learn how to create this website.

If I leave I don’t know what I’ll do.  I don’t have a job waiting for me.  I don’t even really have any skills other than what I’ve been using here.  Plus I like my job here.

If I stay, I won’t learn that much more because given the options of choice powder turns and micro brews, or sitting in a cafe and learning wordpress, I choose POW[1] and cold beer.

I left, and right now I’m happy with that decision.  I think it was the right one.

We all want to be happy with our decisions.  So how do we make sure, when faced with big decisions, that we make the right choice.

To make sure we’re happy with our decisions, we need to figure out where happiness comes from.

I introduce to you… synthetic happiness.

Actually I’ll let Dan Gilbert introduce it to you in his TED Talk.

If you haven’t seen it, watch it.

If you have seen it, watch it again.

He explains that we not only have the ability to create happiness no matter the outcome of the choices we make, but this manufactured happiness is just good as natural happiness[2].

Human beings have something that we might think of as a “psychological immune system.” A system of cognitive processes, largely non-conscious cognitive processes, that help them change their views of the world, so that they can feel better about the worlds in which they find themselves.

So, what does that mean?

It means if I had stayed in Jackson, I’d be skiing waist deep POW yelling “I’m so glad I didn’t leave!!!”

I’d be happy with my choice.

Now I’m confused…

So the decision to leave Jackson was the right one, and the decision to stay in Jackson was the right one?


Repeat – When faced with difficult choices, you will be happy with either decision, because you will naturally change your worldview to feel better about the decision you made.

You’ll have the same capacity for happiness, with either choice.

So that doesn’t help… should I just flip a coin?

Not yet, let’s try something else.

We can’t seem to figure out the right choice.  You’ll be happy with both, they’re both right.

Instead let’s figure out which choice is wrong.  The choice we’ll regret.

Last week I ate a whole medium pizza from domino’s and felt like shit after it.

I regretted it.

But we we’re talking about whether or not to start a pizza company, not whether to eat the 8th slice of pizza.


Most people don’t seem to regret the big decisions they’ve made though.

Remember the four people Dan talked about.

Jim Wright who “lost everything” said he was better off, seeming to have zero regret for the “shady book deal he had done.”  Moreese Bickham said “I don’t have one minute’s regret” after being wrongly in jail for 37 years.

However, there are a few regret’s that we all seem to share.

I’ll get to those in a minute, but first check this out.  In Steve Jobs’ 2005 speech at Stanford, he shared how he made big decisions.

When I was 17, I read a quote that went something like: “If you live each day as if it was your last, someday you’ll most certainly be right.” It made an impression on me, and since then, for the past 33 years, I have looked in the mirror every morning and asked myself: “If today were the last day of my life, would I want to do what I am about to do today?” And whenever the answer has been “No” for too many days in a row, I know I need to change something.

Remembering that I’ll be dead soon is the most important tool I’ve ever encountered to help me make the big choices in life. Because almost everything — all external expectations, all pride, all fear of embarrassment or failure — these things just fall away in the face of death, leaving only what is truly important. Remembering that you are going to die is the best way I know to avoid the trap of thinking you have something to lose. You are already naked. There is no reason not to follow your heart.

When I read this I think… Wow, that’s really inspiring.  I’m going to go live out all my dreams right now.  Or right after I finish this pizza.

Then I wake up from my coma and am not so inspired anymore.

It’s a little unfair anyways.  If I knew I was going to die today I certainly wouldn’t have gone to Starbucks all day to write a blog post that maybe ten people will read.

Plus, how can I really think about being dead soon?  I like the idea, but in the end I know I’m only 25 and probably have at least another 50 years to go.

Maybe we can ask people who are dying soon what they think?

Better yet, I’ll see if Google knows someone who’s already done this.

Bronnie Ware was a nurse for terminal patients for many years.  She listed the biggest regrets her patients had, and this was number one.

I wish I’d had the courage to live a life true to myself, not the life others expected of me.

Bronnie goes on…

This was the most common regret of all. When people realise that their life is almost over and look back clearly on it, it is easy to see how many dreams have gone unfulfilled. Most people had not honoured even a half of their dreams and had to die knowing that it was due to choices they had made, or not made.

Let’s look at some more of Jobs’ speech.

No one wants to die. Even people who want to go to heaven don’t want to die to get there. And yet death is the destination we all share. No one has ever escaped it. And that is as it should be, because Death is very likely the single best invention of Life. It is Life’s change agent. It clears out the old to make way for the new. Right now the new is you, but someday not too long from now, you will gradually become the old and be cleared away. Sorry to be so dramatic, but it is quite true.

Your time is limited, so don’t waste it living someone else’s life. Don’t be trapped by dogma — which is living with the results of other people’s thinking. Don’t let the noise of others’ opinions drown out your own inner voice. And most important, have the courage to follow your heart and intuition. They somehow already know what you truly want to become. Everything else is secondary.

I think he was onto something.

Matthew O’Reilly is a first responder who tells people they’re going to die.  He explains that once people accept death he notices a few patterns.  Most notably, people need to know that their life had meaning.

I’d like to do what I can in life to avoid the regrets that the dying seem to share.  By the dying, I mean you and me and everyone on earth.

So with each big decision, I’ll ask myself two questions in this order.

  1. Is it something I want to do, and not just something others want me to do?
  2. Will it add meaning to my life?

Ruth Chang, a philosopher on decision making, talks about hard choices.

When we choose between options that are on a par[3], we can do something really rather remarkable. We can put our very selves behind an option. Here’s where I stand. Here’s who I am… This response in hard choices is a rational response, but it’s not dictated by reasons given to us. Rather, it’s supported by reasons created by us. When we create reasons for ourselves to become this kind of person rather than that, we wholeheartedly become the people that we are. You might say that we become the authors of our own lives.

So when we make big decisions, we’re really just choosing who we are going to become – what our beliefs will be, what type of friends we will have, what ideas we will value.

From the movie, Jack who chose to get on the plane, chose to become a person who values money, nice cars and suits.  Jack who chose to stay with Kate, chose to become a person who values his family and friends.

So YOU have to figure out who YOU want or don’t want to be.

You’re the author.  How do you want your book to read?


  1. POW = powder.  For those of you unfamiliar with ski lingo, powder is that fresh snow that all skiers crave.
  2. Actually there’s no difference.  Only a perceived difference.
  3. We can’t think about choices like numbers.  Ruth explains that when one choice isn’t better than another, the choices aren’t equal, they’re “on a par.”

About the Author