How To Avoid Life’s Biggest Regret

If you had just one moment left to live, just one chance to do one last thing, what would it be?

Suddenly, your mind would focus and you would know.  Maybe you know now already, if your imagination and your vulnerability are strong enough.

What if you had three moments?  Five? Ten?  A week, a month, a year?

Of course, the irony is that we all have no more than one moment left as far as we’re aware.

And yet.

And yet, when asked what their regrets were, people who were close to death said “unfulfilled dreams”  was by far the biggest regret.

There’s a funny thing about dreams.  They seem both small and impossibly big.

Small, in that we haven’t even begun the work to make them happen.  They’re a whisper in the dark of our minds, just an idea, just a possibility.  They’re no more real than the wind that rushes by our faces.  Existing and then not, coming back and then disappearing again.

Big, in that we see the ones who have followed the dreams to the end, and we can’t imagine how something so small inside of us could grow into something so large.  We want to do standup comedy, and we see Bill Burr standing in a theater of thousands, while they scream and clap and laugh at every single one of his jokes.  We wonder, how on earth… how on earth can my little dream of comedy reach such heights?

Of course, we don’t see the years he sweated it out in the small comedy venues.  The times he got heckled off stage.  The times when he was just starting out.

But still, our minds have a way of looking at the product instead of the process.  And so our dreams stay in the small stage, as we look out in anger, envy, and finally neutral acceptance at those who have lived their dreams to the fullest.


And yet, we all will be in that hospital, hospice, death bed one day.  We will all have to look back, and we will all have regrets.  Will our top regret also be the dreams we haven’t fulfilled?  Will we be like everyone else, or will we look to the message of those whispering to us from their beds right now?

What is it that these people on their deathbeds know better than us?  After all, they had just as little a chance of making it “big” with their dreams as anyone.  Why would something that is so small, a whisper, matter to them so much?  Why would they regret not chasing it?  If most dreams are but whispers, and unlikely to become big, then wasn’t it wise to focus on achievable goals?

Because when we see dreams as small when they are ideas and big when they are achieved, we have it backwards.

When a dream is just an idea, it is expansive.  It is huge.  It is infinite.  Because we haven’t started to give it shape yet, it lives in a world beyond shape.

You see, all your dreams are the wonderful potential of the person you are meant to be, the infinite and utter incredible life you could lead.

In other words, when we turn that infinite, shapeless mass called a dream and we bring it down into the world, we are literally turning the spiritual into the physical.

In other other words, dreams aren’t fulfilled when they are achieved in some grand way.  They are fulfilled at any moment that we choose to live them out in our lives.  At any moment when we say, “I will sit down/stand up/step forward/open my mouth and do this.”

In that sense, the first step towards living a dream is the most powerful, most incredible, most beautiful moment in your life.  Every single time you take a first step towards achieving any dream, you are achieving the equivalent of giving birth.  Something from nothing.  As close to God as humans ever get.


Take that first step, then.  Push aside thoughts of the big results at the end that only few achieve.  Inject yourself with thoughts of the inherent worth of living the life your soul is crying out to live.

One standup show.  One piece of writing.  One business venture.

Start.  And you’ll have already achieved the dreams that those in their death beds are lamenting that they didn’t do.  It is not the finishing that anyone regrets, it is the not beginning.

So begin.






One response to “How To Avoid Life’s Biggest Regret”

  1. Moshe Hendel Avatar
    Moshe Hendel

    Thanks so much for this. This has been on my mind lately, but especially today. I’ve been hearing alot about finding the right balance, but can’t seem to resolve it with the demands of life. Something or more will always give way. Do you have an practical tips about how to give a small shape to large dreams?

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