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Last January, I shared my thoughts on Divine Imperfection: the Joy of Making Mistakesinspired by a Neil Gaiman quote from 2011.

The original post resonated with many people, and I received several private messages and emails with thoughts and comments that folks hesitated to post publicly. And that’s okay too!


A common thread in these private notes was this:

“But is it okay to keep making the same mistakes?”

“Surely you mean just make new mistakes, and not repeat old ones?

My thoughts?

Trying new things unsuccessfully is slightly different from making “true” mistakes repeatedly (e.g. choices that consistently lead to negative outcomes), although some of the underlying factors may be consistent in both.

There is wisdom to be gained from repeating our mistakes… but only if we examine the thoughts and rationale that led us to that same mistake. 

In some cases, folks are not even aware that they are repeating old mistakes, for any number of reasons: they may be operating from a self-limiting belief that they are worthless, undeserving of happiness or are “screw-ups”, leading them to consistent negative outcomes… subconsciously, they may not really want the outcome that their conscious mind is committing too…  they may not have the internal strength or resources to realize that there are other choices to be made… or, they may not be sufficiently self-aware to recognize the repetitive behaviours.

Eventually, the voice of our Wise Inner Self will break through into our conscious mind, with the old or familiar “Oops, I did it again!”

There can be a deep and negative judgment when we witness others (or our Self) make the same mistakes over and over again.

But judgment isn’t productive. 

Standing in judgment may also be an indication of someone’s Shadow side, a reflection of their own fears or beliefs around failure or around the “right” path in life. It may be an indication that there is potential for new insights or growth by reflecting on why one chooses only judgment or criticism on someone else’s journey instead of seeking to understand, to have compassion… or to choose forgiveness if someone’s actions have caused us pain.

Instead of judging, choose to hold space for your Self and others to make different choices, to learn and grow, to move past the failure and ask “okay, now what action can I take that will result in a different outcome?”

Each time we inadvertently or unconsciously make the same mistake, awareness of that choice serves to illuminate our patterns…  and an awareness of our self-limiting thoughts can open us up to new possibilities and enable us to try new ways or paths that will be more successful, productive and rewarding.

This examination of our self-limiting beliefs, and healing them, is also an element of Shadow Work. I have written several posts exploring this concept further, which may support your awareness of your own self-limiting beliefs or shadows:

Transforming Your Shadow with the Third Quarter Moon

Is a “Weakness” merely the Shadow Side of a Strength?

Making the Darkness Conscious

A Yearning for Reflection at Samhain

Those of us in the Northern Hemisphere are in the deep reflective place of Winter. This is a perfect time to tend your Inner Garden, expose the Shadows and self-limiting beliefs, and make new choices or paths for the coming year.