Right now, all over the world, there are well-meaning friends encouraging each other to leave their past behind them, to look to the future with sparkling optimism, and to bury yesteryear’s woes in the sands of time.

However, we ought not forget this ageless proverb: Those who cannot learn from history are doomed to repeat it. This saying, some say, is inherited from this passage by George Santayana (read it slowly):

Progress, far from consisting in change, depends on retentiveness. When change is absolute there remains no being to improve and no direction is set for possible improvement: and when experience is not retained, as among savages, infancy is perpetual. Those who cannot remember the past are condemned to repeat it.¹

Have you ever a exercised rigorous analysis of your biggest regrets? We generally try to forget and “move on” from the consequences of our worst decisions, not go back and revisit them. However, what would be the benefit of dissecting our own regrets in search of common (or casual) traits and patterns? What if we could, as Santayana said, “retain” the past? If we could breakdown our biggest regrets into manageable data sets, would we then not have a helpful tool to help avoid them in the future?

Could analyzing our past regrets be the one of the most effective way of avoiding future ones? Could our past regrets be one of our best assets for making successful future decisions?

I recently tried investigating my own regrets with this tactic in mind. My methodology wasn’t rocket science — nor were the results anything that could published in a peer-reviewed journal — it was just a simple, reflective question: what traits and parameters (if any) do my regrets have in common with each other?

Looking back, I get the sense that most of my regrets are strongly correlated with certain choice scenarios:

Choices made with limited input or based on faulty sources. Trusting the wrong inputs or failing to follow due diligence to verify assumed knowledge has landed me in more than a few situations that I would have rather avoided in hindsight. This reiterates the old adage about assumptions and a donkey’s anus. Failing to ask myself how I know what I “know” has often been costly.²

Choices made with minimal reflection. By reflection I mean something more than merely charting a cost/benefit analysis of an action (although reflection might certainly include this). For me, reflection entails considering a choice or situation beyond the surface of my first gut reaction (we could call this my IER — Initial Emotive Response). Reacting on the basis of my IER seems all-too-often associated with regretted decisions, far too consistently to be a coincidence. (Of course, some of my best best decisions have been driven by my IER, but virtually all of my bad ones have too. It’s complicated.)

Like I said, this is clearly not the stuff of higher academia. However, being cognizant and aware of these correlations might go a long way to avoiding future regrets. If, for instance, I realize that my regrets are more often than not accompanied by a lack of input and reflection, then disciplining myself to apply some knowledge verification and contemplation practice to future decision-making might avoid the kind of decisions I have hitherto regretted the most.

Bad decisions have been given a bad rap — usually deserved, of course, because of their negative consequences — but their importance is grossly abused when we try to repress them altogether. You see, bad choices are good: not only are they a necessary part of life, they’re experiments through which we learn.

Life is a laboratory. In life, as in science, it is important for us to recall, respect, and learn from our negative results.

Those who cannot remember the past are condemned to repeat it.

Your biggest regrets contain a storehouse of wisdom — perhaps some of your most important discoveries — yet you still must dare to explore them.

1. George Santayana, The Life of Reason or, The Phases of Human Progress (London: Archibald Constable & Co. Ltd., 1906) p. 284, emphasis mine [↩]
2. I personally believe this realization ought to foster a disciplined accounting for one’s assertions, as highlighted in the recent post entitled, Cite the Source [↩]