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I have unlimited access to how to live regret free. It’s a job hazard that isn’t included in workman’s comp.

I spend 40 hours a week at a facility that includes a revolving door of volunteers that range in age from 57 to 93.

They’re retired and looking for ways to support the community while keeping monotony at bay. Our site calls to visitors from stateside to worldwide which allows volunteers to mingle with worldwide ways.

In winter, customers dwindle. There are only a few hardy souls who think wintertime is the best time, as I stare at the 2 inches of snow that drifted in this morning.

Since there are few customers to chat with, there is ample opportunity to mingle between the paid and volunteer staff. With less interruptions a wide range of topics gets discussed and dissected. Eventually, one that gurgles up is regret.

Perhaps it’s because I’m a curious sort (is my Ravenclaw showing?) and I ask questions.

Perhaps the sage volunteers want to impart nuggets of wisdom from decades of experience. Or they just want to fill the silence with meaningful insight.

Either way, I have a small reservoir of others’ regrets.

Their lives and lifestyles vary but the sentiment is the same, I should have bought less and traveled more.

Friendly Expectations

There are a couple of ladies who I classify as my favorite. One feisty gal used to work for the CIA, while the other was a bookkeeper when everyone else became a nurse, teacher, or flight attendant.

They lived lives against the grain, though they wouldn’t claim that title unless prodded by a persistent 37-year-old.

I love them for their tenacious work ethic, wit, and spunk. Week after week, I’m drawn to their stories.

A humbling theme is regret. They both regret spending copious amounts of money on clothes, furniture, home décor, and art. While looking back through the lens of time, they would have preferred to use extra funds towards travel.

No regrets about family, friends, or careers but spending on stuff.

As a minimalist who tries to maximize travel, their regrets resonate.

Though my wrinkles and wisdom are far from their own, I feel a twinge of regret too. It’s a lower level because I’ve confronted my values and aggressively adjusted but these ladies are sage with age and locked into lifestyle restrictions.

Their age, or the age of their spouse, has greatly reduced their mobility and health which has diminished their travel options. They can’t adjust their current lifestyle, but they can impart their wisdom to future generations.

Piercing Perspective

Everyone wants to live regret free.

As humans prone to occasional failings, we all have things we should have done differently. Instead of viewing it as a failure, it’s healthier to flip that around and use it as a lesson.

Like in this 100% hypothetical story.

A girl found herself in an on-again, off-again relationship with a guy. Occasionally, she called it quits, but typically he was the one doing the breaking.

The gal was going through a massive lifestyle shift, leaving the military and going to college. Initially, the guy was supportive. When a university acceptance letter arrived and moving to another part of the country became a reality instead of a possibility, he realized that he didn’t love the gal that much.

Per the established default, he broke up the relationship again.

The gal was angry and sad. Instead of sticking around, she left the region. Moving to a new area brought clarity to the frequent relationship failures. The gal used that time to look inside herself and have hard conversations about future dating prospects.

Even if it meant being alone with cats for the rest of her days, she made a vow to not repeat past mistakes. Instead, she wanted to leverage them as lessons to guide better future decisions.

Eventually, it worked. Two years after the big breakup, she would ask a nice guy out over Messager. Years later, they married and had a happily frugal ever after.

A nice, hypothetical, strangely specific story about a girl who turned past mistakes into future caution signs.  

Fearless Forgiveness

The interweb suggests practicing forgiveness when it comes to how to live regret free.

Accepting and forgiving poor choices made in imperfect circumstances seem to go a long way in moving forward in a healthy, productive way.

There is a famous quote that resonates with this sentiment.

Bitterness is like drinking poison and expecting the other person to get sick.

A helpful reminder when I’m practicing forgiving because sometimes forgiveness feels like I’m pulling on wool underwear – uncomfortable, questionable, and smelling sheepish.

Spending time accepting flaws and forgiving, doesn’t wash away regrets, but it does replace toxic thoughts. Our brains can’t throw blame and shame when instead its focused-on forgiving and accepting flawed individuals for making choices with limited time and resources.

Many times, this practice is repeated frequently with unlimited entries. One moment of forgiveness isn’t going to erase years of regrets but revisiting, again and again, layers a healthier foundation.

Any foundation that stands for a lifetime, needs maintenance. Minds need mending too, but instead of concrete and duct tape, it’s accepting and forgiving limitations.

Fixing Failure

In Calgary, there is a site called the Museum of Failure where, “Innovation and progress require an acceptance of failure. The museum aims to stimulate productive discussion about failure and inspire us to take meaningful risks.”

What turns failure into regret? The same process in a goat’s gut, rumination.

When a poor choice, word, or action becomes a consequence cascade that sucks the unsuspecting human into an eddy of regret.

A way to break away from an eddy is to use the experience to make better choices or, my preferred default, to change the current direction.

I’ve changed course a few times because of a regret:

  • Cashing out my TSP to contributing more than 20% of pretax and post-tax pay
  • Traveling little to traveling more
  • Going from a string of exes to happily married
  • Buying stuff to declutter stuff and buying experiences

Turning regret into motivation is how I turn dark into light.

How to Live Regret Free

Regrets are innately human.

A cat doesn’t mourn the loss of catnip.

Geese don’t ruminate on how they aren’t chasing enough bystanders.

I don’t see a dog lamenting about how he didn’t eat enough dog poop.

Perhaps the purpose of regret, the evolutionary suggestion, is turning past hardship and heartache into something better and less painful.

Perhaps it’s motivation to change today so we don’t have to forgive tomorrow.

Or perhaps it’s a reminder that we can be right only so many times before were wrong.

A few regrets over a billion choices.

I’ll take those odds.

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