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On Regrets

Uncle Chuck and Aunt Janie had a difficult marriage. Aunt Janie became disabled a few years after their wedding. Due to brain damage, she became quite irascible at times. They had no physically intimate connection for 22 years, at which point she died. When Chuck had decided to marry Janie, he could have never envisioned the outcome. Nevertheless, he stuck with the marriage.

Did Chuck make the right decision? Did he come to regret it?

The better question is, what drove his decision to stay in the marriage? How much of his decision to stick with his wife came from his own values and beliefs, and to what degree was he influenced by what others around him thought he should do?

When Bronnie Ware, an Australian hospice caregiver, wrote her book, The Top Regrets of the Dying, she recalled the most common misgiving she heard from persons with hours or days to live:

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

There’s an important question hidden in that end-of-life confession: How do we tell the difference between something we genuinely want for ourselves, and that which others want and expect from us?

How often do our choices get blurred by people-pleasing, approval-seeking, and the fear of standing apart from the crowd to follow our own path?

That’s a tension that confronts every one of us.

I don’t know about you, but I love the emotional experience of pleasing others: Gaining their affection or respect by agreeing even when I don’t; interrupting my life pursuits to join their parade, not because I want to, but because I know they want me to.

Have you ever had the experience of designing a goal in your head, or pursuing one, only to have it questioned by others, at which point your goal, even one that is deeply conceived or long sought-after, is quickly abandoned under the weight of others’ expectations?

Acceptance and belonging are deeply a part of our biology – we’re wired to consider the needs, wants, and opinions of those around us, and to compromise where it makes sense for the group.

But the opposite is also true: If we drift too far in the direction of living for others, the resulting lack of autonomy and self-responsibility risks regrets later in life.

Nowhere is this more obvious and impactful than in life’s biggest decisions. I’m referring to those defining forks in the road such as:

  • Deciding to get married, or not

  • Deciding to have/adopt a child, or not

  • Deciding to get divorced, or not

  • Deciding to move to a new geographical location, or not

  • Deciding to leave a job, or change a career, or not

  • Deciding to buy a home, or not

  • Deciding to end a romantic relationship, or not

  • Deciding to care for a family member, or not

When making these decisions, the ones most vulnerable to later regret will likely be those you made on behalf of others, instead of decisions that reflect your own deep wants and needs.

So what does it mean to have the courage to make decisions that are, in Bronnie Ware’s words, “true to myself, not the life others expect of me?”

What might help us eliminate a few of our biggest regrets before our breathing stops?

First, a commitment to self-examination.

Big decision-making moments like the one Chuck made with Janie – when you intentionally choose an outcome that has long-term impact for yourself and others – occur rarely and involve complex considerations. It’s not like buying a car.

Because big decisions are harder to make than small ones, it’s easy to understand why some of us might hesitate, or abdicate, or follow the advice of others, only to regret, later on, what might have been.

The looming question underneath all major life decisions is, ”What do I really want?”

To move in that direction, “internal research” is a good starting point. Recording thoughts and talking with trusted others can produce decisions less subject to regret.

But even when we have a settled direction, there’s no guarantee that a big decision will turn out well. That’s because, unlike buying a car, with most of life’s big decisions, we can’t simply “return the lemon.”

We also can’t control the influence of good and bad fortune, and the biggest wild card of all: the unknown.

Uncle Chuck and Aunt Janie had their lives significantly altered by those unforeseen variables. But Chuck still had to make a decision.

That’s the situation we’re in whenever we’re at the crossroads of a big decision: Get as clear as I can about what I want, realize I will never have all the data or awareness I would like, and take the leap of faith.

Then, keep bringing as much self-awareness as possible to the inevitable curve balls of life, knowing we will not always get our decisions right.

We can reduce our regrets with conscious choosing, but only the perfect – or the delusional - die without at least a few decisions they would make differently.


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