Getting Comfortable with Regret

I was naive. I thought I knew what regret was.

I thought, “be careful, don’t move through life so unhindered, unharnessed, unaware… I’ll do something I may regret.” I believed that regret would come from something I’d do that I hadn’t thought through clearly. I’d feel regret from something I’d done unabashedly. But what about the regret that comes from not doing something?

There appears to be two overarching courses to regret. Regret can stem from having taken an action, and regret can stem from having not taken an action. If there are two courses to regret, then why aren’t there two separate words for this? With regret being one of the most common emotions a human can experience, the naming and framing seems rather narrow.

Sure, each category of experiences — active or inactive — may evoke the same feeling… one of regret. But how those experiences play out are very different. I suspect that I’d be more aware of my inactive regrets if there were a different word for it. Perhaps qualifying the regret as either active or inactive is enough. What do you think? Do you see a marked difference in how you experience regret?

Recently I listened to Daniel Pink discuss his book “The Power of Regret” and he spoke to this distinction of active and inactive regrets. It was so good to hear him speak clearly about something I needed to have named and described. Usually I feel like I have little regret when it comes to actions I’ve taken. As I explore the regret surrounding inaction, I’m noticing a different story.

I’m coming to terms with the fact that I have regrets, more regrets than I thought I had. I’m vacillating between accepting this and denying this. The reality is that we all feel this emotion. There are times when we move through the emotion quickly. There are times when the emotion gets caught up in our thought patterns

In his book, Daniel states that while regret is a negative emotion, it’s not necessarily destructive. Regret can be constructive. It’s normal to have regrets and regrets are functional. These are notions I can get behind. I can see how regret can be constructive. How it can be a reminder of what’s most valued and where to put attention.

Being mindful of thought patterns allows us to know if we’re wading in a pool of regret. Naming the emotion can be elusive, but it’s still felt. The thoughts can be an indicator for accessing what the emotion truly is. Recently, I’ve been catching consistent thoughts of “if only I’d done” this or that.

I allowed these thoughts to play out in various loops. Were the thoughts helping me or hurting me? I needed to get to the core of what was emotionally fueling these thoughts. There was relief in eventually recognizing that the feeling of regret was welling inside me.

According to Daniel, there are four categories of regret that individuals feel:

Foundation — These are regrets where we opt for short-term gains over long-term payoffs. Regretful thinking like: “If only I’d done the work.”

Boldness — These are regrets of inaction, such as not starting a business, asking a crush on a date, or going on trips. Regretful thinking like: “If only I’d taken that risk.”

Moral — These regrets involve taking what our conscience says is a wrong path, such as lying, stealing, or betraying or hurting someone. Regretful thinking like: “If only I’d done the right thing.”

Connection — These regrets stem from “relationships that have come undone or remain incomplete.” Regretful thinking like: “If only I’d reached out.”

The survey conducted for his book conveyed how Connection regrets were the most common, followed by Boldness. Most of us can likely identify one of these categories as the most prevalent for regrets. Which kind of regrets are you facing?

For me, I’m noticing some lapse in my Foundation category. These were the kind of “If only I’d done” thoughts I’d been having recently. It seems I’ve made decisions, whilst good for some reasons, consequently negatively influence some of my own support system and foundation.

I actually feel pretty good for that most common regret category of Connection. But has this inadvertently affected other areas? Yes, as I take inaction with some foundation concerns in order not to have connection regrets. With this framing I can see a more holistic view of how decision making and unintended regrets of inaction take shape in my life.

Okay, what do you think about regret? Now that you’re leaning into these perspectives and expanding the scope of how to view regrets, what next? As you move forward, is it going to be a matter of “feel the awkwardness and do it anyway?

Regarding how to move forward with minimizing Connection regrets, Daniel suggests: “If a relationship you care about has come undone, place the call. Make that visit. Say what you feel. Push past the awkwardness and reach out.” Does this speak to you? Perhaps this is where you can start. If one of the other categories seems more fitting, what can you do to make peace with the decisions you’ve made?



I’m a holistic health coach & writer living in Brooklyn, NY. I’m the creator of assisting others to reach desired health goals.

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James Governale

I’m a holistic health coach & writer living in Brooklyn, NY. I’m the creator of assisting others to reach desired health goals.