How to Live with No Regrets

I have this pact with myself since I was a small boy that I will live my entire life with no regrets. Do you also share this desire with me? I don’t know anyone who takes the contrary approach and wants to live a life with lots of regrets! I don’t know anyone who desires a single regret at all. But for me, this is serious business.

How am I doing on this, you might ask? Well, it’s a bit complex. To arrive at the outcome of a life with no regrets — it’s a journey, and a circuitous one. Let me start with what prompted me to write this piece, and we can use that concrete example as a thread for a better understanding of a life without regret.

I recently lost an old friend who was a very lovable, innocent little brother to me when we were monks together nearly a decade ago. I helped train him and felt a deep, lasting, affectionate connection with him. He suffered a lot in his life, and I didn’t have a clue just how much he suffered until he was gone. It’s most likely that he took his own life. I was devastated to learn of his death, out of the blue one day, and the grief came at me with mounting force. I had also never been in the surreal position to have to reach out and share the news with others who knew him.

When I first heard of his passing, I thought that life had naturally taken us in different directions and I trusted that there is a divine plan for him which is bigger than the awful tragedy that hit. I still feel this way 100%, but what I didn’t count on was the intensity of my own regret.

I’m not used to thinking consciously about my own regret in the first place because I try to live in a way that will preclude its ever coming to me. Moreover, I’ve never been in a situation where I was a caretaker of someone who later left the planet untimely, in abject misery, and by their own hands.

He had reached out to me sporadically over the years, and I have a trail of correspondence between us leading up to just weeks before his departure. It was always his initiative. But the worst thing of all on my conscience was that there were times when I could not get myself together to respond to him until months later, caught in a deluge of messages, and I was never really that anxious to speak with him. I felt responsible.

It was clear that I could not manage the chaos of life well enough to keep up the relationship to the degree he would have desired. And I didn’t have great confidence that I’d be able to continue to inspire him after we left our monastic lives, nor that I could receive inspiration from him.

The effect of all this was I cried a lot. My wife and I held a sacred ceremony in the hopes of benefiting his soul as well as his loved ones. And I had to do a lot of processing within myself, in prayer, and in numerous conversations to try to bear the weight of my guilt in a healthy way. All the while, I needed to remind myself that this is not about me and I’m no savior for anyone — I only want to be the best person I can be for my friend and for all those on my path. Therefore, I’m very determined to learn the lessons, honor this dear soul, and grow the best I can by some grace, sharing the gift of realizations with others thanks to him. Hence, I write this piece as a hopeful offering.

There are so many things I wish I did differently in my life. There are so many things that embarrass me to this day. There are also so many things I’m all the more embarrassed that I’d not be able to do differently because I’m so limited. Every time I’d go over in my mind how I was in relationship with my late friend, I would come up against this very block. I’m not so special that I could conquer my own humanness and the struggles that kept me from being there for him more. Thinking like this humbled me deeply.

I had to reconcile with the fact that I’m not anything great. I had to become grounded, real, humble, as the self really is. And in this way, I could honestly see myself being helpless to have done anything differently.

Then I asked myself the question — what would I have wanted to do differently if I could have? In Nonviolent Communication (NVC), the framework developed by Marshall Rosenberg, there’s a concept of “The Do-Over.” It’s as simple as it sounds — you ask the question I just did and you envision the scene going differently. This practice is so helpful if we actually do it!

When I looked at the past again, I felt a surge of energy. I would have checked in on my friend periodically. I’d have sent him lectures, readings, and quotations that inspired me. I’d have invited him to events that we put on. I’d have spoken with him from time to time. If he was receptive to coaching and it felt right, I’d have found a way to serve him accordingly. There was so much I’d have loved to offer him.

I don’t know that any of it would have kept him alive longer. And he may not have wanted the support or been able to do anything with it. The truth is, had his death come when I was trying to support him so actively, I’d have been much more of a mess, and I have to acknowledge again my own vulnerability and weakness here.

Nevertheless, this opened up my perspective, and it gave me energy to want to serve and become better. It also brought up some frustration and anger. Several times, my friend never responded when I tried to set up a call with him at his own request. And he never told me what he was going through. I had no idea things were so bleak! If I had known this is what was happening, my god, I’d have done something! Anything!

I couldn’t blame him though in spite of the frustration. That was not productive, nor did I have any desire to. And in his situation, the fact that he reached out to me so sweetly always was a testament to his beauty and the beauty of the relationship. It was, however, important to acknowledge and experience everything that was coming up, even the frustration and anger.

I kept thinking — I wish I’d known! But as Devamrita Swami, a senior monk I look up to, shared poignantly when I was a monk myself — “You can only act with the information-base available to you at any given time.” I cling to that insight constantly.

In NVC, there’s a concept called Beneficial Regret. It means we mourn the things we wish had gone better, take responsibility, and try to integrate the new understandings that come for future situations. As NVC trainers Jim and Jori Manske point out, this is meant to be done without self-punishment. They also outline what growth looks like for one successfully practicing Beneficial Regret:

“Consistent willingness to openly own oneʹs part in outcomes that did not meet needs; willingness to feel and express regret; [seeking] learning and growth.”

This resonates deeply with all of our work at Upbuild and my own life experience. The only way out is through. And through means not bypassing. It means going through it, with our hearts. That means feeling the difficult feelings, not avoiding them.

What you resist, persists. Avoiding, as we’re conditioned towards, will not do us any good.

And if we look at what the sacred texts teach in every wisdom tradition around the world — repentance is a core theme. Today, we get the unfortunate image of a religious zealot holding up a punitive finger with burning eyes, and yelling, “Repent!!” But true repentance is something else.

Repentance means remorse. It means my heart feels bad because I wish I could do more. It recognizes our honest limitations. But it’s an alive heart that feels that negativity which points us to where we want to go that we have not yet been.

And it builds authenticity within ourselves as well as deep connection with others by being real and heartfelt. If we didn’t feel bad when other people are hurting or we could have done something more for the good of ourselves or others, we’d be callous. Our hearts call us to feel. And that feeling of care is expressed by regret. Genuine regret respects anyone affected by a situation, including ourselves. And it invites connection to ourselves and to others.

So we are actually meant to repent. We are meant to feel for what others go through and the effects of our actions or the lack thereof. It’s human and it’s healing. The irony is that dancing around trying to live a life without regret will only produce more of what we’re endeavoring to escape in the long run.

I’ve never reflected so much on regret as I have now in the absence of my friend. And I’ve never seen the importance of doing so with the clarity I experience now. Let us make sure we are crystal clear in what we are taking away here for a life with no regrets.

To live with no regrets is processing all the regrets that necessarily come up. It’s owning them. Not wallowing in them or using them as ammunition for my Inner Critic to pulverize me. Not enticing others to rub things in my face because I admit my regrets to them. It’s being with the feeling of remorse, the care that softens my heart and connects me to all others, allowing me to grow wiser.

In summary, it’s not fleeing from, suppressing, or stewing in the guilt of our past actions, but working through the guilt. How do we work through the guilt? It’s as straightforward as acknowledging our regret and desiring to grow from the realizations that come. I can feel what I feel, process the different aspects and complexities, as I’ve tried to here in the case of my lost friend, and mine for lessons, asking, “What would be my Do-Over?”

And if we’re truly honest, regrets are a daily affair. When we look back on our lives, how many of us would want to continue doing all of the things we were doing in the past which we no longer do? Why do we change our ways? We regret the effects of our habits constantly, even in the form of unconsciously wondering how we could have a better experience, become better, or do more. When we regret bad habits or anything that keeps us locked in our present mode, holding us back from further potential, we gain fuel to give up those habits eventually and to reach newer and newer heights.

Regrets never disappear. They serve a purpose. And when we embrace them in this light, paradoxically, we don’t regret anything in life. It is all strongly growing us.