posttitle = Transcending Regrets, Problems, and Mistakes titleClass =title-long len =44

Transcending Regrets, Problems, and Mistakes

One of the biggest things I’ve learned over the past year is how to truly let go of regret.

(Psst: if you’ve got Spotify, hit play on this track before you keep reading. Or here’s a Google Play link. I’ll explain later.)

A few months ago, in September, I went to a tantra yoga workshop called the Fire & Nectar retreat. The event involved a fair bit of yoga and meditation, but what was most powerful for me were the teachings on non-dualism. A lot of it made deep, immediate sense to me, and there were also pieces that were met with a lot of resistance.

One of the most challenging things that our teacher Hareesh said was this:

If you had a chance for a do-over, would you choose for everything to go exactly the same?
If not, you have not yet surrendered.

He clarified that this wasn’t talking about a dualistic sort of surrender, more like surrendering to reality. I seem to recall he was quoting someone, but I can’t find a source in my notes or on the internet. At any rate, this was a thing that he said, and I immediately recognized it as containing a perspective that I didn’t understand. A perspective that I feared.

I recognized it as a perspective that I’d been in a battle with for several years.


This battle existed both as an internal conflict in me, and as a conflict between me and Jean, the leader (or if you will, “wisdom anchor”) of the Upstart Collaboratory for Collaborative Culture Design, a project I’m part of. I had had a lot of perceptions that things should have gone differently, both in terms of the decision-making processes and in terms of outcomes. This was a judgmental form of thinking—as hinted at by the presence of the word “should” in the previous sentence—and judgment is fundamentally at odds with not just how Jean was thinking, but also at odds with how I myself was committed to thinking.

And yet, there it was. What to do?

Starting about a year prior to the retreat, I had done a lot of work to be able to step out of that particular form of judgment, and with substantial amounts of success… temporarily. Then somehow my very basic operating assumptions would interact with something that happened in such a way that it would bring back this frame, this judgment. In those situations, it felt like if I didn’t inhabit that kind of regretful, frustrated relationship with the past, then I wouldn’t be able to shape the future in the ways that I wanted.

And in the ways that we collectively wanted! …although the judgment made it hard to see whatever alignment and resonance was present, and instead magnified the differences in perspective.

What I ended up with from this was a sense that I couldn’t trust Jean to care for the future, because she didn’t share my judgment about the past. If she didn’t agree that we should have done things differently then, how could I trust that she would do things differently in the future?

[EDIT: at the time I wrote this, I hadn’t realized how important it is to respect & honor your own distrust, even if there’s a perspective beyond it. While I stand by the insight in this post and also by how I articulated it, I want to acknowledge in the context of this story that my distrust was actually carrying important information that the insight here didn’t actually supersede! For more on respecting distrust, see posts on NNTD.]

I think that this is a common way of thinking!

And, as I assessed in Beyond “Giving Feedback”: Co-Attending & Attunement, it isn’t the only way, and it may not be ideal for complex situations.

In case you don’t know: the work Jean and I are doing together is definitely complex. It involves the subtle coordination of a bunch of humans, including ourselves, in an improvisational, VUCA context.

But this kind of regret/past-judgment was still a primary lens that I was using for figuring out how to trust someone’s thinking and decision-making, and viewed through that lens, I couldn’t effectively work with Jean. I really wanted to, though, and I felt that something different was possible, so I started doing a lot of work to shift my relationship with regret. The first serious attempt at this was in September 2016, which involved setting aside a few days to do some reading (Leadership is Half the Story, The Zen Leader, and most notably Dave Chapman’s and to talk extensively about this with other people who were part of the project.

And I had a breakthrough related to how I was thinking about problems.

Transcending Problem-Thinking

Some context: David Schnarch, who wrote the book Passionate Marriage, likes to ask the couples he’s counselling this question:

“Why do you think you shouldn’t be having the problems that you’re having?”

These couples tend to feel that somehow they shouldn’t have <whatever problem they have>. Because they… should… have known better. Somehow.

This line of thinking—which is also common in many domains outside of romantic relationships—is the exact same line of thinking that leads to the thought “if I had a do-over, I wouldn’t make the same mistake I did last time.” It’s a frame that leads one to think that somehow if you thought and planned hard enough, you could avoid making any mistakes. While it may be true that some amount of thinking and planning can avoid some amount of mistakes, unless you’re working with a situation you understand perfectly, then this is a foolish notion that will mostly just result in self-blame. It also implies that you have nothing to learn along the way.

Anyway, on Sept 30, 2016, I found myself having a problem that I felt like I shouldn’t be having, but then I found a new way of looking at not just the problem but the whole experience of having the problem.

And suddenly I got a saying that used to annoy me: “each setback is exactly the one you need for your learning right now”.

This annoyed me because viewed from one angle, how could that possibly be the case? How is the universe supposed to know? But that day it hit me like a bolt of lightning that it’s not that the universe throws you a perfectly-shaped problem for you—rather, you go around sculpting the universe into exactly the kinds of problems you don’t know how to solve. It’s that you are the thing that you’re trying to sort out, and so…. in each moment, whatever it is that you haven’t already solved is the next thing to figure out.

When I didn’t understand this, I would skeptically ask, “Well, how could every problem you encounter be exactly the one you need?” but now it’s tautologically obvious to me that the answer is “Because it’s exactly the one you encountered.”

And if you assume (as I used to) that such a process is anything like random, you might say “Come on! What are the odds of that?”

But it’s not random. Nor is it magic. It’s just that obviously, if you could have already mitigated a problem, with your existing knowledge, understanding, skills, habits, etc, then you would have, so the fact that you’re encountering it means it represents whatever is outside of your existing understanding.

(Aside: the teacher from the retreat, Hareesh, has a fantastic blog, and recently he did a series about similar aphorisms, their confused versions, and the related understanding that is true. Here’s “Near Enemy #1: everything happens for a reason“)

Speaking of confusions, there’s a vaguely biblical concept that says “God will never give you more than you can handle”. This is profoundly not the thing I’m talking about. The universe is allowed to kill you.

So your problem isn’t necessarily exactly-the-one-you-need in that sense.

Also, even if it doesn’t kill you, your problem may not actually be optimized for your learning. Your problem is guaranteed to be not a thing you could have averted, but it’s not guaranteed to be a thing that you were just one insight or a small update away from being able to change. It may be very far out of your understanding, not just right on the edges.

I would speculate that some life-navigation strategies will tend to more often encounter problems that are tractable for learning, whereas others may tend to produce encounter that either aren’t directly solveable at all or don’t provide any traction for figuring out how to transcend whatever confusion or lack of understanding led to having that problem. If you’re in the latter situation, you may want to apply this frame on the meta-level and ask “what is it about my approach such that I’m getting object-level problems that aren’t good for learning?” Your problem is then that you have too-hard problems.

Sometimes people may feel a frame that is sort of like this post-problem frame, but it also comes with a notion or even just a feeling that the universe is somehow punishing them for not understanding how to not have the kinds of problems that they’re having. That is… understandable, given how traumatized people are by years of punishment, but it’s neither a necessary nor helpful way of thinking, and it’s definitely not what I’m pointing at.

I’m pointing at a way of thinking about problems where the presence of the problems is itself unproblematic. As Sebastian Marshall put it,

“Most people wish they didn’t have all their problems, so they flee from them. But where are they fleeing to? There’s no “no problem land”—have you studied history at all? Could you name me ONE person in all of history that didn’t have any problems?”
[…] Most people wish they didn’t have problems, but that’s perhaps misguided. You’ll always have problems. What you can work towards, though — note I said “work towards”, not “hope for” — is having MORE INTERESTING AND BIGGER PROBLEMS as your life continues on.

There’s something about the fleeing that Sebastian describes here which seems related to Schnarch’s question, “why do you think you shouldn’t be having the problems that you’re having?” The fleeing person doesn’t want to understand the problem and change so as to transcend the problem, they want to un-have it. They want the problem to go away. They want to not have had the problem in the first place, somehow. Maybe they even like the idea of having more interesting and bigger problems, but feel like they deserve to not have to figure out whatever problems they currently have in order to get bigger ones.

Well… whatever problem you’ve got is the one you need to figure out.

When I first really saw this, it shifted me into a totally different paradigm where I was remarkably free of judgment about the past and present, and I was therefore feeling profoundly open in relation to Jean and excited towards everything that was happening here. I suspect that if I’d heard the bit about do-overs that day, I might have been able to easily make sense of it. But a few days later, while the general insight about problems remained, my basic paradigm had shifted back to what it was before, and it didn’t take long before another incident triggered more frustration.

The Do-Over Koan

For the purposes of this post, we’re now going to fast-forward the story a whole year, straight to the Fire & Nectar retreat. It is worth noting that that year contained an incredible amount of challenge and a commensurate amount of learning, much of which seemed obvious in retrospect but (as evidenced by the fact that we had to go through it) wasn’t obvious in forespect.

So there I was, in September of this year, seated in this sanctuary on a hilltop south of the bay area, on the first full day of an event that I had chosen to go to in part because I had hoped it might help create more space in my relationship with this project and with Jean, and Hareesh said it:

If you had a chance for a do-over, would you choose for everything to go exactly the same?
If not, you have not yet surrendered.

I realized: this is my koan. My puzzle to chew on.

And chew on it I did! I reflected on it a bunch over the next couple of days, and made connections with some of the other teachings. Then I staged a sort of crisis of faith ritual, writing in my journal to really investigate this puzzle.

The place I started was this: who is the “you” in the question “If you had a chance for a do-over, would you choose for everything to go exactly the same?”

Here’s what I wrote in my journal, during the “essential speech” quiet period in the evening:

It sort of seems that I would have to say “of course I would do everything the same—in order not to, I would have to be someone else! (even slightly)”

…and then I wonder if I can’t essentially apply that to the whole cosmos—either as Malcolm, discerning whether or not to demand a different cosmos, or as the cosmos itself, contemplating a grand do-over.

What sort of thought experiment is a do-over anyway?? It seems possible that maybe the whole concept is busted 😕 Not just possible but increasingly so as I think of it. The concept of a do-over is a delusion of some kind. This feels easier to hold than the stance that “I would in fact choose to do it the same.” I think this is what Jean holds, and I’ve looked at it before.

It seems though that this stance, including as it shows up in Jean, does end up representing itself as the surrendered response to the thought experiment. I recall her articulating words to that effect at least… twice?

Anyway, this all feels pretty workable! If I feel around for remaining points of tension… I encounter “counterfactuals”. But ah! Something else that’s juicy:

Feeling into it, I’m getting a sense that being undivided & unconflicted may be incompatible with holding a sense of “would do it differently”.

This, because it holds two selves: one that was, and one that should have been.

I’m now going to meditate on this, and on the grievance-triggers related to Jean & Upstart, for some minutes before bed.

After writing that, I indeed went back into the sanctuary to meditate. The room was dark except for the candles on the altar, and I was the only person in it.

I worked on integrating my new understandings with some thoughts from the past that had been challenging for me to think about without getting worked up. Thoughts about things that I had long felt should have gone differently.

And in that moment, instead of feeling the old frustrations, there was primarily just a deep sadness and compassion for how much I cared. That I was trying really hard, and felt it still wasn’t enough, so I tried to blame others for not trying or not caring enough. But that didn’t actually help. And if I gave up the feeling of needing the present to be different than it already is—which is a crazy sort of need, since it can’t possibly be fulfilled—then I didn’t need to blame anyone.

Even while seeing this, I sometimes found myself pulled back towards the old thought loops of blame, and I repeated to myself, with a hint of desperation, “just be here just be here just be here”. The blame was making me lose track of reality. It was dividing me. And as has been a theme in my writing this year, I care about being undivided.

I wept, and went to bed. My process of integrating that writing carried on through the remainder of the retreat, and into conversations with my friends in the days after. I’m going to close this piece by bringing in something that we fast-forwarded through when jumping from my post-problem insight in Sept’16 to the retreat in Sept’17.

Improv: the Köln Concert

In July of this year, Jean shared one of her favorite pieces of music. It’s the one embedded at the start of the post: solo improv piano, Keith Jarrett’s Köln Concert. After we listened to all 26 minutes of Part I, we read together the first few pages from a book by Tim Harford called Messy, which described the circumstances of the concert:

[17-year-old concert promoter] Vera Brandes was introducing Keith Jarrett and his producer Manfred Eicher to the piano—and it wasn’t going well.

“Keith played a few notes,” recalls Brandes, “Then Eicher played a few notes. They didn’t say anything. They circled the instrument several times and then tried a few keys. Then after a long silence, Manfred came to me and said, ‘If you don’t get another piano, Keith can’t play tonight.'”

Vera Brandes was stunned. [It turned out that instead of the piano Jarrett had requested, all the Opera House had provided was] “this tiny little Bösendorfer, that was completely out of tune, the black notes in the middle didn’t work, the pedals stuck. It was unplayable.”

Brandes tried everything to find a replacement, [but in the end all she could do was get a tuner to make sure the little piano was at least in key.]

Understandably, Jarrett didn’t want to perform. He left and went to wait in his car, leaving Brandes to anticipate the arrival of 1,400 soon-to-be-furious concertgoers. The best day of her life had suddenly become the worst; her enthusiasm for jazz and her precocious entrepreneurial spirit brought the prospect of utter humiliation. Desperate, she caught up with Jarrett and through the window of his car, she begged him to play. The young pianist looked out at the bedraggled German teenager standing in the rain and took pity on her. “Never forget,” Jarrett said. “Only for you.”

A few hours later, as midnight approached, Jarrett walked out to the unplayable piano in front of a packed concert hall, and began.

Keith Jarrett seated at a piano, looking down in reflection

“The minute he played the first note, everybody knew that this was magic,” recalls Brandes.

That night’s performance began with a simple chiming series of notes, then quickly gained complexity as it moved by turns between dynamism and a languid, soothing tone. It was beautiful and strange, and it is enormously popular: the Köln Concert album has sold 3.5 million copies. No other solo jazz album or solo piano album has ever matched that.

When we see skilled performers succeeding in difficult circumstances, we habitually describe them as having triumphed over adversity, or despite the odds. But that’s not always the right perspective. Jarrett didn’t produce a good concert in trying times. He produced the performance of a lifetime, but the shortcomings of the piano actually helped him.

The substandard instrument forced Jarrett away from the tinny high notes and into the middle register. His left hand produced rumbling, repetitive bass riffs as a way of covering up the piano’s lack of resonance. Both of these elements gave the performance an almost trancelike quality. That might have faded into wallpaper music, but Jarrett couldn’t drop anchor in that comfortable musical harbor, because the piano simply wasn’t loud enough.

We read another couple paragraphs, then paused to share reflections. Conveniently, for purposes like this post, we record many of our conversations at Upstart. Here’s the relevant piece of the transcript:

Malcolm: I just have this image too, of him kind of… as we were listening to him play, we were also listening to him get to know this piano.

Jean: Exactly, yeah.

Malcolm: …trying this out, and—euhh, maybe not quite that! Not that there was a specific wincing, per se, at any moment, but a recognition of ‘that won’t work’

Jean: Well but it isn’t “that won’t work” because it’s already part of the performance!

It’s already part of the performance. For better, for worse—for whatever it’s worth—what has happened has happened, and it’s already part of the performance. This is as true of each note Keith Jarrett struck that night as it is of each decision I’ve made, or Jean has made, or you the reader has made. Life is, in general, improv, although much effort goes into both denying this fact and trying to reduce it as much as possible. And yet pretty much any good conversation involves not knowing what will be said until it’s actually being said.

People get stuck though, when they perceive that they’ve somehow gone down a wrong path and that they need to rewind. Which, of course, they can’t, because time goes forward. But because they’re still attached to a notion of how things were supposed to go, a lot of what they’re doing is experienced as a series of correcting mistakes.

Jean asked, during that conversation:

“How do you sustain that shift so you’re not kind of “well I’m trying to kid myself in this” but that really is the frame that you’re coming from which makes that be something different than if you were holding it as a series of correcting mistakes. So somehow there’s a post-mistake element to it.”

Of course, there are lots of situations where a particular act of creation isn’t improvisational with respect to its audience. I’ve made many edits to this blog post while writing it! But there’s a difference between the discernment, “hmm, I think it’ll be clearer if I move this section before this other section” and the perception that it was a mistake to not have put it there in the first place.


I get this now. I am no longer the person who would say the thing that I said in July about Keith Jarrett wincing. It took a lot of work—all of which, apparently, was necessary, given the tools we had at the time. In writing this, I hope that I can shorten and smooth the process for at least a couple people. However, my understanding is that this is the kind of thing that tends to be installed at a pretty core level of the mind, so I suspect that just reading this piece will not be enough, and that there will be lots of further integration required, as you disentangle old thought patterns.

It’s worth it.

It’s been two months since that retreat, and I feel a consistent flow in my relationship with Jean, or in the least-clear moments, still a sense of ease. It’s not just the fact that I’m now seeing things more like how Jean does that’s making things flow more. That helps, but the bigger part is that I’ve finally set aside not the particular tensions that we have but a whole class of strategies in relation to those tensions that have been getting in the way of our ability to feel same-sided.

There are still parts of Jean’s thinking that I don’t understand, and still things that she doesn’t understand about my thinking. There’s still healing to do from the years of misunderstanding. What’s new is twofold. One: that I don’t feel like those need to be fixed before we can start building a consistent basis of trust in our experience of each other. Two: that I actually trust that we can talk about those and resolve them, if that’s needed at some point. (Whereas before the regret or blame would get in the way.)

Being able transcend regret is necessary for transcending blame, which is in turn necessary for effective collaboration. It’s not easy, and we’re figuring it out, and we’re still not there yet, and… that’s not a problem.

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About Malcolm

Constantly consciously expanding the boundaries of thoughtspace and actionspace. Creator of Intend, a system for improvisationally & creatively staying in touch with what's most important to you, and taking action towards it.


Tanya » 28 Nov 2017 » Reply

I feel so much deep resonance with this post.
I actually hold a story that it was the patterns of regret (and the companion pattern of resentment) that were a core factor in taking my mother’s life. And I have been engaged in the project of burning new pathways in my own system that are free of these patterns. (And free of fear of the impacts of those patterns at the same time).
Speaking of burning new neuro pathways…
I have found value in imagining having responded differently to past situations, as a way to grow new brain highways. As studies have shown that athletes who imagine how they would blaze across the finish line, are more likely to do that.
… with role-playing being the more extended, literally embodied version of imagining ourselves into being.

I held space for someone do their first cycle on Sunday and I’m stoked to share this post of yours w them as a way to deepen and build on what they are re-patterning.

Tanya » 28 Nov 2017 » Reply

All that to say,
I am finding it possible to joyfully imagine and Play out what I could have done differently, without regret about what I should have done differently.
AND, I’m so deeply valuing your teasing out the qualitative and structural differences here between these two orientations, because there can be a way in which the “could have” can disguise a slippery “should have” underneath.

Gordon Worley » 8 Dec 2017 » Reply

You might be interested to know that Kierkegaard investigated this in the sense of double regret: you’ll regret something if you do it and you’ll regret it if you don’t. In a sense, every choice creates regret, but rather than being depressing, this is freeing because “regret” becomes nothing more than the dual of choice; the counterfactual choices you could have made. And those counterfactuals always exist no matter what you choose, and further you could not have chosen otherwise anyway because to have chosen differently would be to have been a different person.

Derek » 16 Feb 2023 » Reply

Thanks for writing this up. I’ve been re-reading it every few days, and it’s been helpful in reducing my grip on regrets.

For those who want more of the story behind the Koln Concert, Tim Harford talked about it on an episode of the Ted Radio Hour

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