Life Wisdom - By Words of Taoism - Making Peace With Regret - Life Wisdom #56

Episode Date: August 15, 2026

The question I would like us to sit with is a simple one, and I suspect it has visited almost everyone listening. Why does the life we did not live always seem to have gone better than the one we are living?More resources:Free resources, books and more on ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://wordsoftaoism.com/⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠My Substack Blog:⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://taoismteachings.substack.com/⁠⁠⁠⁠⁠⁠⁠⁠⁠Music I use, as a playlist:⁠⁠⁠ ⁠⁠⁠⁠⁠https://tinyurl.com/spotifyzenplaylist⁠⁠⁠⁠

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Always earn high regular interest rates that grow the more you save and invest. Conditions apply. Visit scotiabank.com slash h-I-SA to learn more. Scotia Bank. You're richer than you think. Welcome to life wisdom. Today, I want to talk about the roads we did not take. We are going to look at that other life closely

at how it is built and what it is made from and why it wins every comparison we put it in. We will look at what regret gets right because some of it is telling the truth and deserves to be heard and we will end somewhere I hope will be more useful than reassurance. This will take us a little while and it is meant to. There's nothing here to write down

and nothing you need to remember. If you are walking or driving or working with your hands, that is a good way to listen to this one. Let it go at the pace it wants to go. Let us start by looking at how the other life actually behaves because it has habits, And once you see them, a great deal changes.

Here is the first thing to notice about the road you did not take. It is beautifully made. The version of you who moved to that city is doing well. The work you set aside turned out to suit you. The relationship you did not pursue would have been the one that lasted. You know all this with a strange confidence, considering that none of it. happened. And now try an experiment because it is more revealing than any argument I could make. Take that other life and try to describe an ordinary Tuesday in it. Not the arrival, not the

highlight, the Tuesday in the seventh month. What time did you get up? What was irritating you that week? Who had disappointed you recently? What was the low-grade financial work? What was the low-grade financial worry running underneath everything. What conversation were you avoiding? For most people, the whole thing dissolves under this question. The other life turns out to have no Tuesdays in it at all. It has a mood. It has a quality of light. It has a general sense of things having gone well. What it does not have is texture, because texture is what a life acquires by being lived, and this one has never been lived by anyone. So when we compare, we are not comparing two lives. We are comparing a life to an atmosphere. Your actual life has every seam showing. You know

exactly where it is worn, because you were there for all of the wearing. You remember the year that was mostly grey. You know which of your friendships took work. You know the compromise you made, in the third year and what it cost. You have complete access to the underside of the fabric. The other life is being shown to you from the front, in good light at a slight distance. No life could win that comparison. A perfectly happy life would lose it,

because the happy life would still have Tuesdays, and the imagined one never will. There is a sharper version of this that most of us have experienced, and it is worth pausing on, because it feels like evidence when it is not. Sometimes you do not have to imagine the other road. You can watch somebody walking down it. Someone you were at school with took the job you turned down.

A cousin moved to the country, you were curious about. A former colleague stayed in the field you left, and you see from a distance how it went for them. And now the other life appears to have stopped being a fantasy. It has a real person in it, with real results, and you can see with your own eyes that it worked, except that you cannot. What you can see is the front of it, which is the only part anyone shows. You are seeing their output and not their cost. You do not know what that job asked of them at home. You do not know what the move did to their marriage, or how many evenings they have spent lonely in a country where they still cannot make jokes. You do not know whether the

field you left has been quietly grinding them down for 11 years. None of that appears in the photograph, and photographs are mostly what we get of other people's lives. And there is a further problem, which is that they are not you. Even if that road did suit them perfectly, roads are not universal. the thing that would have made them happy is not automatically the thing that would have made you happy and it is a strange habit of the mind to assume that a life is a fixed object which works the same way whoever is standing inside it

so watching another person on the road you declined is not the confirmation it feels like it is the same imagined life as before now wearing a real face, which makes it considerably more convincing and no more accurate. If it were only a matter of missing texture, the problem would be manageable. But there is a second unfairness built into the comparison, and it is stranger and harder to see. The person walking around in that other life is you, not the you who made the decision. The you of today, with everything you have learned in the intervening years, dropped into a choice

made by someone who did not know any of it yet. You look back at the decision and you can see, with total clarity, that the safe option was a mistake, or that the exciting one was a trap. You can see it because you now know how things went, and then almost automatically, you hand that knowledge to the younger person standing at the crossroads, and you watch them fail to use it, and you feel a kind of exasperation with them. But they did not have it. That is the entire point, and it is easy to say, and surprisingly hard, to actually believe. They were standing in front of two roads, both of which disappeared into trees after about ten meters.

They made a judgment with the information available, with the fears they had then, with the responsibilities they were carrying, and with the version of themselves they were at that age. The old text puts a distinction here that I find very useful. To know others, it says, is intelligence. To know oneself is clarity. Clarity, in that sense, is not the ability to judge

yourself accurately. It is something closer to seeing yourself truly, including seeing your past self as a real person rather than as a defendant. And a real person at 26 does not have access to what happened at 34. They cannot. Holding them responsible for that is a kind of category error. and it is one that a great many decent people commit against themselves for decades. There is also a quieter version of this that deserves naming. Sometimes we do not blame our younger self for lacking information. We blame them for lacking courage. That accusation feels more legitimate because courage seems like something they could have summoned.

But courage, as we have said before, is not a quantity you simply decide to produce. It comes out of what you have to stand on. And that younger person may have had very little to stand on. They may have been frightened in ways they could not name, or exhausted, or supporting someone, or carrying a fear they inherited long before they were old enough. to examine it. They were not being cowardly. They were being a person at a particular moment with particular weight on them. You are allowed to wish they had chosen differently. That is honest.

What is not honest is the assumption that they easily could have. Now let us go a level down, because underneath the imagined life, there is something driving it. And I think this is what where the real work is. The other life is not really about that city or that job or that person. It is a container. And what we pour into it is everything our actual life has not given us. If your days feel narrow, the other life is spacious. If you feel unseen, the other life is one in which you were recognized. If you are tired, the other life is one in which you would not have been tired. It takes its shape entirely from the shape of what is missing now. This is why the other life changes over the years, which is worth noticing. Ask most people

what their road not taken is at 25, at 40, and at 60, and they will often describe three different roads, or the same road in three different colors. The road is a road. The road is not fixed because it was never really about the road. It is a moving picture of the current absence. And that is genuinely useful information, provided you read it correctly. If you find yourself returning to a particular imagined life, the question worth asking is not whether you should have taken it. That question has no answer and never will. The useful question is, what that imagine life is supplying? Freedom, recognition, adventure, quiet, being close to a place you loved? Because whatever it is supplying, it is telling you something about now, in the present

tense, where you can still act. A person who keeps dreaming of the road that led away from the office is often not dreaming of another career at all. They are dreaming of an hour that belongs to them, and an hour is available. The other career, in most cases, is not. So the imagined life is not a wound to be sealed up and never opened. It is closer to a message that has been badly addressed. It arrives labeled as the past,

and it is almost always about the present. And there is one more feature of these visitations that is worth naming because it does a quiet damage of its own. We tend to carry them alone. Regret is one of the least discussed of the ordinary human experiences. People will tell you about their grief, their worries, their irritations with their families. Very few people will tell you over dinner about the life they think they were supposed to. to have. It feels ungrateful, particularly if the life you did get is a decent one. It feels like a complaint you have not earned the right to make. So it goes underground. And because it goes underground,

each person concludes that they are unusual in having it. You look around at people who seem settled in their lives and you assume they are not carrying an unlived one. They almost all are, the contented ones too, the ones who chose the road you did not, and the ones who chose the same road as you and are further along it. This is not a symptom of having chosen badly. It is a feature of being a creature who can imagine, living a life that can only go one way at a time. Imagination is the same faculty that lets you plan and empathize and hope. It does not switch off when it reaches the past.

That is worth knowing on the afternoons when the other life sits down beside you and you feel faintly ashamed of it. You're not being ungrateful. You're being a person with a working imagination, which is the same equipment that makes everything good in your life. possible. There is a third thing hidden in all this, and it is the deepest of the three, and I want to approach it carefully because it is easy to state and hard to accept. Underneath most regret, if you keep going down, you find a particular belief. The belief is that there

existed somewhere in the branching of your life, a path with no loss in it. a road on which you would have got the things you got and also the things you did not get. That road has never existed for anyone. Every choice you have ever made and every choice you will ever make purchases one thing with another. The stability bought the adventure. The adventure bought the roots. The children bought the freedom. The freedom bought the company.

staying near your family bought the city you were curious about. Going to the city bought the ordinary Sundays with people who are now elderly. None of those are failures of judgment. They are simply the exchange rate of being a finite creature in a finite life, able to be in one place at a time, capable of one direction at a time. So a great deal of what we experience as regret is not actually about the specific choice at all. It is grief about the structure of a human life, arriving in the disguise of a complaint about one particular decision,

and that reframing changes the emotional weather of it considerably. Because if the pain is really about finitude, then no alternative choice. would have prevented it. The other road would have had its own losses, and by now you would be sitting in that life on an ordinary afternoon thinking about this one. I find that oddly comforting rather than bleak. It means you are not paying the price of a mistake. You are paying the price of admission which everyone pays on every road. It is worth sitting. sitting with how total this is, because we tend to accept it in theory and resist it in every particular case. There has never been a human being who got to have both, not one, in the whole

history of the species. Every person who has ever lived has stood at some point in a life that excluded other lives, and every one of them, if they were paying attention, felt the weight of what their own existence had cost them in possibilities, which means that the version of you that keeps appearing on those afternoons, the one who got the city and the family and the work and the years near home, was never on offer, not because you were unlucky, or made a wrong turn, or lacked nerve. That figure could not exist, in the same way,

A square cannot be round. And once you see that clearly, something quietly relaxes. You have not been failing to find a path that other people found. You have been walking the only kind of path there is. There is an old story in this tradition about a farmer whose fortune keeps reversing and whose only reply each time is that no one can say whether it is good, or bad. We usually take that as a story about the future. It is at least as much a story about the past. The confident claim that the other road was better is exactly the claim the farmer refuses to make.

We simply do not know. We cannot know. And regret is, in a sense, the act of pretending we do. Now, I want to be careful here, because there is a version of this reflection that tithe, hips over into something dishonest. And I do not want to offer you that. It would be easy to conclude that all regret is an illusion, that every road is equal, that we should simply let it all go. That is too smooth,

and it does not survive contact with real life. Some regrets are true. Some doors closed because we were careless, or unkind, or too frightened when we did not need to be. Sometimes we did know better and we did it anyway. So it is worth learning to tell the difference because the two kinds ask for completely different responses.

The first kind is regret about outcome. This is where you made a reasonable decision and it went badly. or where the alternative appears attractive only because you have seen how this one turned out. This kind has no lesson in it. There is nothing to extract because you would decide the same way again with the same information. And information is exactly what you did not have. This kind asks only to be mourned and set down. The second kind is regret about conduct.

This is different, and you can usually feel the difference in your body. It is not the wistful ache of the imagined city. It is sharper and more specific, and it tends to involve another person. The thing you said. The support you did not offer. The way you treated someone who deserved better. This kind is not a fantasy at all. It is your own conscience.

working correctly and it has real information in it. And the useful thing about the second kind is that it usually points somewhere you can still go. You cannot repair the specific afternoon. But conduct is a pattern and patterns are still running. If you regret how you treated someone 20 years ago, there is almost certainly a version of that person in your life right now. and you can treat them differently this week.

That is what a conscience is for. It is not there to prosecute you. It is there to steer you, and it is still steering. Someone once described to me the way this landed for them. They had carried for many years a real regret about how little they had been present to a parent in that parents' last long ill. They had been young and frightened of hospitals, and they had visited less than they should have.

No amount of reframing made that stop being true, and they had stopped trying to make it stop being true. What changed, they said, was the day they realized that the regret had been trying to tell them something for two decades, and they had only ever heard it as an accusation. What it was actually saying was that being present to people who are suffering mattered to them enormously. It was not evidence that they were a bad person. It was evidence of a value showing up in the only way a value can show up when it has been contradicted. They started visiting an elderly neighbor, not as penance, and not to balance a ledger, which cannot be balanced.

simply because the thing the regret had been pointing at was still available in the present, with someone else, in a different room. That is regret used well. It does not get to change what happened. It gets to change what happens next. There is something else that deserves attention before we go further, because a great many of our regrets are not about decisions at all. We speak of the roads not taken as though we had stood at every fork and chosen.

In practice, a large part of any life is arrived at rather than chosen. You did not decide to stay in that town for 11 years. You stayed for one more year, and then circumstances made it awkward to leave, and then it was 11. You did not decide to let a friendship end. You were busy in March, and they were busy in June, and nobody made a decision at any point. And now it has been four years. This is how most large outcomes actually happen,

not by a single dramatic turning, but by a long accumulation of small defaults, and none of which felt like a choice at the time. and that changes the character of the regret considerably. You cannot indict yourself for a decision you never made. There was no moment of failure to point at because there was no moment. But it also carries something more useful if you are willing to look at it. If lives are mostly made of drift,

then the same is true of the life you're living right now, which means the material of your future is not made of grand crossroads. It is made of what you do in an unremarkable week, repeatedly without noticing. That is worth knowing, because it puts the attention in a far more useful place. The road not taken is closed. The small defaults of this month are entirely open, and they are, quietly, the way the next day. is being built. There is one more thing worth saying about the imagined life, and it is the least

flattering, so I will say it gently, and you can decide whether it applies to you. Sometimes we keep the other life alive on purpose, not consciously, but there is a comfort in an unlive possibility that a lived one can never provide. As long as the other life remains unlived, it remains perfect. And as long as it remains perfect, some part of you remains a person of great unrealized potential. You're not someone whose life turned out this way. You're someone who could have had that other life and chose otherwise,

or was prevented. That is a surprising, warm blanket. And it costs something to give it up, because giving it up means accepting that this life, the one with the Tuesdays in it, is the actual measure of you. You can see this most clearly in the roads that are still technically open and that we never take. The person who has said for 15 years that they will one day open the shop or move to the coast or write the book, and who is not moving toward it at all. Very often what is being protected is not the plan.

It is the identity of being a person with that plan, which is threatened far more by trying and finding it ordinary than by never trying at all. I say this without any scolding in it because the impulse is entirely human and most of us do some version of it. But it is worth noticing because if a road is genuinely still open, then it is not a regret.

It is a decision you're currently making every day by not making it. And there's a great deal of freedom in that recognition. Some of what we mourn as lost was never lost. It was declined again this morning, and it will be offered again tomorrow. So what do we do with the other life? because it will keep visiting. It is not going to stop arriving on ordinary afternoons, and any advice that depends on its stopping is not going to be much use.

I think there are three small things, and none of them requires you to feel differently, which is fortunate, since we cannot instruct ourselves to feel differently. The first is to notice it as a very, visitor rather than a verdict. The imagined life arrives with an air of great authority, as though it were reporting of fact about your wasted potential. It is not reporting anything. It is a picture, generated by a mind that is very good at generating pictures. You can let it sit down

without agreeing to everything it says. The second is to ask what it is supply. and then to ask whether any of that is available now, in a smaller form. Not the whole other life, a piece of it. The spaciousness, the making, the closeness to a place, the sense of being at the beginning of something. Almost always, a version of it exists in the present at a scale you could actually reach this month. And the third is to give your own life

the same courtesy, you give the imagined one. This is the one people skip, and it is the most important, because the comparison has been rigged in one direction for years, and it can be tilted back a little. Your actual life also contains things that no imagined version would have. The people in it are specific, the friend who knows what you were like at 22, the way your child laughs, which belongs to that particular person and to no other possible person. The competence you built by doing one thing badly for a long time until you were good at it. The evening last spring that you have not thought about since, which was, at the time, entirely sufficient. None of that, would exist on the other road. Something else would, but not that. If you gave the other life the

same scrutiny you give this one, it would collapse in an afternoon. And if you gave this life the same generosity you give the other one, it would look, I suspect, quite a lot better than it currently does. That is not a mental trick, and I'm not asking you to talk yourself into contentment. It is simply a correction of a measurement error. You have been putting one life under a lamp and leaving the other in flattering half-light for years and calling the result an honest assessment. I sometimes picture the whole thing as a gallery.

There's a long room, and on the walls are portraits of every person you might have become, the one who stayed, the one who left, the one who said yes to the offer, the one who called back. They're all extremely well painted and they're all flattering. And if you stand in front of any one of them for long enough, you will begin to feel that you are looking at the person you were supposed to be. But look closely at the paintings and you will notice two things. None of them is signed because no one made them. They were assembled out of your own longing,

and the longing changes, so the paintings change too. And none of them is dated. Not one of those figures ever had a Tuesday. Not one of them ever woke at three in the morning worrying about money, or lost a friend to a slow drift, or sat in a waiting room, or had a difficult decade. They were spared all of it,

and being spared all of it is precisely what makes them beautiful, and precisely what makes them unreal. Then you turn around, and behind you, there is a single portrait, and it is not flattering at all. It has all the wear in it. Everything that happened is in the face,

It is the only one in the building that was painted from life. That is the one you get to keep working on. The others are finished. They were finished before they began because nothing that has not been lived can be added to. And your own is not finished, which is the whole of the good news, and the reason it is worth turning around.

You cannot go back and choose again, but you are choosing today in far smaller ways than the ones you keep replaying, and those small choices are the only material any life has ever been made from. The other roads have no Tuesdays in them. Tomorrow is a Tuesday or something very like one, and it is yours.