How to Let Go: Learning to Deal With Loss

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Recently, my wife and I passed by the spot of one of our first dates. For the next few minutes, we smiled and reminisced and rehashed a small happy sliver of our shared story. That date had been absolutely magical. One of those nights you dream about when you’re an awkward teenager, but as a single young adult, you begin to believe it might never happen.

And then it does. A night that you only get to experience maybe a couple times in your life, if you’re lucky.

And with that realization, to my surprise, I began to experience a faint sort of sadness. I grieved over a tiny loss of myself—that cocky, self-assured 27-year-old who walked into that restaurant having no idea what lay before him. The infinite potential that lay before us. The intensity of emotions that I didn’t know what to do with.

The two people we were that night were now gone. And they would never come back.

I would never get to meet my wife for the first time again.

I would never get to fall wildly in love in a way that both excited and terrified me at the same time.1

There was a sweet, cocky ignorance to my younger self that has been irrevocably lost. And despite being lost for the best reasons, it still made me sad. For a few moments, I silently mourned my past the way one mourns a distant relative’s death.

And then I moved on.

I’m no stranger to loss. I don’t think any of us are. I’ve watched family members and friends die. I’ve had romantic relationships end in a spectacular explosion and I’ve had them end in a long, drawn out silence. I’ve lost friendships, jobs, cities, and communities. I’ve lost beliefs—in both myself and others.

Every loss is a form of death. In every case, there once existed an experience—a thing, an idea, a person—that brought your life meaning. Now it no longer exists.

Coping with loss always involves the same dynamics. In every case—whether it’s the loss of a friendship, a career, a limb, whatever—we are forced to reckon with the fact that we will never experience something or someone again. We are forced to feel an internal emptiness and to accept our pain. We are forced to confront that horrible, horrible word: “Never.”

“Never” hurts because never means that it cannot be changed. And we always like to think that things can be changed. That possibility makes us feel better.

“Just work a little bit harder!”
“You just have to want it enough!”

These phrases give us a lil’ boot in the ass. They say if you don’t like it, get out there and change it.

But “never”? Never means it’s over. Never means it’s gone. Never means forever. And that’s really hard to bear.

You can never bring a dead person back to life. You can never hit ‘reset’ on a broken relationship. You can never fix a wasted youth or redo a past mistake or un-say the words that destroyed a friendship.

When it’s gone, it’s gone. And it will never be the same, no matter what you do. And this, in a real psychological sense, destroys a small piece of you. A piece that must eventually be rebuilt.

Every Loss Is a Partial Loss of Who You Are

One of the most common emails I get from readers is from people who want to get their ex back. Some of them word it more nicely than that—they say they want to “make things up” or “fix things,” but really it comes down to, “He/she left my ass and it hurts. What do I say or do to get them back?”

This question never made sense to me. For one, if there was a tried-and-true way to get an ex back, we would have a) figured it out a long time ago and b) break up or divorce would not exist. The world would be flooded with happily married couples. And I’d probably be out of a job.

But more importantly, trying to “win” back an ex is impossible because even if “it works,” the reformed relationship will never perfectly resemble the one of the past: it will be a fragile, contrived affair, composed of two wholly different and skeptical individuals, replaying the same problems and dramas over and over, while being constantly reminded of why things failed in the first place.

When I think of all of the happy couples I know, you know how many of them say, “Oh, he was a total piece of shit, but then he apologized and bought me cake and flowers and now we’re happily married”?

None of them.2

What these emailers don’t get is that relationships don’t end because two people did something wrong to each other. Relationships end because two people are something wrong for each other.
How to let go - many blowing away

We’ve all been through breakups before. And we’ve all, in our moments of weakness, pined for our exes, written embarrassing emails/text messages, drank too much vodka on a Tuesday night, and silently cried to that one 80s song that reminds us of them.

But why do breakups hurt so bad? And why do we find ourselves feeling so lost and helpless in their wake? This article will be covering coping with all loss, but because the loss of intimate relationships (partners and family members) is by far the most painful form of loss, we will primarily be using those as examples throughout.

But first, we need to understand why loss sucks so bad. So I’m going to whip out an epic bullet point list to set everything straight:

  • To be healthy, functioning individuals, we need to feel good about ourselves. To feel good about ourselves, we need to feel that our time and energy is spent meaningfully. Meaning is the fuel of our minds.3 When you run out of it, everything else stops working.
  • The primary way we generate meaning is through relationships.4 Note that I’ll be using the term “relationship” loosely throughout this article. We don’t just have relationships with other people (although those relationships tend to be the most meaningful to us), we also have relationships with our career, with our community, with groups and ideas that we identify with5, activities we engage in, and so on. All of these relationships can potentially give our lives meaning and, therefore, make us feel good about ourselves.
  • Our relationships don’t just give our lives meaning, they also define our understanding of ourselves. I am a writer because of my relationship with writing. I am a son because of my relationship with my parents. I am an American because of my relationship with my country.6 If any of these things get taken from me—like, let’s say I get shipped to North Korea by accident (oops) and can’t write anymore—it will throw me into a mini identity crisis because the activity that has given my life so much meaning the past decade will no longer be available to me (that and, you know, being stuck in North Korea).
  • When one of these relationships is destroyed, that part of our identity is destroyed along with it. Consequently, the more meaning the relationship added to my life, the more significant its role in my identity, the more crippling the loss will be if/when I lose it. Since personal relationships generally give us the most meaning (and therefore, happiness), these are the relationships that hurt the most when lost.
  • When we lose a relationship, that meaning is stripped away from us. Suddenly this thing that created so much meaning in our life no longer exists. As a result, we will feel a sense of emptiness where that meaning used to be. We will start to question ourselves, to ask whether we really know ourselves, whether we made the right decision. In extreme circumstances, this questioning will become existential. We will ask whether our life is actually meaningful at all. Or if we’re just wasting everybody’s oxygen.7
  • This feeling of emptiness—or more accurately, this lack of meaning—is more commonly known as depression. Most people believe that depression is a deep sadness. This is mistaken. While depression and sadness often occur together, they are not the same thing. Sadness occurs when something feels bad. Depression occurs when something feels meaningless.8 When something feels bad, at least it has meaning. In depression, everything becomes a big blank void. And the deeper the depression, the deeper the lack of meaning, the deeper the pointlessness of any action, to the point where a person will struggle to get up in the morning, to shower, to speak to other people, to eat food, etc.
  • The healthy response to loss is to slowly but surely construct new relationships and bring new meaning into one’s life. We often come to refer to these post-loss periods as “a fresh start,” or “a new me,” and this is, in a literal sense, true. You are constructing a “new you” by adopting new relationships to replace the old.9
  • The unhealthy response to loss is to refuse to admit that part of you is dead and gone. It’s to cling to the past and desperately try to recover it or relive it in some way. People do this because their entire identity and self-respect was wrapped up in that missing relationship. They feel that they are incapable or unworthy of loving and meaningful relationships with someone or something else going forward.
  • Ironically, the fact that many people are not able to love or respect themselves is almost always the reason their relationship failed in the first place.

Unf*ck Your Relationships

Dump the toxic relationship cycle with my free mini course on attachment styles.

    Toxic vs Healthy Relationships

    To dive into why some people have such a hard time letting go, we need to understand a simple dichotomy:

    1. A toxic relationship is when two people are emotionally dependent on each other—that is, they use each other for the approval and respect they are unable to give themselves.
    2. A healthy relationship is when two people are emotionally interdependent with each other—that is, they approve of and respect each other because they approve of and respect themselves.

    Toxic relationships need drama to survive. Toxic people, because they don’t love or respect themselves, are never quite able to completely accept the idea that someone else could love and respect them either. And if someone comes around giving them love and respect, they don’t trust it or won’t accept it. It’s kind of like that old Groucho Marx trope: “I’d never join a club that would have me as a member.”

    Ergo, toxic people are only able to accept affection from people who don’t love and respect them either.10

    Now, when you have an emotional clusterfuck like this—two people who don’t love and respect themselves OR each other—then obviously, they begin to feel really insecure around each other. What if she leaves me? What if she realizes I’m a loser? What if she disapproves of the pizza toppings I ordered?

    As such, these people need a way to consistently test whether or not the other person actually wants to be with them. These tests are accomplished by creating drama.

    Drama is when someone creates unnecessary conflict that generates a false sense of meaning for a short period of time. When a toxic person fucks up their own relationship and their partner forgives them and overlooks it, it causes an otherwise shitty relationship to feel non-shitty for a short period of time. And that feeling causes the relationship to feel really meaningful. They say to themselves, “Wow, I gave his dog away, and he’s still with me. This must be true love.” And everything is rosy and peachy and some other pleasant-sounding color… for a while.

    Because drama doesn’t last. The underlying insecurity remains. So pretty soon, the toxic couple will need another injection of drama to keep the farce of a meaningful relationship going.

    How to let go - couple on a bench with flowers

    Healthy relationships avoid drama because they find that unnecessary conflict detracts from the meaning and importance already generated by the relationship. Healthy people simply don’t tolerate drama. They expect each other to take responsibility for themselves. Only then can they really take care of each other.

    Healthy relationships, instead of inventing conflict to affirm their love and mutual support, minimize conflict to make more room for the love and support that is already there.

    Let’s go back to the example of my nostalgia for when I met my wife. If our relationship was toxic and I were a perpetually insecure fucktard in my relationship, I could have responded to my small amount of sadness and grief by picking a fight with my wife, blaming her for the loss of that excitement and new-relationship passion, bitching at her that things aren’t the way they used to be and it’s her fault.

    The resultant drama would do two things: 1) it would give me a sense of meaning again—here I am, fighting for a more passionate, exciting relationship with my wife! And goddamnit, she has to agree with me and do something about it! And 2) after being a total dickhole to her for an hour or three, the fact that she defended herself, placated me, or made an effort to resolve the (imaginary) conflict, would once again prove to me that she loves me and all would be right in my heart’s world…at least until I started feeling insecure again.

    Another toxic response is to simply decide that if my wife can’t give me that new excitement, then I’ll just go find it outside the marriage. Banging some rando would reaffirm my insecure feelings of being unloved and unwanted. For a while, at least. And I would tell myself all sorts of entitled bullshit, like “I deserve” to feel that newness and excitement with a woman again. And that ultimately, it’s my wife’s fault that my heart (a.k.a., penis) strayed.

    But instead of all this, being the healthy couple we are, I simply mentioned something like, “Wow, weren’t those nights together great? I kind of miss them…” And then silently reminded myself that relationships evolve, that the joy and benefits of love in week three are not the same as the joy and benefits in year three or decade three. And that’s fine. Love grows and expands and changes, and just because you possessed a fleeting excitement, does not mean it was better. Or even necessary at all.

    (Optional) You Might Be in a Toxic Relationship If…

    For those of you freaking out that your relationship might be toxic and ruining your breakfast every morning, here’s a handy little gray box to help you figure it out.

    1. You can’t imagine having a happy life without your relationship.

    A toxic relationship is a deal with the devil. You resign your identity and self-worth to this person or this thing, and in return, that relationship is supposed to offer the meaning and purpose for your life that you so desperately crave. But what you don’t realize is that by sacrificing your identity to one person or thing (or one person-thing, not here to judge), the relationship generates more insecurity, not less. It envelopes your life, demanding all of your time and attention, rendering all other meaning moot, all other relationships worthless.

    If the thought of losing your relationship feels as though your life would be over, then you’re probably cocooned in a toxic relationship.

    And look, it’s not just people who are toxic. Workplaces can be toxic. Family members can be toxic. Groups such as churches, political groups, self-help seminars—you can have a toxic relationship with all of them.11

    2. The relationship harms other relationships in your life.

    Toxic relationships are flames that consume all of the oxygen from our hearts, suffocating the other relationships in our lives. A toxic relationship soon becomes the lens in which you view all other relationships in your life. Nights out with friends are dominated by unloading the drama and baggage you’ve accumulated since you last saw them. You find yourself unable to hold conversations that don’t relate to your relationship for more than a few minutes. Compared to your toxic relationship, the world feels like a cold, bland, grey mess. You couldn’t care less. You find yourself compulsively thinking about your relationship, even in places where it’s irrational or inappropriate—at a basketball game, in the middle of a job interview, while calling your mother on a Tuesday, while listening to your kid’s shitty violin recital. Nothing else matters. Nothing else feels like it should matter.

    When enrapt in a toxic relationship, friends will find you selfish and unbearable, family members will disapprove and then quietly distance themselves. Some friends or family may try to help, telling you that your relationship is hurting you, but this will usually make things worse, not better. Outside people’s attempts to intervene will only be interpreted as more drama to stoke the toxic flame.

    3. The more love you give, the more hurt and angry you become.

    Because the drama is always calling the toxic relationship into question, the relationship demands all of your thought and energy. But then the relationship only punishes you further for this thought and energy, enabling a downward spiral of shittiness. Toxic relationships are black holes. Not only do they suck you in deeper and deeper, but they have their own force of gravity. Any attempt to break away just stokes the drama flame further, which then sucks you right back to where you began.

    Toxic relationships often have a “Damned if you do, damned if you don’t” quality to them. When you’re in them, you can’t wait to get away from them. But when you’re away from them, because you’ve lost your identity, you have no idea what to do without them.

    Why It’s Harder to Let Go of Toxic Relationships Than Healthy Ones

    Toxic relationships are addictive because drama is addictive. Like narcotics or gambling, drama is unpredictable. It is numbing and distracting, and it hits you with unexpected rewards of joy or excitement.

    What’s worse, is that we become desensitized to drama. We need to find greater and greater conflicts to prove to ourselves that we’re loved. The old conflicts will no longer suffice. You started out with a fight about who takes out the garbage. Now he takes out the garbage. But you still feel insecure and unloved. So you start a fight over how often he calls his mother. So he stops calling his mother (around you at least). But that insecurity remains. So you must up the ante again. Time to piss in his favorite pair of shoes and see how he takes that.

    Eventually, the drama reaches a boiling point and the relationship will begin to painfully evaporate, scalding everyone involved.

    But something else happens when we’re caught up in a drama spiral. As we up the ante and the drama increases, we become more emotionally dependent on the person, not less. We invest so much into the drama that we come to believe that our partner is far more important to our well being than they actually are.

    Drama is therefore a psychological prism—a funhouse mirror—skewing the meaning that a relationship brings us. In our eyes, this person or this group or this activity is everything we need, when in reality, it’s probably the one relationship that likely harms us the most.

    Incidentally, people who don’t know how to let go of a relationship are often those who were in a relationship with someone who was either abusive or completely disinterested. That’s because, in these relationships, a breakup changes nothing. When they were together, the person spent all of their time and energy trying to win their partner over. After they split, they continue spending all of their time and energy trying to win their partner over. Same shit, different day.

    Similarly, people who are unable to accept the loss of their relationship will badger their ex and instigate drama with them to re-live the sensation of that relationship. But they need to create that drama again and again to keep that feeling alive.

    Drama, of course, can infect other relationships as well. People create drama at work to overcome their insecurity of not being valuable or appreciated. People create drama with authorities or governments when they feel an existential insecurity. And people create drama with themselves when they imagine they aren’t living up to some sort of past glory.

    I go into a lot more detail about the toxic dynamic that infects relationships, breaking it down into three common patterns and uncovering its roots in your psyche in my Healthy Relationships Course in the Mark Manson Premium Subscription. I also give a step-by-step guide on how to get rid of all the drama. Check it out.

    How to Get Better at Accepting Loss

    Step 1: Understand That Our Memories Lie to Us and Convince Us That EVERYTHING WAS TOTALLY AWESOME BACK THEN, Even Though It Wasn’t

    I graduated university in 2007, a.k.a., the worst job market in four generations. I struggled after school. I had no money. Most of my friends moved away. And damn, did I miss school. School had been easy. It had been fun. And I was good at it.

    Then I went back. I had some friends who were a year behind me, and I spent a day visiting them, hanging out on campus and going to some parties that night.

    And man, it was a downer.

    I realized something: school had actually kind of sucked. I had just forgotten about all the sucky parts and only remembered the good. Pretty soon I couldn’t wait to go back home and get away.

    Our minds have a tendency to only remember the best qualities of our past.12 We delete the tedious and monotonous and just remember the highlight reel.13 Ever meet up with an ex a few years later and wonder to yourself, “Holy shit, me and this person dated?!?” Yeah, that’s because our memories aren’t accurate.14 , 15

    Our brain always thinks that there’s one thing that will make us happy, that there’s one thing that will fix all our problems. But when we find that thing, there’s always one more thing just beyond the horizon. This is known as the hedonic treadmill.16 And the same way we tend to falsely believe that achieving one goal in the future will make us live happily ever after, we also tend to falsely believe that recapturing something in our past will make us live happily ever after.17

    But in both cases, our mind is simply reaching for something to remove it from the present. And the present is where happiness is. You know, buried beneath all the bullshit.

    Step 2: Surround Yourself With People Who Love You and Appreciate You for Who You Are

    So, your mind is like a chair with a bunch of spindly legs. Some legs are bigger than others. And if enough legs get knocked out, you have to replace them.

    Well, relationships are legs on your chair. And when you lose one leg, you need to make the other legs bigger to compensate for its loss. Otherwise, the chair won’t hold your fat ass—which, I guess, in this strange analogy, is your happiness—and you’ll fall over and spill your milkshake.18

    What that means is you have to reconnect with people who care about you. It’s these people and these activities that will carry us through and be the emotional bulwark as we begin the hard process of rebuilding ourselves.

    This sounds easier than it is. Because when you’ve been destroyed by some loss in your life, the last thing you want to do is call up your friends to go get a beer. Or to call mom and admit that you’re a total failure.

    This is particularly difficult for people exiting a toxic relationship. That’s because people who have toxic relationships in one area of life often have toxic relationships in other areas. As a result, they don’t have people who appreciate them unconditionally. Everything is drama. And their breakup in one relationship will often merely be used as another form of drama in others.

    My recommendation: If you’ve lost one toxic relationship, why stop there? Use your mini personal crisis as a litmus test to see who genuinely cares about you and who’s just in it for the drama injections. Good people and good relationships will offer unconditional support. Toxic friends and family members will look to adopt the drama of your loss and make it theirs as well. This just makes everything worse.

    Step 3: Invest in Your Relationship With Yourself

    Generally, people who depend on toxic relationships for their self-worth do so because they’ve never really developed functioning relationships with themselves (and no, excessive masturbation doesn’t count.)

    So what the hell do I mean by “relationship with yourself?”

    Basically, how do you treat your own body, mind, and emotions?

    This is the time to join a gym, to stop eating tubs of ice cream, to get outside and get reacquainted with your old friend called sunshine. It’s the time to sign up for that course you’ve always wanted to sign up for, to read that book that’s been sitting on your nightstand for six months, to finally floss for the first time ever. Now is the time to also let yourself feel sad or angry or guilty without self-judgment.

    And if you find it hard to get motivated to do all these things, use your loss as motivation. If you’re the victim of a disgusting breakup, well, self-improvement is the best revenge against any ex. If you’ve lost someone close to you tragically, imagine what they would have wished for you and go out and live it. If you’ve lost something dear to you in your life, or aged out of a time of your life when you felt important and wanted, commit to building something even better for yourself today.

    Step 4: If You Were Stranded on a Desert Island and Could Do Whatever You Wanted to Do—Do That

    One of the healthiest things you can do after a loss is get back to basics: do something for the simple pleasure of doing it. If no one was around, if you had no obligations on your time or energy at all, what would you spend your time doing? Chances are you aren’t doing much of it. And that’s part of the problem. Get back to it.

    Of course, there are some people who have no idea what they would do with their time if they had no obligations or no one to impress. And this is an incredibly dire sign. It implies that everything they’ve ever done is for the simple sake of pleasing others and/or getting something transactional out of their relationships. No wonder their relationships went south.

    Step 5: If You Lost an Intimate Relationship, Don’t Be Afraid to Stay Single for a While

    After losing an intimate relationship, many people’s natural inclination is to immediately fill the void with either another relationship, or by seeking a bunch of attention, affection, and sex.

    This is a bad idea. As it distracts one from the healthy activities listed above.

    If you’re on the wrong side of a breakup (or even worse, you lose someone to tragedy), even if the relationship was healthy and secure, you need time to recuperate emotionally. And it’s hard to do that if you’re immediately throwing your heart to the next person who comes around.

    Stay single a while. Learn to spend time on yourself again. And only re-enter the dating world when you’re genuinely excited to. Not because you feel like you have to.

    Eventually, Everything Is Lost

    Life is a long series of losses. It’s pretty much the only thing guaranteed in our existence. From moment to moment, year to year, we give up and leave behind former selves that we will never recover. We lose family, friends, relationships, jobs, and communities. We lose beliefs, experiences, perspectives, and passions. And ultimately, we will one day lose our existence entirely.19

    If you think back to a hard time in your life, recognize that to get out of those hard times, you had to accept losses. You had to lose relationships and pursuits, you had to lose a lot of meaning in order to create greater, healthier meaning. In that sense, all growth requires a degree of loss. And all loss incites further growth. The two must occur together.

    People like to see growth as this euphoric, joyous thing. But it’s not. Real change brings a mixture of emotions with it—a grief of what you’ve left behind along with a satisfaction at what you’ve become.20 A soft sadness mixed with a simple joy. That night, my wife and I continued walking. And soon, we came across a new restaurant, just opened, that had new things that we wanted to try, and new experiences we were prepared to share.

    We invited ourselves in.

    How to let go - red rose


    1. Note that I’m not saying that I would never fall in love again. I’m saying that it wouldn’t happen or feel the same way. Not that that’s necessarily a bad thing.
    2. In fact, according to renowned expert researcher John Gottman, half of all marriages that end do so in the first 7 years.
      Gottman, J. M. (1994). What Predicts Divorce?: The Relationship Between Marital Processes and Marital Outcomes. Psychology Press.
    3. Seligman, M., Rashid, T., & Parks, A. C. (2006). Positive Psychotherapy. American Psychologist, 61(8), 774–788.
    4. Technically, I would argue that meaning and relationships are the same thing, but that would lead us down a philosophical rabbit hole that I don’t think either of us want to be in.
    5. Tajfel, H., Turner, J. C., Austin, W. G., & Worchel, S. (1979). An integrative theory of intergroup conflictOrganizational identity: A reader56, 65.
    6. Check out A Game of Giants by Tim Urban from Wait But Why.
    7. I don’t care who you are, I’m happy to share my oxygen with you. I’m just that kind of guy.
    8. National Institute of Mental Health (NIMH). (2016). Depression Basics. NIMH.
    9. Cognitive Behavioral Therapy has been shown to help with depression. You can find more about it here.

      Manber, R., Edinger, J. D., Gress, J. L., Pedro-Salcedo, M. G. S., Kuo, T. F., & Kalista, T. (2008). Cognitive Behavioral Therapy for Insomnia Enhances Depression Outcome in Patients with Comorbid Major Depressive Disorder and Insomnia. Sleep, 31(4), 489–495.

      Tang, T. Z., & DeRubeis, R. J. (1999). Sudden Gains and Critical Sessions in Cognitive-Behavioral Therapy for Depression. Journal of Consulting and Clinical Psychology, 67(6), 894–904.

    10. To learn more about toxic people and how to deal with them, check my audio book, Love is Not Enough. You won’t regret it. Or you might. But probably not. Maybe.
    11. And not to mention online forums or comment sections. Obviously toxic.
    12. Redelmeier, D. A., & Kahneman, D. (1996). Patients’ memories of painful medical treatments: real-time and retrospective evaluations of two minimally invasive procedures. Pain, 66(1), 3–8.
    13. Kardash, C. M., & Scholes, R. J. (1996). Effects of preexisiting beliefs, epistemological beliefs, and need for cognition on interpretation of controversial issues. Journal of Educational Psychology, 88(2), 260.
    14. In his book Stumbling on Happiness, Harvard psychologist Daniel Gilbert discusses how we suck at remembering how something made us feel in the past and guessing at how something will make us feel in the future.
    15. Elizabeth Loftus, one of the world’s foremost researchers in memory, would also be one of the first people to tell you that your memory sucks. Here’s another article to really pile it on. Thanks for nothing memory.
    16. Brickman, P., Coates, D., & Janoff-Bulman, R. (1978). Lottery winners and accident victims: Is happiness relative? Journal of Personality and Social Psychology, 36, 917–927
    17. Although there is some research to suggest nostalgia, in the right circumstances, may be a net positive for mental well-being
    18. Or maybe the milkshake is happiness. I don’t know. I’ve been writing for too long.
    19. Stoic philosophers used to meditate on death as an exercise to gain comfort with our inevitable mortality. It was called Memento Mori, which means ‘Remember Death’
    20. Shuchter, S., & Zisook, S. (1993). The course of normal grief. In M. Stroebe, W. Stroebe, & R. Hansson (Eds.), Handbook of Bereavement: Theory, Research, and Intervention (pp. 23-43). Cambridge: Cambridge University Press.