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Productive and unproductive guilt and suffering

Be motivated by where you need to improve or atone. Don't drag yourself down by falling in love with suffering.

9 min read


Productive and unproductive guilt and suffering

Volkan Olmez/Unsplash

Most of us need periodic reminders to be humble, more questioning and curious, and more open to other people’s ideas and thoughts. Another part of staying grounded is being aware of our mistakes and shortcomings.

As Box CEO Aaron Levie recently said:

We’re going to deal with a lot of challenges, and if we have people who are going to mask those challenges, or not be able to actually address them because they’re just over-confident or have too much ego, we can never succeed as a business, especially in any kind of rapidly changing environment. And frankly people just don’t like working with those kinds of people.

If you are self-questioning and introspective, you’ll inevitably deal with guilt. But there are two types of guilt people tend to grapple with. One is when you’ve done something wrong or failed to live up to your commitments. These can be inadvertent mistakes, the result of impulsive decisions or borne from serious and willful actions that were wrong or hurtful. We have to own those errors, make amends and, especially, try to do better. Learning and growth is part of the cycle. Some of us are bad at this. Almost all of us, me included, can do better.

The second kind of guilt is also common but it’s different — it’s a guilt we needlessly pile on ourselves. You’ll see it when we blame ourselves for things outside of our control, or for things that didn’t go well despite our best efforts. Or, some of us will feel bad about things we think we’ve done or offense we’ve caused, even if those things didn’t happen in that way. This guilt is also present when choose to re-examine the past for flaws and faults alone, failing to appreciate what went well or what we have.

In those moments it’s hard to remember that unproductive self-flagellation is no better than a runaway ego.

Suffering is not a pre-requisite

An illustration of how this guilt can be ingrained in us can be found on Conan O’Brien’s podcast episode with Stephen Colbert. The two talk-show hosts both grew up Catholic, as did I. (Colbert is well-known for teaching Sunday school) That shared upbringing and other environmental and cultural factors led to this statement by O’Brien:

O’Brien: I grew up an anxious person, very anxious person, and struggled with anxiety, and I really thought in a Catholic way that everything anything good had to come through suffering. I really believe that you have to be miserable. And so I was a grind. I was a grind in school, I took everything so seriously. And what happened was I had a natural facility for being silly and funny, but that was just for my friends. I didn’t put any importance on it at all.

And it was only when I stumbled into college and accidentally stumbled into the [Harvard] Lampoon, people valued comedy and I realized — wait a minute, this is something I do for fun but suddenly people are saying hey you know you’re pretty good at this. And this is a valued skill in the world and I didn’t know that. I think I was 18, 19 years old, I had no idea and I didn’t trust it because I could make a whole room full of people laugh and there was no misery beforehand and everyone was happy. ..

“There was no misery beforehand”

Being in comedy has its struggles. as you regularly face rejection and are often without a steady paycheck. But being funny for others is a gift, most of us would agree. And yet O’Brien had built up in his head that misery — suffering — was required for anything good to happen.

Note that this is distinct from the idea that you have to put in the work and time to become great at something. Or that adversity is inevitable and shapes us. I suspect O’Brien’s not alone in this idea that anything good happening is suspicious and can’t be trusted. While O’Brien’s life story suggests he’s overcome a lot of this anxiety, it’s easy to see how this type of guilt leads people to sabotage themselves at work, in relationships, in their health, etc.

Colbert is a kindred spirit, responding “that is a dish that is hitting so many parts of my taste buds right now. That is a bell that is, you know, ringing so many places in my brain.”

Of course, many of us know that Colbert had real suffering as a child, losing his father and two brothers in a plane crash. And he grew up in a devout family where suffering for Christ was “the highest aspiration.” But there is something else here apart from being religious (or not). He goes on:

Colbert: I had a magical thinking —

O’Brien: Yes!

Colbert: I had a magical thinking about suffering and about forbearance and patience … my father and two of my brothers died when I was 10 years old, as you know, and, well, [pause] it would require enormous magic for that not to have happened. Enormous magic. But what kind of brother or son would I be if I didn’t at least attempt the magic, do you know? Because every young questing hero, at first. it’s impossible to bring them back, do you know? You cannot pass through the tunnel that is just a black circle on a wall until the young hero does.

You can understand 10-year-old Colbert going through this exercise, of course. But how many times do we put ourselves through unnecessary suffering, guilt and agony over things with one-millionth the importance?

We embrace “magical thinking” because we want to justify the suffering

This idea of “magical thinking” is something O’Brien and Colbert each, with feeling, urge people listening not to embrace. We don’t need to induce unnecessary suffering and guilt before achieving success. But even still, this idea has a hold on them, as O’Brien elaborates:

O’Brien: My family, who I love very much, they’re magical thinkers, they’re beautiful magical thinkers, they’re crazy magical thinkers, and I’m a crazy magical thinker, and that’s how I grew up, Here’s the thing, here’s the crazy thing —

Colbert: Right, and I know!

O’Brien: You are talking about you went through this pain, and you went through this process, that any normal person would tell you, any therapist — a cognitive therapist would say this suffering is unnecessary, you achieve nothing with this suffering. And I still wrestle with that to this day. Cause I didn’t suffer a tragedy anything million years close to what you suffered, but I felt like I suffered through other things and they felt very powerful to me.

And I engaged in magical thinking and put myself through a lot of torture. And, here’s the crazy thing: What happens when you do that and then magical things start to happen for you?  You can’t see because it’s a podcast, but Stephen just very meaningfully pointed his finger at me as if to say, “You nailed it.” …

Colbert: When you said, ‘here’s the crazy thing’ and I said ‘I know,’ what I meant was it works!

O’Brien: I know! But you know what I hate, I hate, what I hate, I hate that it [expletive] works.

Colbert: Because I don’t recommend it —

O’Brien: I don’t want my children to ever go through it.

Colbert: And I don’t want people out here to want suffering or to even engage in the magical thinking part of the suffering because I think that there are other ways.

Notice the hold this thinking retains on O’Brien, as he says “I hate” over and over to illustrate his struggle with the concept of magical thinking. That said, we don’t need to be middle-aged men or in comedy to fool ourselves into this type of thinking.

I’ll use myself as an example. When I communicate poorly, or am inconsiderate, or betray trust — especially when I know better — I should feel some guilt and a need to remedy and rectify the situation. I should be disappointed in myself when I don’t make the effort to rectify those mistakes and to not repeat them.

But you know what I also spend a lot of time on? Silly things, like some mildly embarrassing, probably funny, misstep or miscue from 25 years ago, when no one else possibly remembers or cares — if they cared then. Or, I’ll take fond memories or memories of accomplishments and instead conjure up regrets because I somehow wish it had been even better. Maybe it’s blaming myself for somehow not foreseeing and overcoming the actions of others. Or, and I’m great at this, procrastinating on something difficult (or not so difficult) when I could just ask for help, connect with someone else and save myself time and stress.

I believe we all have our own versions of this. We have to be better at handling both types of guilt. The tricky part is “how,” and I can’t answer that for you.

But here’s the goal: Hold yourself accountable for the things you know you need to do, especially when your conscience is lighting up. Forgive yourself the rest of the time. You don’t need magical thinking or suffering. The world is difficult enough as it is.


James daSilva is the longtime editor of SmartBrief’s leadership newsletter and blog content, and an even longer-time fan of Conan O’Brien. Contact him at @James_daSilva or by email.

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