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The Question I Ask Myself Every Night

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I Like To Take Long Walks

I find a lot of solace in wandering. It helps me think.

A couple months ago as I was out, I came across a podcast that talked about owning your life and having direction — even if that direction is as small as making tomorrow suck just a little less than today. He argued that the days accumulate, one direction or another, then talked about how so often we let ourselves corrode while enduring shitty circumstances and people. Bad jobs. Toxic bosses. Manipulative relationships. On and on. And the more we come up with excuse after excuse for letting these things remain in our lives, the more we lose ourselves and hollow out our spirit.

I’ve been frustrated with myself. This year has felt like one where a lot has happened to me, but I haven’t done well making things happen. I know I’m not unique in this — this year has hit everyone like a freight train, many much worse. But I related to that corrosion he talked about. It feels like atrophy. Earlier this year, I wasn’t able to work out for a couple months as I waited for a hernia surgery, and then had to wait another few months afterward before I could lift again. I’ve hated that feeling — of losing myself day by day — and I’ve aggressively worked to regain what I’ve lost.

But his words applied to how I felt in my spirit too.

I felt atrophied.

As he continued to talk, I was overwhelmed. For as much as I have valued and taken pride in owning myself, I felt like I still had this gap where I would just let shit happen instead of confronting it. As more and more came to mind from my own life where I did not take initiative, I became more and more furious with myself. I realized that whenever shit inevitably hit the fan, it was never a surprise. The shit would always have been on my radar before, but I would push it off thinking it would take care of itself, wasn’t a big deal, or I could deal with it later if it got worse.


This attitude may have been partly a reaction to the anxiety I had when I was younger, thinking that on principle I shouldn’t worry about things and risk making mountains out of molehills. Maybe there’s some virtue in just letting things ride. Especially this year, seeing how much other people are suffering there’s a sense of “if you can put up, you should shut up.” But as I took that walk, I saw it all so clearly — how weak this attitude was, how weak I was.

I had betrayed my core.

I stomached that feeling that’s a blend of nausea and rage, swearing at myself. No more. No more letting things slide. Ever. Whenever something is in my domain and blips on my radar I must confront it. No more letting any shit fester.

I stopped walking, pulled my phone out, and wrote down a question to ask myself, setting an alarm on it to remind me every night at 10pm. I used some of the phrases that were so impactful from the podcast I listened to — so credit to Jordan Peterson.

“Did you do anything today that made you feel weak or ashamed? Confront fear. A harmless man is not a good man. Good men are dangerous.”

I needed the reminder that harmless people are not good, and that good people are dangerous. Life is dangerous. And to think that good people authentically living in this world could be anything less is the same illusory hope that the naïve cling to in Vegas: I can beat the house (that was also me, age 25 after reading a book on blackjack).

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At First …

The first thing I realized as I asked this question was that it was not effective if I thought about it rationally. I have reasons — no matter how ill-founded — for why I do things. The question was not aimed at finding something I’d mentally overlooked or didn’t understand, but rather at acknowledging an emotion I had dismissed. Had I felt weak or ashamed that day? From there I could figure out what to think, but not vice versa. So I learned to take a few moments to be still and introspective, letting those emotions float up.

And they did.

The first couple nights of asking myself this question I found some immediate answers. I’d been casually dating, which has never really been my thing. I don’t judge people that do, we all have things that work for us and things that don’t work for us. But in the spirit of “what the fuck do I know” I had decided to give it a shot, but it wasn’t me.

Did you do anything that made you feel weak or ashamed?

I felt like I wasn’t being good to the person I’d been seeing since it was only supposed to be casual, I was being too aloof and keeping intentional distance. I kept going back and forth about “what should I do” until I realized this! this is weak! I wasn’t in a spot where I wanted to get deeper into a relationship, so I was forthright about it and then we stopped going out.

This leads to other feelings — loneliness in particular. That feeling when you look around an empty room and can hear the silence. Fuck. And it echoes. There’s a temptation to weigh this feeling against the feelings that originally drove me to answer my question in the first place, and then let the one that feels worst drive me. But I don’t want to be the sum of my most negative emotions, no matter how shitty they feel. I’ve seen in the past that my life is filled with the things I make room for — so I have to operate on the faith that I’ve made space for who I want to be — which is much different than being empty.

But to quote myself from earlier “what the fuck do I know.”

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Each Night I Kept Confronting Myself

What I noticed as I continued to ask myself the question and recognize as things started to accumulate or bother me, I would be more aware of them even during the day as they happened. Instead of reflexively burying something or defaulting to a grin-and-bear-it attitude, I began to catch myself in the act. For instance, if someone said something that seemed off or something at work seemed wrong, I’d speak up. And to clarify, being confrontational isn’t being combative. Sometimes something just needed clarification and I’d completely misunderstood. Other times there was a problem, but we were able to address it.

I found the sooner I would approach an issue, the less an issue it ever became. I felt silly that I’d ever thought it was a good idea to push things off or let things slide. The fear of making mountains out of molehills was completely wrong — this was a necessary responsibility similar to changing my cats’ litter box. If I didn’t do it, poop would pile up.

But What About …

As I kept asking myself the question each night — sometimes old, calcified emotions would rise up that I would immediately bury again. That doesn’t count, it’s their problem not mine. It bothers me because it rightly pisses me off, not because I’m weak or ashamed. But the emotions would keep coming back and became the only answer I had. I’d still deny them. There’s nothing I should do. I don’t need that in my life.

After a while of denying those emotions, I had no other answers to my questions. I could hear a voice in my head say in heavy sarcasm “You must’ve felt great today, huh? Nothing to bother you?” And I would get frustrated with myself again, knowing I’d felt anything but. So I added to the question, adjusting it so that it would help me pick-axe away at my denial.

Did anything disturb my soul? Scare me?

Eventually, as I turned new questions over in my head the right questions would draw out the emotion I was feeling. But the emotions were hard to digest, because they meant that I needed to address long standing hard feelings and awkwardness with some people, especially my family. I would try to rationalize these feelings away, but after several weeks my resistance broke.

And so I set up times to talk. I would visualize how things would go and what I needed to say over and over. As I would drive out to see them, I couldn’t even listen to music. I had to have silence. I had to focus. I made lists of things I could do afterward — partially to promise myself there would be an afterward and that things would be okay.

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So I Opened Myself Up

Each encounter was much less dramatic than I anticipated. Anticlimactic, even. But each one changed me. I don’t know if it goes back to my religion growing up, but I’ll unintentionally think of the body and the spirit as two completely different things. They aren’t. How can thoughts and emotions have physical weight? But they do, and I didn’t anticipate how much weight I had been carrying. My chest literally felt lighter afterward, and my muscles less tense.

For years, when I have been on my own I have had trouble staying in one spot doing one thing. I struggle with focus, because there’s always something else I should be working on. I can’t just enjoy being in a moment. Ever. It drives me crazy because I’ve struggled to even sit down and read. Until now. Whatever that was inside that was always whirring, it fell silent. Now when I am somewhere, I feel present in it. There’s nowhere else to be. The other day I picked up a book, and was stunned when I read through several chapters — just sitting for an hour. I got lost in the book, instead of my mind wandering off and then me setting the book down to wander after it.

What I was most surprised by was that in each situation I typically carried around more hardness and defensiveness than was necessary. I had spoken for other people in my head. I had felt their resentment, disappointment, and anger at one point — then multiplied it and carried it perpetually.

This isn’t the most attractive analogy, but it’s the one that has been on my mind. For insects to grow, they have to get rid of their exoskeleton, because it doesn’t grow with them. Snakes shed their skin for a similar reason: they outgrow it and need to get rid of old parasites that have become embedded in their old skins. There’s something poetic in that. Both insects and snakes may be more vulnerable immediately afterward, but it’s the only way for them to grow. And that feels like what I’m experiencing — I have to let go of my defenses and my hardness. They served their purpose for the time I needed them, but for me to grow I have to let myself be vulnerable.

Photo by John Spalding from Pexels

To Sum It Up

This doesn’t mean that life is easy or that everything is good. I’m sure there will be more conversations. More emotions to address. More everything — especially as this winter is drawing closer and everything looks so bleak. But it does mean that life is a little better, because among the battles I’m fighting — I’ve stopped fighting myself. I make it harder to be my own worst enemy. More than that, each time I confront an issue it’s an exercise in emphasizing my worth — especially to myself. That’s the strength training I’ve needed to address my atrophy.

And there’s no magic in the words or the questions. I’m sure other questions would be more relevant to someone else — these particular ones resonated with me. I think the value is taking the time to be introspective and to challenge yourself. Each day adds up, and in the same way people can drastically transform their physical nature when they discipline themselves, I think the same can be done in all of our nature — mental and emotional.

Also, my questions keep evolving over time, they’re organic. It reminds me of a practice from medieval Christianity in which devotees would take extracts from various sacred or inspirational writings and put them together into one focused theme. The documents were called “florilegium” which in Latin essentially means “gathered flowers.” That’s such powerful imagery to me, to think of different words and passages as flowers and that assembling them together creates a distinct beauty. As I find new ideas, and new questions, I add to my collection. Other times I prune. But each night when my alarm goes off — I read whatever new form the questions have taken.

I share all of this because I’ve been so surprised and impacted by doing this — and hope that it’s something that anyone reading this can take some value from as well. Think up a question or two that checks if you are who you want to be — then set a reminder on your calendar or some other app and do it every night. Not every night is going to be something dramatic or amazing, but it’s about your direction day by day. And sometimes it takes time — weeks or more — to break through some of the dams we’ve set up. Your experience will be uniquely yours, but I can’t imagine that challenging yourself with some emotional introspection would not yield something positive.

I’ll share my own questions. It’s about a paragraph now, and a little clunky, and in some places has changed more into a creed — but it’s meaningful, and things I want to be introspective about to keep at the front of my mind every day.

“Did I do anything today that made me feel weak or ashamed? Did anything disturb my soul? Scare me? Pressure me that I was going to be in trouble? Confront tyranny — don’t let the weak and corrupt win. A harmless man is not a good man. Good men are dangerous. What did I do that was healing and enriching to myself and others?”



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Christopher Guarnera

Christopher Guarnera

Entrepreneur, software developer, and writer. Enthusiast of good stories, interesting conversations, and serendipity.