An Essay About Freedom, Sort Of

It's about other stuff too

For many years, Freedom has been my North Star.

It has been my core value, my Holy Grail, my deepest aspiration. It is the metric against which I measure most of my decisions, whether consciously or subconsciously. My life has largely revolved around its pursuit.

Over the past five years, I have managed to gain a tremendous amount of freedom. In 2017 I was spending six to seven days a week working a miserable job, and I compensated for that misery by digging myself into a cavernous financial hole. I felt about as free as I imagine one does in solitary confinement.

Since then I’ve taken a number of intentional and significant steps to become Free. I changed careers, got my finances in order, and bought a business. Today, my time is entirely mine. I have virtually no external restrictions. By most standards, I have achieved Freedom.

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Throughout the process of working to become Free, though, I’ve had a feeling that started as a muffled whisper but has grown louder as I’ve continued to remove external limitations. For a long time I didn’t quite know what the feeling was, but I did know that it likely challenged my ideas about Freedom and that it made me uncomfortable. I knew this because it was basically the same feeling I had back in 2017 — a frenetic sense that I was in an undersized cage that I needed to break out of, immediately —  and it continued to persist even as I progressively shed any control that external sources had over my life. It put into question the nature of the cage.

This was both puzzling and inconvenient, so I did what any self-respecting man would do: I ignored the feeling and moved forward. When it got louder, I responded with action, doubling down on my efforts to become more free. And when that didn’t work, I tried to achieve or learn or buy or drink the feeling away.

Essentially, I tried to outrun it.

It eventually caught up with me, as these things tend to do. None of us can outrun the truth. This particular truth became clear when I was sitting on the couch with no obligations, nothing on my calendar I didn’t actively choose, and a heart still racing with the inescapable feeling of being shackled in captivity.

I did, in fact, want freedom. Freedom from myself.

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What I mean by this is that my head has not always been a particularly comfortable place to hang out. I have rarely felt at home within myself, and I’ve responded to that internal discomfort by solving external problems.

It’s like living in a really messy house that stresses you out by virtue of its disarray, making you want to just get out so you can be somewhere — anywhere — else. My constant pursuit of freedom and (mostly well-intentioned) distraction was akin to trying to clean the house by cleaning the yard, or buying a vacuum, or reading about cleaning. Those things are all great, but the only way to clean a house is by cleaning the house.

This begs a few questions: What exactly is cleaning the house when the house is your consciousness? How does one go about it? Are there brooms and Clorox wipes for the mind? Are they on sale?

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I’m about as far as one can be from an expert on any of this, but I have recently started to shift into a markedly more comfortable and confident headspace. I attribute this to three things, in roughly increasing order of importance.

The first part lies in that obnoxious, trite word that we’ve become so accustomed to hearing: mindfulness.

It’s impossible to prevent the torrent of thoughts and emotions that our minds produce; our agency lies in how we choose to respond to them. Thousands of years of human experience have taught us that resisting or fighting this Torrent when it becomes unpleasant only amplifies the discomfort and makes things worse over time. Conversely, sitting with it and letting it run its course without trying to interfere seems to weaken it. These kinds of feelings tend to wither under the spotlight of observation. They paradoxically lose their power when we stop resisting them, sort of like internet trolls.

I think we all tend to shy away from this process because the initial period of discomfort involved in sitting with the Torrent is, well, uncomfortable. The idea of mindfulness sounds so frustratingly simple. And based on prior experience, it is. Very rarely does one feel worse after meditating. But simple doesn’t mean easy.

In an age where we have a never-ending supply of ways to distract and numb ourselves from the Torrent without having to use our brains at all — let alone pay attention to what’s going on inside of them — the prospect of sitting alone with our thoughts can be downright terrifying. The barrier to avoidance is lower than it’s ever been, and we have gotten alarmingly accustomed to being able to distract away discomfort on demand.

But that discomfort that we’re avoiding, like most other forms of discomfort, is important for our development. All creatures on this planet grow through adversity; we’re no different. Just as our muscles atrophy when they aren’t regularly under stress, so too does our brain’s ability to manage what life throws at us. When we constantly sweep sources of difficulty or discomfort under the rug, the level of challenge that we’re able to handle gets lower and lower. This is how we end up with things like ‘safe spaces’.

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Mindfulness becomes even more important when you consider that not all forms of avoidance are as overtly or entirely harmful as scrolling through your phone. Consider my pursuit of freedom.

The steps I took to gain external freedom were unquestionably important and valuable. I would still be miserable if I hadn’t done what I did. I’m a Greek Jew, which means that I’m stubborn and enterprising and don’t like to be told what to do. The life that I live today suits me completely and is worlds better than the one I had a few years ago. I wouldn’t trade it for anything.

And therein lies the complexity. Many of the ways that we avoid dealing with our shit are also healthy for and important to us. Life is frustratingly paradoxical that way. My pursuit of freedom was simultaneously crucial for my fulfillment and wellbeing while also serving as a distraction from addressing underlying issues that were making me crazy. I didn’t realize this until I stopped moving and examined what was actually going on.

This is why I’ve begrudgingly hopped on the mindfulness bandwagon. It seems impossible to understate the importance of being able to sit with whatever is going on in our heads. It’s remarkable what happens when we stop fighting or looking away and instead allow the inevitable discomfort to serve us. Our consciousness has a miraculous way of naturally working through all the crap. We have a built-in Brita filter; we just need to give it time and space to operate.

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The second part of my strategy involves having an outlet through which to externalize what’s going on in this filtration process. Language has been one of the most pivotal drivers of human development in the history of our species for a reason: it allows us to turn murky, abstract thoughtstreams into clear, linear concepts. This is not only important for interpersonal communication; it’s also a crucial tool for understanding ourselves and our own narratives. I increasingly believe that not using language for this purpose by writing or talking about our internal lives is actively harmful. It’s analogous to how most things are scarier in the dark. A bunch of messy and weird stuff will inevitably enter our minds on a regular basis, and when we fail to externalize it, we keep it in the dark and reinforce its status as The Scary Unknown. When we bring it into the light, we gain power over it. We start to deal with a known quantity.

My outlet is writing, mostly. Some people go to therapy. Others talk to their friends, or their dogs, or their stuffed animals (I’m not here to judge). It doesn’t have to be some grand or dramatic thing; the point is that the crap in our heads, like the crap in our bodies, needs an outlet. Otherwise, our systems get overwhelmed and we stop functioning properly. Bad news.

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The last and, so far, most important part of my approach is also likely to be the most polarizing. It’s something that I had no interest in hearing for a long time, and I expect many to react similarly. But it has unquestionably caused the most immediate and profound shift in my psyche.

A few weeks I ago I decided to quit drinking for 90 days. I realized that alcohol had been taking more from me than I was getting from it, and I wanted to see what happened if I cut it out. If, after the 90-day period, I didn’t notice any material difference and felt like I was missing something, I’d get back to it and laugh about what a dumb idea it was.

Well, just weeks into this experiment, it would be an understatement to say that I’ve noticed some changes. That constant agitated, restless, frenetic feeling of wanting to escape my own head, the feeling that underscored much of my existence? Gone. Seriously. I look for it, and I can’t find it. It’s been replaced with a sense of calmness, of evenness, of — dare I say — peace?

Having recently read a bunch of ‘Quit Lit’, reflections from others who had varying degrees of problems with alcohol and have gotten sober, this is not surprising. My experience has been quite predictable; there are tons of psychological and biological reasons that alcohol causes the feeling I described. In addition to getting rid of the neurochemical drivers of this feeling, quitting drinking has allowed me to much more easily accomplish both of the other parts of my strategy, mindfulness and externalizing, by removing what was one of the most prominent sources of avoidance and distraction.

I realize that I’ve barely started this experiment and that the adjustment will likely become more difficult over time before it gets easier again. But the results so far are too significant and persistent to ignore.

If this intrigues you, as it did me, send me a message and I’ll suggest some places to start. I have a very close friend who largely inspired this change. She’s experienced similarly incredible benefits over the course of her two years (!!) of sobriety, and she has been an incredible resource and source of support through the beginning of this experiment. I’d love to pay that benevolence forward by pointing you in the direction of people who actually know what they’re talking about.

There are many for whom alcohol is not a problem, and that’s awesome. I’m all for it. I’m just no longer convinced that I’m one of those people. And, given the net positive of the trade-offs thus far, I’m beginning to think I might be okay with that.

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At the end of the day, my challenges around freedom and wellbeing are pretty fantastic problems to have. I have an endless supply of things to be grateful for. I'm very fortunate to have my basic needs met (and then some), an amazing family, and great friends, so I get to spend my time waxing philosophical about the meaning of life and all that shit. This is not lost on me. And in fact, I used to think that this was reason to feel guilty.

But so many of us have all these needs met and are still miserable. This is not just an individual issue; it hurts everyone, including those who are less fortunate. Figuring out how to deal with our problems, however abstract and privileged, helps everyone by allowing us to show up in the world as better versions of ourselves. We're pretty useless when we're racked with anxiety.

With that said, the strategy I shared above is simply what is working for me at the moment. Your mileage may vary. The message to take home is that we often do what we do without knowing why we do it, and our actions can simultaneously be both good and bad for us. Without removing the fog of avoidance and distraction, we are unable to clearly see what is and is not serving us and adjust accordingly. The consequences of this compound negatively over time and can lead to some pretty bad places. On the other hand, when we apply the age-old tools of mindfulness and externalizing (and remove any personal barriers to doing so), we can flip the direction of the compounding cycle from negative to positive. Awesome stuff abounds.

Our ability to examine and question our lives and use what we learn in order to grow is what makes us human. I would argue that this is what Freedom truly is: employing the innate wisdom of our species to progressively shed external and internal sources of imprisonment in order to live a fuller and more meaningful life. To ignore or avoid this ability is to build a very low glass ceiling through which you're constantly forced to watch all the people upstairs having fun. That strikes me as one hell of a tragedy.