Facing Uncertainty: Can Philosophy Help Chicagoans with Anxiety?

Uncertainty is having a moment... in Chicago, in the world, and sometimes, in my head. The weather changes its mind by lunch, and my work email inbox can feel like it’s training for the Chicago Marathon: no warm-up, just go.

Personally, I have always felt uncertain about a lot of things. This is especially true when people around me ask, "Why are you going to a philosophy school? What are you doing in life? How is everything?" I have always felt that what they were truly asking was, "Why are you doing that?" You should be doing this..." whatever "this" is supposed to be.

All the questions people ask, combined with everything in my social media feed, can leave me feeling uncertain and second-guessing my decisions. It is particularly challenging not to compare myself to people who seem “ahead” or “behind.”

So, the question I’ve always had is: Can practical living philosophy offer a real form of help with anxiety here in Chicago?

The truth is, we are each on our own path. Uncertainty is natural; it is part of being human. And while anxiety can show up along the way, it does not have to run the show. If you’ve been trying to out-think the future and feel rushed to have it “figured out," like"everyone else" you’re not alone.

Let me be clear right up front: if you are dealing with clinical or severe anxiety, absolutely do what you need to do and seek professional medical treatment. Philosophy isn't a replacement for a doctor or a therapist. But can it provide us with everyday practices to handle the daily grind in Chicago? The answer is yes. 

The amazing thing is... across Stoicism, Buddhist mindfulness, and existentialist philosophy, there is a shared message: life changes, and the mind hates not knowing.

The good news is that anxiety isn’t the only possible response. When grounded in philosophical practices, uncertainty can become something you navigate without too many trip-ups. And when those falls do happen, and trust me they do (even if you try your best to live like a New Acropolitan and live with philosophy daily), we can finally start calling them what they are: life lessons.

Why uncertainty triggers us (and how philosophy can help with anxiety)

Anxiety often shows up when the mind tries to get certainty where certainty can’t be found. It runs simulations: What if I lose my job? What if this relationship shifts? What if I make the wrong choice and ruin everything forever? What if I choose to support the Sox over the Cubs? Will my family disown me? The mind is dramatic. It would do well in improv, side note; personally, I always wanted to do improv. Maybe soon you’ll see me at Second City Chicago. After all, I’ve heard that the most modern philosophers are now the stand-up comics that go DEEP.

Anyways... continuing on.. philosophical traditions don’t pretend uncertainty is pleasant. They simply teach a more useful relationship with it:

• Stoicism (especially Epictetus) emphasizes distinguishing what’s under your control from what isn’t.

• Buddhist mindfulness trains attention to meet change without clinging or avoidance.

• Existentialist thought highlights that uncertainty is part of freedom—and meaning is something we live into, not something we discover fully formed.

  
  

Different lenses, same direction: less illusion of control, more inner stability. Which is the goal, right?

The Stoic reset: what is (and isn’t) up to you

Epictetus, a former enslaved person who became one of the most influential Stoic teachers, opens his Enchiridion with a clear line: some things are up to us, and some things are not. That distinction is not a slogan it's a daily practice! Or it can be, if you choose to live with philosophy every day.

When we blur the line, we suffer twice:

1. We try to control what can’t be controlled.

2. We neglect what actually can be shaped: our choices, interpretations, and character.

A practical control map for everyday Chicago life

Buddhist mindfulness: meeting change without clinging

Where Stoicism brings clarity, mindfulness brings steadiness. In Buddhist practice, a major cause of suffering is clinging... we cling way too much... to outcomes, to identities, to the way we think things “should” be. We can have wishes and choose to bring about change in our own ways through our own actions, but honestly, things are the way they are, and we cling onto the wrong things. Enter mindfulness.

Mindfulness doesn’t mean “be calm all the time.” Although I definitely try that personally and fail constantly, a calm presence is a mission I love pursuing. True mindfulness, however, means the following:

• noticing what’s happening inside you (sensations, thoughts, emotions),

• without immediately believing every thought,

• and without needing the moment to be different before you can be okay.

In a city that runs fast, mindfulness is quietly rebellious. It’s the choice to pause at the crosswalk of your own mind and actually look both ways before crashing in your mind and crashing out IRL.

A simple mindfulness practice for uncertainty (3 minutes)

1. Name the moment: “Uncertainty is here.”

2. Locate it in the body: tight chest, restless stomach, buzzing thoughts.

3. Breathe with it (not away from it): slow inhale, slower exhale.

4. Label thoughts as thoughts: “planning,” “catastrophizing,” “rehearsing.” Or as one of my personal favorite Buddhists, Thich Naht Hanh, suggests in his book, Being Peace, you can label thoughts as "thinking" and then return to your breath.

5. Return to one anchor: breath, feet on the floor, sound in the room.

You’re not trying to eliminate uncertainty... you’re training your mind not to panic in its presence.

Existential resilience: meaning doesn’t wait for certainty

Existentialist philosophy (think of writers like Jean-Paul Sartre and Simone de Beauvoir) can sound intense, but its core can be surprisingly empowering: life doesn’t hand you a guaranteed script. Although the thought of that sometimes piques my interest, who doesn’t love some free will? (If you don't, let’s have a philosophical conversation!)

That can feel scary to not have a script... until you realize it also means you are not trapped by a script.

From an existential perspective:

• You can’t always choose your circumstances.

• You can always choose your stance, your values, and your next action. (This is it right here)

Uncertainty becomes less of a threat when you stop demanding that the future prove you’ll be okay, and start building “okay” through how you live today. Just like the crazy Chicago weather we find ourselves in, it ebbs and flows, and that is normal; we can’t control it, we can only accept it. How we accept it is the question.

A grounding question for existential clarity

When you don’t know what will happen, ask:

• “What kind of person do I want to be in this situation?”

Not “What’s the perfect outcome?” Not “How do I avoid discomfort?”

Just: Who am I choosing to become? Who am I really?

Three inner practices to build resilience (without pretending everything is fine)

Below are concrete tools you can use this week... between the meetings, on the “CTA” or during a walk along the lakefront.

1) Negative visualization (Stoicism): rehearse reality, reduce panic

Stoics practiced premeditatio malorum... imagining challenges in advance, not to be gloomy, but to be ready and grateful.

Try it gently:

• Imagine one realistic difficulty: a plan changes, a conversation goes poorly, an opportunity doesn’t work out.

• Then ask: “If that happened, what would I do?”

• End with: “And what do I have right now that I appreciate?”

This practice reduces the shock factor. The goal isn’t to expect disaster.. it’s to realize you can meet difficulty without falling apart. This practice right here has helped me grow so much and be “relatively” okay in most situations.

2) Reflective journaling (multiple traditions): clarify the story you’re telling

Journaling isn’t just “dear diary.” It’s philosophy with a pen.

A helpful structure (10 minutes):

• What happened: facts only.

• What I told myself: interpretations, assumptions, fears.

• What I can control next: one action, one attitude, one boundary.

• What matters here: the value at stake (respect, stability, honesty, growth).

Over time, this trains you to separate reality from the mind’s commentary track.

3) Value-based decision making (existential + practical): act with integrity amid unknowns

When outcomes are unclear, values become your compass.

Pick 3–5 “north stars” and keep them simple:

• honesty

• courage

• kindness

• discipline

• service

• wisdom

Then, when stuck, ask:

• “Which option aligns more with my values?”

• “What would I choose if I wasn’t trying to control everyone’s reaction?”

• “What decision lets me respect myself tomorrow morning?”

You may still feel nervous... but you’ll feel less divided inside. The goal is to be conscious.

Bringing it back to daily life: work, relationships, and the future

Uncertainty shows up in predictable places. Here’s how these practices translate.

At work: replace rumination with a next step

• Use the control map: focus on effort and communication, not forecasts.

• Use journaling: clarify what you know vs. what you assume.

• Use values: choose professionalism and courage over avoidance.

In relationships: trade control for honesty

• You can’t control someone’s feelings, but you can control your clarity.

• Mindfulness helps you notice when fear is driving the conversation.

• Stoicism helps you accept outcomes without collapsing your self-worth into them.

About the future: practice small acts of trust

The future isn’t a problem to solve all at once. It’s a direction you walk toward... one step, one day, one choice at a time. When you need a break, go reward yourself with some Deep Dish, because this is Chicago.

A simple weekly resilience plan (for busy Chicagoans)

If you want something doable (not heroic), try this:

1. Twice a week: 10 minutes of reflective journaling

2. Once a week: negative visualization (5 minutes), then gratitude (2 minutes)

3. Daily: 3-minute mindfulness pause (especially before hard conversations)

4. Before decisions: ask the value-based question: “Who am I choosing to be?”

Consistency matters more than intensity. For real for real.

Philosophy as a practice, not just an idea

Resilience isn’t pretending you’re unbothered. It’s learning to face reality without losing your center.

That’s one reason we love practical philosophy at New Acropolis Chicago: it’s not about collecting quotes... it’s about building inner tools for real life, right here in our neighborhoods, relationships, and daily responsibilities. If you’re curious to explore these ideas in community through classes, cultural events, and volunteering, you can learn more at New Acropolis Chicago.

Uncertainty will keep doing what it does. With practice, you can meet it with steadier eyes, a calmer nervous system, and a life guided by something deeper than fear.

Written by Michael Jaurigue, with a bit of help from AI.

When he isn't out walking dogs across Chicago, Michael is a student of philosophy. He currently takes courses at New Acropolis Chicago and volunteers his time writing for the school's blog. He believes wisdom is found by taking knowledge and putting it into action: whether he's dealing with the daily grind or studying philosophy, he tries his best to live out what he learns and share the journey with others. The views in his writing are his own.

Disclaimer: The philosophical practices shared in this post are meant for educational and personal growth purposes. They are not intended as a substitute for professional medical advice, diagnosis, or therapy. Always seek the advice of your mental health professional or other qualified health provider with any questions you may have regarding anxiety or other medical conditions.