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What to do when your comfort zone feels like a prison

Here’s a puzzle for you: what should you do if your comfort zone feels like a prison?

I used to feel this way a lot. My job was comfortable, but I hated it. My hobbies were comfortable, but they bored me. Living in Boston was familiar, but I hated the ceaseless bustle of the city.

I felt like I was perpetually chafing against the edges of my life, haunted by the idea that surely there must be more out there than this.

Maybe you’ve had this problem, too.

Maybe your life is familiar and comfortable… but maybe comfortable is also kind of awful. Maybe you’ve secretly dreamed of running a way to a cabin in the woods and hiding there forever (or at least until things seem less-awful).

Or maybe it’s just me.

But here’s the interesting thing — in the past year almost none of my circumstances have changed. I still have the same job. I still live in the same apartment in the same city.

Nothing has changed materially, and yet today I can say that for the most part I like my job and the city doesn’t really bother me — on good days I sometimes even like living here.

I’ve spent a lot of time thinking about what made this shift possible. And the short answer is always that I did. I changed my relationship to myself, and in doing so I changed my relationship to my job, my life, and my city.

Sometimes it works this way — sometimes uncomfortable circumstances in our life are signposts guiding us to turn inward, to look toward some way in which we are unknowingly creating our own suffering.

And sometimes it’s the opposite — sometimes situations are toxic and we need to get out of them. Sometimes the discomfort is there to help us see that it really is time to move on from a situation in which we have been comfortable for too long.

The more I experience, the more certain I become that truth is always a paradox: do what is easiest, except for when the hardest thing is the right thing for you. Stay put unless it really is time to go. Leave, unless it is time to stay.

Unfortunately, this kind of truth is generally unhelpful — which is why learning to navigate the path to your happiness is ultimately about improving your ability to tell the difference between the loud voice of your fear and the quietest whisper of your heart.

So, with that in mind, here are a few things that have helped to guide me along the way.

The first thing is this: are you moving toward joy or away from discomfort?

I used to believe that moving away from discomfort was the same thing as moving toward joy — that if I reduced my discomfort, I would inevitably experience more joy.

In practice, this never worked out for me. My attempts to make my life more comfortable left me feeling imprisoned rather than free — and today, I no longer believe that this idea to be true.

Because the truth is that we manufacture a lot of our own discomfort.

We tell ourselves scary stories that turn benign situations into nightmares. We create rules about the kind of perfect person we are supposed to be that leave us feeling inadequate and crushingly alone. We are terrified of being vulnerable but angry that our lives are so lacking in meaningful human connection.

The problem is that it’s impossible to move away from the discomfort you create for yourself. If we want these things to change, we have to be the thing that changes.

Otherwise, we inevitably bring our story with us.

I hated my job, but if I’d moved on to a new job, I would have hated that too because the problem wasn’t with my job — it was with my story about what it meant to be a “good employee”.

My job was actually irrelevant — a distraction that I used to avoid facing what was really going on.

Which, again, isn’t to say that you should never move away from discomfort — because sometimes I really believe that you should. But be honest with yourself: are actively moving toward joy or are you just trying to dodge discomfort?

If you’re just trying to dodge discomfort, get really curious about that. What’s the source of your discomfort? Is it really your circumstances (and it might be!), or is it you or how you show up in those circumstances that is causing discomfort?

Because if the problem is really with you (your story, your habits, your mindset), you’re never going to fix it by changing your situation. You’re going to have to face inward and decide to change yourself.

And the second thing is this: what do you need to be okay?

Because sometimes the problem is outside of us, but a lot of the time we’re at least playing a partial role.

Sometimes your boss really is terrible or the situation really is unworkable. But it’s worth asking yourself the question: what do I need to be okay in this situation?

And maybe the answer will just be “LEAVE”, but maybe it won’t be. Maybe some voice inside will whisper that you could learn to set better boundaries, or improve at not taking on another person’s criticism as your own truth.

(Because it’s not the criticism that hurts, so much as the moment just after when we buy into what was said…)

It’s worth asking the question because it is in the asking and the listening that we reclaim our power.

It is in the asking and the listening that we reclaim our right to choose: to choose how we respond, how we show up, how we interact with others, and what we will do moving forward.

Because here’s something I deeply believe to be true: when we trust ourselves to take care of ourselves, even disasters can be handled.

When I trust myself to check-in with myself, to ask myself what I need to be okay, to listen and provide for myself my moments of need — when I trust myself to really do this, I find that it becomes increasingly hard to imagine situations in which I could not find a way to still be okay. There is tremendous freedom in that.

I believe that the definition of empowerment is trusting you to take care of you, over and over and over again.

And when I am able to live like this, suddenly getting out of my comfort zone doesn’t seem quite so scary anymore.

Much love,
Jessica

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