For creatives, entrepreneurs, and the like, there is something stifling about staying in your comfort zone. While your world might seem happy, inside, you crave more. You crave the electric pulse of a true challenge, the thrill of the unknown, the terrifying but beautiful edge where your most ambitious ideas live.
We often tell ourselves that safety is the ultimate goal. We wrap ourselves in the warm blanket of the familiar, waiting for some external authority—a mentor, a partner, society at large—to give us the green light to finally pursue what we actually want. But what if that permission never comes? What if the very safety we cling to is the thing slowly extinguishing our creative fire?
In today’s post, I want to share a recent conversation I had with a brilliant friend who was standing right on that precipice. Grab your journal and let’s explore the insidious nature of the comfort zone, the illusion of permission, and how to finally break free to build a life of genuine, unapologetic happiness.
…my life is sort of shit now. You are successful, and I am successful,
and I’m wondering, are you happy?
(excerpt from an email from Anthony Bourdain to his friend David Choe)
The Reckless Nature of Playing it Safe
Paul looked over my shoulder toward the café door. I kept my focus on him.
“Now there’s someone for you,” he said, ducking his head and nodding forward.
I laughed and didn’t turn around.
“Paul, I’m continually impressed with…a) your ability to dodge the deep question, and b) your relentless obsession with my love life,” I said.
I had just asked Paul whose permission he was waiting for to embark upon his most ambitious dream to date.
“On second thought, nah,” Paul said. “I can tell he lacks your requisite kindness, humor, and creative fire. Pass.”
“Well, now that that’s sorted, let’s get back to you,” I said. “Whose permission are you seeking before you go all in?”
Paul fiddled with the tortoise shell button on his navy blazer sleeve and scratched his thumb across his wrist. I wondered for a second what his body language meant before guessing he was feeling vulnerable and desiring safety. He wanted to stay in his comfort zone.
“Of all the projects I’ve ever done, this one feels the most reckless,” he said. “I’ve been so lucky. At some point, that runs out, right? I’m wondering if rocking the boat in my 50s is smart.”
“Paul, what is it that you really want?” I asked.
Without hesitating, he replied, “To feel the electricity of being on the edge of doing something that feels almost too hard to pull off. Create.”
“Is it possible that not rocking the boat…keeping all the lines wrapped on the pier’s cleats…is slowly dousing the fire within you that makes you, you?”
Paul stared up at the ceiling.
I continued. “And, by not honoring your desire, is it fair to say that that is maybe even more reckless than pursuing your dream? Your passion?”
Paul brought his eyes to mine and said, “Damn, deVille. It’s not even 7 am yet—how do I even figure that out?”
I reached diagonally across the table and tapped the front cover of his journal. “Got a pen with you?” I asked.
Every time I feel myself avoiding the playing field and desiring to hide on the sidelines in my comfort zone, I take myself through a journaling exercise—the very same one I shared with Paul.
The Permission You Seek
If you are feeling as if you are straddling a chasm of indecision, where on one side is the life you desire with your whole heart, and the other side is the land of perceived safety, you might find that this exercise reveals enormous clarity.
Warning: Stepping out of your comfort zone to disrupt what is familiar (but no longer aligned) is not for the faint of heart. However, I can assure you that on the other end of the journey lies a freedom that many of us have never tasted.
Ready? Get out your journal and a pen. Write your answers to the following questions without lifting your pen from the page. Notice how your body feels when you answer honestly, without censoring.
- What approval are you still waiting for before you fully commit to your ambitions, whether they are creative, professional, or deeply personal? Pause and examine that.
- Who, in your mind, holds the authority to validate your path? Is it an old cautionary tale from a parent, a well-meaning loved one, cultural messaging, or some idealized version of success or stability you have constructed?
- Now, challenge those assumptions: What if no one is actually coming to grant that permission? What would shift if you consciously chose to become the source of your own approval? Not in a vague, motivational sense, but in a tangible, lived way. How would you behave differently tomorrow if you had already been given the green light?
- Consider what self-permission might look like in practice. Could it take the form of a daily ritual, time blocked off that is non-negotiable, treated with the same respect as a meeting with someone important? Could it mean setting boundaries that protect your creative energy, or creating systems that make showing up inevitable rather than optional?
In other words, how can you design your environment, your schedule, and your habits so that they do not just allow your dreams, but actively reinforce that you are already authorized to pursue them?
Leaving the Emotional Comfort Zone
And for those who are in a strange, gray world in their personal life, routinely asking themselves, Should I stay, or should I go?…
Ask yourself this: Are you waiting for certainty, for timing to feel perfect, for someone else to affirm that it is okay to want more?
Because choosing love—real, expansive, aligned love—often requires you to leave your emotional comfort zone, an act of courage that looks disruptive from the outside. It might mean ending something that still sort of works (but you’ve outgrown the identity that once fit) or stepping into unfamiliar emotional territory without guarantees.
How can you design your life, your routines, your relationships, your standards, in a way that reflects not who you have been, but who you are ready to become?
The Courage to Begin
Everything begins in the simple, brave decision to make a move.
We have stood at this edge long enough to know what hesitation feels like. It is familiar, almost comforting, wrapped in logic and what-ifs. Yet somewhere beneath all of that is a knowing, a pull that has not faded, a vision that keeps returning no matter how many times we try to set it aside.
There will never be a moment when every piece falls neatly into place before we begin. Clarity arrives in chunks, unfolding because we stepped forward. Confidence does not appear fully formed. It grows each time we choose to act despite the uncertainty.
Imagine looking back on this very moment from a future where you chose to begin. The strength you discovered because you needed it. The life that expanded because you allowed it to.
You are far more ready than you have been willing to admit.
Take the step. Send the message. Make the call. Start the thing that has been waiting for your courage to catch up with your desire. Let it be imperfect. Let it be real. Let it be yours.
The life we keep imagining is built in the moments when we decide that this is the day we begin.
