I Don’t Know (and That’s Okay)

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By Jon Ray

Several years ago, I joined a mastermind group that brought tears to my eyes and hope to my soul. It was a private group for entrepreneurs looking to become more emotionally honest with themselves, the people in their lives, and with reality in general so that we might collectively move through challenges with a new kind of ease and grace.

After one meeting, I was bowled over. Why? Because I recognized in that first session that I had been in resistance to “not knowing” my entire life.

Not knowing was just too uncomfortable to acknowledge as a reality. I’ve always been the smart guy who knows. When I was a little kid my parents used to tell me and everyone else:

“Jon knows everything.”

When I was a teenager they said the same thing, albeit in a more accusatory fashion:

“Oh, you just think you know everything!”

In the entryway of our small 3-bedroom home, as a child, was a leather bound set of Encyclopedia Britannicas. I consumed these. I was (and am) addicted to information.

Feed me!

The internet came out when I was still young. I found information on a million topics via a 2,400-baud modem connecting into the BBS bulletin board system that ultimately became the internet. Those modem screeches were orgasmic—a gateway to knowledge. To this day, I consume several books a month, purchase any course I can get my hands on, go to every workshop, watch every motivational or instructional video—and read user’s manuals! When you’re reading the fine-print in user’s manuals and terms of service agreements, you’ve got an obsession. But here’s the thing: I thought that’s what you did to become proactive in your growth. And to a certain extent, that obsession with learning and the insatiable curiosity I have about all things—a belief that I can evolve—has served me very well. Where it started to get unhealthy and become an emotional addiction was when I had to have the information to feel worthy. I had to know everything about a subject to feel important. I had to know everything about a situation before I could take the next step. The unknown has historically scared the *expletives* out of me. Because to feel safe, I needed the control that more information has always offered me. A thirst for that information has certainly helped me seek out ways to heighten my awareness, while encouraging me to develop a keen intuition. But not knowing something? That’s always been a big no-no for me. That’s the cue for me to bow out, turn the other direction, tell a big ol’ lie, and absolutely avoid the discomfort of the unknown. “You can’t not know, Jon. Find it before you’re found out!“ This is something I’ve muttered to myself frequently over the years. It’s a kind of mania. It’s a way of saying that being out of control is unacceptable. And, of course, anyone familiar with the power of surrender recognizes that the grace and beauty of surrender doesn’t arrive until we’re willing to embrace the unknown.

It’s fun to search; to solve puzzles. It’s important to keep going without giving up. But my motivations around searching were misguided for quite a long time. I was seeking, not because I was joyously enjoying the present-time unfolding. No, I was seeking because I was desperately trying to avoid “not knowing”. Not knowing creates a silence where too much existential truth might start to flow in—and that’s deeply uncomfortable for someone who needs to feel in control all the time. That’s why all my life I’ve sought after knowledge and avoided not knowing. That was a disservice to myself and my growth. That avoidance prevented me from leaning into edges and opportunities that would have provided me with greater increase and capacity. But since we don’t know what we don’t know (and I guess that’s kind of the point, here), I went 30 years without even recognizing that my addiction to knowledge and control was in direct conflict with my creative and spiritual growth. I could feel that I was resisting something, but I always thought it was more tangible, like not having the right career, diet, relationships, or income level. You know—I was putting the blame out there somewhere because “out there” is less icky than having to take a hard look within. I could see out there, and that’s why I kept staring it down. It had nothing to do with seeking the truth, and everything to do with the fact that as long as I was looking out there, I didn’t have to get real with myself about my own internal discomfort. Because knowledge and truth are different things.

“Not knowing” was a label I gave to my fear. I was afraid that I might not be accepted for who I really was. I was afraid no one would ever love the real me. I was afraid I might not have what it takes to be an artist. I was afraid people might ridicule me. My resistance to not knowing was a string being pulled by a puppet master named fear. By ignoring my fear, I stuck only to things I could control (things I could know). Instead of moving towards the unknown, I was simply regurgitating other people’s truths, never landing on any of my own. I was playing it safe because that felt better than the fear of failure. This is the irony in all of this because anyone who’s ever achieved success in anything repeatedly will tell you that it’s never about perfection, it’s about process and persistence. Everyone fails. You fall, then you get up. Fall. Back up again. It’s never about “not falling” but rather, can I get up, learn from the past, iterate, and optimize towards a more successful outcome. The great mentors I see modeling this for me are not concerned with failure, they actually lean into it. Because not knowing is uncomfortable. Until it isn’t.

Over the last few years, I’ve continued to allow the feelings of all that old, bypassed uncertainty and fear to come to the surface and express within me. I’ve made it a practice to process the discomfort of any given moment and accept it wholly. The more I accept not knowing and build out a space for it within me, the more pure my desires become, as they rise to the surface. And that’s useful in business, finance, life, and love! As I align with uncertainty, rather than manically spinning over it—clarity presents itself. Simple solutions show up in unexpected ways and with perfect timing. These are things I’ve heard people say my entire life, but only in the last few years have I really found them at any kind of gut level. By moving knowledge from something that is theoretical, existing only in the mental plane, and finding it down in my body as experience—by giving my discomfort space to fully express—knowledge has become something more embodied and real, not just a mental model to be debated. So now a new, strange hope bubbles up, not from having the control of a “right” strategy, but from a deeper place that says,

“You’re already on the path. Let it come as it will. Enjoy it.”

I’ve heard mystics, magicians, and miracle workers talk about that kind of acceptance and hope for much of my life, but it was always a muddled mental concept to me. Because come to find out, really knowing it requires a complete relinquishment of control. It requires surrender. It’s in my acceptance of not knowing, in embracing my fears, that a new kind of space and capacity arises. Something which points to a new path for exploration: that knowing isn’t everything—not knowing can also be the way.


Jon Ray is a heart-centered copywriter and digital marketing consultant for high-level executives and awakening entrepreneurs. He teaches a simple practice—feel your feelings—as a way to unlock creative potential and show up as a more powerful and profitable leader.

Jon has used these techniques to lead large teams at Google, in the real estate space,

and now running his digital marketing agency, Awaken Entrepreneur. As a recovering alcoholic and addict, he points towards emotional processing as the primary way to release “white-knuckle sobriety” and truly step into a place of peaceful expansion.

Email: whoisjonray@gmail.com



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