The Duality of Letting Go

Julie Penner
4 min readOct 31, 2020

“Just let it roll off your back….” “Forgive and forget….” “Just let it go.”

I’ve never been good at letting go. I tend to fight more than I need to and hold a grudge longer than I care to admit. On a spectrum from easy-going to my- way-is-best, I know I my natural tendency is to fall closer to the opinionated, dictatorial jackass end. Letting go always kind of felt like giving in or giving up. In that sense, the stubborn part of me that held a grudge also gave me the grit to keep going when things were hard, and that grudge-holding, stubborn AF grit was just the kind of delayed gratification required to get me to a lot of good things in life.

I am not alone. Some of you recognize a part of yourself here. The fighter, the challenger persona, maybe it worked for you too. It helped you get hard things done. It powered you through when things got difficult, when others were not strong enough to continue. Your resolve proved worthwhile, probably at big breakthroughs in your life: It was hard. You fought your way through. You were better off for it.

My college athlete days. When “tough as nails” worked for me.

It definitely worked for me. As an athlete. As a double major in college and again in grad school. In my career. Fighting upstream worked for me.

And, it’s exhausting. Sometimes even self-destructive. How does the saying go?

Holding a grudge is like drinking poison and waiting for the other person to die.”

It would be so much easier to go with rather than go against if I could just LET IT GO already! (Yes, I see the irony in not letting go of how best to let go. This is the depth of me not wanting to let go.)

This “tough as nails” strategy for winning has evolved in so many ways in my mid-thirties. From being more emotionally expressive, to practicing a language of appreciation, to holding my stories more lightly. “The Work” for me has led to a softer version of my warrior persona, and I’m better off for it, as are the people in my orbit. But this growth edge around letting go still feels like part of my edge that I don’t really know how to do without. Who would I be without my ability to be incredibly stubborn? Consciously or unconsciously, that thought is holding me back.

But I’m ready. And I now I can see, even experience, the freedom that comes with letting go. When I don’t clench so tightly to what “should be”, anything is possible. That’s intellectually obvious, but profound when embodied. It was this summer that I had an experience with art that helped me get it.

I was in my studio working on an assignment from my pottery class: make a Jomon pot. It involved draping coils of clay lavishly on a ceramic cylinder in creative patterns. I was at a loss for where to start. What was “right?” I didn’t know, and I did not want an ugly or stupid-looking pot. I sat there, clay in hand, stumped, with the potter’s version of a blank canvas. Until I changed my story- “I guess I’ll just start and see where it goes….”

The “blank canvas” problem.

No plan. No direction. Just freedom. Going with what feels right next. It was an incredible feeling to trust that whatever happened next was exactly what was meant to unfold. And sure, there was editing along the way, but it felt like absolute freedom to me. I had let go. I noticed that as soon as I let a thought creep into my inner dialog about what it “should be” that sense of freedom vanished. I had to let go and just be with that clay, in the moment, to feel that freedom. It was a simple but startling moment. And I appreciated the outcome:

A 360 view of my finished (but unfired) Jomon pot.

Now I can see letting go not as a giving in or a giving up, but a dropping of a constraint. I can be lighter, fight less, and feel more free. This is the duality of letting go. We may give up what we were so attached to thinking or feeling or dreaming, but then we are open to everything. That is the trade we can make when we let go.

The next time someone asks you, “What are you ready to let go of?” hear it as “Where are you most open to something new?”

I know I will. And, I still need practice letting go. I have hard, engrained habits around holding tightly. I practice it best with my art, holding space for the unfolding of what a piece wants to become. I’m sure there are other ways to practice letting go, I’m curious if you know one!

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Julie Penner

Founder and author of Soul of Startups and #Ruleof5. Venture Partner at Frazier Group. EIR at Telluride Venture Network. Coach. Facilitator. Challenger.