At the Threshold of Transition
By: Jesse C Vaughan
Tags: Cofounders, Life Lessons, Startup, Career Change, Transitions

Photo by Dan-Cristian Pădureț on Unsplash

I am at an inflection point in my life and I find it difficult to capture my thoughts and emotions in cohesive prose, so inspired by Richard Feynman’s book, Surely You’re Joking, Mr. Feynman!, I’m going to try to create a collage of sorts, a compilation of rambling anecdotes and reflections that when read together will hopefully provide a portrait of this liminal moment in my life and the insights I’m drawing from it.

If I’m honest, I don’t expect anyone to read these words. Writing them serves their own purpose. But taking a queue from my lovely wife, Jen, maybe one day an unborn child of ours will see this series of posts and use them as a way to connect with a past version of their father. If anyone else finds some small benefit or insight from these ramblings, that’s gravy.

An ending and a beginning

What we call the beginning is often the end And to make an end is to make a beginning. The end is where we start from. T. S. Eliot

My dad passed away in June of this year, three days after my grandmother. The experience was like jumping into a cold body of water in that it was a shock to the system. When I came up for air, a lot seemed clear that wasn’t before.

For the first time in a long time, I decided to take a few weeks off from working. The combination of grief and cold-turkey withdrawal from work was eye opening. I started working with a therapist. My motto became, “don’t let this crisis go to waste.”

On the other side of the trauma, I had a different relationship to Landed, the company I helped co-found five years ago. I came to realize that I am most energized when I am creating something from nothing and that my greatest days of building at Landed were behind me. With this realization, I knew I could no longer be a full-time operator within Landed. I needed to hand over the reins.

Since August, I doubled-down on hiring. With the hiring and onboarding phase coming to a close, I will once again be facing a blank canvas in the new year.

Uncertainty in transition

After a number of sleepless nights, Jen recommended an interview by First Round Capital with Sasha Orloff. This article was hugely valuable to me. Not only did it normalize what I was going through but it also gave me some things I could take action on.

In particular, Orloff recommended making space for the transition itself. He also suggested William Bridges’ book Transitions: Making Sense of Life’s Changes. I’m a slow reader but I tore through it.

One of my main takeaways from Bridges’ book was that most of us default to either dragging out an ending or jumping into a new beginning. Few of us spend enough time in the space between.

The Gods have two ways of dealing harshly with us — the first is to deny us our dreams, and the second is to grant them. Oscar Wild

Listening to the voice of a thin silence

If you have ever surfed, you will understand when I say I feel like I’m paddling out to sea in a large swell — crossing wave after wave, filled with anticipation and uncertainty. All one can do is make a commitment to continue pulling themselves into deeper water.

I’ve never been very good at embracing transitions. My tendency is to jump into what is next; to grasp at my own self-importance. After all, to lean into the liminal moment is inherently unmooring. Yet, a subtle reframe of this uncanny moment is that it is a privilege.

Inspired by Orloff’s “100 days to have 100 coffee chats,” I have decided that I would spend 100 days of reflection, relationship building, and learning. Understandably, a number of people have asked me, “but really, what are you going to be doing?!” The answer is, “really, I don’t know yet.”

Maybe a few lines from Rumi can explain better than me:

Listen, and feel the beauty of your separation, the unsayable absence. There is a moon inside every human being. Learn to be companions with it. Give more of your life to this listening.

Or, maybe the story of Elijah meeting God in a cave after walking 40 days and 40 nights (I Kings 19:9–13):

There he [Elijah] went into a cave, and there he spent the night…There was a great and mighty wind, splitting mountains and shattering rocks by the power of Adonai; but God was not in the wind. After the wind — an earthquake; but God was not in the earthquake. After the earthquake — fire; but God was not in the fire. And after the fire — a voice of a thin silence [0]. When Elijah heard it, he wrapped his mantle about his face and went out and stood at the entrance of the cave. Then a voice addressed him: “Why are you here, Elijah?”

I believe that inspiration comes when we listen to the “voice of a thin silence” that arises from within us in these moments of transition. I will be listening.

[0] this phrase in hebrew is usually translated as a “soft murmuring sound” but I prefer this literal translation.