Tell me about the time you felt most alive
“I had just left the company I founded,” he said. “My instinct was to jump straight into another startup, but I knew it was important to give myself a month. I remember near the end of that month, there was a moment. Halfway up a mountain hike in Patagonia, I stopped at a plateau and looked out over the expanse of glaciers. I looked back down the mountain, at how far I’d come. I looked up at where I was going next. I knew I’d keep climbing, but for just that moment I was all alone, between everything.”
There’s a question I like to ask when facilitating T-Groups. Once the CEOs have gotten to know one another a bit, and have determined that I’m weird but harmless, I ask them to tell the group about the time when they felt most alive.
“It was the end of my time in Asia, when we almost died riding in a truck,” she said. “I’d been living there for a couple months after college, just experiencing other parts of the world, and I think it was our last day or the day before that. Either way, I’d be returning home soon, back to the world and my life. It was pouring, I remember. The kind of freezing rain that makes you blow through your windshield fluid in 20 miles. Our taxi driver was battling mud-slides, and we almost flipped the truck. I remember that moment, and thinking I’d never felt more alive.”
In my experience with hundreds of founders, I’ve learned that the times we feel the most alive are rare. They happen when we’re inside a liminal space, in the midst of a transition between what was and what will be. These are the circumstances or situations we remember for years, the ones that still give us chills.
We spend most of our lives looking only a few feet ahead, at our next goal, or a few feet behind at the latest accomplishment or mistake, each place a mile-marker on our way to Somewhere Important. We fall into a sort of autopilot in this mode, everyday life. We know who we are and where we’re going, and each day is another step toward that destination, or away from it.
But every once in a while we get a chance to pick our heads up and look around. Occasionally, something happens that jars us out of our daily marching and gives us occasion to take stock. In these moments, we step off the path we’ve been on and, with objectivity, finally see it for what it is. At the same time, if we’re lucky, we also see ourselves for who we truly are. Maybe for the first time.
“It was when I finally knew we’d done it,” she said. “I’d been pulling 100-hour weeks for a month getting ready for the kickoff. It felt less like building an airplane while flying it, more building a train while pushing it. The day before, of course, everything went wrong. Our speaker pulled out, it turned out we didn’t have enough space and had to find a bigger room at the last minute, just everything. But we did it. And I remember standing in the back on the day of the kickoff, and just looking out at the crowd of smiling people. I knew we had so much work to do after this day, but at that moment, I remember thinking, ‘I can’t believe we did it.’ It felt like I could do anything.”
In these moments, we look backward and see who we’ve been. With joy or regret, we observe our past self as something separate, as “not I.” Sometimes, we even see that who we’ve always been has no hold over us any longer. We realize that we have a choice to be different, and we’re surprised to realize that we’ve always had that choice, even though it never seemed like it before.
And at the same time, we look forward, and we see all that we can be. We see the possibility of something different, or better. Of successes to come. Expansion. With hope or resistance (but nearly always with fear), we allow ourselves to feel the sensations of who we might become, and maybe catch a glimpse of just how infinite we actually are. How we’ve always had the entire Universe available to us, even when it seemed we had only one or two options.
In these liminal spaces, the rote answers that make up our daily reality are loosened, and we’re awake, just for a minute, to the fundamental question of life. Of ourselves. Robbed of our everyday answers, these moments of pregnant ungroundedness are those in which we feel the most alive.
“I was outside on my back deck, bawling my eyes out and hoping that the neighbors wouldn’t be too freaked,” he said. “I’d just stepped away from the company I’d been CEO of for the last decade. I knew something was off, but I didn’t know what until I read a Brene Brown article that talked about the ‘Midlife Unraveling.’ I saw my own journey in that article, the person I’d tried to be for my company; the person who’d died when I left; the vacuum left behind. That moment I think was the first I’d realized that I wasn’t who I’d been striving so hard to be. That life could be more than that.”
Don’t look at the sun; you’ll go blind
Ironically, we spend most of our lives avoiding these moments. Uncertainty makes us feel alive, but it also makes us uncomfortable. So we busily button ourselves up, shine our companies, our relationships, and our resumes, removing all imperfections and options. We spend countless hours convincing ourselves we’re on the right path. That we know the answers to everything that matters. That everything is going to turn out just as we planned.
Of course we don’t know, really. And we worry about that fact, sometimes. That we might run out of cash, might not close that deal, whatever. We worry that we might not be enough, and we might not get what we want. Or we wonder, what if things could be different? Touching this foundational lack of control, through worry or wonder, gives us the opportunity to wake up. To lean into the uncomfortable question of our existence, and in so doing experience one of those moments that make us feel truly alive.
Sometimes we do. Sometimes circumstances align in just such a way that we catch a glimpse of the infinite within us, and are indelibly marked by the experience. Changed utterly by it, sometimes.
But mostly, faced with the question of our lives all at once, we (I, if I’m being honest) race with faceless others to find the next answer. The next salve of certainty, in a milestone, a compliment, or a white picket fence.
Creating liminal spaces
This topic isn’t new -- the power of liminal space, and the importance of intentionally creating it in your life. It just feels that way because of the cultural bubble we’ve (I’ve) been living in, in which virtue is only a measure of productivity. Liminal space is actually the oldest topic in the book, and as close to perennial human wisdom as it gets. From Richard Rohr’s brilliant book “Adam’s Return:”
“As the Jewish tradition brilliantly intuited: if at least one-seventh of life is not consciousness, presence, and naked human being, the other six days will be caught up as human doings that have little depth, meaning, or final effect. If at least one-seventh of life is somehow Sabbath and sabbatical, the rest will take care of itself. Without daily, weekly, and yearly choices for liminal space, our whole lives eventually become liminoid and we end up just doing time.”
An unfinished piece
Read this piece ten times and you’ll still find no answers. No “four easy steps to feeling more alive” (see bullet #5 below). It’s uncomfortable, publishing something this way. But today, now, I’m writing not for comfort or acclaim, but simply to feel alive.
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