Tell me about the time you felt most alive

A surprising truth about the moments that stick with us for a lifetime

Welcome Entrepreneurs. I’m so glad you’re here.

Since it’s inception, SMS has always been first and foremost a creative outlet. A place to exercise my writing muscle, and work out my own journey on the page. I intend for it to remain that. But I’ve also discovered that it’s a great way to connect with interesting people building impactful things, who are trying to do so in a way that’s sustainable, and Good for as many people as possible. As I reflect, I think I appreciate the people I’ve met as a result of this site just as much as my own creative expression.

So if you’re one of the folks who’s reached out to me in response to an article and established a friendship, thank you.

And if you’re a longtime reader but haven’t yet said hello, I want to encourage you to send me a note. Introduce yourself, tell me about what you’re building, or just share a topic you’d like to discuss on SMS.

Either way, I’d love to hear from you.

Onto this week’s essay.

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.

(HT: Julie Mosow, Christine Cauthen, Alex Azoury & Foster for editing!)

Liked this article? I’d be honored if you’d share with others who might find it valuable. 


Who is Ryan Vaughn? 

I’m an executive coach for startup founders, a role in which I get to help high-performing founders design a more conscious life and expand into extraordinary leaders. I’m a 3x Founder/CEO who’s raised $20m+ in VC and built a market-changing company, as well as two other companies that taught me things. I’m an avid writer, meditator (decade+ practice), reader, athlete, father, husband, amateur physicist, student of leadership, and adventurer. I’m also none of those things. But I am glad that you’re here.  If that’s not enough, here’s a more detailed bio.


One: The Modern Curriculum

Reimagining school is not new (although nobody has yet done so successfully and at scale, so it's also not irrelevant). I loved this reimagining from Seth Godin. If there were a school I could send my boys to that taught these things…man. I'd move there. Almost makes me want to homeschool. 


Two: World, Meet Blue Dot

One of the things that inspires me most about America right now is the way we've mobilized the VC-fueled-innovation-engine toward the climate crisis. I know there are still deniers (smh), but those with the ability to do something are increasingly doing so. I was inspired by the latest example: a friend of mine who is a coach, Andy Sparks, just dedicated his entire practice to supporting founders tackling the climate crisis. As he said, he wanted to be able to tell his grandkids that "I was in the ring doing something about it, even if we failed. I was doing something." 


Three: It’s Time To Replace Ambition With Adaptation

I've realized that, for the most part, my ambition is driven primarily by fear. The fear of being left out, of not being enough, and of falling behind. Realizing its illusory source, I spent a good deal of time resisting my ambition, an approach through which I naturally worked myself into a bind. If you relate, kudos because it's tough to even step outside ambition long enough to see it clearly, but more to the point I suggest reading this article about how one might transmute ambition into something with more sustainable meaning. It spoke to me. 


Four: The Lean Startup

In case you needed a reminder why Lean Startup exists, I happened upon this nugget in Adam Grant's "Think Again". Apparently they did a study in which two groups of entrepreneurs were given the exact same resources and training curriculum to build a cohort of very similar businesses. The only difference was that one group was also trained in the Lean Startup methodology. 

Five: Affectations of Authority - AoA (@visakanv)

One of the best ways to get clicks as a writer is to speak with authority (earned or unearned are the same), and offer quick fixes. “Here are the 10 ways to do this” or “The easy way to do that.” In conversations with various people about my writing this is advice I’m often given, and for good reason: it works. But also, it’s gross. And wrong. And I hadn’t put the effort into describing why it is such a turnoff for me, so I was glad to see this thread from a really good Twitter follow, Visa.

Good validation to keep prioritizing truth in all its nuance, even if it misses the masses.



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