“What do you do?” a gray-haired man in a blue blazer asked me. 

I watched his eyes drift from my face to my name card. Looking closely at it, he squinted. I imagined he must be confused, not at my name, but at the fact that under my name there was no company association or title like there was on every other tag I had seen that evening.

In the National Parks, I tell people I’m on a year-long adventure through our country’s wild places. There, the answer is usually met with excitement. But here, it felt too embarrassing to say aloud. I was in Chicago, mingling with business executives, entrepreneurs, tech investors, and distinguished professors – surely he’d think I was a joke if I said “I’m on a journey”. So, instead I froze. 

This freezing compounded my feelings of shame. It’s not like I should have been surprised to get the question. It’s basic small talk in the business world, but for me the question (though not actually intended that way) had the result of feeling accusatory – with the result that even before I spoke I felt put on trial, proven guilty, and sentenced to irrelevance. 

But taking a step back, why was I away from the wild this week, talking to a man in business attire in downtown Chicago? Because I was at the Twin Global annual conference for global leaders in innovation. Hmm… that probably still doesn’t answer the question does it. In fact, it’s probably just confused you more. After all, as you all know, I am not a global leader, nor do I know much about innovation. I’ve never even worked in tech. And while I may have gone to MIT for graduate school – the last time I conducted an experiment in a science lab was as a junior in high school. 

So why was I there? I was there as a guest of a dear friend, Ralph, who (unlike me) is an extraordinary visionary, and who generously invited me to join him as his guest for the conference. He was certain it would be an important part of my journey. “You are going to love it. It’s going to open up a lot for you,” he told me, “And when we are there you should just go do your thing. We don’t need to do things together. We can catch up when it’s over.” 

I didn’t immediately see the connection to my journey, but something deep inside me told me to say yes – to him and to the experience – and so I did. 

However, in the days leading up to the conference I began feel a nagging fear – was “saying yes” a mistake? Afterall, I have no experiences or insights to offer the other attendees about innovation. Moreover, I probably won’t even understand the subject matter. I don’t know anything about AI, blockchain, CRISPR, or moonshots beyond the buzz words. Given that, I’d hate for my friend to waste his generosity on me; or even worse, for me to embarrass him.

And so, with all of these fears swirling in my mind, I fumbled to answer the business man’s simple question, “What do you do?” by casually invoking my old “prestigious” job title and role, as if the mere incantation of those words held secret power to let someone rich and powerful like him know, “I deserve to be here.” 

But it immediately backfired. Not only did I feel small as I said it, but I saw instantly he was rightly unimpressed. It turned out he worked in my old industry, but was much, much more senior in it than I ever was. In my old role, I would have been a peon to him. We made some more small talk and then headed separate ways. I felt ashamed. I was a total impostor. 

As people milled out, I isolated myself at a standing cocktail table, not even trying to engage with others – hiding behind a look of rapt intensity as I scrolled through my Instagram feed like a banker working through his inbox. 

Of course, the first day of the conference had many positive moments too – a profound and beautiful conversation with my friend Ralph, several fascinating speakers, a few moments of connection with strangers which didn’t revolve around work, but the moment when I was asked, “what do you do?” was all I could think about as I walked home. 

The following morning, as I got up and dressed in my nice slacks and suit coat, I felt deflated.  I tried to cheer myself up by reminding myself of how much I had to be grateful for, that good things often happen at unexpected times, and that challenging moments are an opportunity to learn about the world and yourself. But as I looked into the mirror, I felt embarrassed at what I saw. I felt like a child play-acting in adult clothes. This same uniform used to give me so much swagger, but looking at myself now I saw clearly that none of it fit anymore. The pants seemed to balloon around my waist. The jacket was too tight in certain places, and too loose elsewhere. 

Throughout this journey people often have asked me, “What are you going to do when it’s over?” Despite what I’ve written previously, when I’m most scared it’s easy for me to think: “What I did before.” Though I wanted to use this time to explore new ideas, in my deepest heart I sometimes wonder if my time away from “real life”, will merely help me re-enter “real life” as a version 1.02 of my old self. Metaphorically, I’ll put my old uniform in the closet for a year; do a bunch of working out; and then when the time comes to put it back on, I will; and though it’s the same suit, at least I’ll look better than ever before after so much exercise.

But this week, the absurdity of that notion stared comically at me as I looked into the mirror. As my Matrix referencing, Buddhist cab driver told me on the very first day of the journey, “You can’t take the red pill and expect to come back the same.” This year is not a vacation from real life. This year is real life! At times, it feels more real than the life I lived before. And now having lived it, I can never view my old world and cares the same. Of course, I don’t fit into my old suit anymore!

And with that, I began to laugh at myself, literally. I took off my old “work” clothes, and instead put on a plaid shirt and a pair of jeans. This felt right. This is who I’ve become. And so, when I re-entered the auditorium, I saw the sea of blazers, and thought if people were looking at me wondering, “what is he doing here?” I don’t care. 

Walking in that day I felt the weight of needing to prove myself lifted. I realized I was there not because of my degrees or my old job; I was there solely because of my friend’s generosity and care for me. Whether deserved or not, I belonged because he invited me. Those were the rules. That may not make sense, but it is the system. Given that, the best thing I could do is honor his generosity, show up as I am, be fully present, respect the people I meet, and open myself to whatever truths emerge.

And that is what I did. Now inhabiting my own skin, I felt at ease introducing myself to strangers as an interloper, a wanderer, a writer, and a young man in casual clothes on an emerging journey. Yes, I had a career before and that shapes who I am, but it is not the defining attribute of who I am now, nor is it central to who I am becoming. 

Sure, when I said this, some people rolled their eyes and quickly moved on. But more often than not, I found myself deep in conversations after doing so. At times, the conversations veered into the philosophical implications of the days’ panels – how can Hegel help us understand our historical moment, what does it mean to be human as the line between man and machine is becoming blurred, and what ethical responsibilities do inventors have for their creations – but more often our connections quickly become personal.

And it was there, in those personal conversations, when I gave up the need to prove myself, when I showed up as I am, and when I led with vulnerability that many of these brilliant innovators opened up to me as well – sharing stories about their own unexpected job transitions, failed businesses, and unanswered questions. I even discovered many other “sabbatical-ers” who were in the midst of their own wanderings. In discovering these fellow searchers, I felt so buoyed up.

When the conference was over I ran around the hall looking for all the people I had met. As I saw them, many of us made plans to see each again -- not because we had urgent business to do, but because we knew we had more life to share. And as we said goodbye, there were no firm hand shakes, only hugs.

As we drove to the airport I felt so energized. True, I still cannot tell you what my professional identity will be a year from now. But despite that, Ralph was right – being at TWIN was an important step in my journey, and so much has opened up for me. I have new ideas to wrestle with, I met new people who inspired and comforted me, I gained new insights into who I am becoming, and I feel renewed conviction about the path I’m on. 

So now, on the other side of TWIN, I can’t help but ask myself again: “What do you do?”

To which I proudly and publicly answer: I wander freely, I am vulnerable with strangers, I easily make new friends, I read widely, I grapple with new ideas, I write about my experiences, I photograph the places I see in order to inspire others to conserve our wild lands, and I hug people I just met at business conferences… it may not sound like much, and it won’t get me onto any Forbes 40 under 40 lists, but you know what? For the first time in my adult life, I feel pretty darn happy about what I do and who I am becoming.