In his 2005 commencement address at Stanford University, the late Founder of Apple Steve Jobs famously reflected on the connecting dots of life. And the profound and, if we’re lucky, gratifying ways in which the dots connect, and begin to make sense, when we reflect back on the many seasons of our lives.

“If I had never dropped out,” Jobs said eighteen years ago this week while reflecting on his decision to drop out of Reed College in Oregon, “I would have never dropped in on this calligraphy class, and personal computers might not have the wonderful typography that they do. Of course it was impossible to connect the dots looking forward when I was in college. But it was very, very clear looking backward 10 years later.”

“Again, you can’t connect the dots looking forward; you can only connect them looking backward,” Jobs emphasized. “So you have to trust that the dots will somehow connect in your future. You have to trust in something — your gut, destiny, life, karma, whatever. This approach has never let me down, and it has made all the difference in my life.”

Wise words that don’t easily leave us.

But how do we build that trust, faith and steel in the midst of our lives, and not just at reflective junctures? How do we intuit that our chosen paths - some short, some long, some connecting personal dots and others connecting professional dots - are indeed in stride with our calling? What is our calling? And as we make decision after decision, how do we assure ourselves that we’re tracking on, and then fully present for, a path sure to fill our hearts down the road?

One answer that Jobs, a polymath who embraced arts and artists, might concur with: the humanities.

While chronicling Jobs’ final product launch event, biographer Walter Isaacson illuminated a North Star at the center of the former Apple CEO’s world view: “Jobs ended, as he had often done, with a slide of a street sign showing the corner of Technology Street and Liberal Arts Street. ‘It’s in Apple’s DNA that technology alone is not enough,’ he said, ‘that it’s technology married with liberal arts, married with the humanities, that yields us the result that makes our heart sing’.”

I’m often asked: “What are the humanities?” In their simplest terms, the humanities constitute the big tent of all human experiences - educational and otherwise - that expose us to the human other: from art and anthropology to philosophy and politics, from literature and linguistics to mythology and music.

But it’s the mind-multiplying, soul-soaring impact the humanities has on us that’s worth sitting with. What kind of impact? T.S. Eliot once said that “genuine poetry can communicate before it’s understood,” so a short poem that aspires to be genuine will do.

Awe and wonder,
In the other

“Awe and wonder … in the other,” I often answer when asked about the humanities, always proud of my six-word poem and creative writing debut. Indeed, committing to the humanities triggers the cultivation of a superpower in each of us: a sustained and habitual sense of awe and wonder in human others - and all others - which in turns leads to growing skills and sensibilities of curiosity, empathy, introspection, storytelling (storylistening, too), imagination, communication, vision, leadership.

And, over time, intuition about the world - and oneself - and a kind of soulful stewardship.

These capacities are, of course, hugely universal: indeed, they are as critical for the protagonists connecting the dots looking forward in our technology landscape, like Jobs decades ago, as they are for all of us wrestling with life’s daily dilemmas and delights.

While much of the public inquiry pertaining to the liberal arts, in the United States and elsewhere, centers on the decline of undergraduate humanities majors, in the fall of 2022 I started convening conversations around a separate strand of questions at Virginia Tech, a leading research university whose motto - “Ut Prosim, That I May Serve” - has created a magnanimous culture of giving across the institution:

“What if we thought about this differently?,” I wondered. “If the highest forms of human leadership necessarily involve drawing on the very best of what the humanities teach us, what if we began building an Executive Leadership Degree in the Humanities? What might a world - and a technology landscape - in which we’ve created new leadership credentials, currency and credibility around humanities sensibilities, and not merely business and technical skills, look like?”

It seemed to me that in a world where computing and commercial skills were increasingly within reach, the leadership superpower of the future, across fields and functions, might just reside with those with a deep sense of their own intuition, compass and light - and an equal depth of feeling for human others near and far. And that this message might be particularly resonant today with those who’ve already lived and led in the complicated real world composed of humans, if not one day with undergraduates as well.

As The New Yorker’s March 6, 2023 cover story mentioned in passing, “There are people in their thirties and forties who have been stay-at-home parents, or they work. And they are committed to the humanities.. they have an idea about the value of liberal-arts education.. it’s a matter of life experience. What someone who has been in the grind of life wants to learn more isn’t necessarily linear algebra.”

And so, after twenty years as an entrepreneur and executive in and around technology, I joined with inspired colleagues and advisors at Virginia Tech to launch the Institute for Leadership in Technology, a new, one-year, low-residency fellowship for rising stars in and around our inescapably-digital landscape. Drawing on the magic only a structured, shared, serious liberal arts experience can provide, our purpose is to instill heightened skills and sensibilities emanating from the humanities in those who connect the dots, and lead the disruptions, in and around technology.

While the response from people around the world has been heartening since our April 2023 launch, ultimately time will test our own intuition as we connect the dots of our Institute in real time, building and flying concurrently.

But, at base, can we connect the dots looking forward? As we climb life’s mountains, can we feel awe and wonderment in between the basecamps, summits and inevitable falls?

Jobs gave us his answer in his commencement remarks, but the example of his life encourages us to look deeper. For it seems that he was, after all, a remarkable example of the sensibilities that accrue and accumulate when drawing on the liberal arts and humanities in life’s page-by-page plot, and not merely at chapter’s end. Awe and wonder in the other as a relentless line-by-line, day-by-day, product-by-product habit always in service of higher understanding, beauty and legacy.

Indeed, even Jobs’ last words before passing, according to his sister, channeled this enlightening, lifelong spirit of awe and wonderment, which should recall for all of us what it means to be unabashedly human before the dots have connected:

“Oh wow. Oh wow. Oh wow.”