Thinking Different(ly)

Last year, Stanford University uploaded a copy of Steve Jobs’ 2005 commencement speech. It was apparently shared and viewed far and wide with many people praising its inspiration and insight. I missed it because, well, school. I’m just getting around to seeing it now. And I agree, it is inspirational and just the type of thing a recent college graduate wants to hear.

Here’s the thing: it is also the type of thing a seasoned professional might need to hear. It is a great reminder about the importance of loving what we do, feeling like it matters, wanting to wake up each morning and go do it. For me, it is a nice reminder of why I questioned my situation four years ago and decided a significant change was in order. And it comes just as I prepare to head to Washington, DC to finish up my graduate program.

Apple's ad campaign from 1997-2002.

Jobs is one of the most impactful people in modern times. He is praised for his insight, genius, can-do spirit, and determination to shake up the status quo through technology that is supposed to improve our lives. This is as applicable to the iPhone as it is to the Apple IIe I first tinkered with in middle school. So, no surprise that Stanford University would invite one of Silicon Valley’s most illustrious figures to speak to its graduates.

The address, like Jobs and his apparent approach to everything, is a mixture of pragmatism, elegance, and challenging existing views. It is only fifteen minutes long – very little fluff – and he imparts three important pieces of advice couched in very personal and colorful stories from his life. Like the old Apple ads, his speech invites the listener to “think different.”

As I listened, I noticed parallels to what Jobs said and some of the ideas I return to here. I encourage you to watch the video, but here are his main points.

1. You connect the dots by looking backward. You cannot connect them looking forward. There is a thread that runs from Jobs’ decision to drop out of college to founding Apple. He never saw how a curiosity about a calligraphy class would connect to a world-changing technology brand, but he listened to his instincts and followed his passion to do just that. Had he followed the path others suggested, his outcome would have been different.

I have two quibbles with his point. First, you can connect the dots looking forward. It’s called planning. The plan may not work out and adjustment may be necessary, but one can at least try to identify the dots. Second, connecting the dots looking backward is simply history, asking “how did I get here?” Even someone in an unenviable position can do that. I think the larger question is, “what do you do with the result of those connected dots?”


That is where I think Jobs is on point. I’m clearly an advocate of pursuing one’s passion, and that doing so can yield remarkable results in one’s life. If I never joined an improv group while in college, I would not have been doing a show one weekend where my going to church introduced me to missionaries working in Jamaica, an introduction that took me to that very country and that has led me to where I am now. Follow you interests and trust the dots will connect even when others question what you’re doing.

Who knows where I'd be had I never checked out improv comedy? (The Studio 013 Refugees in 1998)

2. Keep looking for your passion and don’t settle. Jobs focuses this story on his ouster from Apple. It hurt, but it was necessary because it freed him to try new things in technology, a field where he had found his passion. He challenges the audience to never settle, even when things don’t go the way they want. He urges them to keep fighting to find that which inspires them.

I heard more than a grain of truth in this story. I thought my pursuit of a more fulfilling career would keep me in Chicago and that my then-girlfriend would be a part of that long-term vision. Then the relationship ended. My plan collapsed and I was crushed. I could have settled and gone back to what I knew, but instead kept looking for what would inspire me. And that’s the challenge: staying present and persistent when it comes to being inspired about our vocations; the place we will make (arguable) the biggest time investment of our lives.

3. Death is a great motivator. Jobs advises his audience begin with the idea that life is short, they too will someday be old, and that everyone in that stadium had the same destination. Being very aware of our eventual demise can sharpen our decision making. The unnecessary falls away when you ask, if the end of my life were in sight, would I be doing what I’m doing now? Because none of us knows the time allotted us, we cannot afford to waste it doing something that does not inspire us.

I don’t have a near-death story. Jobs framed his words through his experience of cancer. However, I do recall various moments in my life where I imagined my future self in a monotonous, lifeless, prescribed scenario where I was having no real impact on much of anything. In short, I feared I would waste my shot at life. When I thought about quitting, I tried a visualization exercise where I thought about what people might say about me at my funeral based on my life to that point versus what I would want them to say. The space between those things was a large impetus for quitting and setting me on this path, a path whose end remains largely vague but that I trust will work out.

I consider these all very good points for further thought about living with intention and awareness. What we perceive as the limits to pushing past what we think we are supposed to do, or the situations in which we find ourselves, are usually the well-worn paths of others. The heart rate amps up a bit when we think of moving beyond that, even an inch. Find that space and keep yourself in it. I’m trying to and remain grateful to those of you reminding me to do so.

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#Fulfillment

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© 2020 by Mark Konold