Jobs and the Art of Standing Out

April 8, 2015

“You can’t connect the dots looking forward; you can only connect them looking backwards. So you have to trust that the dots will somehow connect in your future.” — Steve Jobs

It’s a brisk spring morning here in New York and I’ve just poured my first full cup of coffee in a while. And…dang — caffeine really works when the body hasn’t used it in a while.

This has been an interesting week and I’ve been thinking a lot about the Steve Jobs quote above. For millennials who are entering into their life’s work or are reinventing themselves, it’s terrifying to take a leap of faith or follow your gut.

Trust me, I feel the same way. The Traveling Cup has grown so much in the past few months and it’s been incredible. But I still love my full-time teaching job. It’s rewarding for one because my students inspire me to be more and do more, and the job security really helps when my family depends on me.

This week David Ralph interviewed me on his British podcast called Join Up Dots and we spent a lot of time talking about connecting the dots. On the show, I had the unique opportunity to go back in time and offer advice to my former teenage self. It was fun and here’s what I said,

“Hey dude — right now, you’re probably sitting there in class staring out at the trees wondering how the heck this high school class lesson is going to help you in your life. Well, here’s the truth…it’s probably not. Your intuition is right. The school design is entirely outdated. Learn to listen to your intuition, but focus more on your mindset. Sure, that class isn’t really helping you, but staring out at the trees isn’t either. Be present. If you’re in a class be in the class. If you’re walking out in the woods, be in nature. Commit 100% to what it is that you’re doing. Mindset is everything.”

Side Note: I’ve been re-reading my wife’s novel and her ninja fantasy fiction writing skills just had me imagining…what if I really could pass a note through time to my former self? How would that alter the space time continuum!?


The three books I’m reading this week have everything to do with connecting the dots.

Steve Jobs by Walter Isaacson is the biography on Steve Jobs’. I’m amazed at how Isaacson was able to piece together all the many dots in Job’s life, including interviews with former girlfriends, parents, and burned business partners.

The Art of Work by Jeff Goins lays out a strategy for how anyone can discover what it is that they were meant to do.

Stand Out by Dorie Clark shows how a person can stand out and become the go-to expert in their field.

It’s interesting connecting the dots between these three books. Goins shows readers how to find out what it is that they are meant to do. Clark shows readers how to stand out after a person decides what it is that they want to do with their career. And Jobs…well, his story serves as a perfect model for trusting in your gut and taking risks. If you know Jobs’ story, there were many times when he was just starting out that he followed his gut even when others couldn’t understand why.

What about you? Where are you along the journey of connecting the dots? Are you on the path to discovering what it is that you were meant to do or are you working on standing out and becoming a go-to expert?

The Traveling Cup © 2016