Connecting the Dots and Finding What You Love

I’ve recently begun prepping for a talk I’m giving next month at our local Scrum User Group (ScrumRVA), and I stumbled across Steve Jobs’ 2005 Stanford commencement speech. I first watched this about 10 years ago and was deeply inspired as I was undergoing a transitional phase in my life and career.   As I listened to his address again, I was struck by his transparency and vulnerability. This was clearly a reflective and personal account, giving us a glimpse into the mind of one of the greatest leaders and entrepreneurs of our time. This time around, I want to capture for posterity how his words have inspired me to connect the dots and continue seeking what I love.

Drop out of things that don’t interest you and drop in on the things that do.

Steve dropped out of college after not seeing the value in spending his parents’ life savings when he had no idea what he wanted to do in life and no idea how college was going to help him figure it out. He dropped out of Reed College after 6 months, but stayed around campus for 18 months as a “drop in”. By dropping out, he was able to stop taking the required classes that didn’t interest him and he could drop in on the classes that did. A Calligraphy class he took during those 18 months would go on to shape the design and typography used in the Mac 10 years later, a strategy copied by Microsoft and now ubiquitous across the PC industry.

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. Believing that the dots will connect somewhere down the road will give you the confidence to follow your heart, even when it leads you off the well-worn path. And that will make all the difference.”

This hit me like a ton of bricks. I spend so much time trying to connect the dots and plan my future steps and activities. I spend so much time worrying about things that are outside of my control. I instinctively need to have contingency plans and scenarios accessible at any point and time and spend so many cycles chasing these situations which almost never materialize.

Steve talked about believing in “something” (gut, karma, etc.) and trusting that it’s all going to work out. For those who don’t know me, I’m a Christian, and Steve’s words helped me remember that I’m here for a reason and a purpose. I do believe that God has a plan, and in the end, everything will work out for the good so I truly don’t have to worry. 

Finding what you love.

In recounting his firing from Apple, Steve shared that sometimes life is going to hit you in the head with a brick and the key is not to lose faith. He said that the only thing that kept him going was that he loved what he did which gave him the strength to move forward.

Steve goes on to share whether it’s at work or in our personal life, we’ve got to find what we love and follow hard after it. We spend a large part of our lives at work, and the only way to be satisfied is to do great work (he’s referred to it as dong the best work of you life). And the only way to do great work is to love what you do. He admonishes if you haven’t found what you love yet, keep looking and don’t settle. You’ll know in your heart once you find it, so never settle for less.

If you live each day as if it was your last, someday you’ll most certainly be right.

Steve heard that quote as a teen and it stuck with him. For 33 years, he looked in the mirror each day and asked himself, “If today were the last day of my life, would I want to do what I’m about to do today?” Whenever the answer has been ‘no’ for too many days in a row, I know I need to change something.”

At the time of this speech, Steve had learned of his cancer a year before and was treatable with surgery. It would be 6 years later that Steve would lose his battle, but his sobering reminder was that death is a destination we all share:

“Because almost everything: external expectations, pride, all fear of embarrassment or failure, just fall away in the face of death — leaving only what is truly important. Remembering you are going to die is the best way to avoid the trap of thinking you have something to lose. You are already naked and there is no reason to not follow your heart.” 

“Follow you heart and intuition.”

“They somehow already know what you truly want to become. Everything else is secondary.” — Steve Jobs

These were among his closing statements and really resonated deeply with me. How often do we really follow our heart and intuition? In some instances, we don’t have the psychological safety to truly be vulnerable and acknowledge what’s on our hearts and minds. Maybe folks will laugh. Or think that we’re crazy. Does it really matter? We have one life and when we finally reach that final destination, do we really want to have any regrets?

Watching this talk has renewed my focus and desire to pursue what I love. And that’s serving people and organizations in discovering a better version of themselves. As an Agile Coach, I’m blessed and fortunate to have found something I truly love and if today were my last day on earth, I’m doing exactly what I want to do. The only change I do want to make is moving my area of focus into nonprofits and faith-based organizations.

I’ve seen Scrum literally transform lives and organizations, and my heart is telling me the next 10 years will be filled with opportunities to help transform even move lives and organizations through reimagining and transforming the world of work in nonprofits and charities.

Onward and upward!