The Leap to What You Love
And why it’s so damn scary
On August 13th, my family and I buried my 93 year old Grandpa — “Pa.”
He was the most present, curious and loving man I’ve ever known.
If you knew Pa, you knew his love for sharing knowledge. He could tell you the secret to flossing your teeth; why vinyl records sound so good; how to turn a light into a laser.
But with me, Pa shared more than just fun facts. We had a special bond that was strengthened by his imparting of valuable life lessons.
The most important lesson he taught me happened four years ago.
It was on an evening at my Granny and Pa’s home. I was in a rut — confused about my purpose in life and disconnected from the work I was doing. I was in a position where I needed to make an important decision about the direction of my business. I told Pa about the challenges I was facing.
He took me aside, sat me down and very gently said,
“Whatever decision you make, just be sure that it allows you to do something you love.” I watched a tear form in his eye as he told me he wished he had considered this at my age.
Later that night, I made a scary decision that would throw me into the unknown and change my career, but I knew it would better position me to do what I loved. The regret behind Pa’s words gave me the courage to make that decision — which proved to be one of the most important of my life.
(I went from running a record label to leaping into the tech investment world — a process that was just as intimidating as it was gratifying. Last year, Pa’s words held true when I decided to leave that company to start completely fresh).
Earlier this month, I flew to LA to see Pa. He was weak from pneumonia and he sat with his eyes closed.
Sitting next to him while he rested, I told my Granny about the influence that Pa had on me from that talk four years ago. I told her about the challenges that came with transitioning out of my company; the self doubt and fear that filled me as I opened myself up to find purpose beyond the industries I worked in for 9 years.
I told her that after a good deal of discomfort, I’m now doing work that I genuinely love. It continues to be challenging and at times can be gut-wrenching, but I’m connected to a purpose that allows me to give my greatest gifts: building communities and businesses around human connection.
I told her that I have Pa to thank for this.
We looked over at Pa and his eyes were wide open. Granny asked him if he had heard what I had just said. He nodded slowly and told us that he heard every word. In his soft voice he said,
“Doing what you love is not easy. It takes courage and continuous sacrifice, but it can not be ignored. You must spread this message to others.”
With a heavy heart, he reminded me that he deeply regretted not challenging himself in this way more throughout his career.
Pa was a brilliant and accomplished laser optic engineer. I wondered what he would have done differently — how his career would have been more in-line with his aspirations if he had acted on this advice.
Before we were able to continue the conversation, Pa told me he wanted to rest. I helped him into bed and sat by his side as he slept.
That was the last time we spoke.
Pa’s final words touched me deeply. When I spoke about this at a recent Medi Club gathering, a friend shared a study on the most common regrets of the dying. The top regret from the study: “I wish I had pursued my dreams and aspirations.”
These past few days since Pa’s funeral, I’ve been asking myself why this regret is so common.
In his book The Way of the Superior Man, David Deida writes, “Feel what you want to give most as a gift to the world, and do what you can to give it today. Every moment waited is a moment wasted, and each wasted moment degrades your clarity of purpose.”
But why have so many people waited? What is keeping us from doing what we love?
It’s so easy to just put it off until later, or wait until that pay raise kicks in, or start fresh in the new year, etc etc.
Pulling from my own experience, there have been three big challenges/questions on my path to purpose:
- Failure — among our top fears as humans is failure. If pursuing what we love doesn’t work out, what does that mean for our self image, our reputations, our finances and our loved ones?
- Expectations — we tend to live the life that others expect us to live. If we leave our jobs or jump into a new career/passion, what will our friends, families and colleagues think?
- Uncertainty— we get hooked on living in comfort and playing it safe. If we push ourselves to step out of this zone, how will we be able to operate if we’re in a constant state of vulnerability and uncertainty? What if we’re not able to discover what we really love doing?
Understanding these obstacles is a key piece to being able to actualize our dreams and aspirations. To truly give ourselves to doing what we love, we must be willing to let go of expectations, embrace failure and step into uncertainty...now.
Without the proper tools and mindset, the discomfort can be paralyzing, and leave us putting off doing what we love until it’s too late.
I’ve developed a handful of practices that have helped me bridge the gap from the comfort zone to the magic zone, navigate obstacles and keep my head up during low points. Here a few of them:
Connect with gratitude — After reading The How of Happiness, I learned that science now shows that we have the ability to control 40% of our happiness based on a practice of daily gratitude. Connecting with gratitude is single handedly my most powerful tool when I’m feeling self-doubt, fear, anger or envy. Every morning I write down 5 things I’m grateful for — this helps me keep a positive foundation throughout my day.
Drop the comparisons — I tend to compare my internal situations to what I perceive externally from others — a process that does nothing but create suffering. When I find myself comparing my situation to the successes of my peers, I remind myself that I’m wasting energy. To stop comparisons, I re-focus my energy on self-compassion and put my belief back into my own unique path.
Own my mindset —I used to think that positive thinking was a forced way of looking at reality, until my negative thinking recently brought me to one of the lowest points in my life. USC Business School Professor Ira Falk says, “If you think you can’t, you won’t. If you think you can, there’s a good chance you will.” Shifting my mindset to a positive one has allowed me to take control of my moods, my work and my impact on the world.
Recently, I’ve been seeing many of my peers leaving companies and switching professions to align themselves with what they love. I hope to see more honest dialogue around the challenges confronted on this path.
As we remember Pa and the many others who have shared his message, we can honor their lives by taking risks and giving ourselves permission to do what we truly love. There will never be a perfect time to leap. Start the process now — and consider what a gift it will be to come to the end of our days with one less dying regret.
Thank you Pa for everything you taught me.