I took this picture in a bonsai garden when I was a senior in college. The night before I’d caught a flight on a whim from Pittsburgh, PA to San Francisco. Graduation was just around the corner and I was deeply questioning my direction. It struck me as ironic that even this exotic garden was telling me to Please Stay On Path. It was my first time in Northern California. In part the trip was for a boy, but in part it was fueled by something more subconscious. It was about something more primal. It stemmed from a deep need to believe that life could contain possibility and that my path could be meaningful.

Over a decade has passed since that spontaneous, late night, cross-country flight and I now live in San Francisco. A lot has changed, but one thing that hasn’t is my thirst for life and my pursuit of discovery. Over the years, I’ve found that this perspective flies in the face of convention. To this day I’m often reminded to please stay on path.

Life doesn’t have to be linear.

There’s this widely held notion of how we’re meant to progress in life. We all know the drill: college, job, promotion, marriage, mortgage, children, repeat, etc. The problem with this cultural narrative, however, is that we’re living in a time where change is both constant and necessary. Staying on path is not particularly authentic anymore. In fact, it’s pretty limiting. (more…)

Many automatically equate being an entrepreneur or an independent creative with freedom and working for the corporate world with being beholden to an endless, soulless rat race. I know that for a long time, I was guilty of this assumption myself. Recently, however, I started a job with a new group at a massive tech company. For the first time in almost five years I have a boss and for the first time in my life I’m working for a corporation.

What has struck me and surprised me about the experience is that I actually feel a far greater sense of freedom than I ever expected to. (more…)

Last night I got lost. Instead of showing up at an event, I found myself on the porch of one of the most interesting homes in San Francisco, having a passionate conversation with two complete strangers. They weren’t meant to be there either.

Earlier that evening, I’d set out to meet a friend and arrived at the address, only to find a quiet and seemingly empty, large Victorian home. Not long after, a random guy arrived and asked if I was there for dinner. (more…)

The way we frame our reality determines the possibilities we see, which in turn determines the actions that we take. This is just one of the many reasons why storytelling is such a powerful tool. Stories tell us about how we assign meaning to the world. They enable us to reconcile with our past and shape our future. They serve as a means to navigate our journey and connect with people and possibilities along the way.

Stories can also hinder us. I used to (and sometimes still do) turn to my career to tell my story. I allowed jobs that didn’t fulfill me to define my worth and without fail, this always left me feeling small. I also experienced the other extreme. (more…)

This space contained one of the most challenging, defining and inspiring periods of my life. In the 2+ years that I lived here, not a single day passed that I didn’t think about the pursuit of happiness, human potential and how to help people live authentic, fulfilling and engaged lives.

Today I’m closing a chapter. I certainly know a lot more than when this all began. I’ve gone through the hard work of living out some of these questions myself. I can’t say that I have the answer and I don’t know what’s next, but I want to make room to find out.

During the past week I’ve savored, I’ve purged, I’ve remembered, I’ve questioned, I’ve committed, I’ve cleared it out. I’ve felt immense gratitude and I’ve let go. The boxes are packed. The movers have come and gone. And now as I glance around this empty home one last time, I’m reminded of a poem by Lao Tzu and I make room for not.

The Uses of Not

Thirty spokes
meet in the hub.
Where the wheel isn’t
is where it’s useful.

Hollowed out,
clay makes a pot.
Where the pot’s not
is where it’s useful.

Cut doors and windows
to make a room.
Where the room isn’t,
there’s room for you.

So the profit in what is
is in the use of what isn’t.

-Lao Tzu

During my last week in Cape Town I woke up on a sunny morning and drove to the southern most tip of South Africa. The winds were wild and intense. The landscape became more barren and beautiful. As we neared Cape of Good Hope, we drove along a turquoise coastline and stumbled upon a group of windswept ostriches by the sea. It was one of the most beautiful things I’ve seen in a long time… I can’t quite explain it, except that the moment expanded the boundaries of how I understand natural beauty. There was a raw elegance to it that was strikingly beautiful and immensely energizing.

In reflecting back to the weeks leading up to my trip, I was pretty exhausted. A year of living in uncertainty had taught me a tremendous amount, but I was ready to change modalities. I arrived in South Africa with a long backlog of ideas waiting to explode, but instead of attempting to churn through them, I rested. I did nothing. I explored. I wandered aimlessly through markets, met new people, read fiction in cafes, went on walks, painted flowers in Kirstenbosch Gardens, took naps, visited cheetahs, drank tea, watched the ocean and had long conversations with an old friend. I allowed myself to slip into a cycle of restoration and positive flow. (more…)

There’s something I’ve always loved about international flights and that feeling of being completely unreachable. It’s the sense that you’re neither here nor there. It’s the rare pause where time doesn’t seem to exist. It’s the quiet relief that comes with disconnecting. It’s losing yourself as you give into sleep and slip in and out of dreams. It’s wholehearted permission to just allow yourself to be in the in-between.

It’s been a year since this all started… I can’t claim to have been actively job searching the whole time. There have been consulting projects and breaks along the way. I have, however, been actively in transition the whole time. I guess you could also just call that living.

A few weeks ago, an unexpected opportunity popped up that I was truly excited about. It wasn’t for a full time position, but it was a project with people who I respect and admire, at a company that I really like and believe in. It seemed promising and this time I really wanted it. (more…)

On a warm fall day in October 2012, I laced up my sneakers and found myself running through Golden Gate Park deep in thought. I had recently shut down my startup Joyo, a coaching platform focused on careers and happiness. After many months of running on empty in every imaginable way, I was completely exhausted and ironically not at my happiest. I had pushed hard to realize my dream, but in the process of doing so lost the very thing that I was so adamantly chasing after in the first place.

With each step I took that afternoon, I came closer and closer to the conclusion that I was done running. I was done striving for some far out and elusive state of having “made it.” I was done living for later. I was done with feeling insanely tired all of the time. F-it. I wanted to live now. I wanted to be joyous in the moment, regardless of what that made me. Maybe I’d be less interesting. Maybe my resume would be less sexy. Who knows? I didn’t have the answer. All I knew is that I had to change the way that I lived. Both the rewards of success and the lessons of failure would always feel irrelevant to me, if it meant losing the ability to wake up every morning and feel deeply alive. (more…)

#1. Confessions of a Job Seeker – Sept. 2012

This series is based on a design journal that I kept between 09/12 – 02/13.

I started a company about careers and happiness called Joyo Inc. We didn’t make it and I became a job seeker myself. When I realized that I’d literally become my own user, I couldn’t help but see the irony in my situation. At first I wasn’t sure what to do about it, but then I realized that I had an important choice to make. I could see my situation as failure and admit defeat or I could see my circumstances as a gift and an opportunity to live my way to the answer. I chose the latter, and here I am.

#2. Confessions of a Job Seeker – Sept. 2012
This series is based on a design journal that I kept between 09/12 – 02/13. New? Start here.

On the morning of September 28^th, I was so bummed that I didn’t want to get out of bed. I didn’t see the point. This attitude contrasted sharply with the way that I normally jumped up in the morning to get after this dream that I cared so much about. I’d promised myself that I’d start my job search though, so I pulled my laptop into bed and half committed to taking action (rule #1 to being an entrepreneur). Between getting on Facebook and halfheartedly job searching on LinkedIn, I was not feeling awesome. I went back to what I had learned while working on Joyo: start by taking small steps. This worked. I was up and back at it, slowly, but surely.