Cape Town, South Africa, September 2018

Sailing Oroboro Podcast — Episode 1

Quitting Our Jobs

Before Oroboro, before the ocean, there was a question: could you actually do it? In this episode, Francesco and Yuka explain what it takes to walk into an office and resign — and why it turned out to be nothing like they expected.

Quitting our jobs was one of the hardest things we've ever done, especially because we loved what we were doing - well, the greater portion thereof.

With our jobs, we also leave behind the security and comfort of our established lives. What about friends? What about health insurance? Mortgage? How long will our savings last? Who will offer us another job if we stay out of the workforce for so long? These and many other questions kept us often awake at night.

But a dream stays a dream if you are too scared to chase it. And most people's dreams remains just that. Fear of the unknown keeps them away from unfolding the possibilities in life.

And in the end, it's not the years in your life that count. It's the life in your years.

Yuka at her office — surrounded by international flags and elephant figurines, the Silicon Valley tech world we were about to leave behind

Yuka at her office — surrounded by international flags and elephant figurines, the Silicon Valley tech world we were about to leave behind

Francesco at eBay, celebrating the launch of Fresh Feed — one of the last projects before leaving

Francesco at eBay, celebrating the launch of Fresh Feed — one of the last projects before leaving

We spent countless hours planning and dreaming about the next step in our lives. So we thought that when it was finally going to be time to quit our jobs, we would be prepared, and it would be easy. We were wrong. It hasn't been easy at all.

As soon as we learned the exact date for the splash of our boat, we decided to turn in our resignations. Because we worked in the same industry - it's a small world, we thought it would be better to do it at exactly the same time. So we picked up a date and a time that worked well for both of us. When that day come, we went through the details one last time during breakfast, and we left home with one mission: going to the office and quit. Once we did it, we felt sad, but also relieved.

Alea iacta est (The die is cast)

My eBay badge — the last day I would ever need it

My eBay badge — the last day I would ever need it

We gave our employers generous notice, and that gave both of our teams enough time to search for our successors. A long notice also helped us, because we had enough time to catch up with and say goodbye to all the people we've worked with during the course of the years. And they are a lot!

So now here we are now: jobless. For the first time in our lives since college. No more intelligent conversations with our peers under the fluorescent. No more presentations, staff meetings, one-on-ones, V2MOMs, status reports, performance reviews and compliance trainings.

Saying goodbye to our beloved house was not easy

Saying goodbye to our beloved house was not easy

Friends and coworkers are asking me how my last day at work feels like. Well, to me it feels exactly like when I graduated from college.

As a matter of fact, as soon as I got home after my last day at the office this afternoon, Yuka welcomed me saying: Congratulations! I asked: What for? And she said: you've just graduated from eBay.

She is absolutely right!

What we shipped to Cape Town

What we shipped to Cape Town

Home — the last familiar view before the adventure began

Home — the last familiar view before the adventure began