Lessons learned from my year off
After 8 years of working as Kevin Spacey’s Chief of Staff, I was depressed. It was an amazing job and I had some incredible experiences but I yearned for a new challenge where I could continue to grow and learn. About a year ago I plucked up the courage to resign and this blog post details the most valuable learning from my year off.
Trying lots of things
Over the course of the year, I experimented with a lot of business ideas. I spent a couple of months writing a sci-fi book but I got stuck at 40,000 words and decided I needed to be a better writer before continuing. I tested a bunch of startup ideas including an online marketplace selling celebrities services. Want Elton John to sing at your birthday? No problem, for the bargain price of $5,000,000 you can have him….. After some market research, i decided this idea was not viable because it didn’t solve a strong enough pain point for the celebrity. I tried to start a cybersecurity business helping celebrities protect themselves from hackers. I tried my hand at being one of those youtube celebrities but after I made a couple of videos I realized it didn’t light a fire in my belly. After a while, i decided I needed more experience before setting out on my own so I interviewed for jobs at 50 tech companies including Google and AirBnB.
Here is one of the silly videos I made.
Everyone has an opinion but yours is the only one that matters
Before I quit my parents came to visit me in New York. We walked around central park in the fall and I told them I was thinking about leaving. They thought it was a terrible idea. They said I was lucky to be where I was and most people would kill to be in my position earning my salary. This made me feel terrible. If I stayed I knew I would feel bored but if I left I might find myself working in a job I hated making no money. I considered my parent’s advice but ultimately I made the decision to resign. They were not the only people sewing doubt in my mind. My husband also questioned my process and suggested I compromise. He thought I was considering too many options. To him, it looked like I was all over the place not finishing anything but ultimately I knew this process of trial and error was the best way to figure out what I wanted. My husband and parents love me so I knew their suggestions were made with the best intentions but it was tough to stay positive with everyone’s opinion flying around.
Perseverance pays off
After 8 months of experimenting / being unemployed, I began to worry that I had fucked everything up. I couldn’t seem to land any of the jobs I wanted and I had failed multiple times to get my own business off the ground. It’s an understatement to say I regretted leaving my old job and I was seriously doubting myself. I was very down in the dumps but it turns out everything came together 2 months later.
I’ve just accepted a job offer at AirBnB in San Fransisco and my cybersecurity business is finally starting to see some traction so I’m going to try and run the business on the side. Robin Wright and Neil Patrick Harris are interested in hiring me to do their cybersecurity and a prominent member of the White House National Security Council Cybersecurity Division has joined me as an advisor.
This year off was valuable for many reasons but the most important lesson I’ve learned is to make your own decisions and persevere. As I was going through the process I doubted myself many times but at the end of the day, no one knew more about my situation than I did. Success doesn’t happen overnight, I realized now that every failure was just another step towards success.
