It's time to ask the hard questions. What matters most to you?


Six years ago, I was in San Francisco (cue the Full House house) presenting to the marketing team at Apple as part of my interviews with them. Yes, Apple. It went great, but after I walked out of the doors of their campus, it hit me that I never wanted to be that far away from family.

I’ve experienced the “only a plane ride away” thing before when I was living in Japan and my brother died unexpectedly, and I learned the hard way that “only a plane ride away” is still a plane ride away.

So after my realization in San Fran, I decided I’d only considered companies that were on the east coast. After getting an incredible offer from Pepsi, I turned it down. While it would put me closer to home, it didn’t feel right to me. They reached out to again a couple of months later, and I turned it down again.

I asked myself hard questions, if these incredible companies with powerhouse marketing teams weren’t it, then what was “it”? I started thinking about the things that matter most to me.

At the time, I didn’t want to leave Vermont. And while asking myself the hard questions I thought about how insane it is that we build our lives around work ー it determines where we live, who we meet, when (and how much time) we get to spend time with our loved ones, and really, the entire path of our lives. That felt wrong to me.

It was then that I decided to start my own business and become a free agent as a freelancer. Free. And it really was my freedom. I got to work when and where I wanted. I got to spend more time with my family. I got to sleep in my aunt’s hospital room of Dana Farber for a week or two as she underwent a clinical trial for the cancer that later took her life. It’s time I cherish with all of my heart. Later that summer, I got to spend the full seven days on family vacation without having to come late or leave early for a work event. The list goes on and on.

For me, making that decision to go on my own was the best choice I ever made. Sure, I sometimes wonder how things would have been different. And of course, this whole freelance thing isn’t always rainbows and cupcakes. It’s not for everyone. But it works for me, and being able to design my life is something I never take for granted.

So what matters most to you? No matter what you choose for yourself remember that work is a fulfilling and vital part of our lives. But it should only ever be a part of it.

And if you’ve wrestled with an idea in your head, a voice you’ve been quieting, a dream for someday ー DO IT. Today. Now. Go. You’ll never know if you don’t try.