I was sitting in a dream circle in a small village in Guatemala when it hit me — my biggest revelation in the year since I left the company I founded.
I had spent the trip surrounded by local women who earn a modest living making beautiful pieces of jewelry to sell in the States, and they invited me and everyone within earshot, to join this circle and draw their dreams.
This is not typically my scene. First off, drawing gives me massive anxiety. Things like meditation freak me out, and I would say silence in general is unwelcome in my world.
But there I was, with my piece of paper, a stack of colored pencils, my lackluster drawing skills and 10 minutes to draw my most far-reaching dreams.
It was a strange feeling to be asked that question in a room full of women whose lives are so dramatically different than mine, women who work so hard just to keep food on table. I feel extremely grateful to have achieved some of my most ambitious dreams. That doesn’t happen very often, and I felt a tinge of guilt at the prospect of having to stand in the center of that circle and say that success had afforded me a new dream: to help other women do the same.
But in the end, that’s what I drew — in stick figures and rainbows. And I thought it came out pretty good.
Until I saw what everyone else had done.
The other women in the group had drawn these beautiful, creative images with shape and texture. Mine was comprised entirely of straight lines and circles. It was the most binary drawing you’ve ever seen. I had even drawn that rainbow with perfectly straight lines. Who does that?
And I realized something: My dream is to be less binary.
It’s a revelation I’ve been working toward the entire year since I left WebDAM, the company I bootstrapped for 10 years. The company I ultimately sold to Shutterstock. The company that was my life for a very long time.
The first day after I left, I sat at my desk — technically unemployed for the first time in my adult life — and stared at a blank piece of paper, wondering, “What do I do now?” I knew I wanted to escape the grind and refresh, but how?
So I made a list. I decided I would get in better shape, spend more time outdoors, write, cook more, learn Spanish, do more volunteer work.
And for the most part, I didn’t do any of it.
It’s been a year, and despite spending 10 days in Guatemala and 3 weeks in Spain, I don’t know any Spanish. I still don’t have an interest in cooking — despite how joyful the Food Network makes it look. And this is my first real piece of writing since leaving work so I’m definitely not killing it in that department, either. As someone passionately committed to working and hitting my goals, this should be a major blow to my identity.
And yet, it’s not. As I look back on that list, it looks like a litany of stock New Year’s resolutions — a very binary exercise in personal transformation.
What I did accomplish this past year mattered so much more.
I didn’t volunteer in the way I thought I would — giving my time at soup kitchens or toy drives — but I did do more strategic philanthropic work with NGOs. I went to Guatemala with both a for-profit, for-purpose company and a nonprofit organization. I got deeply involved in a political campaign. I organized fundraising and social events for causes I believe in.
I spent two months traveling Europe with my husband and two small children — 14 cities in eight weeks. I unplugged, finally, and had an intense but amazing family adventure.
I started advising a whole range of startups — everything from social ventures to enterprise software companies. And I recaptured the rush I get from the entrepreneurial community.
Most important, I focused on relationships. That’s one of the biggest sacrifices we make as entrepreneurs — with children, with friends, with family. So I joined the PTA (yes, that PTA). I embraced the founders I met. I had parties. And I’ve built an incredible and diverse community of people I didn’t have a year ago. I love Silicon Valley and the tech community — but I have found a unique pleasure in building relationships with people who bring new perspectives and insights.
So I didn’t plow through my list with my typical workaholic zeal, but I did let life lead me to where I am supposed to be. I relinquished control (not easy for me) and rode the wave. So often in life, we set goals based on how we think we should live. We pledge to read more or run a 5k, but we don’t stop to consider why we want to do it.
Here is what I have learned: If we stop for just a moment, if we focus on being present and intentional and if we listen to what inspires us, we can accomplish a hell of a lot more than a 5k. Dreams becomes more than straight lines and circles, black and white.
So am I still seeing the world in black and white? Yes. But I am on the journey to Technicolor. And I have those women in that dream circle in Guatemala to thank for that.