Chapter 4: Dreaming Takes Resilience

“We’re going to get you food.”

I think that was the second sentence she spoke to me as I hopped into her car at San Francisco airport. I had hugged the neck of Laura Hale, a friend and client of my branding business for over a year and agreed “food” was a great idea.

Food does not begin to describe what I sat down to in the middle of a walled in Palo Alto garden restaurant on that afternoon. The crust was crisp and slightly blackened, a white sauce warmed it and crack black pepper scattered about its edges and in the very center of it was a sunny side up egg. I cut a slice and closed my eyes as the first bite went down. I was in pizza heaven. She laughed into her salad across the table and offered me some. I refused as politely as one can when their mouth is stuffed with pizza ambrosia.

Shhhh…I’m in heaven.

I told her about the trip thus far and she caught me up on a recent large dinner party which had brought her joy and her family,. Things were not going as she had planned but her life was very full and I loved the life I saw in her eyes.

A few hours later we sat down to discuss her start-up, Generation Grit, and her own Kickstarter which had raised quite a lot of money but had not been completely funded. I was fascinated by her story. I knew she wasn’t a newbie when it came to startups. She was the first official employee of bates, so I began there.

“What was it like building someone else’s big dream?” I asked her over my chamomile.

The sunlight lit her head as tilted it to one side and remembered, “It was amazing. I loved it. I loved building someone else’s dream. Online shopping wasn’t exactly what I wanted to focus my entire life on but it was a really fun job. It’s great being a part of something that started and wasn’t an insta-success. It was a long hard route to figure out. It was a lot of trial and error and listening to people, because things look different in real life than how you imagine them in your head.”

She had worked for them fifteen years before this conversation we were having and I remembered her mentioning earlier how they had just sold the company. “At one point the two of them even stepped down to serve on the board and hiring a CEO who could take it to the next level,” she said.

Handing over your dream to someone else sounded like a painful task to me.

She agreed, “I’m glad I got to see it from afar. From where I was sitting, they did it beautifully and it was all about what made the most sense for the company.”

They sounded like the kind of people who were willing to say “the dream is more important than my role in the dream.” We discussed how difficult that is for most people.We see that in tech. We see that in business all the time; people who just run their companies into the ground.

This led me to ask about her startup, Generation Grit.

She began it to encourage resilience in children, specifically boys, ages 9–12, and it has evolved. I asked her if it felt like the company was her dream or the concept or idea is was her dream? I wondered if she was an activist for these ideas and Generation Grit was just the vehicle for her to present them to the world.

“It is absolutely the idea of living an adventure for kids,” she replied, “it is also about building and creating something. The two come together in Generation Grit and the Kickstarter that we did was really a test for the market to see if this was something people wanted. It was a mixed message. I could argue both sides. I could see my dreams of building things and the passion I have around the issues fulfilled other ways but I’d love to see it happen this way.”

She seemed to have come to a place of peace but I couldn’t help but think that it had to be really hard when you have seen one particular method for making your dream come true and it doesn’t appear to be working itself out.

I wondered what it would take to get her from where she was at to making choices about the future of the company. Laughing, she admitted that she wondered the same thing. I asked her if she was waiting to make the decision because it was a difficult one or because it just wasn’t the right time.

“I’m trying to sit in the awkward space of not knowing either way,”

she answered, after getting up to let the dog out into the still green grass. “The day the Kickstarter ended I knew exactly what I was going to do. I needed to talk to people involved in the campaign and get their feedback while it was really fresh. I needed people who love me to be willing to say the hard things. I needed to talk to the uberfans who were super excited and hear what their feelings were really about. I did all that and it was so helpful. Now I’m sitting in that messy place realizing no matter what happens, there is no perfect answer. There is the element of what I want to do and there is the element of what makes sense given all that information I was able to get. Now I’m just sitting with it.”

Her answer sounded healthy if very uncomfortable to me and the next question seemed to flow out of that. “How is that affecting the other parts of your life?”

She was quick to respond to this, “I have a ton of pent up creativity. I’m just dying to work on something. There are other ways for it to come out besides Generation Grit. It completely affects everything. It affects me at my identity level. If I am not an entrepreneur doing a startup along with my family and everything, who am I and what’s enough?”

I sat there for a moment remembering the shuttle driver at LAX asking me that very question about I was. I remembered having a terrible answer and I wondered if she had a better one, if she had figured it out yet.

“It always comes back to being the beloved child of God,” she said. “It’s at the core of everything and that’s enough. That’s a great place to operate from because then I can pursue the dreams without it tanking me. It may tank me momentarily but it won’t for long. Acting that way doesn’t come naturally for me. I have to remind myself and I have people in my life who point me there when it gets shaky.”

Any dream worth having will be bigger than you.

It’s going to be bigger and wider and deeper than you and at some point you’re going to have to be willing to step out of its way so that it (and you) can grow. That’s painful and maybe a little bit ugly. But the other side of it is worth it. Dreaming is an ever evolving adventure. It will mutiny on you and you’re going to have to ride it out. Be resilient.